S-3/A

QuickLinks -- Click here to rapidly navigate through this document

As filed with the Securities and Exchange Commission on October 2, 2003

Registration Statement No. 333-108711

SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

AMENDMENT NO. 1
TO
FORM S-3
REGISTRATION STATEMENT
UNDER THE SECURITIES ACT OF 1933

Lehman Brothers Holdings Inc.	Delaware	13-3216325
(Exact name of Registrant as specified in its charter)	(State or other jurisdiction of incorporation or organization)	(I.R.S. Employer Identification No.)

745 Seventh Avenue New York, New York 10019 (212) 526-7000 (Address, including Zip Code, and Telephone Number, including area code, of registrant's principal executive offices)	Thomas A. Russo, Esq. Lehman Brothers Holdings Inc. 745 Seventh Avenue New York, New York 10019 (212) 526-7000 (Name, address, including zip code, and telephone number, including area code, of agent for service for registrant)
Copies to:
Barrett S. DiPaolo, Esq. Lehman Brothers Holdings Inc. 399 Park Avenue New York, New York 10022	Andrew R. Keller, Esq. Simpson Thacher & Bartlett LLP 425 Lexington Avenue New York, New York 10017

        Approximate date of commencement of proposed sale to the public: From time to time after the effective date of this Registration Statement, as determined by market conditions.

        If the only securities being registered on this form are being offered pursuant to dividend or interest reinvestment plans, please check the following box. o

        If any of the securities being registered on this form are to be offered on a delayed or continuous basis pursuant to Rule 415 under the Securities Act of 1933 other than securities offered only in connection with dividend or interest reinvestment plans, check the following box. ý

        If this Form is filed to register additional securities for an offering pursuant to Rule 462(b) under the Securities Act, please check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering. o

        If this Form is a post-effective amendment filed pursuant to Rule 462(c) under the Securities Act, check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering. o

        If delivery of the prospectus is expected to be made pursuant to Rule 434, please check the following box. o

        The Registrant hereby amends this Registration Statement on such date or dates as may be necessary to delay its effective date until the Registrant shall file a further amendment which specifically states that this Registration Statement shall thereafter become effective in accordance with Section 8(a) of the Securities Act of 1933 or until the Registration Statement shall become effective on such date as the Commission, acting pursuant to said Section 8(a), may determine.

INTRODUCTORY NOTE

        This Registration Statement contains a form of prospectus supplement relating to the full and unconditional guarantee by Lehman Brothers Holdings of debt securities previously issued and hereafter issuable by Lehman Brothers Inc. To the extent required, the information in the applicable prospectus and this prospectus supplement will be updated at the time of each future offering. Upon each such offering, a prospectus supplement to the applicable prospectus of Lehman Brothers Inc. will be filed.

The information in this prospectus supplement is not complete and may be changed. We may not sell these securities until the registration statement filed with the Securities and Exchange Commission is effective. This prospectus supplement is not an offer to sell these securities and it is not soliciting an offer to buy these securities in any jurisdiction where the offer or sale is not permitted.

SUBJECT TO COMPLETION, DATED OCTOBER 2, 2003

PROSPECTUS SUPPLEMENT
(To prospectus dated May 6, 1998)
(To prospectus dated November 9, 1993)
(To prospectus dated May 20, 1985)

Full and Unconditional Guarantee By

LEHMAN BROTHERS HOLDINGS INC.
of Debt Securities of
Lehman Brothers Inc.

        The following terms will generally apply to the full and unconditional guarantee issued by Lehman Brothers Holdings of $1,684,438,000 of debt securities of Lehman Brothers Inc. issued and outstanding as of the date of this prospectus supplement and $1,795,000,000 aggregate principal amount of debt securities of Lehman Brothers Inc. to be sold from time to time using this prospectus supplement, together with a prospectus supplement relating to a specific series of debt securities and an attached prospectus. Lehman Brothers Inc. is a wholly owned subsidiary of Lehman Brothers Holdings and a broker-dealer registered under the Securities Exchange Act of 1934. Specific terms for each guaranteed debt security to be sold will be provided in a prospectus supplement and an attached prospectus, together with this prospectus supplement.

        Lehman Brothers Holdings may offer the guaranteed debt securities through underwriters, dealers or agents or by themselves directly.

        The securities may be sold through, or through underwriting syndicates managed by, Lehman Brothers Inc. alone or with one or more other underwriters. The applicable prospectus supplement sets forth or will set forth the names of the specific managing underwriter or underwriters and the members of the underwriting syndicate, if any, involved in the sale of the securities in respect of which this prospectus supplement is being delivered.

        This prospectus supplement, together with a prospectus supplement relating to a specific series of debt securities and an attached prospectus, may also be used by affiliates of Lehman Brothers Holdings in connection with offers and sales of securities related to market-making transactions at negotiated prices related to prevailing market prices at the time of sale or otherwise. These affiliates may act as principal or agent in such transactions.

        Neither the Securities and Exchange Commission nor any state securities commission has approved or disapproved of these securities or determined if this prospectus supplement is truthful or complete. Any representation to the contrary is a criminal offense.

LEHMAN BROTHERS

                                                 , 2003

TABLE OF CONTENTS

Where You Can Find More Information About Lehman Brothers Holdings	S-3
Lehman Brothers Holdings	S-4
Ratio of Earnings to Fixed Charges	S-4
Use of Proceeds	S-4
Description of the Guarantees	S-4
Certain United States Federal Income Tax Consequences	S-6
Plan of Distribution	S-13
ERISA Considerations	S-15
Experts	S-16
Legal Matters	S-16

        You should only rely on the information contained or incorporated by reference in this prospectus supplement, the prospectus supplement relating to a specific series of debt securities and an attached prospectus. Lehman Brothers Holdings has not authorized any other person to provide you with different information. If anyone provides you with different or inconsistent information, you should not rely on it. Lehman Brothers Holdings is not making an offer to sell these securities in any jurisdiction where the offer or sale is not permitted. You should assume that the information appearing in this prospectus supplement, the prospectus supplement relating to a specific series of debt securities and an attached prospectus, as well as information Lehman Brothers Holdings previously filed with the Securities and Exchange Commission and incorporated herein by reference, is accurate only as of the date of the applicable document. The business, financial condition, results of operations and prospects of Lehman Brothers Holdings may have changed since that date.

S-2

WHERE YOU CAN FIND MORE INFORMATION
ABOUT LEHMAN BROTHERS HOLDINGS

        Lehman Brothers Holdings files annual, quarterly and current reports, proxy statements and other information with the Securities and Exchange Commission (the "SEC"). These SEC filings are available to the public over the Internet at the SEC's web site at www.sec.gov. You may read and copy any document we file at the SEC's public reference room at Room 1024, 450 Fifth Street, N.W., Washington, D.C. 20549. Please call the SEC at 1-800-SEC-0330 for further information on the public reference room.

        Lehman Brothers Holdings filed a registration statement on Form S-3 with the SEC covering the guarantees offered by this prospectus supplement. For further information on Lehman Brothers Holdings and the offered securities, you should refer to the registration statement and its exhibits. Lehman Brothers Inc. has also filed registration statements concerning the debt securities that will be guaranteed by Lehman Brothers Holding. This prospectus supplement summarizes material provisions of the offered guarantees, and the prospectus supplement relating to a specific series of debt securities and an attached prospectus summarize material provisions of the offered debt securities and related indentures. Because this prospectus supplement and the prospectus supplement relating to a specific series of debt securities and an attached prospectus may not contain all the information that you may find important, you should review the full text of the registration statements and their exhibits. Lehman Brothers Holdings and Lehman Brothers Inc. have included copies of the documents summarized in this prospectus supplement and the prospectus supplement relating to a specific series of debt securities and an attached prospectus in exhibits to the respective registration statements of which this prospectus supplement and the prospectus are a part.

        The SEC allows Lehman Brothers Holdings to "incorporate by reference" the information Lehman Brothers Holdings files with them, which means important information can be disclosed to you by referring you to those documents. The information incorporated by reference is considered to be a part of this prospectus supplement, and information that Lehman Brothers Holdings files later with the SEC will automatically update and supersede this information. In all cases, you should rely on the later information over different information included in this prospectus supplement. Lehman Brothers Holdings incorporates by reference the documents listed below and any future filings made with the SEC under Sections 13(a), 13(c), 14, or 15(d) of the Securities Exchange Act of 1934 shall be incorporated by reference in this prospectus until the later of (1) the completion of the offering of the securities described in this prospectus supplement and (2) the date affiliates of Lehman Brothers Holdings stop offering securities pursuant to this prospectus supplement:

•

the Annual Report on Form 10-K for the year ended November 30, 2002;



•

the Quarterly Reports on Form 10-Q for the quarters ended February 28, 2003 and May 31, 2003; and



•

the Current Reports on Form 8-K filed on December 11, December 19 and December 23, 2002 (two filings), January 9, March 17, March 20, March 21, April 29, May 1, May 2, May 8 (two filings), May 13, May 20, May 27, June 2, June 19, June 24, July 1, July 10, July 14, July 22, August 26, August 27, September 10, 2003 September 16 and September 23.

        You may also request a copy of any or all of the information that has been incorporated by reference in this prospectus supplement, free of cost, by writing or telephoning Lehman Brothers Holdings at the following address and telephone number:

Lehman Brothers Holdings Inc.
Office of the Corporate Secretary
399 Park Avenue
New York, New York 10022
(212) 526-0858

S-3

LEHMAN BROTHERS HOLDINGS

        Lehman Brothers Holdings together with its subsidiaries ("Lehman Brothers") is one of the leading global investment banks, serving institutional, corporate, government and high net-worth individual clients and customers. Lehman Brothers' worldwide headquarters in New York and regional headquarters in London and Tokyo are complemented by offices in additional locations in the United States, Europe, the Middle East, Latin America and the Asia Pacific region. Lehman Brothers is engaged primarily in providing financial services. Other businesses in which Lehman Brothers is engaged represent less than 10 percent of consolidated assets, revenues or pre-tax income.

        Lehman Brothers' business includes capital raising for clients through securities underwriting and direct placements, corporate finance and strategic advisory services, private equity investments, securities sales and trading, research, and the trading of foreign exchange and derivative products and certain commodities. Lehman Brothers acts as a market-maker in all major equity and fixed income products in both the United States and international markets. Lehman Brothers is a member of all principal securities and commodities exchanges in the United States, as well as the NASD, and holds memberships or associate memberships on several principal international securities and commodities exchanges, including the London, Tokyo, Hong Kong, Frankfurt, Paris and Milan stock exchanges.

        Lehman Brothers provides a full array of capital market products and advisory services worldwide. Through Lehman Brothers' investment banking, trading, research, structuring and distribution capabilities in equity and fixed income products, Lehman Brothers continues its focus of building its client/customer business model. These "customer flow" activities represent a majority of Lehman Brothers' revenues. In addition to its customer flow activities, Lehman Brothers also takes proprietary positions, the success of which is dependent on its ability to anticipate economic and market trends. Lehman Brothers believes its customer flow orientation mitigates its overall revenue volatility.

        Lehman Brothers Holdings is a Delaware corporation, incorporated on December 29, 1983. Its executive offices are located at 745 Seventh Avenue, New York, New York 10019, and its telephone number is (212) 526-7000.

RATIO OF EARNINGS TO FIXED CHARGES

        The following table shows Lehman Brothers Holdings' consolidated ratio of earnings to fixed charges for each of the five most recent fiscal years and the most recent interim period:

						Six Months Ended May 31, 2003
	Year Ended November 30,
	1998	1999	2000	2001	2002
Ratio of Earnings to Fixed Charges	1.07	1.12	1.14	1.11	1.13	1.23

USE OF PROCEEDS

        Lehman Brothers Holdings will not receive directly any proceeds from any offered guarantees. For a discussion of the use of proceeds to be received by Lehman Brothers Inc. from any offering of debt securities, see "Use of Proceeds" in the prospectus supplement relating to a specific series of debt securities and an attached prospectus.

DESCRIPTION OF THE GUARANTEES

        The following description of the terms of the guarantees of Lehman Brothers Holdings supplements the description of the terms and provisions of the debt securities of Lehman Brothers Inc. set forth in the prospectus supplement relating to a specific series of debt securities and an attached prospectus. Terms used

S-4

in this prospectus supplement will have the meanings described in the prospectus supplement relating to a specific series of debt securities and an attached prospectus, unless otherwise specified.

        The prospectus supplement relating to a specific series of debt securities of Lehman Brothers Inc. to be issued in the future will contain the specific information and terms for that offering. You should read carefully the particular terms of a series of debt securities in the specific prospectus supplement. That prospectus supplement may also add, update or change information contained in an attached prospectus. It is important for you to consider the information contained in this prospectus supplement and the specific prospectus supplement and an attached prospectus relating to your debt securities in making your investment decision.

Guarantees

        The guarantees are to be issued under the respective senior or senior subordinated indentures described in the specific prospectus supplement and an attached prospectus between Lehman Brothers Inc. and the respective trustees named therein, each as amended and supplemented to date and as further amended and supplemented by a supplemental indenture among Lehman Brothers Inc., Lehman Brothers Holdings, as guarantor, and the applicable trustee setting forth the terms of the guarantee, all of which are included or incorporated by reference as exhibits to the registration statement of which this prospectus supplement forms a part. This prospectus supplement, the prospectus supplement relating to a specific series of debt securities and an attached prospectus briefly summarize the material provisions of the indentures and the debt securities and guarantees. You should read the more detailed provisions of the applicable indenture, including the defined terms, for provisions that may be important to you.

        A form of each debt security, reflecting the particular terms and provisions of a series of offered debt securities, has been filed with the SEC or will be filed with the SEC at the time of the offering and incorporated by reference in the registration statement of which this prospectus supplement forms a part. You can obtain a copy of any form of debt security when it has been filed by following the directions on page S-3 or by contacting the applicable trustee.

        Payment of the principal of and premium, if any, and interest on the debt securities of Lehman Brothers Inc. described in the prospectus supplement relating to a specific series of debt securities and an attached prospectus will be fully and unconditionally guaranteed by Lehman Brothers Holdings, which is the parent corporation of Lehman Brothers Inc. Lehman Brothers Holdings will guarantee the full and prompt payment of the principal of, premium, if any, and interest on the debt securities of Lehman Brothers Inc. when and as the same become due and payable, whether at maturity, upon redemption or purchase, by declaration of acceleration or otherwise. The guarantee provides that upon a default in payment of principal of and premium, if any, and interest on the debt securities of Lehman Brothers Inc., the holder of the debt security may institute legal proceedings directly against Lehman Brothers Holdings without first proceeding against Lehman Brothers Inc.

        A guarantee issued by Lehman Brothers Holdings of senior debt securities or of senior subordinated debt securities of Lehman Brothers Inc. will be an unsecured obligation of Lehman Brothers Holdings ranking equally with all unsecured and unsubordinated indebtedness of Lehman Brothers Holdings.

        You should refer to the most recent report on Form 10-K or Form 10-Q of Lehman Brothers Holdings filed with the SEC and incorporated by reference in this prospectus supplement to obtain the most recent financial information about Lehman Brothers Holdings. The indentures do not limit the amount of additional debt or guarantees or other contingent liabilities that Lehman Brothers Holdings may issue or incur or limit Lehman Brothers Holdings ability to mortgage, pledge or place a lien or security interest or other encumbrance of any of its assets.

        The guarantees are unsecured obligations of Lehman Brothers Holdings. Since Lehman Brothers Holdings is a holding company, its cash flow and consequent ability to satisfy its obligations under the

S-5

offered guarantees are dependent upon the earnings of its subsidiaries and the distribution of those earnings or loans or other payments by those subsidiaries to Lehman Brothers Holdings. Lehman Brothers Holdings' subsidiaries (other than Lehman Brothers Inc. as issuer) will have no obligation to pay any amount in respect of the guarantees or debt securities or to make any funds available therefor.

        Dividends, loans and other payments by Lehman Brothers Inc. and certain other subsidiaries are restricted by net capital and other rules of various regulatory bodies. Additionally, the ability of Lehman Brothers Holdings to participate as an equity holder in any distribution of assets of any subsidiary is subordinate to the claims of creditors of the subsidiary, except to the extent that any claims Lehman Brothers Holdings may have as a creditor of the subsidiary are judicially recognized.

        Lehman Brothers Holdings and its affiliates maintain bank accounts, borrow money and have other customary banking relationships and other business relationships with the trustees in the ordinary course of business.

CERTAIN UNITED STATES FEDERAL INCOME TAX CONSEQUENCES

        The following is a summary of the material United States federal income tax consequences of the purchase, ownership and disposition of debt securities as of the date of this prospectus supplement and replaces the discussion of tax consequences in any prospectus supplement relating to a specific series of debt securities dated prior to the date of this prospectus supplement and an attached prospectus. (In this summary, references to the debt securities include the guarantees thereof.) Except where noted, this summary deals only with debt securities held as capital assets by United States holders (as defined below) and does not deal with special situations. For example, this summary does not address:

•

tax consequences to holders who may be subject to special tax treatment, such as dealers in securities or currencies, financial institutions, tax-exempt entities, real estate investment trusts, regulated investment companies, insurance companies, or traders in securities that elect to use a mark-to-market method of accounting for their securities holdings;



•

tax consequences to persons holding debt securities as part of a hedging, integrated, conversion or constructive sale transaction or a straddle;



•

tax consequences to United States holders of debt securities whose "functional currency" is not the U.S. dollar;



•

certain expatriates who are holders of our debt securities;



•

alternative minimum tax consequences, if any; or



•

any state, local or foreign tax consequences.

        The discussion below is based upon the provisions of the Internal Revenue Code of 1986, as amended (the "Code"), the Treasury regulations promulgated under the Code, and rulings and judicial decisions as of the date of this prospectus. Those authorities may be changed, perhaps retroactively, so as to result in United States federal income tax consequences different from those discussed below. The discussion set forth below also assumes that all debt securities constitute debt for United States federal income tax purposes. If any debt security did not constitute debt for United States federal income tax purposes, the tax consequences of the ownership of such debt security could differ materially from the tax consequences described herein. Lehman Brothers Inc. has summarized or will summarize any special United States federal tax considerations relevant to a particular issue of the debt securities in the specific prospectus supplement relating to your debt securities.

        If a partnership holds debt securities, the tax treatment of a partner will generally depend upon the status of the partner and the activities of the partnership. If you are a partner of a partnership holding debt securities, you should consult your tax advisor.

S-6

        If you are considering the purchase of debt securities, you should consult your own tax advisor concerning the federal income tax consequences to you and any consequences arising under the laws of any other taxing jurisdiction.

Consequences to United States Holders

        The following is a summary of certain United States federal tax consequences that will apply to you if you are a United States holder of debt securities.

        Certain consequences to "non-United States holders" of debt securities are described under "—Consequences to Non-United States Holders" below.

        "United States holder" means a beneficial owner of a debt security that is for United States federal income tax purposes:

•

a citizen or resident of the United States;



•

a corporation or partnership created or organized in or under the laws of the United States or any political subdivision of the United States;



•

an estate the income of which is subject to United States federal income taxation regardless of its source;



•

a trust that (x) is subject to the primary supervision of a court within the United States and one or more United States persons have the authority to control all substantial decisions of the trust or (y) has a valid election in effect under applicable United States Treasury regulations to be treated as a United States person.

Payments of Interest

        Except as set forth below, interest on a debt security will generally be taxable to you as ordinary income from domestic sources at the time it is paid or accrued in accordance with your method of accounting for tax purposes.

Original Issue Discount

        If you own debt securities issued with original issue discount ("OID"), you will be subject to special tax accounting rules, as described in greater detail below. In that case, you should be aware that you generally must include OID in gross income in advance of the receipt of cash attributable to that income. However, you generally will not be required to include separately in income cash payments received on the debt securities, even if denominated as interest, to the extent those payments do not constitute qualified stated interest, as defined below. Notice will be given in the applicable prospectus supplement when Lehman Brothers Inc. determines that a particular debt security will be an OID debt security.

        A debt security with an issue price that is less than the "stated redemption price at maturity" (the sum of all payments to be made on the debt security other than "qualified stated interest") generally will be issued with OID if that difference is at least 0.25% of the stated redemption price at maturity multiplied by the number of complete years to maturity. The "issue price" of each debt security in a particular offering will be the first price at which a substantial amount of that particular offering is sold to the public. The term "qualified stated interest" means stated interest that is unconditionally payable in cash or in property, other than debt instruments of the issuer, and the interest to be paid meets all of the following conditions:

•

it is payable at least once per year;



•

it is payable over the entire term of the debt security; and

S-7

•

it is payable at a single fixed rate or, subject to certain conditions, based on one or more interest indices.

        Lehman Brothers Inc. will give you notice in the applicable prospectus supplement when it determines that a particular debt security will bear interest that is not qualified stated interest.

        If you own a debt security issued with "de minimis" OID, which is discount that is not OID because it is less than 0.25% of the stated redemption price at maturity multiplied by the number of complete years to maturity, you generally must include the de minimis OID in income at the time payments, other than qualified stated interest, on the debt securities are made in proportion to the amount paid. Any amount of de minimis OID that you have included in income will be treated as capital gain.

        Certain of the debt securities may contain provisions permitting them to be redeemed prior to their stated maturity at our option and/or at your option. OID debt securities containing those features may be subject to rules that differ from the general rules discussed herein. If you are considering the purchase of OID debt securities with those features, you should carefully examine the applicable prospectus supplement and should consult your own tax advisor with respect to those features since the tax consequences to you with respect to OID will depend, in part, on the particular terms and features of the debt securities.

        If you own OID debt securities with a maturity upon issuance of more than one year, you generally must include OID in income in advance of the receipt of some or all of the related cash payments using the "constant yield method" described in the following paragraph. This method takes into account the compounding of interest. The accruals of OID on an OID debt security will generally be less in the early years and more in the later years.

        The amount of OID that you must include in income if you are the initial United States holder of an OID debt security is the sum of the "daily portions" of OID with respect to the debt security for each day during the taxable year or portion of the taxable year in which you held that debt security ("accrued OID"). The daily portion is determined by allocating to each day in any "accrual period" a pro rata portion of the OID allocable to that accrual period. The "accrual period" for an OID debt security may be of any length and may vary in length over the term of the debt security, provided that each accrual period is no longer than one year and each scheduled payment of principal or interest occurs on the first day or the final day of an accrual period. The amount of OID allocable to any accrual period is an amount equal to the excess, if any, of:

•

the debt security's adjusted issue price at the beginning of the accrual period multiplied by its yield to maturity, determined on the basis of compounding at the close of each accrual period and properly adjusted for the length of the accrual period, over



•

the aggregate of all qualified stated interest allocable to the accrual period.

        OID allocable to a final accrual period is the difference between the amount payable at maturity, other than a payment of qualified stated interest, and the adjusted issue price at the beginning of the final accrual period. The "adjusted issue price" of a debt security at the beginning of any accrual period is equal to its issue price increased by the accrued OID for each prior accrual period, determined without regard to the amortization of any acquisition or bond premium, as described below, and reduced by any payments made on the debt security (other than qualified stated interest) on or before the first day of the accrual period. Under these rules, you will have to include in income increasingly greater amounts of OID in successive accrual periods. Lehman Brothers Inc. is required to provide information returns stating the amount of OID accrued on debt securities held of record by persons other than corporations and other exempt holders.

S-8

        Floating rate debt securities are subject to special OID rules. In the case of an OID debt security that is a floating rate debt security, both the "yield to maturity" and "qualified stated interest" will be determined solely for purposes of calculating the accrual of OID as though the debt security will bear interest in all periods at a fixed rate generally equal to the rate that would be applicable to interest payments on the debt security on its date of issue or, in the case of certain floating rate debt securities, the rate that reflects the yield to maturity that is reasonably expected for the debt security. Additional rules may apply if:

•

the interest on a floating rate debt security is based on more than one interest index; or



•

the principal amount of the debt security is indexed in any manner.

        This discussion does not address the tax rules applicable to debt securities with an indexed principal amount. If you are considering the purchase of floating rate OID debt securities or securities with indexed principal amounts, you should carefully examine the applicable prospectus supplement and should consult your own tax advisor regarding the United States federal income tax consequences to you of holding and disposing of those debt securities.

        You may elect to treat all interest on any debt security as OID and calculate the amount includible in gross income under the constant yield method described above. For purposes of this election, interest includes stated interest, acquisition discount, OID, de minimis OID, market discount, de minimis market discount and unstated interest, as adjusted by any amortizable bond premium or acquisition premium. You should consult with your own tax advisor about this election.

Short-term Debt Securities

        In the case of debt securities having a term of one year or less, all payments, including all stated interest, will be included in the stated redemption price at maturity and will not be qualified stated interest. As a result, you will generally be taxed on the discount instead of stated interest. The discount will be equal to the excess of the stated redemption price at maturity over the issue price of a short-term debt security, unless you elect to compute this discount using tax basis instead of issue price. In general, individuals and certain other cash method United States holders of short-term debt securities are not required to include accrued discount in their income currently unless they elect to do so, but may be required to include stated interest in income as the income is received. United States holders that report income for United States federal income tax purposes on the accrual method and certain other United States holders are required to accrue discount on short-term debt securities (as ordinary income) on a straight-line basis, unless an election is made to accrue the discount according to a constant yield method based on daily compounding. If you are not required, and do not elect, to include discount in income currently, any gain you realize on the sale, exchange or retirement of a short-term debt security will generally be ordinary income to you to the extent of the discount accrued by you through the date of sale, exchange or retirement. In addition, if you do not elect to currently include accrued discount in income, you may be required to defer deductions for a portion of your interest expense with respect to any indebtedness attributable to the short-term debt securities.

Market Discount

        If you purchase a debt security, other than an OID debt security, for an amount that is less than its stated redemption price at maturity, or, in the case of an OID debt security, its adjusted issue price, the amount of the difference will be treated as "market discount" for United States federal income tax purposes, unless that difference is less than a specified de minimis amount. Under the market discount rules, you will be required to treat any payment, other than qualified stated interest, on, or any gain on the sale, exchange, retirement or other disposition of, a debt security as ordinary income to the extent of the market discount that you have not previously included in income and are treated as having accrued on the debt security at the time of its payment or disposition.

S-9

        In addition, you may be required to defer, until the maturity of the debt security or its earlier disposition in a taxable transaction, the deduction of all or a portion of the interest expense on any indebtedness attributable to the debt security. You may elect, on a bond-by-bond basis, to deduct the deferred interest expense in a tax year prior to the year of disposition. You should consult your own tax advisor before making this election.

        Any market discount will be considered to accrue ratably during the period from the date of acquisition to the maturity date of the debt security, unless you elect to accrue on a constant interest method. You may elect to include market discount in income currently as it accrues, on either a ratable or constant interest method, in which case the rule described above regarding deferral of interest deductions will not apply.

Acquisition Premium, Amortizable Bond Premium

        If you purchase an OID debt security for an amount that is greater than its adjusted issue price but equal to or less than the sum of all amounts payable on the debt security after the purchase date other than payments of qualified stated interest, you will be considered to have purchased that debt security at an "acquisition premium." Under the acquisition premium rules, the amount of OID that you must include in gross income with respect to the debt security for any taxable year will be reduced by the portion of the acquisition premium properly allocable to that year.

        If you purchase a debt security (including an OID debt security) for an amount in excess of the sum of all amounts payable on the debt security after the purchase date other than qualified stated interest, you will be considered to have purchased the debt security at a "premium" and, if it is an OID debt security, you will not be required to include any OID in income. You generally may elect to amortize the premium over the remaining term of the debt security on a constant yield method as an offset to interest when includible in income under your regular accounting method. If you do not elect to amortize bond premium, that premium will decrease the gain or increase the loss you would otherwise recognize on disposition of the debt security.

Sale, Exchange and Retirement of Debt Securities

        Your tax basis in a debt security will, in general, be your cost for that debt security, increased by OID, market discount or any discount with respect to a short-term debt security that you previously included in income, and reduced by any amortized premium and any cash payments on the debt security other than qualified stated interest. Upon the sale, exchange, retirement or other disposition of a debt security, you will recognize gain or loss equal to the difference between the amount you realize upon the sale, exchange, retirement or other disposition (less an amount equal to any accrued qualified stated interest that you did not previously include in income, which will be taxable as such) and the adjusted tax basis of the debt security. Except as described above with respect to certain short-term debt securities or with respect to market discount, or with respect to foreign currency debt securities or contingent payment debt securities, that gain or loss will be capital gain or loss. Capital gains of individuals derived in respect of capital assets held for more than one year are eligible for reduced rates of taxation. The deductibility of capital losses is subject to limitations.

Tax Consequences of Satisfaction and Discharge

        Lehman Brothers Inc. may legally discharge its obligations under the debt securities as more fully described under "Description of Senior Debt Securities—Satisfaction and Discharge" in the applicable prospectus. Such a discharge would generally for United States federal income tax purposes constitute the retirement of the debt securities and the issuance of new obligations. As a result, you would realize gain or loss (if any) on this exchange, which would be recognized subject to certain possible exceptions.

        Even though federal income tax on the deemed exchange may be imposed on you, you would not receive any cash until the maturity or an earlier redemption of the debt securities, except for any current interest payments.

S-10

        Following the legal discharge, the debt securities might be subject to withholding, backup withholding and/or information reporting and might be issued with OID.

        Any gain realized would generally not be taxable to non-United States holders under the circumstances outlined below under "Consequences to Non-United States Holders—United States Federal Income Tax."

        Under current federal income tax law, a covenant defeasance generally would not be treated as a taxable exchange of the debt securities. You should consult your own tax advisor as to the tax consequences of a defeasance and discharge and a covenant defeasance, including the applicability and effect of tax laws other than the United States federal income tax law.

Consequences to Non-United States Holders

        The following is a summary of certain United States federal tax consequences that will apply to you if you are a non-United States holder of debt securities. "Non-United States holder" means a beneficial owner of a debt security that is not a United States holder.

        Special rules may apply to some non-United States holders, such as "controlled foreign corporations," "passive foreign investment companies," "foreign personal holding companies" and corporations that accumulate earnings to avoid United States federal income tax, that are subject to special treatment under the Code. These entities should consult their own tax advisors to determine the United States federal, state, local and other tax consequences that may be relevant to them.

United States Federal Withholding Tax

        The 30% United States federal withholding tax will not apply to any payment of principal or interest, including OID, on debt securities under the portfolio interest rule provided that:

•

interest paid on the debt security is not effectively connected with your conduct of a trade or business in the United States;



•

you do not actually or constructively own 10% or more of the total combined voting power of all classes of voting stock of Lehman Brothers Inc. within the meaning of the Code and United States Treasury regulations;



•

you are not a controlled foreign corporation that is related to Lehman Brothers Inc. through stock ownership;



•

you are not a bank whose receipt of interest on the debt securities is described in section 881(c)(3)(A) of the Code; and



•

either (a) you provide your name and address on an Internal Revenue Service ("IRS") Form W-8BEN (or successor form), and certify, under penalties of perjury, that you are not a United States person or (b) you hold your debt securities through certain foreign intermediaries, and you satisfy the certification requirements of applicable United States Treasury regulations.

        Special certification rules apply to certain non-United States holders that are entities rather than individuals. If you cannot satisfy the requirements described above, payments of premium, if any, and interest, including OID, made to you will be subject to the 30% United States federal withholding tax, unless you provide Lehman Brothers Inc. with a properly executed:

•

IRS Form W-8BEN (or successor form) claiming an exemption from, or reduction in, withholding under the benefit of an applicable income tax treaty;



•

IRS Form W-8ECI (or successor form) stating that interest paid on the debt securities is not subject to withholding tax because it is effectively connected with your conduct of a trade or business in the United States.

S-11

        Except as discussed below, the 30% United States federal withholding tax generally will not apply to any gain that you realize on the sale, exchange, retirement or other disposition of debt securities.

United States Federal Income Tax

        If you are engaged in a trade or business in the United States and premium, if any, or interest, including OID, on the debt securities is effectively connected with the conduct of that trade or business, you will be subject to United States federal income tax on that premium, interest and OID on a net income basis (although exempt from the 30% withholding tax, provided certification and disclosure requirements discussed above under "—United States Federal Withholding Tax" are satisfied) in the same manner as if you were a United States holder. In addition, if you are a foreign corporation, you may be subject to a branch profits tax equal to 30% (or lower applicable income tax treaty rate) of your earnings and profits for the taxable year, subject to adjustments. For this purpose, any premium and interest, including OID, on debt securities will be included in your earnings and profits.

        You generally will not be subject to United States federal income tax on the disposition of a debt security unless:

•

the gain is effectively connected with your conduct of a trade or business in the United States; or



•

you are an individual who is present in the United States for 183 days or more in the taxable year of that disposition, and certain other conditions are met.

United States Federal Estate Tax

        Your estate will not be subject to United States federal estate tax on debt securities beneficially owned by you at the time of your death provided that:

•

any payment to you on the debt securities would be eligible for exemption from the 30% United States federal withholding tax under the portfolio interest rule described in the bullet points under "—United States Federal Withholding Tax," without regard to the certification requirements of the fifth bullet point; and



•

interest on those debt securities would not have been, if received at the time of your death, effectively connected with the conduct by you of a trade or business in the United States.

Information Reporting and Backup Withholding

United States Holders

        In general, information reporting requirements will apply to certain payments of principal, interest, OID and premium paid on debt securities and to the proceeds of sale of a debt security made to you (unless you are an exempt recipient such as a corporation). A 28% backup withholding tax will apply to such payments if you fail to provide a taxpayer identification number or a certification of exempt status, or if you fail to report in full dividend and interest income.

        Any amounts withheld under the backup withholding rules will be allowed as a refund or a credit against your United States federal income tax liability provided the required information is furnished to the IRS.

Non-United States Holders

        If you are a non-United States holder of debt securities, Lehman Brothers Inc. must report annually to the IRS and to you the amount of payments Lehman Brothers Inc. makes to you and the tax withheld with respect to such payments, regardless of whether withholding was required. Copies of the information returns reporting such payments and withholding may also be made available to the tax authorities in the country in

S-12

which you reside under the provisions of an applicable income tax treaty. You will not be subject to backup withholding regarding payments Lehman Brothers Inc. makes to you provided that it does not have actual knowledge or reason to know that you are a United States person and it has received from you the statement described above in the fifth bullet point under "—United States Federal Withholding Tax."

        In addition, you will be subject to information reporting and, depending on the circumstances, backup withholding regarding the proceeds of the sale of a debt security made within the United States or conducted through United States-related intermediaries, unless the payor receives the statement described above and does not have actual knowledge or reason to know that you are a United States person, or you otherwise establish an exemption.

        Any amounts withheld under the backup withholding rules will be allowed as a refund or a credit against your United States federal income tax liability provided the required information is furnished to the IRS.

PLAN OF DISTRIBUTION

        Lehman Brothers Inc. and Lehman Brothers Holdings may offer or may have offered the offered securities in one or more of the following ways from time to time:

•

to or through underwriters or dealers;



•

by itself directly;



•

through agents; or



•

through a combination of any of these methods of sale.

        Any such underwriters, dealers or agents may include Lehman Brothers Inc. or affiliates of Lehman Brothers Inc. and Lehman Brothers Holdings.

        The prospectus supplement relating to a particular offering of securities sets forth or will set forth the terms of such offering, including:

•

the name or names of any underwriters, dealers or agents;



•

the purchase price of the offered securities and the proceeds to Lehman Brothers Inc. and Lehman Brothers Holdings from such sale;



•

any underwriting discounts and commissions or agency fees and other items constituting underwriters' or agents' compensation, which in the aggregate will not exceed 8 percent of the gross proceeds of the offering;



•

the initial public offering price;



•

any discounts or concessions to be allowed or reallowed or paid to dealers; and



•

any securities exchanges on which such offered securities may be listed.

        Any initial public offering prices, discounts or concessions allowed or reallowed or paid to dealers may be changed from time to time.

        If underwriters are used in an offering of offered securities, such offered securities will be acquired by the underwriters for their own account and may be resold from time to time in one or more transactions, including negotiated transactions, at a fixed public offering price (which may be changed); at market prices prevailing at the time of sale; at prices related to prevailing market prices; or at varying prices determined at the time of sale. The securities may be either offered to the public through underwriting syndicates represented by one or more managing underwriters or by one or more underwriters without a syndicate. In connection with those sales, underwriters may be deemed to have received compensation from Lehman

S-13

Brothers Inc. or Lehman Brothers Holdings in the form of underwriting discounts and commissions and may also receive commissions from purchasers of the securities for whom they may act as agents. Underwriters may resell the securities to or through dealers, and those dealers may receive compensation in the form of discounts, concessions or commissions from the underwriters and/or commissions from purchasers for whom they may act as agent. The applicable prospectus supplement will include any required information about underwriting compensation paid to underwriters, and any discounts, concessions or commissions underwriters allow to participating dealers, in connection with an offering of securities. Unless otherwise set forth in the prospectus supplement, the underwriters will not be obligated to purchase offered securities unless specified conditions are satisfied, and if the underwriters do purchase any offered securities, they will purchase all offered securities.

        In connection with underwritten offerings of the offered securities and in accordance with applicable law and industry practice, underwriters may over-allot or effect transactions that stabilize, maintain or otherwise affect the market price of the offered securities at levels above those that might otherwise prevail in the open market, including by entering stabilizing bids, effecting syndicate covering transactions or imposing penalty bids, each of which is described below.

•

A stabilizing bid means the placing of any bid, or the effecting of any purchase, for the purpose of pegging, fixing or maintaining the price of a security.



•

A syndicate covering transaction means the placing of any bid on behalf of the underwriting syndicate or the effecting of any purchase to reduce a short position created in connection with the offering.



•

A penalty bid means an arrangement that permits the managing underwriter to reclaim a selling concession from a syndicate member in connection with the offering when offered securities originally sold by the syndicate member are purchased in syndicate covering transactions.

        These transactions may be effected on the NYSE, in the over-the-counter market, or otherwise. Underwriters are not required to engage in any of these activities, or to continue such activities if commenced.

        If dealers are utilized in the sale of offered securities, Lehman Brothers Inc. and Lehman Brothers Holdings will sell such offered securities to the dealers as principals. The dealers may then resell such offered securities to the public at varying prices to be determined by such dealers at the time of resale. The names of the dealers and the terms of the transaction will be set forth in the prospectus supplement relating to that transaction.

        Offered securities may be sold directly by Lehman Brothers Inc. and Lehman Brothers Holdings to one or more institutional purchasers, or through agents designated by Lehman Brothers Inc. or Lehman Brothers Holdings from time to time, at a fixed price or prices, which may be changed, or at varying prices determined at the time of sale. Any such agent may be deemed to be an underwriter as that term is defined in the Securities Act. Any agent involved in the offer or sale of the offered securities in respect of which this prospectus is delivered will be named, and any commissions payable by Lehman Brothers Inc. and Lehman Brothers Holdings to such agent will be set forth, in the prospectus supplement relating to that offering. Unless otherwise indicated in such prospectus supplement, any such agent will be acting on a best efforts basis for the period of its appointment.

        If so indicated in the applicable prospectus supplement, Lehman Brothers Inc. and Lehman Brothers Holdings will authorize agents, underwriters or dealers to solicit offers from certain types of institutions to purchase offered securities from Lehman Brothers Inc. and Lehman Brothers Holdings at the public offering price set forth in such prospectus supplement pursuant to delayed delivery contracts providing for payment and delivery on a specified date in the future. Such contracts will be subject only to those conditions set forth in the prospectus supplement and the supplement will set forth the commission payable for solicitation of such contracts.

S-14

        Lehman Brothers Inc. is a member of NASD Inc. and may participate in distributions of the offered securities. Accordingly, offerings of offered securities in which Lehman Brothers Inc. participates will conform to the requirements set forth in Rule 2720 of the Conduct Rules of the NASD. Furthermore, any underwriters offering the offered securities will not confirm sales to any accounts over which they exercise discretionary authority without the prior approval of the customer.

        Underwriters, dealers and agents may be entitled, under agreements with Lehman Brothers Inc. and Lehman Brothers Holdings, to indemnification by Lehman Brothers Inc. and Lehman Brothers Holdings relating to material misstatements and omissions. Underwriters, dealers and agents, as well as their affiliates and associates, may be customers of or lenders to, engage in transactions with, or perform services for, Lehman Brothers Inc. and Lehman Brothers Holdings and their affiliates in the ordinary course of business.

        Each series of offered securities will be a new issue of securities and will have no established trading market. Any underwriters to whom offered securities are sold for public offering and sale may make a market in such offered securities, but such underwriters will not be obligated to do so and may discontinue any market making at any time without notice. The offered securities may or may not be listed on a national securities exchange. No assurance can be given that there will be a market for the offered securities.

Market-Making Transactions

        This prospectus supplement, together with a prospectus supplement relating to a specific series of debt securities and an attached prospectus may also be used by affiliates of Lehman Brothers Holdings in connection with offers and sales of securities related to market-making transactions at negotiated prices related to prevailing market prices at the time of sale or otherwise. These affiliates may act as principals or agents in such transactions, including as agent for the counterparty in a transaction in which these affiliates act as principal, or as agent for both counterparties in a transaction in which these affiliates do not act as principal. These affiliates may receive compensation in the form of discounts and commissions, including from both counterparties in some cases. These affiliates have no obligation to make a market in any of the offered securities and may discontinue any market-making activities at any time without notice, in their sole discretion.

ERISA CONSIDERATIONS

        Lehman Brothers Holdings has subsidiaries, including Lehman Brothers Inc., that provide services to many employee benefit plans. Lehman Brothers Holdings and any direct or indirect subsidiary of Lehman Brothers Holdings may each be considered a "party in interest" within the meaning of the Employee Retirement Income Security Act of 1974 ("ERISA"), and a "disqualified person" under corresponding provisions of the Internal Revenue Code of 1986 (the "Code"), relating to many employee benefit plans. "Prohibited transactions" within the meaning of ERISA and the Code may result if any offered securities are acquired by an employee benefit plan relating to which Lehman Brothers Holdings or any direct or indirect subsidiary of Lehman Brothers Holdings is a party in interest, unless such offered securities are acquired pursuant to an applicable exemption. Any employee benefit plan or other entity subject to such provisions of ERISA or the Code proposing to acquire the offered securities should consult with its legal counsel.

        Any person proposing to acquire the offered securities will be deemed to have represented, by its purchase and holding of the offered securities, that either (i) no portion of the assets used by it to acquire and hold the offered securities constitutes assets of any employee benefit plan that is subject to Title I of ERISA, of plans, individual retirement accounts or other arrangement that are subject to Section 4975 of the Code, or provisions under any federal, state, local, non-U.S. or other laws or regulations that are similar to such provisions of ERISA or the Code, or an entity whose underlying assets are considered to include "plan assets" of such plans, accounts or arrangements, or (ii) the purchase and holding of the offered securities will not constitute a non-exempt prohibited transaction under Section 406 of ERISA or Section 4975 of the Code or a similar violation under any applicable similar laws.

S-15

EXPERTS

        The consolidated financial statements and financial statement schedule of Lehman Brothers Holdings as of November 30, 2002 and 2001, and for each of the years in the three-year period ended November 30, 2002, have been audited by Ernst & Young LLP, independent certified public accountants, as set forth in their report on the consolidated financial statements. The consolidated financial statements and accountant's report are incorporated by reference in Lehman Brothers Holdings' annual report on Form 10-K for the year ended November 30, 2002, and incorporated by reference in this prospectus supplement. The consolidated financial statements of Lehman Brothers Holdings referred to above are incorporated by reference in this prospectus supplement in reliance upon such report given on the authority of Ernst & Young LLP as experts in accounting and auditing. To the extent that Ernst & Young LLP audits and reports on consolidated financial statements of Lehman Brothers Holdings issued at future dates, and consents to the use of their report thereon, such consolidated financial statements also will be incorporated by reference in this prospectus supplement in reliance upon their report given on said authority.

LEGAL MATTERS

        The validity of the securities offered by this prospectus supplement will be passed upon for Lehman Brothers Holdings by Barrett S. DiPaolo, Associate General Counsel of Lehman Brothers Holdings. Mr. DiPaolo beneficially owns, or has rights to acquire under Lehman Brothers Holdings' employee benefit plans, an aggregate of less than 1% of Lehman Brothers Holdings' common stock. The validity of the securities offered by this prospectus supplement will be passed upon for any underwriters or agents by Simpson Thacher & Bartlett LLP, New York, New York. Simpson Thacher & Bartlett LLP from time to time acts as counsel for Lehman Brothers Holdings and its subsidiaries.

S-16

PART II

INFORMATION NOT REQUIRED IN PROSPECTUS

Item 14. Other Expenses of Issuance and Distribution

        The following are the estimated expenses to be incurred and paid by Lehman Brothers Holdings Inc. (the "Registrant") in connection with the offerings described in this Registration Statement (other than underwriting discounts and commissions).

SEC registration fee		$	2,815
Legal fees and expenses			50,000	*
Accounting fees and expenses			50,000	*
Transfer Agent and Trustee fees and expenses			30,000	*
NASD filing fee			3,980	*
Blue Sky qualification fees and expenses			5,000	*
Miscellaneous fees and expenses			8,205	*
	Total	$	150,000

*

Estimated and subject to future contingencies

Item 15. Indemnification of Directors and Officers

        The Registrant is a Delaware corporation. Section 145 of the General Corporation Law of the State of Delaware (the "DGCL") empowers a Delaware corporation to indemnify any persons who are, or are threatened to be made, parties to any threatened, pending, or completed legal action, suit, or proceedings, whether civil, criminal, administrative, or investigative, by reason of the fact that such person is or was a director, officer, employee or agent of such corporation or is or was serving at the request of such corporation as a director, officer, employee or agent of another corporation or enterprise. The indemnity may include expenses (including attorney's fees), judgments, fines and amounts paid in settlement actually and reasonably incurred by such person in connection with such action, suit, or proceeding, provided that such officer or director acted in good faith and in a manner such person reasonably believed to be in or not opposed to the corporation's best interests, and, for criminal proceedings, had no reasonable cause to believe such person's conduct was illegal, provided that, in an action by or in the right of a corporation, a corporation may indemnify only for expenses and no indemnification is permitted without judicial approval if the officer, director, employee or agent is adjudged to be liable to the corporation in the performance of such person's duty. Under the DGCL, where a present or former officer or director is successful on the merits or otherwise in the defense of any action referred to above, Lehman Brothers Holdings must indemnify such person against the expenses which such person actually and reasonably incurred.

        Lehman Brothers Holdings' by-laws provide that Lehman Brothers Holdings will indemnify each of its present and former directors, officers, employees and agents, and each person who is or was serving at the request of the corporation as a director, officer, member, manager, partner, trustee, fiduciary, employee or agent of another corporation or other enterprise, to the extent and in the manner permitted by Delaware law, subject to certain limitations and procedures. Lehman Brothers Holdings must (in the case of a present or former director or officer) and may (in the case of any other person referred to above) pay expenses in advance of the final disposition of a proceeding upon receipt of an undertaking by or on behalf of such indemnified person to repay such amount if it shall ultimately be determined that he or she is not entitled to be indemnified by Lehman Brothers Holdings.

        Lehman Brothers Holdings' certificate of incorporation provide that the liability of its directors to Lehman Brothers Holdings or its stockholders for monetary damages for breach of fiduciary duty will be eliminated to the fullest extent permissible under Delaware law except for (a) breaches of duty of loyalty to

II-1

Lehman Brothers Holdings or its stockholders, as the case may (b) acts or omissions not in good faith or which involve intentional misconduct or a knowing violation of law, (c) the payment of unlawful dividends or unlawful stock repurchases or redemptions or (d) for any transaction from which the director derives an improper personal benefit.

        The effect of these provisions is to eliminate the rights of Lehman Brothers Holdings or its stockholders to recover monetary damages against a director for breach of fiduciary duty of care as a director (including breaches resulting from negligent or grossly negligent behavior) except in certain limited situations. These provisions do not limit or eliminate the rights of Lehman Brothers Holdings or its stockholders to seek non-monetary relief such as an injunction or rescission in the event of a breach of a director's fiduciary duty of care. In addition, these provisions do not alter the liability of directors under federal securities law.

        Lehman Brothers Holdings have each purchased liability insurance for its officers and directors as permitted by Section 145 of the General Corporation Law of the State of Delaware. The directors, officers and employees of Lehman Brothers Inc. are also insured against fiduciary liabilities under the Employee Retirement Income Security Act of 1974.

        Any underwriting agreement or agency agreement with respect to an offering of securities registered hereunder will provide for indemnification of the Registrant and its officers and directors who signed this Registration Statement by the underwriters or agents, as the case may be, against certain liabilities including liabilities under the Securities Act of 1933, as amended (the "Securities Act").

Item 16. Exhibits

        The Exhibit Index beginning on page E-1 is hereby incorporated by reference.

Item 17. Undertakings

        (a)   The undersigned Registrant hereby undertakes:

        (1)   To file, during any period in which offers or sales are being made, a post-effective amendment to this Registration Statement:

          (i)  To include any prospectus required by section 10(a)(3) of the Securities Act;

        (ii)  To reflect in the prospectus any facts or events arising after the effective date of the Registration Statement (or the most recent post-effective amendment thereof) which, individually or in the aggregate, represent a fundamental change in the information set forth in the Registration Statement. Notwithstanding the foregoing, any increase or decrease in volume of securities offered (if the total dollar value of securities offered would not exceed that which was registered) and any deviation from the low or high end of the estimated maximum offering range may be reflected in the form of prospectus filed with the Commission pursuant to Rule 424(b) if, in the aggregate, the changes in volume and price represent no more than a 20 percent change in the maximum aggregate offering price set forth in the "Calculation of Registration Fee" table in the effective registration statement;

       (iii)  To include any material information with respect to the plan of distribution not previously disclosed in the Registration Statement or any material change to such information in the Registration Statement;

provided, however, that the undertakings set forth in paragraphs (i) and (ii) above do not apply if the information required to be included in a post-effective amendment by those paragraphs is contained in periodic reports filed by the Registrant pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934 that are incorporated by reference in the Registration Statement.

II-2

        (2)   That, for the purposes of determining any liability under the Securities Act, each such post-effective amendment shall be deemed to be a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall be deemed to be the initial bona fide offering thereof.

        (3)   To remove from registration by means of a post-effective amendment any of the securities being registered which remain unsold at the termination of the offering.

        (b)   The undersigned Registrant hereby undertakes that, for purposes of determining any liability under the Securities Act, each filing of the Registrants' annual reports pursuant to Section 13(a) or Section 15(d) of the Securities Exchange Act of 1934 that is incorporated by reference in the Registration Statement shall be deemed to be a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall be deemed to be the initial bona fide offering thereof.

        Insofar as indemnification for liabilities arising under the Securities Act may be permitted to directors, officers and controlling persons of the Registrant pursuant to the foregoing provisions, or otherwise, the Registrant has been advised that in the opinion of the Securities and Exchange Commission, such indemnification is against public policy as expressed in the Securities Act and is, therefore, unenforceable. In the event that a claim for indemnification against such liabilities (other than the payment by the Registrant of expenses incurred or paid by a director, officer or controlling person of the Registrant in the successful defense of any action, suit or proceeding) is asserted by such director, officer or controlling person in connection with the securities being registered, the Registrant will, unless in the opinion of its counsel the matter has been settled by controlling precedent, submit to a court of appropriate jurisdiction the question whether such indemnification by it is against public policy as expressed in the Securities Act and will be governed by the final adjudication of such issue.

II-3

SIGNATURES

        Pursuant to the requirements of the Securities Act of 1933, the Registrant certifies that it has reasonable grounds to believe that it meets all of the requirements for filing on Form S-3 and has duly caused this Registration Statement to be signed on its behalf by the undersigned, thereunto duly authorized, in the City of New York, State of New York, on October 2, 2003.

LEHMAN BROTHERS HOLDINGS INC.
By:	/s/ BARRETT S. DIPAOLO
	Name: Title:	Barrett S. DiPaolo Vice President

        Pursuant to the requirements of the Securities Act of 1933, this Registration Statement has been signed below by the following persons in the capacities indicated.

Dated: October 2, 2003

Signature	Title
* Richard S. Fuld, Jr.	Chief Executive Officer and Chairman of the Board of Directors (principal executive officer)
* David Goldfarb	Chief Financial Officer and Executive Vice President (principal financial and accounting officer)
* Michael L. Ainslie	Director
* John F. Akers	Director
* Roger S. Berlind	Director
* Thomas H. Cruikshank	Director
* Sir Christopher Gent	Director
* Henry Kaufman	Director
* John D. Macomber	Director
* Dina Merrill	Director

*By:
/s/  BARRETT S. DIPAOLO Barrett S. DiPaolo
Attorney-in-fact

II-4

EXHIBIT INDEX

Exhibit Number	Description		Filed Herewith(—); to Be Filed By Amendment; Previously Filed; or Incorporated By Reference to
1(a)	—	Form of Underwriting Agreement (including Delayed Delivery Contract) for Debt Securities and Guarantees	To be filed by amendment or by Current Report on Form 8-K
4(a)	—	Indenture, dated as of March 1, 1996, between Lehman Brothers Inc. and Bank One Trust Company, N.A. (as successor in interest to The First National Bank of Chicago), as Trustee, with respect to Lehman Brothers Inc.'s Senior Subordinated Debt Securities (the "1996 Senior Subordinated Indenture") (including the form of Senior Subordinated Debt Security to be issued thereunder)	Exhibit 4(a) to Post-Effective Amendment No. 2 to Registration Statement No. 33-63613 filed on April 12, 1996
4(b)	—	First Supplemental Indenture, dated as of April 19, 1996, to the 1996 Senior Subordinated Indenture	Exhibit 4(b) to Registration Statement No. 33-08319 filed on July 17, 1996
4(c)	—	Form of Second Supplemental Indenture among Lehman Brothers Inc., Lehman Brothers Holdings Inc., as guarantor, and Bank One Trust Company, N.A. (as successor in interest to The First National Bank of Chicago), as Trustee, to the 1996 Senior Subordinated Indenture	—
4(d)	—	Indenture, dated as of October 23, 1995, between Lehman Brothers Inc. and The Bank of New York, as Trustee, with respect to the Lehman Brothers Inc.'s Senior Debt Securities (the "Senior Indenture")	Exhibit 4(o) to Lehman Brothers Inc.'s Registration Statement No. 33-63613 filed on October 23, 1995
4(e)	—	Form of First Supplemental Indenture among Lehman Brothers Inc., Lehman Brothers Holdings Inc., as guarantor, and The Bank of New York, as Trustee, to the Senior Indenture	—
4(f)	—	Form of Indenture between Lehman Brothers Inc. and U.S. Bank National Association (as successor in interest to 33-28381 filed on April 27, 1989 Continental Bank, National Association), as Trustee, with respect to Lehman Brothers Inc.'s Senior Subordinated Debt Securities (the "1989 Senior Subordinated Indenture") (including the form of Senior Subordinated Debt Securities issued thereunder)	Exhibit 4.3 to Lehman Brothers Inc.'s Registration Statement No. 33-28381 filed on April 27, 1989

E-1

4(g)	—	First Supplemental Indenture, dated as of June 21, 1989, between Lehman Brothers Inc. and U.S. Bank National Association (as successor in interest to Continental Bank, National Association), as Trustee	Exhibit 4(b) to Lehman Brothers Inc.'s Post-Effective Amendment No. 3 to Registration Statement No. 33-63613
4(h)	—	Second Supplemental Indenture, dated as of October 3, 1990, between Lehman Brothers Inc. and U.S. Bank National Association (as successor in interest to Continental Bank, National Association), as Trustee	Exhibit 4(c) to Lehman Brothers Inc.'s Registration Statement No. 33-51837
4(i)	—	Third Supplemental Indenture, dated as of December 2, 1992, between Lehman Brothers Inc. and U.S. Bank National Association (as successor in interest to Continental Bank, National Association), as Trustee	Exhibit 4(d) to Lehman Brothers Inc.'s Registration Statement No. 33-51837
4(j)	—	Fourth Supplemental Indenture, dated as of December 30, 1992, between Lehman Brothers Inc. and U.S. Bank National Association (as successor in interest to Continental Bank, National Association), as Trustee	Exhibit 4(e) to Lehman Brothers Inc.'s Registration Statement No. 33-51837
4(k)	—	Fifth Supplemental Indenture, dated as of January 14, 1993, between Lehman Brothers Inc. and U.S. Bank National Association (as successor in interest to Continental Bank, National Association), as Trustee	Exhibit 4(f) to Lehman Brothers Inc.'s Registration Statement No. 33-51837
4(l)	—	Sixth Supplemental Indenture, dated as of May 17, 1993, between Lehman Brothers Inc. and U.S. Bank National Association (as successor in interest to Continental Bank, National Association), as Trustee	Exhibit 4(g) to Lehman Brothers Inc.'s Registration Statement No. 33-51837
4(m)	—	Seventh Supplemental Indenture, dated as of November 17, 1993, between Lehman Brothers Inc. and U.S. Bank National Association (as successor in interest to Continental Bank, National Association), as Trustee	Exhibit 4(h) to Lehman Brothers Inc.'s Registration Statement No. 33-51837
4(n)	—	Eighth Supplemental Indenture, dated as of December 23, 1993, between Lehman Brothers Inc. and U.S. Bank National Association (as successor in interest to Continental Bank, National Association), as Trustee	Exhibit 4(i) to Lehman Brothers Inc.'s Registration Statement No. 33-51837

E-2

4(o)	—	Form of Ninth Supplemental Indenture between Lehman Brothers Inc. and U.S. Bank National Association (as successor in interest to Continental Bank, National Association), as Trustee	Exhibit 4(j) to Lehman Brothers Inc.'s Registration Statement No. 33-51837
4(p)	—	Form of Tenth Supplemental Indenture among Lehman Brothers Inc., Lehman Brothers Holdings Inc., as guarantor, and U.S. Bank National Association (as successor in interest to Continental Bank, National Association), as Trustee, to the 1989 Senior Subordinated Indenture	—
4(q)	—	Indenture, dated as of October 1, 1984, between Lehman Brothers Inc. and HSBC Bank USA (as successor in interest to Marine Midland Bank, N.A.), as Trustee with respect to Lehman Brothers Inc.'s Senior Subordinated Debt Securities (the "1984 Senior Subordinated Indenture") (including the form of Senior Subordinated Debt Securities to be issued thereunder).	Previously Filed
4(r)	—	Form of First Supplemental Indenture among Lehman Brothers Inc., Lehman Brothers Holdings Inc., as guarantor, and HSBC Bank USA (as successor in interest to Marine Midland Bank, N.A.), as Trustee, to the 1984 Senior Subordinated Indenture	—
4(s)	—	Form of Senior Debt Securities	Exhibit 4(p) to Lehman Brothers Inc.'s Registration Statement No. 33-63613 filed on October 23, 1995
5(a)	—	Opinion and consent of Barrett S. DiPaolo, Esq. as to the validity of the Guarantees	Previously Filed
12(a)	—	Computation of ratio of earnings to fixed charges	Exhibit 12 to Lehman Brothers Holdings Quarterly Report on Form 10-Q for the six months ended May 31, 2003 filed July 15, 2003
23(a)	—	Consent of Barrett S. DiPaolo, Esq.	Previously Filed
23(b)	—	Consent of Ernst & Young LLP, Independent Auditors	—
24(a)	—	Powers of Attorney of Lehman Brothers Holdings	Previously Filed

E-3

QuickLinks

INTRODUCTORY NOTE
TABLE OF CONTENTS
WHERE YOU CAN FIND MORE INFORMATION ABOUT LEHMAN BROTHERS HOLDINGS
LEHMAN BROTHERS HOLDINGS
RATIO OF EARNINGS TO FIXED CHARGES
USE OF PROCEEDS
DESCRIPTION OF THE GUARANTEES
CERTAIN UNITED STATES FEDERAL INCOME TAX CONSEQUENCES
PLAN OF DISTRIBUTION
ERISA CONSIDERATIONS
EXPERTS
LEGAL MATTERS
PART II INFORMATION NOT REQUIRED IN PROSPECTUS
SIGNATURES
EXHIBIT INDEX

EX-4.(C)

QuickLinks -- Click here to rapidly navigate through this document

Exhibit 4(c)

LEHMAN BROTHERS INC.,

LEHMAN BROTHERS HOLDINGS INC.,

as Guarantor,

AND

BANK ONE TRUST COMPANY, N.A.,

as Trustee

FORM OF SECOND SUPPLEMENTAL INDENTURE

Dated as of                         , 2003

        SECOND SUPPLEMENTAL INDENTURE, dated as of                         , 2003 (the "Supplemental Indenture"), among LEHMAN BROTHERS INC., a corporation duly organized and existing under the laws of the State of Delaware (the "Company"), LEHMAN BROTHERS HOLDINGS INC., a corporation duly organized and existing under the laws of the State of Delaware, as guarantor (the "Guarantor"), and BANK ONE TRUST COMPANY, N.A. (as successor in interest to The First National Bank of Chicago), a national banking corporation duly organized and existing under the laws of the United States, as trustee (the "Trustee").

RECITALS

        The Company has duly authorized the execution and delivery of an Indenture, dated as of March 1, 1996, between the Company and the Trustee, as amended and supplemented by the First Supplemental Indenture dated as of April 19, 1996, between the Company and the Trustee (together, the "Indenture"), to provide for the issuance from time to time of its unsecured senior subordinated debentures, notes or other evidences of indebtedness to be issued in one or more series (the "Securities") unlimited as to principal amount, to bear such rates of interest, to mature at such time or times, to be issued in one or more series and to have such other provisions as in the Indenture provided.

        The Guarantor has determined that it is in its best interests to fully and unconditionally guarantee the due and punctual payment of the principal (including any amount in respect of original issue discount) of, and premium, if any, and interest, if any, on all outstanding and future Securities and the due and punctual payment of the sinking fund payments, if any, and analogous obligations, if any, provided for pursuant to the terms of such Securities, when and as the same shall become due and payable;

        The Company and the Guarantor have duly authorized the execution and delivery of this Supplemental Indenture to provide for the guarantee by the Guarantor of the Securities;

        All acts and things necessary to make this Supplemental Indenture a valid agreement of the Company and of the Guarantor, in accordance with its terms and with the terms of the Indenture, have been done and performed.

NOW, THEREFORE, THIS SUPPLEMENTAL INDENTURE WITNESSETH:

        For and in consideration of the premises, and of the sum of one dollar duly paid to the Company and the Guarantor by the Trustee at the execution and delivery of these presents, the receipt whereof is hereby acknowledged, the Company and the Guarantor covenant and agree, for the equal and proportionate benefit of all holders of the Securities with the Trustee to supplement the Indenture as follows:

Section 1. AMENDMENTS TO THE INDENTURE

        1.1    Amendment to Section 1.1 of the Indenture.    Section 1.1 of the Indenture is hereby amended by deleting the definitions of "Board of Directors," "Board Resolution," "Officers' Certificate," "Opinion of Counsel" and "Vice President" and inserting the following definitions, in the appropriate alphabetical sequence:

        "Board of Directors" means the board of directors of the Company or the Guarantor, as the case may be, or any committee of either Board duly authorized to act hereunder or any directors and/or officers of the Company or the Guarantor, as the case may be, to whom that board or committee shall have delegated its authority.

        "Board Resolution" means a copy of a resolution certified by the Secretary or an Assistant Secretary of the Company or the Guarantor, as the case may be, to have been duly adopted by the Board of Directors and to be in full force and effect on the date of such certification, and delivered to the Trustee.

        "Guarantee" means the full and unconditional guarantee by the Guarantor set forth in Article 15.

        "Guarantor" means Lehman Brothers Holdings Inc., a corporation duly organized and existing under the laws of the State of Delaware.

        "Guarantor Order" or "Guarantor Request" means a written request or order signed in the name of the Guarantor by its Chairman of the Board, any Vice Chairman of the Board, its President or a Vice President, and by its Treasurer, an Assistant Treasurer, its Secretary or an Assistant Secretary, and delivered to the Trustee.

        "Officers' Certificate" means a certificate signed by the Chairman of the Board, any Vice Chairman of the Board, the President or a Vice President, and by the Treasurer, and Assistant Treasurer, the Secretary or an Assistant Secretary, of the Company or the Guarantor, as the case may be, and delivered to the Trustee.

        "Opinion of Counsel" means a written opinion of counsel, who may be counsel for or employed by the Company or the Guarantor, as the case may be, and who shall be acceptable to the Trustee.

        "Vice President", when used with respect to the Company, the Guarantor or the Trustee, means any vice president, whether or not designated by a number or a word or words added before or after the title "vice president."

        1.2    Amendment to Section 1.2 of the Indenture.    Section 1.2 of the Indenture is hereby amended by inserting the following paragraph as the new second paragraph thereto:

        "Upon any application or request by the Guarantor to the Trustee to take any action under any provision of this Indenture, the Guarantor shall furnish to the Trustee an Officers' Certificate stating that all conditions precedent, if any, provided for in this Indenture relating to the proposed action have been complied with and an Opinion of Counsel stating that in the opinion of such counsel all such conditions precedent, if any, have been complied with, except that in the case of any such application or request as to which the furnishing of such documents is specifically required by any provision of this Indenture relating to such particular application or request, no additional certificate or opinion need by furnished."

        1.3    Amendment to Section 1.3 of the Indenture.    Section 1.3 of the Indenture is hereby amended by inserting the following paragraph as the new third paragraph thereof:

        "Any certificate or opinion of an officer of the Guarantor may be based, insofar as it relates to legal matters, upon a certificate or Opinion of Counsel, or representations by counsel, unless such officer knows, or in the exercise of reasonable care should know, that the certificate or opinion or representations with respect to the matters upon which his certificate or opinion is based are erroneous. Any such certificate or Opinion of Counsel or representation by counsel may be based, insofar as it relates to factual matters, upon a certificate or opinion of, or representations by, an officer or officers of the Guarantor stating that the information with respect to such factual matters is in the possession of the Guarantor, unless such counsel knows, or in the exercise of reasonable care should know, that the certificate or opinion or representations with respect to such matters are erroneous."

        1.4    Amendment to Section 1.5 of the Indenture.    (a) Section 1.5 of the Indenture is hereby amended by deleting the current section heading thereof and replacing it with the following:

        "Notices, Etc., to Trustee, Company or Guarantor"

2

        (b)   Section 1.5 of the Indenture is hereby amended by deleting the word "or" at the end of paragraph (1), deleting the period and inserting the word ", or" at the end of paragraph (2) and inserting the following paragraph as the final paragraph thereof:

        "(3) the Guarantor by the Trustee or by any Holder shall be sufficient for every purpose hereunder if in writing and mailed, first-class postage prepaid, to the Guarantor addressed to it at 745 Seventh Avenue, New York, New York 10019, attention: Treasurer or at any other address previously furnished in writing to the Trustee by the Guarantor."

        1.5    Amendment to Section 3.1 of the Indenture.    Section 3.1 of the Indenture is hereby amended by deleting the word "and" at the end of paragraph (14), redesignating paragraph (15) as paragraph (16) and inserting the following paragraph in proper numerical order:

        "(15) the terms and provisions of the Guarantee, to the extent that such provisions differ from those set forth herein; and"

        1.6    Amendment to Section 3.3 of the Indenture.    (a) Section 3.3 of the Indenture is hereby amended by deleting the word "and" at the end of subparagraph (b), deleting the period and inserting the word "; and" at the end of subparagraph (c) and inserting the following paragraph as the new subparagraph (d) thereof:

        "(d) that the Guarantee of such Securities, when the Securities are authenticated and delivered by the Trustee and issued by the Company in the manner and subject to any conditions specified in such Opinion of Counsel, will constitute a valid and legally binding obligation of the Guarantor, enforceable in accordance with its terms, subject to the effects of bankruptcy, insolvency, fraudulent conveyance, reorganization, moratorium and other similar laws relating to or affecting creditors' rights generally, general equitable principles (whether considered in a proceeding in equity or at law) and an implied covenant of good faith and fair dealing."

        (b)   Section 3.3 of the Indenture is hereby amended by inserting the words "or Guarantee" immediately following the words "No Security" at the beginning of the final paragraph of the section.

        1.7    Amendment to Section 3.5 of the Indenture.    Section 3.5 of the Indenture is hereby amended by deleting the fourth paragraph and inserting in lieu thereof the following paragraph:

        "All Securities issued upon any registration of transfer or exchange of Securities shall be the valid obligations of the Company evidencing the same debt, and entitled to the same benefits under this Indenture (including the Guarantee), as the Securities surrendered upon such registration of transfer or exchange."

        1.8    Amendment to Section 3.8 of the Indenture.    Section 3.8 of the Indenture is hereby amended by inserting the words ", the Guarantor" immediately following the words "the Company" in each place such words appear.

        1.9    Amendment to Section 5.3 of the Indenture.    Section 5.3 of the Indenture is hereby amended by deleting the final paragraph in its entirety and inserting in lieu thereof the following paragraph:

        "Any money deposited with the Trustee of such series or any Paying Agent, or then held by the Company or the Guarantor in trust for the payment of the principal of (and premium, if any) or interest on any Security of any series and remaining unclaimed for two years after such principal (and premium, if any) or interest has become due and payable shall be paid to the Company on Company Request or the Guarantor on Guarantor Request, or (if then held by the Company or the Guarantor) shall be discharged from such trust; and the Holder of such Security shall thereafter, as an unsecured general creditor, look only to the Company and the Guarantor for payment thereof, and all liability of such Trustee or such Paying Agent with respect to such

3

trust money, and all liability of the Company or the Guarantor as trustee thereof, shall thereupon cease; provided, however, that such Trustee or such Paying Agent, before being required to make any such repayment, may at the expense of the Company cause to be published once, in a newspaper published in the English language, customarily published on each Business Day and of general circulation in the Borough of Manhattan, The City of New York, notice that such money remains unclaimed and that, after a date specified therein, which shall not be less than 30 days from the date of such publication, any unclaimed balance of such money then remaining will be repaid to the Company or the Guarantor."

        1.10    Amendment to Section 5.6 of the Indenture.    Section 5.6 of the Indenture is hereby amended by inserting the following paragraphs as the new third, fourth and fifth paragraphs respectively thereof:

        "The Guarantor will deliver to the Trustee, within 120 days after the end of each fiscal year of the Guarantor ending after the date hereof, an Officers' Certificate of the Guarantor, stating whether or not to the best knowledge of the signers thereof the Guarantor is in default in the performance and observance of any of the terms, provisions and conditions of this Indenture, and if the Guarantor shall be in default, specifying all such defaults and the nature and status thereof of which they may have knowledge. For purposes of this Section 5.6, any such default shall be determined without regard to any period of grace or requirement of notice provided under this Indenture.

        In addition, the Guarantor shall file with the Trustee written notice of the occurrence of any default or Event of Default within five Business Days of its becoming aware of any such default or Event of Default.

        Such Officers' Certificate or written notice of the Company and the Guarantor may be in the form of one certificate or notice signed by the appropriate officers of the Company and the Guarantor."

        1.11    Amendment to Section 6.2 of the Indenture.    Section 6.2 of the Indenture is hereby amended by inserting the words "or the Guarantor" immediately following the words "including the Company" therein.

        1.12    Amendment to Section 7.1 of the Indenture.    Section 7.1 of the Indenture is hereby amended by deleting the reference to subparagraph (g) in the introductory sentence and inserting in lieu thereof a reference to subparagraph (h), by deleting the word "or" at the end of subparagraph (f) and by inserting the following paragraph immediately prior to the final period at the end of subparagraph (g) thereof:

        "; or

        (h)   the dissolution or insolvency of the Guarantor or the making of an assignment for the benefit of creditors by the Guarantor or the commencement of any proceedings (by petition, application, answer, consent or otherwise) by the Guarantor to be adjudicated a bankrupt or for the appointment of a receiver or trustee or similar officer for it or for a substantial part of its property or for reorganization, an arrangement, composition or other relief under the Bankruptcy Act or the taking of corporate action by the Guarantor for any such purpose, or any marshalling of the assets or liabilities of the Guarantor or the commencement against the Guarantor of any of the aforementioned proceedings and in such latter case the consent thereto by the Guarantor or its admission of the material allegations thereof or the continuance of such proceedings undismissed for a period of 60 days."

        1.13    Amendment to Section 7.11 of the Indenture.    Section 7.11 of the Indenture is hereby amended by inserting the words ", the Guarantor" immediately following the words "subject to any determination in such proceeding, the Company" therein.

4

        1.14    Amendment to Section 7.16 of the Indenture.    Section 7.16 of the Indenture is hereby amended by inserting the words "or the Guarantor" immediately following the words "suit instituted by the Company" therein.

        1.15    Amendment to Section 7.17 of the Indenture.    Section 7.17 of the Indenture is hereby amended by deleting the words "the Company" in each place of the two places where such words appear and inserting in each place in lieu thereof the words "each of the Company and the Guarantor"

        1.16    Amendment to Section 9.4 of the Indenture.    (a) Section 9.4 of the Indenture is hereby amended by deleting the current section heading thereof and replacing it with the following:

        "Reports by Company and Guarantor"

        (b)   Section 9.4 of the Indenture is hereby amended by redesignating the first paragraph thereof as subsection (a) and by inserting the following paragraph as the new subsection (b) thereof:

        "(b) The Guarantor shall:

        (1)   file with the Trustee for the Securities of each series, within 15 days after the Guarantor is required to file the same with the Commission, copies of the annual reports and of the information, documents and other reports (or copies of such portions of any of the foregoing as the Commission may from time to time by rules and regulations prescribe) which the Guarantor may be required to file with the Commission pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934; or, if the Guarantor is not required to file information, documents or reports pursuant to either of said Sections, then it shall file with such Trustee and the Commission, in accordance with rules and regulations prescribed from time to time by the Commission, such of the supplementary and periodic information, documents and reports which may be required pursuant to Section 13 of the Securities Exchange Act of 1934 in respect of a security listed and registered on a national securities exchange as may be prescribed from time to time in such rules and regulations;

        (2)   file with such Trustee and the Commission, in accordance with rules and regulations prescribed from time to time by the Commission, such additional information, documents and reports with respect to compliance by the Guarantor with the conditions and covenants of this Indenture as may be required from time to time by such rules and regulations; and

        (3)   transmit by mail to all Holders, as their names and addresses appear in the Security Register, within 30 days after the filing thereof with the Trustee, such summaries of any information, documents and reports required to be filed by the Guarantor pursuant to paragraphs (1) and (2) of this Section 9.4(b) as may be required by rules and regulations prescribed from time to time by the Commission.

        1.17    Amendment to Section 10.1 of the Indenture.    Section 10.1 of the Indenture is hereby amended by redesignating the first paragraph thereof as subsection (a) and by inserting the following paragraph as the new subsection (b) thereof:

        "(b) Nothing contained in this Indenture or in any of the Securities shall prevent any consolidation or merger of the Guarantor with or into any other corporation or corporations (whether or not affiliated with the Guarantor), or successive consolidations or mergers in which the Guarantor or its successor or successors shall be a party or parties, or shall prevent any sale or transfer (or successive sales or transfers) of the property and assets of the Guarantor (or of its successor or successors) as an entirety or substantially as an entirety, to any other corporation (whether or not affiliated with the Guarantor) authorized to acquire the same; provided, however, that the corporation formed by such consolidation or into which the Guarantor shall have been merged or which shall have acquired such property and assets shall be a corporation organized

5

under the laws of the United States or of any State thereof; and provided, further, and the Guarantor hereby covenants and agrees, that upon any such consolidation, merger, sale or transfer, the Guarantee of the due and punctual payment of the principal of (and premium, if any) and interest, if any, on all of the Securities, according to their tenor, and the due and punctual performance and observance of all the terms, covenants and conditions of this Indenture to be kept or performed by the Guarantor, shall be expressly assumed, by an indenture supplemental hereto, satisfactory in form to the Trustee for the Securities of each series, executed and delivered to such Trustee by the corporation formed by such consolidation, or into which the Guarantor shall have been merged, or by the corporation which shall have acquired such property and assets; and in the event of any such sale or transfer, the predecessor Guarantor shall be released from all liability hereunder and under the Securities and may be dissolved, wound up and liquidated at any time thereafter."

        1.18    Amendment to Section 10.2 of the Indenture.    Section 10.2 of the Indenture is hereby amended by redesignating the first and second paragraphs thereof as subsection (a) and by inserting the following two paragraphs as the new subsection (b) thereof:

        "(b) In case of any such consolidation, merger, sale or transfer and upon the execution by the successor corporation of an indenture supplemental hereto, as provided in Section 10.1(b), such successor corporation shall succeed to and be substituted for the Guarantor, with the same effect as if it had been named herein as the party of the first part; and any order, certificate, statement, request, instructions, advice or resolutions of the Board of Directors or officers of the Guarantor provided for in this Indenture may be made by like officials of such successor corporation.

        Nothing contained in this Indenture or in any of the Securities shall prevent the Guarantor from merging into itself, or acquiring by purchase or otherwise all or any part of the property of, any other corporation (whether or not affiliated with the Guarantor)."

        1.19    Amendment to Section 11.1 of the Indenture.    (a) Section 11.1 of the Indenture is hereby amended by inserting the words "the Guarantor, when authorized by a Board Resolution," immediately following the words "the Company, when authorized by a Board Resolution," in the introductory sentence thereof.

        (b)   Section 11.1 of the Indenture is hereby amended by redesignating subparagraphs (3), (4), (5), (6), (7), (8), (9) and (10), respectively, as new subparagraphs (5), (6), (7), (8), (9), (10), (11) and (12), respectively, and by inserting the following paragraphs in proper numerical order:

        "(3) to evidence the succession of another corporation to the Guarantor, and the assumption by any such successor of the covenants of the Guarantor herein and in the Securities, if applicable; or

        "(4) to add to the covenants of the Guarantor for the benefit of the Holders of all or any series of Securities (and if such covenants are to be for the benefit of less than all series of Securities, stating that such covenants are expressly being included solely for the benefit of such series) or to surrender any right or power herein conferred upon the Guarantor; or"

        1.20    Amendment to Section 11.2 of the Indenture.    Section 11.2 of the Indenture is hereby amended by inserting the words "the Guarantor, when authorized by a Board Resolution," immediately following the words "the Company, when authorized by a Board Resolution," in the introductory sentence thereof.

Section 2. GUARANTEE

        2.1    Addition of New Article 15 of the Indenture.    Article 15 of the Indenture is hereby created and the following shall be inserted therein:

6

ARTICLE FIFTEEN

THE GUARANTEES

        Section 15.1    Except as otherwise set forth in a supplemental indenture or provided in or pursuant to a Board Resolution and set forth in an Officers' Certificate, the Guarantor hereby unconditionally guarantees to the Holder of the Securities of each series authenticated and delivered by the Trustee, and to the Trustee on behalf of each such Holder, the due and punctual payment of the principal (including any amount in respect of original issue discount) of, and premium, if any, and interest, if any, on such Securities and the due and punctual payment of the sinking fund payments, if any, and analogous obligations, if any, provided for pursuant to the terms of such Securities, when and as the same shall become due and payable, whether at maturity or upon redemption or upon declaration of acceleration or otherwise, according to the terms of such Securities and of the Indenture and this Supplemental Indenture. The Guarantor agrees that in case of default by the Company in the payment of any such principal (including any amount in respect of original issue discount), premium, interest, sinking fund payment, or analogous obligation, the Guarantor shall duly and punctually pay the same, as if such payment were made by the Company. The Guarantor hereby agrees that its obligations hereunder shall be absolute and unconditional, irrespective of any extension of the time for payment of any such Security, any modification of any such Security or any supplemental indenture or Board Resolution and Officers' Certificate relating thereto, any invalidity, irregularity or unenforceability of any such Security or the Indenture or this Supplemental Indenture, any failure or delay to enforce the same or any waiver, modification, consent or indulgence granted to the Company with respect thereto by the Holder of such Security or the Trustee, or any other circumstances which may otherwise constitute a legal or equitable discharge of a surety or guarantor.

        The Guarantor further agrees that the Guarantee herein constitutes a guarantee of payment when due (and not a guarantee of collection) and waives (to the extent that it may lawfully do so) any right to require that any resort be had by any Holder or the Trustee to any security held for payment of the Guarantee.

        The Guarantor hereby waives (to the extent that it may lawfully do so) diligence, presentment, demand of payment, filing of claims with a court in the event of merger or bankruptcy of the Company, any right to require a demand or proceeding first against the Company, protest or notice with respect to any such Security or the indebtedness evidenced thereby and all demands whatsoever, and covenants that this Guarantee will not be discharged as to any such Security except by payment in full of the principal (including any amount payable in respect of original issue discount) of, and premium, if any, and interest, if any, and payment of the sinking fund payments, if any, and analogous obligations, if any, thereon.

        The Guarantor agrees that the Guarantee with respect to each series of Securities shall remain in full force and effect until payment in full of all the Securities of such series. The Guarantor further agrees that the Guarantee herein shall continue to be effective or be reinstated, as the case may be, if at any time payment, or any part thereof, of the principal (including any amount payable in respect of original issue discount) of, and premium, if any, and interest, if any, and payment of the sinking fund payments, if any, and analogous obligations, if any, on any series of Securities is rescinded or must otherwise be restored by any Holder or the Trustee upon the bankruptcy or reorganization of the Company or otherwise.

        The Guarantor further agrees that, as between it, on the one hand, and the Holders and the Trustee, on the other hand, (x) the maturity of the obligations guaranteed hereby may be accelerated as provided in Article Seven for the purposes of any Guarantee herein, notwithstanding any stay, injunction or other prohibition preventing such acceleration in respect of the obligations guaranteed hereby, and (y) in the event of any declaration of acceleration of the obligations guaranteed hereby as

7

provided in Article Seven, such obligations (whether or not due and payable) shall forthwith become due and payable by the Guarantor for the purposes of this Section 15.01.

        The Guarantor shall be subrogated to all rights of the Holders of the Securities of a series against the Company in respect of any amounts paid by the Guarantor on account of such Security pursuant to the provisions of the Guarantees or this Indenture; provided, however, that the Guarantor agrees that it shall not be entitled to any right of subrogation in relation to the Holders until payment in full of the principal (including any amount payable in respect of original issue discount) of, and premium, if any, and interest, if any, and payment of the sinking fund payments, if any, and analogous obligations, if any, on all Securities of such series. The Guarantor hereby waives (to the extent that it may lawfully do so) any and all rights to which it may be entitled, by operation of law or otherwise, upon making any payment hereunder (i) any right to which it may be entitled to have the assets of the Company first be used and depleted as payment of the Company's or the Guarantor's obligations hereunder prior to any amounts being claimed from or paid by the Guarantor hereunder; or (ii) to receive any payment, in the nature of contribution or for any other reason, from any other obligor with respect to such payment.

Section 3. MISCELLANEOUS

        3.1    Continuance of Indenture.    This Supplemental Indenture supplements the Indenture and shall be a part of and subject to all the terms thereof. The Indenture, as supplemented by this Supplemental Indenture, shall continue in full force and effect.

        3.2    Defined Terms.    All capitalized terms used in this Supplemental Indenture which are defined in the Indenture, but not otherwise defined herein, shall have the same meanings assigned to them in the Indenture.

        3.3    Conflict with Trust Indenture Act.    If any provision of this Supplemental Indenture limits, qualifies or conflicts with the duties imposed by any of Sections 310 through 317, inclusive, of the Trust Indenture Act through the operation of Section 318(c) thereof, such imposed duties shall control.

        3.4    Separability Clause.    In case any provision in this Supplemental Indenture shall be invalid, illegal or unenforceable, the validity, legality and enforceability of the remaining provisions shall not in any way be affected or impaired thereby.

        3.5    Benefits of Indenture.    Nothing in this Supplemental Indenture, express or implied, shall give to any Person, other than the parties hereto and their successors hereunder and the Holders any benefit or any legal or equitable right, remedy or claim under this Supplemental Indenture.

        3.6    Governing Law.    This Supplemental Indenture shall be governed by and construed in accordance with the laws of the State of New York.

        3.7    The Trustee.    The recitals contained herein shall be taken as the statements of the Company and the Guarantor, and the Trustee assumes no responsibility for their correctness. The Trustee makes no representations as to the validity or sufficiency of this Supplemental Indenture.

        3.8    Successors and Assigns of Company and Guarantor Bound By Supplemental Indenture.    All the covenants, stipulations, promises and agreements contained in this Supplemental Indenture by or on behalf of the Company or the Guarantor shall bind their successors and assigns, whether so expressed or not, and the provisions hereof shall bind the heirs, executors, administrators, successors and assigns of the Holders.

        3.9    Acts of Board, Committee or Officer of Successor Corporation Valid.    Any act or proceeding by any provision of this Supplemental Indenture authorized or required to be done or performed by any board, committee or officer of the Company or the Guarantor shall and may be done and performed with like force and effect by the like board, committee or officer of any corporation that shall at the time be the lawful successor of the Company or the Guarantor, as the case may be.

        3.10    Counterparts.    This Supplemental Indenture may be executed in any number of counterparts, each of which shall be an original; but such counterparts shall together constitute but one and the same instrument.

        Bank One Trust Company, N.A. hereby accepts the trusts in this Supplemental Indenture declared and provided, upon the terms and conditions hereinabove set forth.

8

        IN WITNESS WHEREOF, Lehman Brothers Inc. has caused this Supplemental Indenture to be signed and acknowledged by its Chairman of the Board, one of its Vice Chairmen of the Board, its President, its Treasurer or one of its Vice Presidents, Lehman Brothers Holdings Inc. has caused this Supplemental Indenture to be signed and acknowledged by its Chairman of the Board, one of its Vice Chairmen of the Board, its President, its Treasurer or one of its Vice Presidents, and Bank One Trust Company, N.A., as Trustee, has caused this Supplemental Indenture to be signed and acknowledged by one its authorized officers, and its corporate seal to be affixed hereunto, and the same to be attested by one of its authorized officers, as of the day and year first above written.

LEHMAN BROTHERS INC.
By:	Name: Title:
LEHMAN BROTHERS HOLDINGS INC., as Guarantor
By:	Name: Title:
BANK ONE TRUST COMPANY, N.A., as Trustee
By:	Authorized Officer

9

QuickLinks

Exhibit 4(c)

RECITALS
ARTICLE FIFTEEN THE GUARANTEES

EX-4.(E)

QuickLinks -- Click here to rapidly navigate through this document

Exhibit 4(e)

LEHMAN BROTHERS INC.,

LEHMAN BROTHERS HOLDINGS INC.,

as Guarantor,

AND

THE BANK OF NEW YORK,

as Trustee

FORM OF FIRST SUPPLEMENTAL INDENTURE

Dated as of            , 2003

        FIRST SUPPLEMENTAL INDENTURE, dated as of                        , 2003 (the "Supplemental Indenture"), among LEHMAN BROTHERS INC., a corporation duly organized and existing under the laws of the State of Delaware (the "Company"), LEHMAN BROTHERS HOLDINGS INC., a corporation duly organized and existing under the laws of the State of Delaware, as guarantor (the "Guarantor"), and THE BANK OF NEW YORK, a New York banking corporation, as trustee (the "Trustee").

W I T N E S S E T H:

        WHEREAS, The Company has duly authorized the execution and delivery of an Indenture, dated as of October 23, 1995, between the Company and the Trustee, as amended and supplemented, to provide for the issuance from time to time of its unsecured notes or other evidences of indebtedness to be issued in one or more series (the "Securities"), as in the Indenture provided, up to such principal amount or amounts as may from time to time be authorized in or pursuant to one or more resolutions of the Board of Directors; and

        WHEREAS, the Guarantor has determined that it is in its best interests to fully and unconditionally guarantee the due and punctual payment of the principal (including any amount in respect of original issue discount) of, and premium, if any, and interest, if any, on all outstanding and future Securities and the due and punctual payment of the sinking fund payments, if any, and analogous obligations, if any, provided for pursuant to the terms of such Securities, when and as the same shall become due and payable; and

        WHEREAS, the Company and the Guarantor have duly authorized the execution and delivery of this Supplemental Indenture to provide for the guarantee by the Guarantor of the Securities of the Company under the Indenture; and

        WHEREAS, all acts and things necessary to make this Supplemental Indenture a valid agreement of the Company and of the Guarantor according to its terms have been done and performed, and the execution and delivery of this Supplemental Indenture have in all respects been duly authorized,

        NOW, THEREFORE, THIS SUPPLEMENTAL INDENTURE WITNESSETH:

        That in order to declare the terms and conditions upon which the Securities are, and are to be, authenticated, issued and delivered, and in consideration of the premises, of the purchase and acceptance of the Securities by the Holders thereof and of the sum of one dollar duly paid to it by the Trustee at the execution and delivery of these presents, the receipt whereof is hereby acknowledged, the Company and the Guarantor covenant and agree with the Trustee for the equal and proportionate benefit of the respective Holders from time to time of the Securities or of any series thereof, to supplement the Indenture as follows:

Section 1.    AMENDMENTS TO THE INDENTURE

        1.1    Amendment to Section 101 of the Indenture.    Section 101 of the Indenture is hereby amended by deleting the definitions of "Board of Directors," "Board Resolution," "Officers' Certificate," "Opinion of Counsel" and "Vice President" and inserting the following definitions, in the appropriate alphabetical sequence:

"Board of Directors" means either the board of directors of the Company or the Guarantor, as the case may be, or any committee of either board duly authorized to act hereunder or any directors and/or officer of the Company or the Guarantor, as the case may be, to whom such board or committee shall have delegated its authority.

"Board Resolution" means a copy of a resolution certified by the Secretary or an Assistant Secretary of the Company or the Guarantor, as the case may be, to have been duly adopted by the Board of Directors and to be in full force and effect on the date of such certification, and delivered to the Trustee.

"Guarantee" means the full and unconditional guarantee by the Guarantor set forth in Article 14.

"Guarantor" means Lehman Brothers Holdings Inc., a corporation duly organized and existing under the laws of the State of Delaware.

"Guarantor Order" or "Guarantor Request" means a written request or order signed in the name of the Guarantor by its Chairman of the Board, any Vice Chairman of the Board, its President or a Vice President, and by its Treasurer, an Assistant Treasurer, its Secretary or an Assistant Secretary, and delivered to the Trustee.

"Officers' Certificate" means a certificate signed by the Chairman of the Board, any Vice Chairman of the Board, the Chief Executive Officer, and Vice Chairman of the Board, the President or a Vice President, and by the Treasurer, an Assistant Treasurer, the Secretary or an Assistant Secretary of the Company or the Guarantor, as the case may be, and delivered to the Trustee.

"Opinion of Counsel" means a written opinion of counsel, who may be counsel for (including an employee of) the Company or the Guarantor, as the case may be, and who shall be acceptable to the Trustee.

"Vice President", when used with respect to the Company, the Guarantor or the Trustee, means any vice president, whether or not designated by a number or a word or words added before or after the title "vice president".

        1.2    Amendment to Section 102 of the Indenture.    Section 102 of the Indenture is hereby amended by inserting the following paragraph as the new second paragraph thereto:

        "Upon any application or request by the Guarantor to the Trustee to take any action under any provision of this Indenture, the Guarantor shall furnish to the Trustee an Officers' Certificate stating that all conditions precedent, if any, provided for in this Indenture relating to the proposed action have been complied with and an Opinion of Counsel stating that in the opinion of such counsel all such conditions precedent, if any, have been complied with, except that in the case of any such application or request as to which the furnishing of such documents is specifically required by any provision of this Indenture relating to such particular application or request, no additional certificate or opinion need be furnished."

        1.3    Amendment to Section 103 of the Indenture.    Section 103 of the Indenture is hereby amended by inserting the following paragraph as the new third paragraph thereof:

        "Any certificate or opinion of an officer of the Guarantor may be based, insofar as it relates to legal matters, upon a certificate or opinion of, or representations by, counsel, unless such officer knows, or in the exercise of reasonable care should know, that the certificate or opinion or representations with respect to the matters upon which his certificate or opinion is based are erroneous. Any such certificate or Opinion of Counsel may be based, insofar as it relates to factual matters, upon a certificate or opinion of, or representations by, an officer or officers of the Guarantor stating that the information with respect to such factual matters is in the possession of the Guarantor, unless such counsel knows, or in the exercise of reasonable care should know, that the certificate or opinion or representations with respect to such matters are erroneous."

        1.4    Amendment to Section 105 of the Indenture.    (a) Section 105 of the Indenture is hereby amended by deleting the current section heading thereof and replacing it with the following:

"Notices, Etc., to Trustee, Company or Guarantor"

2

        (b)   Section 105 of the Indenture is hereby amended (i) by deleting the word "or" at the end of paragraph (1), (ii) by deleting the period and inserting the word ", or" at the end of paragraph (2) and (iii) by inserting the following paragraph as the final paragraph thereof:

        "(3)    the Guarantor by the Trustee or by any Holder shall be sufficient for every purpose hereunder (unless otherwise herein expressly provided) if in writing and mailed, first-class postage prepaid, to the Guarantor addressed to it at 745 Seventh Avenue, New York, New York 10019, attention: Treasurer, or at any other address previously furnished in writing to the Trustee by the Guarantor."

        1.5    Amendment to Section 115 of the Indenture.    Section 115 of the Indenture is hereby amended by inserting the following paragraph as the new second paragraph thereof:

        "No recourse shall be had for the payment of the Guarantee of the principal of (and premium, if any) or the interest, if any, on any Security or coupon of any series, or for any claim based thereon, or upon any obligation, covenant or agreement of this Indenture, against any incorporator, stockholder, officer or director, as such, past, present or future, of the Guarantor or of any successor corporation, either directly or indirectly through the Guarantor or any successor corporation, whether by virtue of any constitution, statute or rule of law or by the enforcement of any assessment or penalty or otherwise; it being expressly agreed and understood that this Indenture and the Guarantee of all the Securities and coupons of each series are solely corporate obligations, and that no personal liability whatever shall attach to, or is incurred by, any incorporator, stockholder, officer or director, past, present or future, of the Guarantor or of any successor corporation, either directly or indirectly through the Guarantor or any successor corporation, because of the incurring of the indebtedness hereby authorized or under or by reason of any of the obligations, covenants or agreements contained in this Indenture, or to be implied herefrom therefrom; and that all such personal liability is hereby expressly released and waived as a condition of, and as part of the consideration for, the execution of this Indenture."

        1.6    Amendment to Section 301 of the Indenture.    Section 301 of the Indenture is hereby amended by adding the words "or the Guarantor" immediately following the words "covenant of the Company" in paragraph (20) and by deleting the word "and" at the end of paragraph (26), redesignating paragraph (27) as paragraph (28) and inserting the following paragraph in proper numerical order:

        "(27)    the terms and provisions of the Guarantee, to the extent that such provisions differ from those set forth herein; and"

        1.7    Amendment to Section 303 of the Indenture.    (a) Section 303 of the Indenture is hereby amended (i) by deleting the word "and" at the end of subparagraph (c), (ii) by redesignating subparagraph (d) as subparagraph (e) and (iii) by inserting the following paragraph as the new subparagraph (d) thereof:

        "(d)    that the Guarantee of such Securities, together with any coupons appertaining thereto, when the Securities are authenticated and delivered by the Trustee and issued by the Company in the manner and subject to any conditions specified in such Opinion of Counsel, will constitute valid and legally binding obligations of the Guarantor, enforceable in accordance with their terms, subject to the effects of bankruptcy, insolvency, fraudulent conveyance, reorganization, moratorium and other similar laws relating to or affecting creditors' rights generally, general principles of equity (whether considered in a proceeding at law or in equity) and by an implied covenant of good faith and fair dealing."

        (b)   Section 303 of the Indenture is hereby amended by inserting the word ", Guarantee" immediately following the words "No Security" at the beginning of the seventh paragraph of such section.

3

        1.8    Amendment to Section 305 of the Indenture.    Section 305 of the Indenture is hereby amended by deleting the eleventh paragraph in its entirety and inserting in lieu thereof the following paragraph:

        "All Securities issued upon any registration of transfer or exchange of Securities shall be the valid obligations of the Company evidencing the same debt, and entitled to the same benefits under this Indenture (including the Guarantee), as the Securities surrendered upon such registration of transfer or exchange."

        1.9    Amendment to Section 308 of the Indenture.    Section 308 of the Indenture is hereby amended by inserting the words ", the Guarantor" immediately following the words "the Company" in each place such words appear.

        1.10    Amendment to Section 402 of the Indenture.    Section 402 of the Indenture is hereby amended (i) by inserting the words "or the Guarantor" immediately following the words "including the Company" in subparagraph (a) thereof; (ii) by inserting the words "or the Guarantor, as the case may be," immediately following the words "or pay to the Company" in subparagraph (c) thereof; and (iii) by inserting the words "or Guarantor Request" immediately following the words "upon Company Request" in subparagraph (c) thereof.

        1.11    Amendment to Section 501 of the Indenture.    Section 501 of the Indenture is hereby amended by redesignating subparagraph (7) as subparagraph (9) and by inserting the following paragraphs in proper numerical order:

        "(7)    the entry by a court having jurisdiction in the premises of (A) a decree or order for relief in respect of the Guarantor in an involuntary case or proceeding under any applicable Federal or State bankruptcy, insolvency, reorganization or other similar law or (B) a decree or order adjudging the Guarantor a bankrupt or insolvent, or approving as properly filed a petition seeking reorganization, arrangement, adjustment or composition of or in respect of the Guarantor under any applicable Federal or State law, or appointing a custodian, receiver, liquidator, assignee, trustee, sequestrator or other similar official of the Guarantor or of any substantial part of its property, or ordering the winding up or liquidation of its affairs, and the continuance of any such decree or order for relief or any such other decree or order unstayed and in effect for a period of 60 consecutive days; or

        (8)    the commencement by the Guarantor of a voluntary case or proceeding under any applicable Federal or State bankruptcy, insolvency, reorganization or other similar law or of any other case or proceeding to be adjudicated a bankrupt or insolvent, or the consent by it to the entry of a decree or order for relief in respect of it in an involuntary case or proceeding under any applicable Federal or State bankruptcy, insolvency, reorganization or other similar law or to the commencement of any bankruptcy or insolvency case or proceeding against it, or the filing by it of a petition or answer or consent seeking reorganization or relief under any applicable Federal or State law, or the consent by it to the filing of such petition or to the appointment of or taking possession by a custodian, receiver, liquidator, assignee, trustee, sequestrator or similar official of the Guarantor or of any substantial part of its property, or the making by it of an assignment for the benefit of creditors, or the admission by it in writing of its inability to pay its debts generally as they become due, or the taking of corporate action by the Guarantor in furtherance of any such action; or"

        1.12    Amendment to Section 509 of the Indenture.    Section 509 of the Indenture is hereby amended by inserting the words ", the Guarantor" immediately following the words "subject to any determination in such proceeding, the Company".

        1.13    Amendment to Section 514 of the Indenture.    Section 514 of the Indenture is hereby amended by inserting the words "or the Guarantor" immediately following the words "suit instituted by the Company".

4

        1.14    Amendment to Section 515 of the Indenture.    Section 515 of the Indenture is hereby amended by deleting the words "the Company" in each place of the two places where such words appear and inserting in each place in lieu thereof the words "each of the Company and the Guarantor".

        1.15    Amendment to Section 704 of the Indenture.    (a) Section 704 of the Indenture is hereby amended by deleting the current section heading thereof and replacing it with the following:

"Reports by Company and Guarantor"

        (b) Section 704 of the Indenture is hereby amended by redesignating the first paragraph thereof as subsection (a) and by inserting the following paragraph as the new subsection (b) thereof:

"(b)    The Guarantor shall:

(1)    file with the Trustee, within 15 days after the Guarantor is required to file the same with the Commission, copies of the annual reports and of the information, documents and other reports (or copies of such portions of any of the foregoing as the Commission may from time to time by rules and regulations prescribe), which the Guarantor may be required to file with the Commission pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934; or, if the Guarantor is not required to file information, documents or reports pursuant to either of said Sections, then it shall file with the Trustee and the Commission, in accordance with rules and regulations prescribed from time to time by the Commission, such of the supplementary and periodic information, documents and reports which may be required pursuant to Section 13 of the Securities Exchange Act of 1934 in respect of a security listed and registered on a national securities exchange as may be prescribed from time to time in such rules and regulations;

(2)    file with the Trustee and the Commission, in accordance with rules and regulations prescribed from time to time by the Commission, such additional information, documents and reports with respect to compliance by the Guarantor with the conditions and covenants of this Indenture as may be required from time to time by such rules and regulations; and

(3)    transmit, within 30 days after the filing thereof with the Trustee, to the Holders of Securities, in the manner and to the extent provided in Section 703(c) with respect to reports pursuant to Section 703(a), such summaries of any information, documents and reports required to be filed by the Guarantor pursuant to paragraphs (1) and (2) of this Section as may be required by rules and regulations prescribed from time to time by the Commission."

        1.16    Amendment to Section 801 of the Indenture.    (a) Section 801 of the Indenture is hereby amended by deleting the current section heading thereof and replacing it with the following:

"Company and Guarantor May Consolidate, Etc., Only on Certain Terms"

        (b)    Section 801 of the Indenture is hereby amended by redesignating the first paragraph thereof as subsection (a) and by inserting the following paragraph as the new subsection (b) thereof:

        "(b)    The Guarantor shall not consolidate with or merge into any other corporation or convey, transfer or lease its properties and assets substantially as an entirety to any Person, and the Guarantor shall not permit any Person to consolidate with or merge into the Guarantor or convey, transfer or lease its properties and assets substantially as an entirety to the Guarantor, unless:

(1)    in case the Guarantor shall consolidate with or merge into another corporation or convey, transfer or lease its properties and assets substantially as an entirety to any Person, the corporation formed by such consolidation or into which the Guarantor is merged or the Person which acquires by conveyance or transfer, or which leases, the properties and assets of the Guarantor substantially as an entirety shall be a corporation organized and existing under

5

the laws of the United States of America, any State thereof or the District of Columbia and shall expressly assume, by an indenture supplemental hereto, executed and delivered to the Trustee, in form satisfactory to the Trustee, the due and punctual payment of the principal of (and premium, if any) and interest, if any, (including all Additional Amounts, if any, payable pursuant to Section 1008) on all the Securities and any related coupons and the performance of every covenant of this Indenture on the part of the Guarantor to be performed or observed;

(2)    immediately after giving effect to such transaction and treating any indebtedness which becomes an obligation of the Guarantor or a Subsidiary as a result of such transaction as having been incurred by the Guarantor or such Subsidiary at the time of such transaction, no Event of Default, and no event which, after notice or lapse of time or both, would become an Event of Default, shall have occurred and be continuing;

(3)    the successor corporation assuming the Guarantee shall have agreed, by supplemental indenture, to indemnify the individuals liable therefor for the amount of United States Federal estate tax paid solely as a result of such assumption in respect of Guarantee held by individuals who are not citizens or residents of the United States at the time of their death; and

(4)    the Guarantor has delivered to the Trustee an Officers' Certificate and an Opinion of Counsel, each stating that such consolidation, merger, conveyance, transfer or lease and, if a supplemental indenture is required in connection with such transaction, such supplemental indenture, complies with this Article and that all conditions precedent herein provided for relating to such transaction have been complied with."

        1.17    Amendment to Section 802 of the Indenture.    Section 802 of the Indenture is hereby amended by inserting the following paragraph as the new second paragraph thereof:

6

"Upon any consolidation by the Guarantor with or merger by the Guarantor into any other corporation or any conveyance, transfer or lease of the properties and assets of the Guarantor substantially as an entirety in accordance with Section 801, the successor corporation formed by such consolidation or into which the Guarantor is merged or to which such conveyance, transfer or lease is made shall succeed to, and be substituted for, and may exercise every right and power of, the Guarantor under this Indenture with the same effect as if such successor corporation had been named as the Guarantor herein, and thereafter, except in the case of a lease, the predecessor corporation shall be relieved of all obligations and covenants under this Indenture, the Securities and any related coupons."

        1.18    Amendment to Section 901 of the Indenture.    (a) Section 901 of the Indenture is hereby amended by inserting the words "the Guarantor, when authorized by a Board Resolution," immediately following the words "the Company, when authorized by a Board Resolution," in the introductory sentence thereof.

(b)

Section 1101 of the Indenture is hereby amended by redesignating subparagraphs (3), (4), (5), (6), (7), (8), (9), (10) and (11), respectively, as new subparagraphs (5), (6), (7), (8), (9), (10), (11), (12) and (13), respectively, and by inserting the following subparagraphs in proper numerical order:

"(3) to evidence the succession of another corporation to the Guarantor and the assumption by any such successor of the covenants of the Guarantor herein and in the Securities; or

"(4) to add to the covenants of the Guarantor for the benefit of the Holders of all or any series of Securities and any related coupons (and if such covenants are to be for the benefit of less than all series of Securities, stating that such covenants are expressly being included solely for the benefit of such series) or to surrender any right or power herein conferred upon the Guarantor; or"

        1.19    Amendment to Section 902 of the Indenture.    Section 902 of the Indenture is hereby amended by inserting the words "the Guarantor, when authorized by a Board Resolution," immediately following the words "the Company, when authorized by a Board Resolution," in the introductory sentence thereof.

        1.20    Amendment to Section 1003 of the Indenture.    Section 1003 of the Indenture is hereby amended by deleting the final paragraph in its entirety and inserting in lieu thereof the following paragraph:

"Any money deposited with the Trustee or any Paying Agent, or then held by the Company or the Guarantor, in trust for the payment of the principal of (and premium, if any) or interest, if any, on any Security of any series and remaining unclaimed for two years after such principal (and premium, if any) or interest, if any, has become due and payable shall, unless otherwise required by mandatory provisions of applicable escheat or abandoned or unclaimed property law as determined by the Company, be paid to the Company on Company Request or the Guarantor on Guarantor Request, or (if then held by the Company or the Guarantor) shall be discharged from such trust; and the Holder of such Security or any coupon appertaining thereto shall thereafter, as an unsecured general creditor, look only to the Company or the Guarantor for payment thereof, and all liability of the Trustee or such Paying Agent with respect to such trust money, and all liability of the Company or the Guarantor as trustee thereof, shall thereupon cease; provided, however, that the Trustee or such Paying Agent, before being required to make any such repayment, may at the expense of the Company cause to be transmitted once, in the manner and to the extent provided in Section 106, notice that such money remains unclaimed and that, after a date specified

7

therein, which shall not be less than 30 days from the date of such publication, any unclaimed balance of such money then remaining will be repaid to the Company or the Guarantor."

        1.21    Amendment to Section 1006 of the Indenture.    Section 1006 of the Indenture is hereby amended by inserting the following paragraphs as the new third, fourth and fifth paragraphs respectively thereof:

"The Guarantor will deliver to the Trustee, within 120 days after the end of each fiscal year of the Guarantor ending after the date hereof, an officers' certificate of the principal executive officer, principal financial or principal accounting officer of the Guarantor, stating whether or not to the best knowledge of the signers thereof the Guarantor is in default in the performance and observance of any of the terms, provisions and conditions of this Indenture and, if the Guarantor shall be in default, specifying all such defaults and the nature and status thereof of which they may have knowledge. For purposes of this Section 1006, any such default shall be determined without regard to any period of grace or requirement of notice provided under this Indenture.

In addition, the Guarantor shall file with the Trustee written notice of the occurrence of any default or Event of Default within five Business Days of its becoming aware of any such default or Event of Default.

Such officers' certificate or written notice of the Company and the Guarantor may be in the form of one certificate or notice signed by the appropriate officers of the Company and the Guarantor."

Section 2. GUARANTEE

        2.1    Addition of New Article 14 of the Indenture.    Article 14 of the Indenture is hereby created and the following shall be inserted therein:

ARTICLE FOURTEEN
THE GUARANTEES

        Section1401.    Except as otherwise set forth in a supplemental indenture or provided in or pursuant to a Board Resolution and set forth in an Officers' Certificate, the Guarantor hereby unconditionally guarantees to the Holder of the Securities of each series authenticated and delivered by the Trustee, and to the Trustee on behalf of each such Holder, the due and punctual payment of the principal (including any amount in respect of original issue discount) of, and premium, if any, and interest, if any, on such Securities and the due and punctual payment of the sinking fund payments, if any, and analogous obligations, if any, provided for pursuant to the terms of such Securities, when and as the same shall become due and payable, whether at maturity or upon redemption or upon declaration of acceleration or otherwise, according to the terms of such Securities and of the Indenture and this Supplemental Indenture. The Guarantor agrees that in case of default by the Company in the payment of any such principal (including any amount in respect of original issue discount), premium, interest, sinking fund payment, or analogous obligation, the Guarantor shall duly and punctually pay the same, as if such payment were made by the Company. The Guarantor hereby agrees that its obligations hereunder shall be absolute and unconditional, irrespective of any extension of the time for payment of any such Security, any modification of any such Security or any supplemental indenture or Board Resolution and Officers' Certificate relating thereto, any invalidity, irregularity or unenforceability of any such Security or the Indenture or this Supplemental Indenture, any failure or delay to enforce the same or any waiver, modification, consent or indulgence granted to the Company with respect thereto by the Holder of such Security or the Trustee, or any other circumstances which may otherwise constitute a legal or equitable discharge of a surety or guarantor.

8

        The Guarantor further agrees that the Guarantee herein constitutes a guarantee of payment when due (and not a guarantee of collection) and waives (to the extent that it may lawfully do so) any right to require that any resort be had by any Holder or the Trustee to any security held for payment of the Guarantee.

        The Guarantor hereby waives (to the extent that it may lawfully do so) diligence, presentment, demand of payment, filing of claims with a court in the event of merger or bankruptcy of the Company, any right to require a demand or proceeding first against the Company, protest or notice with respect to any such Security or the indebtedness evidenced thereby and all demands whatsoever, and covenants that this Guarantee will not be discharged as to any such Security except by payment in full of the principal (including any amount payable in respect of original issue discount) of, and premium, if any, and interest, if any, and payment of the sinking fund payments, if any, and analogous obligations, if any, thereon.

        The Guarantor agrees that the Guarantee with respect to each series of Securities shall remain in full force and effect until payment in full of all the Securities of such series. The Guarantor further agrees that the Guarantee herein shall continue to be effective or be reinstated, as the case may be, if at any time payment, or any part thereof, of the principal (including any amount payable in respect of original issue discount) of, and premium, if any, and interest, if any, and payment of the sinking fund payments, if any, and analogous obligations, if any, on any series of Securities is rescinded or must otherwise be restored by any Holder or the Trustee upon the bankruptcy or reorganization of the Company or otherwise.

        The Guarantor further agrees that, as between it, on the one hand, and the Holders and the Trustee, on the other hand, (x) the maturity of the obligations guaranteed hereby may be accelerated as provided in Article Seven for the purposes of any Guarantee herein, notwithstanding any stay, injunction or other prohibition preventing such acceleration in respect of the obligations guaranteed hereby, and (y) in the event of any declaration of acceleration of the obligations guaranteed hereby as provided in Article Seven, such obligations (whether or not due and payable) shall forthwith become due and payable by the Guarantor for the purposes of this Section 1401.

        The Guarantor shall be subrogated to all rights of the Holders of the Securities of a series against the Company in respect of any amounts paid by the Guarantor on account of such Security pursuant to the provisions of the Guarantees or this Indenture; provided, however, that the Guarantor agrees that it shall not be entitled to any right of subrogation in relation to the Holders until payment in full of the principal (including any amount payable in respect of original issue discount) of, and premium, if any, and interest, if any, and payment of the sinking fund payments, if any, and analogous obligations, if any, on all Securities of such series. The Guarantor hereby waives (to the extent that it may lawfully do so) any and all rights to which it may be entitled, by operation of law or otherwise, upon making any payment hereunder (i) any right to which it may be entitled to have the assets of the Company first be used and depleted as payment of the Company's or the Guarantor's obligations hereunder prior to any amounts being claimed from or paid by the Guarantor hereunder; or (ii) to receive any payment, in the nature of contribution or for any other reason, from any other obligor with respect to such payment.

Section 3. MISCELLANEOUS

        3.1    Continuance of Indenture.    This Supplemental Indenture supplements the Indenture and shall be a part of and subject to all the terms thereof. The Indenture, as supplemented by this Supplemental Indenture, shall continue in full force and effect.

        3.2    Defined Terms.    All capitalized terms used in this Supplemental Indenture which are defined in the Indenture, but not otherwise defined herein, shall have the same meanings assigned to them in the Indenture.

9

        3.3    Conflict with Trust Indenture Act.    If any provision of this Supplemental Indenture limits, qualifies or conflicts with the duties imposed by any of Sections 310 through 317, inclusive, of the Trust Indenture Act through the operation of Section 318(c) thereof, such imposed duties shall control.

        3.4    Successors and Assigns.    All covenants and agreements in this Supplemental Indenture by the Company or the Guarantor shall bind its successors and assigns, whether so expressed or not.

        3.5    Separability Clause.    In case any provision in this Supplemental Indenture shall be invalid, illegal or unenforceable, the validity, legality and enforceability of the remaining provisions shall not in any way be affected or impaired thereby.

        3.6    Governing Law.    This Supplemental Indenture and the Securities and coupons shall be governed by and construed in accordance with the laws of the State of New York.

        3.7    The Trustee.    The recitals contained herein shall be taken as the statements of the Company and the Guarantor, and the Trustee assumes no responsibility for their correctness. The Trustee makes no representations as to the validity or sufficiency of this Supplemental Indenture.

        3.8    Execution in Counterparts.    This Supplemental Indenture may be executed in any number of counterparts, each of which shall be an original, but such counterparts shall together constitute but one and the same instrument.

        The Bank of New York hereby accepts the trusts in this Supplemental Indenture declared and provided, upon the terms and conditions hereinabove set forth.

10

        IN WITNESS WHEREOF, Lehman Brothers Inc. has caused this Supplemental Indenture to be signed and acknowledged by its Chairman of the Board, one of its Vice Chairmen of the Board, its President or one of its Vice Presidents, Lehman Brothers Holdings Inc. has caused this Supplemental Indenture to be signed and acknowledged by its Chairman of the Board, one of its Vice Chairmen of the Board, its President or one of its Vice Presidents, and The Bank of New York, as Trustee, has caused this Supplemental Indenture to be signed and acknowledged by one its authorized officers, and its corporate seal to be affixed hereunto, and the same to be attested by one of its authorized officers, as of the day and year first above written.

LEHMAN BROTHERS INC.
By:	Name: Title:

LEHMAN BROTHERS HOLDINGS INC., as Guarantor
By:	Name: Title:

THE BANK OF NEW YORK, as Trustee
By:	Authorized Officer

11

QuickLinks

Exhibit 4(e)

EX-4.(P)

QuickLinks -- Click here to rapidly navigate through this document

Exhibit 4(p)

LEHMAN BROTHERS INC.,

LEHMAN BROTHERS HOLDINGS INC.,

as Guarantor,

AND

U.S. BANK NATIONAL ASSOCIATION,

as Trustee

FORM OF TENTH SUPPLEMENTAL INDENTURE

Dated as of                         , 2003

        TENTH SUPPLEMENTAL INDENTURE, dated as of                    , 2003 (the "Supplemental Indenture"), among LEHMAN BROTHERS INC., a corporation duly organized and existing under the laws of the State of Delaware (the "Company"), LEHMAN BROTHERS HOLDINGS INC., a corporation duly organized and existing under the laws of the State of Delaware, as guarantor (the "Guarantor"), and U.S. BANK NATIONAL ASSOCIATION (as successor in interest to Continental Bank, National Association), a national banking corporation duly organized and existing under the laws of the United States, as trustee (the "Trustee").

RECITALS

        The Company has duly authorized the execution and delivery of an Indenture, dated as of June 14, 1989, between the Company and the Trustee, as amended and supplemented by (i) the First Supplemental Indenture, dated as of June 21, 1989, between the Company and the Trustee, (ii) the Second Supplemental Indenture, dated as of October 3, 1990, between the Company and the Trustee, (iii) the Third Supplemental Indenture, dated as of December 2, 1992, between the Company and the Trustee, (iv) the Fourth Supplemental Indenture, dated as of December 30, 1992, between the Company and the Trustee, (v) the Fifth Supplemental Indenture, dated as of January 14, 1993, between the Company and the Trustee, (vi) the Sixth Supplemental Indenture, dated as of May 17, 1993, between the Company and the Trustee, (vii) the Seventh Supplemental Indenture, dated as of November 17, 1993, between the Company and the Trustee and (ix) the Ninth Supplemental Indenture between the Company and the Trustee (collectively, the "Indenture"), to provide for the issuance from time to time of its unsecured senior subordinated debentures, notes or other evidences of indebtedness to be issued in one or more series (the "Securities") unlimited as to principal amount, to bear such rates of interest, to mature at such time or times, to be issued in one or more series and to have such other provisions as in the Indenture provided.

        The Guarantor has determined that it is in its best interests to fully and unconditionally guarantee the due and punctual payment of the principal (including any amount in respect of original issue discount) of, and premium, if any, and interest, if any, on all outstanding and future Securities and the due and punctual payment of the sinking fund payments, if any, and analogous obligations, if any, provided for pursuant to the terms of such Securities, when and as the same shall become due and payable;

        The Company and the Guarantor have duly authorized the execution and delivery of this Supplemental Indenture to provide for the guarantee by the Guarantor of the Securities;

        All acts and things necessary to make this Supplemental Indenture a valid agreement of the Company and of the Guarantor, in accordance with its terms and with the terms of the Indenture, have been done and performed.

NOW, THEREFORE, THIS SUPPLEMENTAL INDENTURE WITNESSETH:

        For and in consideration of the premises, and of the sum of one dollar duly paid to the Company and the Guarantor by the Trustee at the execution and delivery of these presents, the receipt whereof is hereby acknowledged, the Company and the Guarantor covenant and agree, for the equal and proportionate benefit of all holders of the Securities with the Trustee to supplement the Indenture as follows:

Section 1. AMENDMENTS TO THE INDENTURE

        1.1    Amendment to Section 101 of the Indenture.    Section 101 of the Indenture is hereby amended by deleting the definitions of "Board of Directors," "Board Resolution," "Company," "Officers' Certificate," "Opinion of Counsel" and "Vice President" and inserting the following definitions, in the appropriate alphabetical sequence:

        "Board of Directors" means the board of directors of the Company or the Guarantor, as the case may be, the executive committee thereof or any other committee of either board of directors duly authorized to act hereunder.

        "Board Resolution" means a copy of a resolution certified by the Secretary or an Assistant Secretary of the Company or the Guarantor, as the case may be, to have been duly adopted by the Board of Directors and to be in full force and effect on the date of such certification, and delivered to the Trustee.

        "Company" means Lehman Brothers Inc., and subject to the provisions of Article Ten, shall also include its successors and assigns.

        "Guarantee" means the full and unconditional guarantee by the Guarantor set forth in Article 15.

        "Guarantor" means Lehman Brothers Holdings Inc., a corporation duly organized and existing under the laws of the State of Delaware.

        "Guarantor Order" or "Guarantor Request" means a written request or order signed in the name of the Guarantor by its Chairman of the Board, any Vice Chairman of the Board, its President or a Vice President, and by its Treasurer, an Assistant Treasurer, its Secretary or an Assistant Secretary, and delivered to the Trustee.

        "Officers' Certificate" means a certificate signed by the Chairman of the Board, any Vice Chairman of the Board, the President or a Vice President, and by the Treasurer, and Assistant Treasurer, the Secretary or an Assistant Secretary, of the Company or the Guarantor, as the case may be, and delivered to the Trustee.

        "Opinion of Counsel" means a written opinion of counsel, who may be counsel for or employed by the Company or the Guarantor, as the case may be, and who shall be acceptable to the Trustee.

        "Vice President", when used with respect to the Company, the Guarantor or the Trustee, means any vice president, whether or not designated by a number or a word or words added before or after the title "vice president."

        1.2    Amendment to Section 102 of the Indenture.    Section 102 of the Indenture is hereby amended by inserting the following paragraph as the new second paragraph thereto:

        "Upon any application or request by the Guarantor to the Trustee to take any action under any provision of this Indenture, the Guarantor shall furnish to the Trustee an Officers' Certificate stating that all conditions precedent, if any, provided for in this Indenture relating to the proposed action have been complied with and an Opinion of Counsel stating that in the opinion of such counsel all such conditions precedent, if any, have been complied with, except that in the case of any such application or request as to which the furnishing of such documents is specifically required by any provision of this Indenture relating to such particular application or request, no additional certificate or opinion need be furnished."

        1.3    Amendment to Section 103 of the Indenture.    Section 103 of the Indenture is hereby amended by inserting the following paragraph as the new third paragraph thereof:

        "Any certificate or opinion of an officer of the Guarantor may be based, insofar as it relates to legal matters, upon a certificate or Opinion of Counsel, or representations by counsel, unless such officer knows, or in the exercise of reasonable care should know, that the certificate or opinion or representations with respect to the matters upon which his certificate or opinion is based are erroneous. Any such certificate or Opinion of Counsel or representation by counsel may be based, insofar as it relates to factual matters, upon a certificate or opinion of, or representations by, an officer or officers of the Guarantor stating that the information with respect to such factual matters is in the possession of the Guarantor, unless such counsel knows, or in the

2

exercise of reasonable care should know, that the certificate or opinion or representations with respect to such matters are erroneous."

        1.4    Amendment to Section 105 of the Indenture.    (a) Section 105 of the Indenture is hereby amended by deleting the current section heading thereof and replacing it with the following:

        "Notices, Etc., to Trustee, Company or Guarantor"

        (b)   Section 105 of the Indenture is hereby amended by deleting the word "or" at the end of paragraph (1), deleting the period and inserting the word ", or" at the end of paragraph (2) and inserting the following paragraph as the final paragraph thereof:

        "(3) the Guarantor by the Trustee or by any Holder shall be sufficient for every purpose hereunder if in writing and mailed, first-class postage prepaid, to the Guarantor addressed to it at 745 Seventh Avenue, New York, New York 10019, attention: Treasurer or at any other address previously furnished in writing to the Trustee by the Guarantor."

        1.5    Amendment to Section 301 of the Indenture.    Section 301 of the Indenture is hereby amended by deleting the word "and" at the end of paragraph (10), redesignating paragraph (11) as paragraph (12) and inserting the following paragraph in proper numerical order:

        "(11) the terms and provisions of the Guarantee, to the extent that such provisions differ from those set forth herein; and"

        1.6    Amendment to Section 303 of the Indenture.    (a) Section 303 of the Indenture is hereby amended by deleting the word "and" at the end of subparagraph (b), deleting the period and inserting the word "; and" at the end of subparagraph (c) and inserting the following paragraph as the new subparagraph (d) thereof:

        "(d) that the Guarantee of such Securities, when the Securities are authenticated and delivered by the Trustee and issued by the Company in the manner and subject to any conditions specified in such Opinion of Counsel, will constitute a valid and legally binding obligation of the Guarantor, enforceable in accordance with its terms, subject to the effects of bankruptcy, insolvency, fraudulent conveyance, reorganization, moratorium and other similar laws relating to or affecting creditors' rights generally, general equitable principles (whether considered in a proceeding in equity or at law) and an implied covenant of good faith and fair dealing."

        (b)   Section 303 of the Indenture is hereby amended by inserting the words "or Guarantee" immediately following the words "No Security" at the beginning of the final paragraph of the section.

        1.7    Amendment to Section 305 of the Indenture.    Section 305 of the Indenture is hereby amended by deleting the fourth paragraph and inserting in lieu thereof the following paragraph:

        "All Securities issued upon any registration of transfer or exchange of Securities shall be the valid obligations of the Company evidencing the same debt, and entitled to the same benefits under this Indenture (including the Guarantee), as the Securities surrendered upon such registration of transfer or exchange."

        1.8    Amendment to Section 308 of the Indenture.    Section 308 of the Indenture is hereby amended by inserting the words ", the Guarantor" immediately following the words "the Company" in each place such words appear.

        1.9    Amendment to Section 503 of the Indenture.    Section 503 of the Indenture is hereby amended by deleting the final paragraph in its entirety and inserting in lieu thereof the following paragraph:

        "Any money deposited with the Trustee or any Paying Agent, or then held by the Company or the Guarantor in trust for the payment of the principal of (and premium, if any) or interest on any

3

Security of any series and remaining unclaimed for three years after such principal (and premium, if any) or interest has become due and payable shall be paid to the Company on Company Request or the Guarantor on Guarantor Request, or (if then held by the Company or the Guarantor) shall be discharged from such trust; and the Holder of such Security shall thereafter, as an unsecured general creditor, look only to the Company and the Guarantor for payment thereof, and all liability of the Trustee or such Paying Agent with respect to such trust money, and all liability of the Company or the Guarantor as trustee thereof, shall thereupon cease; provided, however, that the Trustee or such Paying Agent, before being required to make any such repayment, may at the expense of the Company cause to be published once, in a newspaper published in the English language, customarily published on each Business Day and of general circulation in the Borough of Manhattan, The City of New York, notice that such money remains unclaimed and that, after a date specified therein, which shall not be less than 30 days from the date of such publication, any unclaimed balance of such money then remaining will be repaid to the Company or the Guarantor."

        1.10    Amendment to Section 506 of the Indenture.    Section 506 of the Indenture is hereby amended by inserting the following paragraphs as the new second and third paragraphs respectively thereof:

        "The Guarantor will deliver to the Trustee, within 120 days after the end of each fiscal year of the Guarantor ending after the date hereof, an Officers' Certificate, stating whether or not to the best knowledge of the signers thereof the Guarantor is in default in the performance and observance of any of the terms, provisions and conditions of this Indenture, and if the Guarantor shall be in default, specifying all such defaults and the nature and status thereof of which they may have knowledge. For purposes of this Section 506, any such default shall be determined without regard to any period of grace or requirement of notice provided under this Indenture.

        Such Officers' Certificate or written notice of the Company and the Guarantor may be in the form of one certificate or notice signed by the appropriate officers of the Company and the Guarantor."

        1.11    Amendment to Section 602 of the Indenture.    Section 602 of the Indenture is hereby amended by inserting the words "or the Guarantor" immediately following the words "including the Company" therein.

        1.12    Amendment to Section 701 of the Indenture.    Section 701 of the Indenture is hereby amended by deleting the reference to subparagraph (g) in the introductory sentence and inserting in lieu thereof a reference to subparagraph (h), by deleting the word "or" at the end of subparagraph (f) and by inserting the following paragraph immediately prior to the final period at the end of subparagraph (g) thereof:

        "; or

        (h)   the dissolution or insolvency of the Guarantor or the making of an assignment for the benefit of creditors by the Guarantor or the commencement of any proceedings (by petition, application, answer, consent or otherwise) by the Guarantor to be adjudicated a bankrupt or for the appointment of a receiver or trustee or similar officer for it or for a substantial part of its property or for reorganization, an arrangement, composition or other relief under the Bankruptcy Act or the taking of corporate action by the Guarantor for any such purpose, or any marshalling of the assets or liabilities of the Guarantor or the commencement against the Guarantor of any of the aforementioned proceedings and in such latter case the consent thereto by the Guarantor or its admission of the material allegations thereof or the continuance of such proceedings undismissed for a period of 60 days."

4

        1.13    Amendment to Section 711 of the Indenture.    Section 711 of the Indenture is hereby amended by inserting the words ", the Guarantor" immediately following the words "subject to any determination in such proceeding, the Company" therein.

        1.14    Amendment to Section 716 of the Indenture.    Section 716 of the Indenture is hereby amended by inserting the words "or the Guarantor" immediately following the words "suit instituted by the Company" therein.

        1.15    Amendment to Section 717 of the Indenture.    Section 717 of the Indenture is hereby amended by deleting the words "the Company" in each place of the two places where such words appear and inserting in each place in lieu thereof the words "each of the Company and the Guarantor"

        1.16    Amendment to Section 904 of the Indenture.    (a) Section 904 of the Indenture is hereby amended by deleting the current section heading thereof and replacing it with the following:

        "Reports by Company and Guarantor"

        (b)   Section 904 of the Indenture is hereby amended by redesignating the first paragraph thereof as subsection (a) and by inserting the following paragraph as the new subsection (b) thereof:

        "(b) The Guarantor shall:

        (1)   file with the Trustee for the Securities of each series, within 15 days after the Guarantor is required to file the same with the Commission, copies of the annual reports and of the information, documents and other reports (or copies of such portions of any of the foregoing as the Commission may from time to time by rules and regulations prescribe) which the Guarantor may be required to file with the Commission pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934; or, if the Guarantor is not required to file information, documents or reports pursuant to either of said Sections, then it shall file with such Trustee and the Commission, in accordance with rules and regulations prescribed from time to time by the Commission, such of the supplementary and periodic information, documents and reports which may be required pursuant to Section 13 of the Securities Exchange Act of 1934 in respect of a security listed and registered on a national securities exchange as may be prescribed from time to time in such rules and regulations;

        (2)   file with such Trustee and the Commission, in accordance with rules and regulations prescribed from time to time by the Commission, such additional information, documents and reports with respect to compliance by the Guarantor with the conditions and covenants of this Indenture as may be required from time to time by such rules and regulations; and

        (3)   transmit by mail to all Holders, as their names and addresses appear in the Security Register, within 30 days after the filing thereof with the Trustee, such summaries of any information, documents and reports required to be filed by the Guarantor pursuant to paragraphs (1) and (2) of this Section 904(b) as may be required by rules and regulations prescribed from time to time by the Commission.

        1.17    Amendment to Section 1001 of the Indenture.    Section 1001 of the Indenture is hereby amended by redesignating the first paragraph thereof as subsection (a) and by inserting the following paragraph as the new subsection (b) thereof:

        "(b) Nothing contained in this Indenture or in any of the Securities shall prevent any consolidation or merger of the Guarantor with or into any other corporation or corporations (whether or not affiliated with the Guarantor), or successive consolidations or mergers in which the Guarantor or its successor or successors shall be a party or parties, or shall prevent any sale or transfer (or successive sales or transfers) of the property and assets of the Guarantor (or of its

5

successor or successors) as an entirety or substantially as an entirety, to any other corporation (whether or not affiliated with the Guarantor) authorized to acquire the same; provided, however, that the corporation formed by such consolidation or into which the Guarantor shall have been merged or which shall have acquired such property and assets shall be a corporation organized under the laws of the United States or of any State thereof; and provided, further, and the Guarantor hereby covenants and agrees, that upon any such consolidation, merger, sale or transfer, the Guarantee of the due and punctual payment of the principal of (and premium, if any) and interest, if any, on all of the Securities, according to their tenor, and the due and punctual performance and observance of all the terms, covenants and conditions of this Indenture to be kept or performed by the Guarantor, shall be expressly assumed, by an indenture supplemental hereto, satisfactory in form to the Trustee, executed and delivered to the Trustee by the corporation formed by such consolidation, or into which the Guarantor shall have been merged, or by the corporation which shall have acquired such property and assets; and in the event of any such sale or transfer, the predecessor Guarantor shall be released from all liability hereunder and under the Securities and may be dissolved, wound-up and liquidated at any time thereafter."

        1.18    Amendment to Section 1002 of the Indenture.    Section 1002 of the Indenture is hereby amended by redesignating the first and second paragraphs thereof as subsection (a) and by inserting the following two paragraphs as the new subsection (b) thereof:

        "(b) In case of any such consolidation, merger, sale or transfer and upon the execution by the successor corporation of an indenture supplemental hereto, as provided in Section 1001(b), such successor corporation shall succeed to and be substituted for the Guarantor, with the same effect as if it had been named herein as the party of the first part; and any order, certificate, statement, request, instructions, advice or resolutions of the Board of Directors or officers of the Guarantor provided for in this Indenture may be made by like officials of such successor corporation.

        Nothing contained in this Indenture or in any of the Securities shall prevent the Guarantor from merging into itself, or acquiring by purchase or otherwise all or any part of the property of, any other corporation (whether or not affiliated with the Guarantor)."

        1.19    Amendment to Section 1101 of the Indenture.    (a) Section 1101 of the Indenture is hereby amended by inserting the words "the Guarantor, when authorized by a Board Resolution," immediately following the words "the Company, when authorized by a Board Resolution," in the introductory sentence thereof.

        (b)   Section 1101 of the Indenture is hereby amended by redesignating subparagraphs (3), (4), (5), (6), (7), (8), (9) and (10), respectively, as new subparagraphs (5), (6), (7), (8), (9), (10), (11) and (12), respectively, and by inserting the following paragraphs in proper numerical order:

        "(3) to evidence the succession of another corporation to the Guarantor and the assumption by any such successor of the covenants of the Guarantor herein and in the Securities, if applicable; or

        "(4) to add to the covenants of the Guarantor for the benefit of the Holders of all or any series of Securities (and if such covenants are to be for the benefit of less than all series of Securities, stating that such covenants are expressly being included solely for the benefit of such series) or to surrender any right or power herein conferred upon the Guarantor; or"

        1.20    Amendment to Section 1102 of the Indenture.    Section 1102 of the Indenture is hereby amended by inserting the words "the Guarantor, when authorized by a Board Resolution," immediately following the words "the Company, when authorized by a Board Resolution," in the introductory sentence thereof.

Section 5. GUARANTEE

        2.1    Addition of New Article 15 of the Indenture.    Article 15 of the Indenture is hereby created and the following shall be inserted therein:

6

ARTICLE FIFTEEN

THE GUARANTEES

        SECTION 1501 Except as otherwise set forth in a supplemental indenture or provided in or pursuant to a Board Resolution and set forth in an Officers' Certificate, the Guarantor hereby unconditionally guarantees to the Holder of the Securities of each series authenticated and delivered by the Trustee, and to the Trustee on behalf of each such Holder, the due and punctual payment of the principal (including any amount in respect of original issue discount) of, and premium, if any, and interest, if any, on such Securities and the due and punctual payment of the sinking fund payments, if any, and analogous obligations, if any, provided for pursuant to the terms of such Securities, when and as the same shall become due and payable, whether at maturity or upon redemption or upon declaration of acceleration or otherwise, according to the terms of such Securities and of the Indenture and this Supplemental Indenture. The Guarantor agrees that in case of default by the Company in the payment of any such principal (including any amount in respect of original issue discount), premium, interest, sinking fund payment, or analogous obligation, the Guarantor shall duly and punctually pay the same, as if such payment were made by the Company. The Guarantor hereby agrees that its obligations hereunder shall be absolute and unconditional, irrespective of any extension of the time for payment of any such Security, any modification of any such Security or any supplemental indenture or Board Resolution and Officers' Certificate relating thereto, any invalidity, irregularity or unenforceability of any such Security or the Indenture or this Supplemental Indenture, any failure or delay to enforce the same or any waiver, modification, consent or indulgence granted to the Company with respect thereto by the Holder of such Security or the Trustee, or any other circumstances which may otherwise constitute a legal or equitable discharge of a surety or guarantor.

        The Guarantor further agrees that the Guarantee herein constitutes a guarantee of payment when due (and not a guarantee of collection) and waives (to the extent that it may lawfully do so) any right to require that any resort be had by any Holder or the Trustee to any security held for payment of the Guarantee.

        The Guarantor hereby waives (to the extent that it may lawfully do so) diligence, presentment, demand of payment, filing of claims with a court in the event of merger or bankruptcy of the Company, any right to require a demand or proceeding first against the Company, protest or notice with respect to any such Security or the indebtedness evidenced thereby and all demands whatsoever, and covenants that this Guarantee will not be discharged as to any such Security except by payment in full of the principal (including any amount payable in respect of original issue discount) of, and premium, if any, and interest, if any, and payment of the sinking fund payments, if any, and analogous obligations, if any, thereon.

        The Guarantor agrees that the Guarantee with respect to each series of Securities shall remain in full force and effect until payment in full of all the Securities of such series. The Guarantor further agrees that the Guarantee herein shall continue to be effective or be reinstated, as the case may be, if at any time payment, or any part thereof, of the principal (including any amount payable in respect of original issue discount) of, and premium, if any, and interest, if any, and payment of the sinking fund payments, if any, and analogous obligations, if any, on any series of Securities is rescinded or must otherwise be restored by any Holder or the Trustee upon the bankruptcy or reorganization of the Company or otherwise.

        The Guarantor further agrees that, as between it, on the one hand, and the Holders and the Trustee, on the other hand, (x) the maturity of the obligations guaranteed hereby may be accelerated as provided in Article Seven for the purposes of any Guarantee herein, notwithstanding any stay, injunction or other prohibition preventing such acceleration in respect of the obligations guaranteed hereby, and (y) in the event of any declaration of acceleration of the obligations guaranteed hereby as

7

provided in Article Seven, such obligations (whether or not due and payable) shall forthwith become due and payable by the Guarantor for the purposes of this Section 1501.

        The Guarantor shall be subrogated to all rights of the Holders of the Securities of a series against the Company in respect of any amounts paid by the Guarantor on account of such Security pursuant to the provisions of the Guarantees or this Indenture; provided, however, that the Guarantor agrees that it shall not be entitled to any right of subrogation in relation to the Holders until payment in full of the principal (including any amount payable in respect of original issue discount) of, and premium, if any, and interest, if any, and payment of the sinking fund payments, if any, and analogous obligations, if any, on all Securities of such series. The Guarantor hereby waives (to the extent that it may lawfully do so) any and all rights to which it may be entitled, by operation of law or otherwise, upon making any payment hereunder (i) any right to which it may be entitled to have the assets of the Company first be used and depleted as payment of the Company's or the Guarantor's obligations hereunder prior to any amounts being claimed from or paid by the Guarantor hereunder; or (ii) to receive any payment, in the nature of contribution or for any other reason, from any other obligor with respect to such payment.

Section 3. MISCELLANEOUS

        3.1    Continuance of Indenture.    This Supplemental Indenture supplements the Indenture and shall be a part of and subject to all the terms thereof. The Indenture, as supplemented by this Supplemental Indenture, shall continue in full force and effect.

        3.2    Defined Terms.    All capitalized terms used in this Supplemental Indenture which are defined in the Indenture, but not otherwise defined herein, shall have the same meanings assigned to them in the Indenture.

        3.3    Conflict with Trust Indenture Act.    If any provision of this Supplemental Indenture limits, qualifies or conflicts with another provision hereof which is required to be included in this Supplemental Indenture by any of the provisions of the Trust Indenture Act, such required provision shall control.

        3.4    Separability Clause.    In case any provision in this Supplemental Indenture shall be invalid, illegal or unenforceable, the validity, legality and enforceability of the remaining provisions shall not in any way be affected or impaired thereby.

        3.5    Benefits of Indenture.    Nothing in this Supplemental Indenture, express or implied, shall give to any Person, other than the parties hereto and their successors hereunder and the Holders any benefit or any legal or equitable right, remedy or claim under this Supplemental Indenture.

        3.6    Governing Law.    This Supplemental Indenture shall be governed by and construed in accordance with the laws of the State of New York.

        3.7    The Trustee.    The recitals contained herein shall be taken as the statements of the Company and the Guarantor, and the Trustee assumes no responsibility for their correctness. The Trustee makes no representations as to the validity or sufficiency of this Supplemental Indenture.

        3.8    Successors and Assigns of Company and Guarantor Bound By Supplemental Indenture.    All the covenants, stipulations, promises and agreements contained in this Supplemental Indenture by or on behalf of the Company or the Guarantor shall bind their successors and assigns, whether so expressed or not, and the provisions hereof shall bind the heirs, executors, administrators, successors and assigns of the Holders.

        3.9    Acts of Board, Committee or Officer of Successor Corporation Valid.    Any act or proceeding by any provision of this Supplemental Indenture authorized or required to be done or performed by any board, committee or officer of the Company or the Guarantor shall and may be done and performed with like force and effect by the like board, committee or officer of any corporation that shall at the time be the lawful successor of the Company or the Guarantor, as the case may be.

        3.10    Counterparts.    This Supplemental Indenture may be executed in any number of counterparts, each of which shall be an original; but such counterparts shall together constitute but one and the same instrument.

        U.S. Bank National Association hereby accepts the trusts in this Supplemental Indenture declared and provided, upon the terms and conditions hereinabove set forth.

8

        IN WITNESS WHEREOF, Lehman Brothers Inc. has caused this Supplemental Indenture to be signed and acknowledged by its Chairman of the Board, one of its Vice Chairmen of the Board, its President or one of its Vice Presidents, Lehman Brothers Holdings Inc. has caused this Supplemental Indenture to be signed and acknowledged by its Chairman of the Board, one of its Vice Chairmen of the Board, its President or one of its Vice Presidents, and U.S. Bank National Association, as Trustee, has caused this Supplemental Indenture to be signed and acknowledged by one its authorized officers, and its corporate seal to be affixed hereunto, and the same to be attested by one of its authorized officers, as of the day and year first above written.

LEHMAN BROTHERS INC.
By:	Name: Title:
LEHMAN BROTHERS HOLDINGS INC., as Guarantor
By:	Name: Title:
U.S. BANK NATIONAL ASSOCIATION, as Trustee
By:	Authorized Officer

9

QuickLinks

Exhibit 4(p)

RECITALS
ARTICLE FIFTEEN THE GUARANTEES

EX-4.(R)

QuickLinks -- Click here to rapidly navigate through this document

Exhibit 4(r)

LEHMAN BROTHERS INC.,

LEHMAN BROTHERS HOLDINGS INC.,

as Guarantor,

AND

HSBC BANK USA,

as Trustee

FORM OF FIRST SUPPLEMENTAL INDENTURE

Dated as of                         , 2003

        FIRST SUPPLEMENTAL INDENTURE, dated as of                    , 2003 (the "Supplemental Indenture"), among LEHMAN BROTHERS INC., a corporation duly organized and existing under the laws of the State of Delaware (the "Company"), LEHMAN BROTHERS HOLDINGS INC., a corporation duly organized and existing under the laws of the State of Delaware, as guarantor (the "Guarantor"), and HSBC BANK USA (as successor in interest to Marine Midland Bank, N.A.), a banking corporation duly organized and existing under the laws of the State of New York, as trustee (the "Trustee").

RECITALS

        The Company has duly authorized the execution and delivery of an Indenture, dated as of October 1, 1984 (the "Indenture"), between the Company and the Trustee, as amended and supplemented, to provide for the issuance from time to time of its unsecured senior subordinated debentures, notes or other evidences of indebtedness to be issued in one or more series (the "Securities") unlimited as to principal amount, to bear such rates of interest, to mature at such time or times, to be issued in one or more series and to have such other provisions as in the Indenture provided.

        The Guarantor has determined that it is in its best interests to fully and unconditionally guarantee the due and punctual payment of the principal (including any amount in respect of original issue discount) of, and premium, if any, and interest, if any, on all outstanding and future Securities and the due and punctual payment of the sinking fund payments, if any, and analogous obligations, if any, provided for pursuant to the terms of such Securities, when and as the same shall become due and payable;

        The Company and the Guarantor have duly authorized the execution and delivery of this Supplemental Indenture to provide for the guarantee by the Guarantor of the Securities;

        All acts and things necessary to make this Supplemental Indenture a valid agreement of the Company and of the Guarantor, in accordance with its terms and with the terms of the Indenture, have been done and performed.

NOW, THEREFORE, THIS SUPPLEMENTAL INDENTURE WITNESSETH:

        For and in consideration of the premises, and of the sum of one dollar duly paid to the Company and the Guarantor by the Trustee at the execution and delivery of these presents, the receipt whereof is hereby acknowledged, the Company and the Guarantor covenant and agree, for the equal and proportionate benefit of all holders of the Securities with the Trustee to supplement the Indenture as follows:

Section 1. AMENDMENTS TO THE INDENTURE

        1.1    Amendment to Section 101 of the Indenture.    Section 101 of the Indenture is hereby amended by deleting the definitions of "Board of Directors," "Board Resolution," "Company," "Officers' Certificate," "Opinion of Counsel" and "Vice President" and inserting the following definitions, in the appropriate alphabetical sequence:

        "Board of Directors" means the board of directors of the Company or the Guarantor, as the case may be, the executive committee thereof or any other committee of either board of directors duly authorized to act hereunder.

        "Board Resolution" means a copy of a resolution certified by the Secretary or an Assistant Secretary of the Company or the Guarantor, as the case may be, to have been duly adopted by the Board of Directors and to be in full force and effect on the date of such certification, and delivered to the Trustee.

        "Company" means Lehman Brothers Inc., and subject to the provisions of Article Ten, shall also include its successors and assigns.

        "Guarantee" means the full and unconditional guarantee by the Guarantor set forth in Article 15.

        "Guarantor" means Lehman Brothers Holdings Inc., a corporation duly organized and existing under the laws of the State of Delaware.

        "Guarantor Order" or "Guarantor Request" means a written request or order signed in the name of the Guarantor by its Chairman of the Board, any Vice Chairman of the Board, its President or a Vice President, and by its Treasurer, an Assistant Treasurer, its Secretary or an Assistant Secretary, and delivered to the Trustee.

        "Officers' Certificate" means a certificate signed by the Chairman of the Board, any Vice Chairman of the Board, the President or a Vice President, and by the Treasurer, and Assistant Treasurer, the Secretary or an Assistant Secretary, of the Company or the Guarantor, as the case may be, and delivered to the Trustee.

        "Opinion of Counsel" means a written opinion of counsel, who may be counsel for or employed by the Company or the Guarantor, as the case may be, and who shall be acceptable to the Trustee.

        "Vice President", when used with respect to the Company, the Guarantor or the Trustee, means any vice president, whether or not designated by a number or a word or words added before or after the title "vice president."

        1.2    Amendment to Section 102 of the Indenture.    Section 102 of the Indenture is hereby amended by inserting the following paragraph as the new second paragraph thereto:

        "Upon any application or request by the Guarantor to the Trustee to take any action under any provision of this Indenture, the Guarantor shall furnish to the Trustee an Officers' Certificate stating that such action is authorized or permitted by this Indenture and that all conditions precedent, if any, provided for in this Indenture relating to the proposed action have been complied with and an Opinion of Counsel stating that in the opinion of such counsel all such conditions precedent, if any, have been complied with, except that in the case of any such application or request as to which the furnishing of such documents is specifically required by any provision of this Indenture relating to such particular application or request, no additional certificate or opinion need by furnished."

        1.3    Amendment to Section 103 of the Indenture.    Section 103 of the Indenture is hereby amended by inserting the following paragraph as the new third paragraph thereof:

        "Any certificate or opinion of an officer of the Guarantor may be based, insofar as it relates to legal matters, upon a certificate or Opinion of Counsel, or representations by counsel, unless such officer knows, or in the exercise of reasonable care should know, that the certificate or opinion or representations with respect to the matters upon which his certificate or opinion is based are erroneous. Any such certificate or Opinion of Counsel or representation by counsel may be based, insofar as it relates to factual matters, upon a certificate or opinion of, or representations by, an officer or officers of the Guarantor stating that the information with respect to such factual matters is in the possession of the Guarantor, unless such counsel knows, or in the exercise of reasonable care should know, that the certificate or opinion or representations with respect to such matters are erroneous."

        1.4    Amendment to Section 105 of the Indenture.    (a) Section 105 of the Indenture is hereby amended by deleting the current section heading thereof and replacing it with the following:

        "Notices, Etc., to Trustee, Company or Guarantor"

2

        (b)   Section 105 of the Indenture is hereby amended by deleting the word "or" at the end of paragraph (1), deleting the period and inserting the word ", or" at the end of paragraph (2) and inserting the following paragraph as the final paragraph thereof:

        "(3) the Guarantor by the Trustee or by any Holder shall be sufficient for every purpose hereunder if in writing and mailed, first-class postage prepaid, to the Guarantor addressed to it at 745 Seventh Avenue, New York, New York 10019, attention: Treasurer or at any other address previously furnished in writing to the Trustee by the Guarantor."

        1.5    Amendment to Section 301 of the Indenture.    Section 301 of the Indenture is hereby amended by deleting the word "and" at the end of paragraph (10), redesignating paragraph (11) as paragraph (12) and inserting the following paragraph in proper numerical order:

        "(11) the terms and provisions of the Guarantee, to the extent that such provisions differ from those set forth herein; and"

        1.6    Amendment to Section 303 of the Indenture.    (a) Section 303 of the Indenture is hereby amended by deleting the word "and" at the end of subparagraph (b), deleting the period and inserting the word "; and" at the end of subparagraph (c) and inserting the following paragraph as the new subparagraph (d) thereof:

        "(d) that the Guarantee of such Securities, when the Securities are authenticated and delivered by the Trustee and issued by the Company in the manner and subject to any conditions specified in such Opinion of Counsel, will constitute a valid and legally binding obligation of the Guarantor, enforceable in accordance with its terms, subject to the effects of bankruptcy, insolvency, fraudulent conveyance, reorganization, moratorium and other similar laws relating to or affecting creditors' rights generally, general equitable principles (whether considered in a proceeding in equity or at law) and an implied covenant of good faith and fair dealing."

        (b)   Section 303 of the Indenture is hereby amended by inserting the words "or Guarantee" immediately following the words "No Security" at the beginning of the final paragraph of the section.

        1.7    Amendment to Section 305 of the Indenture.    Section 305 of the Indenture is hereby amended by deleting the fourth paragraph and inserting in lieu thereof the following paragraph:

        "All Securities issued upon any registration of transfer or exchange of Securities shall be the valid obligations of the Company evidencing the same debt, and entitled to the same benefits under this Indenture (including the Guarantee), as the Securities surrendered upon such registration of transfer or exchange."

        1.8    Amendment to Section 308 of the Indenture.    Section 308 of the Indenture is hereby amended by inserting the words ", the Guarantor" immediately following the words "the Company" in each place such words appear.

        1.9    Amendment to Section 503 of the Indenture.    Section 503 of the Indenture is hereby amended by deleting the final paragraph in its entirety and inserting in lieu thereof the following paragraph:

        "Any money deposited with the Trustee or any Paying Agent, or then held by the Company or the Guarantor in trust for the payment of the principal of (and premium, if any) or interest on any Security of any series and remaining unclaimed for three years after such principal (and premium, if any) or interest has become due and payable shall be paid to the Company on Company Request or the Guarantor on Guarantor Request, or (if then held by the Company or the Guarantor) shall be discharged from such trust; and the Holder of such Security shall thereafter, as an unsecured general creditor, look only to the Company and the Guarantor for payment thereof, and all liability of the Trustee or such Paying Agent with respect to such trust money, and

3

all liability of the Company or the Guarantor as trustee thereof, shall thereupon cease; provided, however, that the Trustee or such Paying Agent, before being required to make any such repayment, may at the expense of the Company cause to be published once, in a newspaper published in the English language, customarily published on each Business Day and of general circulation in the Borough of Manhattan, The City of New York, notice that such money remains unclaimed and that, after a date specified therein, which shall not be less than 30 days from the date of such publication, any unclaimed balance of such money then remaining will be repaid to the Company or the Guarantor."

        1.10    Amendment to Section 506 of the Indenture.    Section 506 of the Indenture is hereby amended by inserting the following paragraphs as the new second and third paragraphs respectively thereof:

        "The Guarantor will deliver to the Trustee, within 120 days after the end of each fiscal year of the Guarantor ending after the date hereof, an Officers' Certificate, stating whether or not to the best knowledge of the signers thereof the Guarantor is in default in the performance and observance of any of the terms, provisions and conditions of this Indenture, and if the Guarantor shall be in default, specifying all such defaults and the nature and status thereof of which they may have knowledge. For purposes of this Section 506, any such default shall be determined without regard to any period of grace or requirement of notice provided under this Indenture.

        Such Officers' Certificate or written notice of the Company and the Guarantor may be in the form of one certificate or notice signed by the appropriate officers of the Company and the Guarantor."

        1.11    Amendment to Section 602 of the Indenture.    Section 602 of the Indenture is hereby amended by inserting the words "or the Guarantor" immediately following the words "including the Company" therein.

        1.12    Amendment to Section 701 of the Indenture.    Section 701 of the Indenture is hereby amended by deleting the reference to subparagraph (g) in the introductory sentence and inserting in lieu thereof a reference to subparagraph (h), by deleting the word "or" at the end of subparagraph (f) and by inserting the following paragraph immediately prior to the final period at the end of subparagraph (g) thereof:

        "; or

        (h)   the dissolution or insolvency of the Guarantor or the making of an assignment for the benefit of creditors by the Guarantor or the commencement of any proceedings (by petition, application, answer, consent or otherwise) by the Guarantor to be adjudicated a bankrupt or for the appointment of a receiver or trustee or similar officer for it or for a substantial part of its property or for reorganization, an arrangement, composition or other relief under the Bankruptcy Act or the taking of corporate action by the Guarantor for any such purpose, or any marshalling of the assets or liabilities of the Guarantor or the commencement against the Guarantor of any of the aforementioned proceedings and in such latter case the consent thereto by the Guarantor or its admission of the material allegations thereof or the continuance of such proceedings undismissed for a period of 60 days."

        1.13    Amendment to Section 711 of the Indenture.    Section 711 of the Indenture is hereby amended by inserting the words ", the Guarantor" immediately following the words "subject to any determination in such proceeding, the Company" therein.

        1.14    Amendment to Section 716 of the Indenture.    Section 716 of the Indenture is hereby amended by inserting the words "or the Guarantor" immediately following the words "suit instituted by the Company" therein.

4

        1.15    Amendment to Section 717 of the Indenture.    Section 717 of the Indenture is hereby amended by deleting the words "the Company" in each place of the two places where such words appear and inserting in each place in lieu thereof the words "each of the Company and the Guarantor"

        1.16    Amendment to Section 904 of the Indenture.    (a) Section 904 of the Indenture is hereby amended by deleting the current section heading thereof and replacing it with the following:

        "Reports by Company and Guarantor"

        (b)   Section 904 of the Indenture is hereby amended by redesignating the first paragraph thereof as subsection (a) and by inserting the following paragraph as the new subsection (b) thereof:

        "(b) The Guarantor shall:

        (1)   file with the Trustee for the Securities of each series, within 15 days after the Guarantor is required to file the same with the Commission, copies of the annual reports and of the information, documents and other reports (or copies of such portions of any of the foregoing as the Commission may from time to time by rules and regulations prescribe) which the Guarantor may be required to file with the Commission pursuant to Section 13 or Section 15(d) of the Securities Exchange Act of 1934; or, if the Guarantor is not required to file information, documents or reports pursuant to either of said Sections, then it shall file with such Trustee and the Commission, in accordance with rules and regulations prescribed from time to time by the Commission, such of the supplementary and periodic information, documents and reports which may be required pursuant to Section 13 of the Securities Exchange Act of 1934 in respect of a security listed and registered on a national securities exchange as may be prescribed from time to time in such rules and regulations;

        (2)   file with such Trustee and the Commission, in accordance with rules and regulations prescribed from time to time by the Commission, such additional information, documents and reports with respect to compliance by the Guarantor with the conditions and covenants of this Indenture as may be required from time to time by such rules and regulations;

        (3)   transmit by mail to all Holders, as their names and addresses appear in the Security Register, within 30 days after the filing thereof with the Trustee, such summaries of any information, documents and reports required to be filed by the Guarantor pursuant to paragraphs (1) and (2) of this Section 904(b) as may be required by rules and regulations prescribed from time to time by the Commission; and

        (4)   delivery of such reports, information and documents to the Trustee is for informational purposes only and the Trustee's receipt of such shall not constitute constructive notice of any information contained therein or determinable from information contained therein, including the Guarantor's compliance with any of its covenants hereunder (as to which the Trustee is entitled to rely exclusively on Officers' Certificates).

        1.17    Amendment to Section 1001 of the Indenture.    Section 1001 of the Indenture is hereby amended by redesignating the first paragraph thereof as subsection (a) and by inserting the following paragraph as the new subsection (b) thereof:

        "(b) Nothing contained in this Indenture or in any of the Securities shall prevent any consolidation or merger of the Guarantor with or into any other corporation or corporations (whether or not affiliated with the Guarantor), or successive consolidations or mergers in which the Guarantor or its successor or successors shall be a party or parties, or shall prevent any sale or transfer (or successive sales or transfers) of the property and assets of the Guarantor (or of its successor or successors) as an entirety or substantially as an entirety, to any other corporation (whether or not affiliated with the Guarantor) authorized to acquire the same; provided, however,

5

that the corporation formed by such consolidation or into which the Guarantor shall have been merged or which shall have acquired such property and assets shall be a corporation organized under the laws of the United States or of any State thereof; and provided, further, and the Guarantor hereby covenants and agrees, that upon any such consolidation, merger, sale or transfer, the Guarantee of the due and punctual payment of the principal of (and premium, if any) and interest, if any, on all of the Securities, according to their tenor, and the due and punctual performance and observance of all the terms, covenants and conditions of this Indenture to be kept or performed by the Guarantor, shall be expressly assumed, by an indenture supplemental hereto, satisfactory in form to the Trustee, executed and delivered to the Trustee by the corporation formed by such consolidation, or into which the Guarantor shall have been merged, or by the corporation which shall have acquired such property and assets; and in the event of any such sale or transfer, the predecessor Guarantor shall be released from all liability hereunder and under the Securities and may be dissolved, wound-up and liquidated at any time thereafter."

        1.18    Amendment to Section 1002 of the Indenture.    Section 1002 of the Indenture is hereby amended by redesignating the first and second paragraphs thereof as subsection (a) and by inserting the following two paragraphs as the new subsection (b) thereof:

        "(b) In case of any such consolidation, merger, sale or transfer and upon the execution by the successor corporation of an indenture supplemental hereto, as provided in Section 1001(b), such successor corporation shall succeed to and be substituted for the Guarantor, with the same effect as if it had been named herein as the party of the first part; and any order, certificate, statement, request, instructions, advice or resolutions of the Board of Directors or officers of the Guarantor provided for in this Indenture may be made by like officials of such successor corporation.

        Nothing contained in this Indenture or in any of the Securities shall prevent the Guarantor from merging into itself, or acquiring by purchase or otherwise all or any part of the property of, any other corporation (whether or not affiliated with the Guarantor)."

        1.19    Amendment to Section 1101 of the Indenture.    (a) Section 1101 of the Indenture is hereby amended by inserting the words "the Guarantor, when authorized by a Board Resolution," immediately following the words "the Company, when authorized by a Board Resolution," in the introductory sentence thereof.

        (b)   Section 1101 of the Indenture is hereby amended by redesignating subparagraphs (3), (4), (5), (6), (7), (8), (9) and (10), respectively, as new subparagraphs (5), (6), (7), (8), (9), (10), (11) and (12), respectively, and by inserting the following paragraphs in proper numerical order:

        "(3) to evidence the succession of another corporation to the Guarantor and the assumption by any such successor of the covenants of the Guarantor herein and in the Securities, if applicable; or

        "(4) to add to the covenants of the Guarantor for the benefit of the Holders of all or any series of Securities (and if such covenants are to be for the benefit of less than all series of Securities, stating that such covenants are expressly being included solely for the benefit of such series) or to surrender any right or power herein conferred upon the Guarantor; or"

        1.20    Amendment to Section 1102 of the Indenture.    Section 1102 of the Indenture is hereby amended by inserting the words "the Guarantor, when authorized by a Board Resolution," immediately following the words "the Company, when authorized by a Board Resolution," in the introductory sentence thereof.

Section 2. GUARANTEE

        2.1    Addition of New Article 15 of the Indenture.    Article 15 of the Indenture is hereby created and the following shall be inserted therein:

6

ARTICLE FIFTEEN

THE GUARANTEES

        SECTION 1501    Except as otherwise set forth in a supplemental indenture or provided in or pursuant to a Board Resolution and set forth in an Officers' Certificate, the Guarantor hereby unconditionally guarantees to the Holder of the Securities of each series authenticated and delivered by the Trustee, and to the Trustee all payments due to the Trustee from the Company under Section 807 hereof, and on behalf of each such Holder, the due and punctual payment of the principal (including any amount in respect of original issue discount) of, and premium, if any, and interest, if any, on such Securities and the due and punctual payment of the sinking fund payments, if any, and analogous obligations, if any, provided for pursuant to the terms of such Securities, when and as the same shall become due and payable, whether at maturity or upon redemption or upon declaration of acceleration or otherwise, according to the terms of such Securities and of the Indenture and this Supplemental Indenture. The Guarantor agrees that in case of default by the Company in the payment of any such principal (including any amount in respect of original issue discount), premium, interest, sinking fund payment, or analogous obligation, the Guarantor shall duly and punctually pay the same, as if such payment were made by the Company. The Guarantor hereby agrees that its obligations hereunder shall be absolute and unconditional, irrespective of any extension of the time for payment of any such Security, any modification of any such Security or any supplemental indenture or Board Resolution and Officers' Certificate relating thereto, any invalidity, irregularity or unenforceability of any such Security or the Indenture or this Supplemental Indenture, any failure or delay to enforce the same or any waiver, modification, consent or indulgence granted to the Company with respect thereto by the Holder of such Security or the Trustee, or any other circumstances which may otherwise constitute a legal or equitable discharge of a surety or guarantor.

        The Guarantor further agrees that the Guarantee herein constitutes a guarantee of payment when due (and not a guarantee of collection) and waives (to the extent that it may lawfully do so) any right to require that any resort be had by any Holder or the Trustee to any security held for payment of the Guarantee.

        The Guarantor hereby waives (to the extent that it may lawfully do so) diligence, presentment, demand of payment, filing of claims with a court in the event of merger or bankruptcy of the Company, any right to require a demand or proceeding first against the Company, protest or notice with respect to any such Security or the indebtedness evidenced thereby and all demands whatsoever, and covenants that this Guarantee will not be discharged as to any such Security except by payment in full of the principal (including any amount payable in respect of original issue discount) of, and premium, if any, and interest, if any, and payment of the sinking fund payments, if any, and analogous obligations, if any, thereon.

        The Guarantor agrees that the Guarantee with respect to each series of Securities shall remain in full force and effect until payment in full of all the Securities of such series. The Guarantor further agrees that the Guarantee herein shall continue to be effective or be reinstated, as the case may be, if at any time payment, or any part thereof, of the principal (including any amount payable in respect of original issue discount) of, and premium, if any, and interest, if any, and payment of the sinking fund payments, if any, and analogous obligations, if any, on any series of Securities is rescinded or must otherwise be restored by any Holder or the Trustee upon the bankruptcy or reorganization of the Company or otherwise.

        The Guarantor further agrees that, as between it, on the one hand, and the Holders and the Trustee, on the other hand, (x) the maturity of the obligations guaranteed hereby may be accelerated as provided in Article Seven for the purposes of any Guarantee herein, notwithstanding any stay, injunction or other prohibition preventing such acceleration in respect of the obligations guaranteed

7

hereby, and (y) in the event of any declaration of acceleration of the obligations guaranteed hereby as provided in Article Seven, such obligations (whether or not due and payable) shall forthwith become due and payable by the Guarantor for the purposes of this Section 1501.

        The Guarantor shall be subrogated to all rights of the Holders of the Securities of a series against the Company in respect of any amounts paid by the Guarantor on account of such Security pursuant to the provisions of the Guarantees or this Indenture; provided, however, that the Guarantor agrees that it shall not be entitled to any right of subrogation in relation to the Holders until payment in full of the principal (including any amount payable in respect of original issue discount) of, and premium, if any, and interest, if any, and payment of the sinking fund payments, if any, and analogous obligations, if any, on all Securities of such series. The Guarantor hereby waives (to the extent that it may lawfully do so) any and all rights to which it may be entitled, by operation of law or otherwise, upon making any payment hereunder (i) any right to which it may be entitled to have the assets of the Company first be used and depleted as payment of the Company's or the Guarantor's obligations hereunder prior to any amounts being claimed from or paid by the Guarantor hereunder; or (ii) to receive any payment, in the nature of contribution or for any other reason, from any other obligor with respect to such payment.

Section 3. MISCELLANEOUS

        3.1    Continuance of Indenture.    This Supplemental Indenture supplements the Indenture and shall be a part of and subject to all the terms thereof. The Indenture, as supplemented by this Supplemental Indenture, shall continue in full force and effect.

        3.2    Defined Terms.    All capitalized terms used in this Supplemental Indenture which are defined in the Indenture, but not otherwise defined herein, shall have the same meanings assigned to them in the Indenture.

        3.3    Conflict with Trust Indenture Act.    If any provision of this Supplemental Indenture limits, qualifies or conflicts with another provision hereof which is required to be included in this Supplemental Indenture by any of the provisions of the Trust Indenture Act, such required provision shall control.

        3.4    Separability Clause.    In case any provision in this Supplemental Indenture shall be invalid, illegal or unenforceable, the validity, legality and enforceability of the remaining provisions shall not in any way be affected or impaired thereby.

        3.5    Benefits of Indenture.    Nothing in this Supplemental Indenture, express or implied, shall give to any Person, other than the parties hereto and their successors hereunder and the Holders any benefit or any legal or equitable right, remedy or claim under this Supplemental Indenture.

        3.6    Governing Law.    This Supplemental Indenture shall be governed by and construed in accordance with the laws of the State of New York.

        3.7    The Trustee.    The recitals contained herein shall be taken as the statements of the Company and the Guarantor, and the Trustee assumes no responsibility for their correctness. The Trustee makes no representations as to the validity or sufficiency of this Supplemental Indenture.

        3.8    Successors and Assigns of Company and Guarantor Bound By Supplemental Indenture.    All the covenants, stipulations, promises and agreements contained in this Supplemental Indenture by or on behalf of the Company or the Guarantor shall bind their successors and assigns, whether so expressed or not, and the provisions hereof shall bind the heirs, executors, administrators, successors and assigns of the Holders.

        3.9    Acts of Board, Committee or Officer of Successor Corporation Valid.    Any act or proceeding by any provision of this Supplemental Indenture authorized or required to be done or performed by any board, committee or officer of the Company or the Guarantor shall and may be done and performed

8

with like force and effect by the like board, committee or officer of any corporation that shall at the time be the lawful successor of the Company or the Guarantor, as the case may be.

        3.10    Counterparts.    This Supplemental Indenture may be executed in any number of counterparts, each of which shall be an original; but such counterparts shall together constitute but one and the same instrument.

        HSBC Bank USA hereby accepts the trusts in this Supplemental Indenture declared and provided, upon the terms and conditions hereinabove set forth.

9

        IN WITNESS WHEREOF, Lehman Brothers Inc. has caused this Supplemental Indenture to be signed and acknowledged by its Chairman of the Board, one of its Vice Chairmen of the Board, its President or one of its Vice Presidents, Lehman Brothers Holdings Inc. has caused this Supplemental Indenture to be signed and acknowledged by its Chairman of the Board, one of its Vice Chairmen of the Board, its President or one of its Vice Presidents, and HSBC Bank USA, as Trustee, has caused this Supplemental Indenture to be signed by one its authorized officers, as of the day and year first above written.

LEHMAN BROTHERS INC.
By:	Name: Title:
LEHMAN BROTHERS HOLDINGS INC., as Guarantor
By:	Name: Title:
HSBC BANK USA, as Trustee
By:	Name: Title:

10

QuickLinks

Exhibit 4(r)

RECITALS
ARTICLE FIFTEEN THE GUARANTEES

EX-23.(B)

QuickLinks -- Click here to rapidly navigate through this document

Exhibit 23(b)

[Letterhead of Ernst & Young LLP]

Consent of Independent Auditors

        We consent to the reference to our firm under the caption "Experts" in Amendment No. 1 to the Registration Statement (Form S-3 No. 333-108711) and related Prospectus of Lehman Brothers Holdings Inc. (the "Company") and to the incorporation by reference therein of our report dated January 10, 2003 with respect to the consolidated financial statements and financial statement schedule of the Company included in its Annual Report on Form 10-K for the year ended November 30, 2002, filed with the Securities and Exchange Commission.

New York, New York
October 2, 2003

QuickLinks

Exhibit 23(b)

Consent of Independent Auditors