S-1/A

As filed with the Securities and Exchange Commission on  November 4, 2003

File No. 333-108739

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

________________

AMENDMENT NO. 1

TO

FORM S-1

ON

FORM S-3

REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933

________________

21^st CENTURY HOLDING COMPANY

(Exact name of registrant as specified in its charter)

Florida	65-0248866
(State or other jurisdiction of incorporation or organization)	(I.R.S. Employer Identification No.)

4161 N.W. 5^th Street, Plantation, FL 33317, (954) 581-9993

(Address, including zip code, and telephone number, including area code,

of registrant’s principal executive offices)

________________

Richard A. Widdicombe

Chief Executive Officer

21^st Century Holding Company

4161 N.W. 5^th Street

Plantation, FL 33317

(954) 581-9993

(Name, address, including zip code, and telephone number,

including area code, of agent for service)

Copies to:

A. Jeffry Robinson, P.A.

Broad and Cassel

201 South Biscayne Boulevard

Miami Center, Suite 3000

Miami, Florida 33131

Telephone: (305) 373-9400

Telecopier: (305) 373-9443

________________

Approximate date of commencement of proposed sale to the public:

As soon as practicable after this Registration Statement becomes effective.

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

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. [X]

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. [  ]

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. [  ]

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

CALCULATION OF REGISTRATION FEE

Title of Each Class of Securities to Be Registered	Amount to Be Registered	Proposed Maximum Offering Price per Share	Proposed Maximum Aggregate Offering Price	Amount of Registration Fee
Common Stock, $.01 par value	38,543 shares	$18.84 (1)	$726,150.12	$58.74(2)

(1)

Estimated solely for the purpose of calculating the registration fee in accordance with Rule 457 under the Securities Act.

(2)

Previously paid.

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 this registration statement shall become effective on such date as the Securities and Exchange Commission, acting pursuant to said Section 8(a), may determine.

THE INFORMATION CONTAINED HEREIN IS SUBJECT TO COMPLETION OR AMENDMENT. A REGISTRATION STATEMENT RELATING TO THESE SECURITIES HAS BEEN FILED WITH THE SECURITIES AND EXCHANGE COMMISSION. WE MAY NOT SELL THESE SECURITIES UNTIL THE REGISTRATION STATEMENT FILED WITH THE SECURITIES AND EXCHANGE COMMISSION IS EFFECTIVE. THIS PROSPECTUS IS NOT AN OFFER TO SELL THE SECURITIES AND IT IS NOT SOLICITING AN OFFER TO BUY THESE SECURITIES IN ANY STATE IN WHICH THE OFFER OR SALE IS NOT PERMITTED.

SUBJECT TO COMPLETION, NOVEMBER 4, 2003

PROSPECTUS

38,543  SHARES OF COMMON STOCK

21ST CENTURY HOLDING COMPANY

This prospectus covers 38,543  shares of our common stock issued by us as payment of principal and interest due on our 6% Senior Subordinated Notes due July 31, 2006.  We will not receive any proceeds from the sale of the common stock.  We will pay our out-of-pocket expenses, legal and accounting fees, and the other expenses of registering these shares for resale.

The shareholders named in this prospectus may offer and sell these shares at any time using a variety of different methods. The actual number of shares sold and the prices at which the shares are sold will depend upon the market prices at the time of those sales; therefore, we have not included in this prospectus information about the price to the public of the shares or the proceeds to the selling shareholders.

Our common stock is traded on the Nasdaq National Market under the symbol "TCHC." On November 3, 2003, the last reported sale price of the common stock on the Nasdaq National Market was $18.03 per share.

The shares of common stock offered hereby involve a high degree of risk and should be considered only by such persons capable of bearing the economic risk of such investment. You should carefully consider the "Risks of Investing in Our Shares" section beginning on page 3 of this prospectus.

Neither the SEC nor any state securities commission has approved or disapproved of these securities or passed upon the adequacy or accuracy of the prospectus. Any representation to the contrary is a criminal offense.

The date of this prospectus is November ___, 2003.

TABLE OF CONTENTS

	Page
PROSPECTUS SUMMARY	1
RISKS OF INVESTING IN OUR SHARES	3
Our revenues and operating performance may fluctuate with business cycles in the property and casualty insurance industry.	3
If we are unable to continue our growth because our capital must be used to pay greater than anticipated claims, our financial results may suffer.	3
The maximum credit commitment under our revolving loan was reduced by our lender and could be subject to further review and reduction, which would adversely affect our available working capital.	3
We may not obtain the necessary regulatory approvals to expand the types of insurance products we offer or the states in which we operate.	4
If our ratings are downgraded or withdrawn, we may be unable to write or renew desirable insurance policies or obtain adequate reinsurance, which would limit or halt our growth and harm our business.	4
Although we follow the industry practice of reinsuring a portion of our risks, our costs of obtaining reinsurance have increased and we may not be able to successfully alleviate risk through reinsurance arrangements.	4
Our investment portfolio may suffer reduced returns or losses, which would significantly reduce our earnings.	5
Our loss reserves may be inadequate to cover our actual liability for losses, causing our results of operations to be adversely affected.	5
Legislation may be enacted that would limit our ability to increase our premiums or cancel, reduce or non-renew our existing policies, which could reduce our revenues or increase our claims losses.	6
We are subject to significant government regulation, which can limit our growth and increase our expenses, thereby reducing our earnings.	6
We rely on agents, most of whom are independent agents or franchisees, to write our insurance policies, and if we are not able to attract and retain independent agents and franchisees, our revenues would be negatively affected.	6
Our primary insurance product, nonstandard automobile insurance, historically has a higher frequency of claims than standard automobile insurance, thereby increasing our potential for loss exposure beyond what we would be likely to experience if we offered only standard automobile insurance.	7
Florida’s personal injury protection insurance statute contains provisions that favor claimants, causing us to  experience a higher frequency of claims than might otherwise be the case if we operated only outside of Florida.	7
Our business strategy is to avoid competition in our automobile insurance products based on price to the extent possible. This strategy, however, may result in the loss of business in the short term.	7
With operations concentrated in Florida, we could be adversely affected by unpredictable catastrophic events such as hurricanes and tropical storms.	8
Our president and chief executive officer are key to the strategic direction of our company. If we were to lose the services of either of them, our business could be harmed.	8
The trading of our warrants may negatively affect the trading prices of our common stock if investors purchase and exercise the warrants to facilitate other trading strategies, such as short selling.	8
Our largest shareholders control approximately 32% of the voting power of our outstanding common stock, which could discourage potential acquirors and prevent changes in management.	9
We have authorized but unissued preferred stock, which could affect rights of holders of common stock.	9
Our articles of incorporation and bylaws and Florida law may discourage takeover attempts and may result in entrenchment of management.	9
As a holding company, we depend on the earnings of our subsidiaries and their ability to pay dividends to the holding company as the primary source of our income.	10

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TABLE OF CONTENTS

(continued)

	Page
USE OF PROCEEDS	11
SELLING SHAREHOLDERS	11
HOW THE SHARES MAY BE DISTRIBUTED	12
LEGAL MATTERS	13
EXPERTS	13
WHERE YOU CAN FIND MORE INFORMATION	13
INCORPORATION OF CERTAIN INFORMATION BY REFERENCE	14
INDEMNIFICATION OF DIRECTORS AND OFFICERS	15

ABOUT THIS PROSPECTUS

You should rely only on the information contained in this prospectus. No dealer, salesperson or other person is authorized to give any information that is not contained in this prospectus. This prospectus is not an offer to sell nor is it seeking an offer to buy these shares in any jurisdiction where the offer or sale is not permitted. The information contained in this prospectus is correct only as of the date of this prospectus, regardless of the time of the delivery of this prospectus or any sale of these shares.

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PROSPECTUS SUMMARY

This is only a summary and does not contain all of the information that may be important to you. You should read the more detailed information contained in this prospectus and all other information, including the financial information and statements with notes, as discussed in the “Where You Can Find More Information” section of this prospectus.

Overview

We are a vertically integrated insurance holding company, which, through our subsidiaries, controls substantially all aspects of the insurance underwriting, distribution and claims process. We underwrite personal automobile insurance, general liability insurance, flood insurance, homeowners’ insurance, and mobile home property and casualty insurance in the State of Florida through our wholly owned subsidiaries, Federated National Insurance Company and American Vehicle Insurance Company. American Vehicle was approved in August 2003 to be a foreign insurer in the State of Georgia. During the year ended December 31, 2002, 83.42%, 13.75% and 2.83% of the policies we underwrote were for personal automobile insurance, homeowners’ insurance, and mobile home property and casualty insurance, respectively. We internally process claims made by our own a nd third-party insureds through our wholly owned claims adjusting company, Superior Adjusting, Inc. We also offer premium financing to our own insureds through our wholly owned subsidiary, Federated Premium Finance, Inc.

We market and distribute our own and third-party insurers’ products and our other services primarily in Central and South Florida, through a network of 23 agencies owned by Federated Agency Group, Inc., a wholly owned subsidiary, 42 franchised agencies, and approximately 125 independent agents. Through our wholly owned subsidiary, FedUSA, Inc., we franchise agencies under the FedUSA name. As of September 30, 2003, franchises were granted for 43 FedUSA agencies, of which 37 were operating. We intend to focus our future expansion efforts for our agency network on franchised agencies.

Assurance Managing General Agents, Inc., a wholly owned subsidiary, acts as Federated National’s and American Vehicle’s exclusive managing general agent. Assurance MGA currently provides all underwriting policy administration, marketing, accounting and financial services to Federated National, American Vehicle and our agencies, and participates in the negotiation of reinsurance contracts.

We offer electronic tax filing services through Express Tax Service, Inc., an 80%-owned subsidiary, as well as franchise opportunities for these services. As of September 30, 2003, there were 158 franchises granted in ten states. Revenue is generated through franchise sales, collection of royalties on tax preparation fees, incentives from business partners as well as fees from the preparation of income tax returns and income tax refund anticipation loans. In addition, Express Tax offers tax preparation services through more than 500 licensees nationwide, acting as sales representatives.

We believe that we can be distinguished from our competitors because we generate revenue from substantially all aspects of the insurance underwriting, distribution and claims process. We provide quality service to both our agents and insureds by utilizing an integrated computer system, which links our insurance and service entities. Our computer and software systems allow for automated premium quotation, policy issuance, billing, payment and claims processing and enables us to continuously monitor substantially all aspects of our business. Using these systems, our agents can access a customer’s driving record, quote a premium, offer premium financing and, if requested, generate a policy on-site. We believe that these systems have facilitated our ability to market and underwrite insurance products on a cost-efficient basis, allow our owned and fran chised agencies to be a “one stop” shop for insurance, tax preparation and other services, and will enhance our ability to expand in Florida and to other states.

Our primary products are nonstandard and standard personal automobile insurance. Of the total auto premiums we received in 2002, 96.7% were for nonstandard insurance policies and 3.3% were for standard insurance policies. The former is principally provided to insureds who are unable to obtain preferred or standard insurance coverage because of their payment history, driving record, age, vehicle type or other factors, including market conditions for preferred or standard risks. The latter is principally provided to insureds who present an average risk profile in terms of payment history, driving record, vehicle and other factors. We believe that industry-wide underwriting standards for standard insurance coverage have become more restrictive, thereby requiring more drivers to seek coverage in the nonstandard automobile insurance market. We believe that these factors have contributed to an increase in the size of the nonstandard personal automobile insurance market.

We currently underwrite and sell insurance in Florida and Georgia; however, we intend to expand to other selected states and we have applied to obtain licenses to underwrite and sell personal automobile insurance in Alabama and North Carolina. We also expect to apply in Louisiana to obtain licenses to underwrite and sell homeowner’s and general liability policies. We will select additional states for expansion based on a number of criteria, including the size of the personal automobile insurance market, statewide loss results, competition and the regulatory climate. Our ability to expand into other states will be subject to receiving prior regulatory approval of each state. Certain states impose operating requirements upon licensee applicants, which may impose burdens on our ability to obtain a license to conduct insurance business in those other states. There can be no assurance that we will be able to obtain the required licenses, and the failure to do so would limit our ability to expand geographically.

Our executive offices are located at 4161 N.W. 5th Street, Plantation, Florida and our telephone number is (954) 581-9993.

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RISKS OF INVESTING IN OUR SHARES

You should carefully consider the following risks, in addition to the other information presented in this prospectus or incorporated by reference into this prospectus, before making an investment decision. If any of these risks or uncertainties actually occur, our business, results of operations, financial condition, or prospects could be substantially harmed, which would adversely affect your investment.

Risks Related to Our Business

Our revenues and operating performance may fluctuate with business cycles in the property and casualty insurance industry.

Historically, the financial performance of the property and casualty insurance industry has tended to fluctuate in cyclical patterns characterized by periods of significant competition in pricing and underwriting terms and conditions, which is known as a “soft” insurance market, followed by periods of lessened competition and increasing premium rates, which is known as a “hard” insurance market.  Although an individual insurance company’s financial performance is dependent on its own specific business characteristics, the profitability of most property and casualty insurance companies tends to follow this cyclical market pattern, with profitability generally increasing in hard markets and decreasing in soft markets.  At present, we are experiencing a “hard” market in our automobile and property sectors. &nbs p;We cannot predict, however, how long these market conditions will persist.  If we were to experience a “soft” market, increased price competition would likely cause us to have to reduce our premiums in order to maintain our market share, which would result in a decrease in our revenues.

If we are unable to continue our growth because our capital must be used to pay greater than anticipated claims, our financial results may suffer.

We have grown rapidly over the last few years.  Our future growth will depend on our ability to expand the types of insurance products we offer and the geographic markets in which we do business.  We believe that our company is sufficiently capitalized to operate our business as it now exists and as we currently plan to expand it.  Our existing sources of funds include our revolving loan from Flatiron Funding Company LLC, sales of our securities such as our recent private placement of $7,500,000 of our senior subordinated notes, and our earnings from operations and investments.  Unexpected catastrophic events in our market areas could result in greater claims losses than anticipated, which could require us to limit or halt our growth while we redeploy our capital to pay these unanticipated claims.

The maximum credit commitment under our revolving loan was reduced by our lender and could be subject to further review and reduction, which would adversely affect our available working capital.

In September 2002, the maximum credit commitment under our revolving loan agreement was reduced to $4.0 million from $7.0 million due to the A.M. Best Company ratings of third-party insurance carriers for which we were financing policies at that time.  Although we have stopped financing policies for third-party carriers and have changed other aspects of our business so that the higher credit commitment is currently unnecessary, our lender could

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determine to further reduce our available credit.  If that occurs and we are not able to obtain working capital from other sources, then we would have to restrict our growth and, possibly, our operations.

We may not obtain the necessary regulatory approvals to expand the types of insurance products we offer or the states in which we operate.

We currently have applications pending in Alabama and North Carolina to underwrite and sell automobile insurance and expect to file an application in Louisiana to underwrite and sell homeowners’ and general liability insurance.  The insurance regulators in any of these states may request additional information, add conditions to the license that we find unacceptable, or deny our application.  This would delay or prevent us from operating in that state.  If we want to operate in any additional states, we must file similar applications for licenses, which we may not be successful in obtaining.

If our ratings are downgraded or withdrawn, we may be unable to write or renew desirable insurance policies or obtain adequate reinsurance, which would limit or halt our growth and harm our business.

Third-party rating agencies assess and rate the ability of insurers to pay their claims. These financial strength ratings are used by the insurance industry to assess the financial strength and quality of insurers. These ratings are based on criteria established by the rating agencies and reflect evaluations of each insurer’s profitability, debt and cash levels, customer base, adequacy and soundness of reinsurance, quality and estimated market value of assets, adequacy of reserves, and management. Ratings are based upon factors of concern to agents, reinsurers and policyholders and are not directed toward the protection of investors, such as purchasers of our common stock.

In 2002, A.M. Best Company assigned Federated National a B rating (“Fair,” which is the seventh of 14 rating categories) and American Vehicle a B+ rating (“Very Good,” which is the sixth of 14 rating categories).  Federated National and American Vehicle are rated “A” (“Unsurpassed,” which is first of six ratings) by Demotech, Inc.  If our financial condition deteriorates, we may not maintain our ratings.  A downgrade or withdrawal of our ratings could severely limit or prevent us from writing or renewing desirable insurance policies or from obtaining adequate reinsurance.

Although we follow the industry practice of reinsuring a portion of our risks, our costs of obtaining reinsurance have increased and we may not be able to successfully alleviate risk through reinsurance arrangements.

We follow the insurance industry practice of reinsuring a portion of our risks and paying for that protection based upon premiums received on all policies subject to this reinsurance.  Our business depends on our ability to transfer or “cede” significant amounts of risk insured by us. Reinsurance makes the assuming reinsurer liable to the extent of the risk ceded. Both Federated National and American Vehicle currently cede approximately 40% of their premiums from automobile insurance policies to Transatlantic Reinsurance Company.  Federated National also obtains reinsurance for its property insurance policies on the private market in Bermuda and

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London and through the Florida Hurricane Catastrophe Fund.  The Florida Hurricane Catastrophe Fund reinsures Federated National for liabilities resulting from a storm causing damage totaling $5.5 million to $39.0 million in the aggregate, which we believe constitutes an event expected to occur no more often than once in a period of 100 years.

Because we currently obtain a material portion of our reinsurance from one reinsurer, we are also subject to credit risk with respect to that reinsurer, as the ceding of risk does not relieve us of liability to our insureds regarding the portion of the risk that has been reinsured, if the reinsurer fails to pay for any reason. The insolvency of our primary reinsurer or any of our other current or future reinsurers, or their inability otherwise to pay claims, would increase the claims that we must pay, thereby significantly harming our results of operations. In addition, prevailing market conditions have limited the availability and increased the cost of reinsurance, which has increased our costs and reduced our profitability.

Our investment portfolio may suffer reduced returns or losses, which would significantly reduce our earnings.

As do other insurance companies, we depend on income from our investment portfolio for a substantial portion of our earnings. A significant decline in investment yields in our investment portfolio caused by fluctuations in interest rates or volatility in the stock market, or a default by issuers of securities that we own, could adversely affect the value of our investment portfolio and the returns that we earn on our portfolio, thereby substantially harming our financial condition and results of operations. During the time that normally elapses between the receipt of insurance premiums and any payment of insurance claims, we invest the funds received, together with our other available capital, primarily in fixed-maturity investments and equity securities, in order to generate investment income. In 2002, our interest and dividends earned totaled $1.3&nb sp;million, or 27 % of our total net income of $4.6 million.

We experienced net realized investment losses of $1,369,961 for 2002, $2,911,658 for 2001 and $109,256 for 2000. The net realized losses experienced in 2001 and 2000 were primarily a function of the widely publicized declines in the industrial common stock valuations. As a result of the declines in the equity markets in 2001, we acquired securities in the more conservative and highly rated industrial bond markets in late 2001 and the first half of 2002. During 2002, we incurred a $2,000,000 decline in value of our investment in WorldCom, Inc. bonds. This write down is reflected in the $1,369,961 loss incurred in 2002. We have been experiencing a declining interest rate environment during the past three years. The effect on our bond portfolio of this declining interest rate environment has been to decrease our yields to maturity and the interest income generated accordingly.

Our loss reserves may be inadequate to cover our actual liability for losses, causing our results of operations to be adversely affected.

We maintain reserves to cover our estimated ultimate liabilities for loss and loss adjustment expenses. These reserves are estimates based on historical data and statistical projections of what we believe the settlement and administration of claims will cost based on facts and circumstances then known to us. Actual losses and loss adjustment expenses, however, may vary significantly from our estimates. For example, after we compared our reserve levels to our actual claims for the prior years, we increased our liability for loss and loss adjustment expenses by $90,874 for 2002, by $2,568,476 for 2001, and by $1,444,556 for 2000. These increases reflected primarily our loss experience under our personal automobile policies.

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Because of the uncertainties that surround estimated loss reserves, we cannot be certain that our reserves will be adequate to cover our actual losses. If our reserves for unpaid losses and loss adjustment expenses are less than actual losses and loss adjustment expenses, we will be required to increase our reserves with a corresponding reduction in our net income in the period in which the deficiency is identified. Future loss experience substantially in excess of our reserves for unpaid losses and loss adjustment expenses could substantially harm our results of operations and financial condition.

Legislation may be enacted that would limit our ability to increase our premiums or cancel, reduce or non-renew our existing policies, which could reduce our revenues or increase our claims losses.

Legislation has been proposed from time to time in Florida, which is where our operations are now primarily located, that would limit our ability to increase our premiums or that would restrict our ability to cancel, reduce or non-renew existing policies.  If one or more of these proposals are enacted in Florida, or in any other state in which we conduct significant business operations, our results of operations could be materially adversely affected if we are not able to increase our premiums to offset higher expenses or if we are not able to cancel, reduce or non-renew existing policies where our claims experience has been unacceptably high.

We are subject to significant government regulation, which can limit our growth and increase our expenses, thereby reducing our earnings.

We are subject to laws and regulations in Florida, our state of domicile, and Georgia, and will be subject to the laws of any other state in which we conduct business in the future. These laws and regulations cover all aspects of our business and are generally designed to protect the interests of insurance policyholders. For example, these laws and regulations relate to licensing requirements, authorized lines of business, capital surplus requirements, allowable rates and forms, investment parameters, underwriting limitations, restrictions on transactions with affiliates, dividend limitations, changes in control, market conduct, and limitations on premium financing service charges. The cost to monitor and comply with these laws and regulations adds significantly to our cost of doing business. Further, if we do not comply with the laws and regulations a pplicable to us, we may be subject to sanctions or monetary penalties by the applicable insurance regulator.

We rely on agents, most of whom are independent agents or franchisees, to write our insurance policies, and if we are not able to attract and retain independent agents and franchisees, our revenues would be negatively affected.

We currently market and distribute Federated National’s, American Vehicle’s and third-party insurers’ products and our other services through a network of 23 agencies that we own, 42 agencies that we franchise to others, and approximately 125 independent agents. Approximately 51% of our insurance products are sold through agents employed by us and franchised agents and approximately 49% of our products are sold through independent agents. Many of our competitors also rely on independent agents. As a result, we must compete with other insurers for independent agents’ business and with other franchisors of insurance agencies for franchisees. Our competitors may offer a greater variety of insurance products, lower premiums for insurance coverage, or higher commissions to their agents. If our products, pricing and

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commissions do not remain competitive, we may find it more difficult to attract business from independent agents and to attract franchisees for our agencies to sell our products. A material reduction in the amount of our products that independent agents sell would negatively affect our revenues.

Our primary insurance product, nonstandard automobile insurance, historically has a higher frequency of claims than standard automobile insurance, thereby increasing our potential for loss exposure beyond what we would be likely to experience if we offered only standard automobile insurance.

Nonstandard automobile insurance, which is our primary product, is provided to insureds who are unable to obtain preferred or standard insurance coverage because of their payment histories, driving records, age, vehicle types, or prior claims histories. This type of automobile insurance historically has a higher frequency of claims than does preferred or standard automobile insurance policies, although the average dollar amount of the claims is usually smaller under nonstandard insurance policies. As a result, we are exposed to the possibility of increased loss exposure and higher claims experience than would be the case if we offered only standard automobile insurance.

Florida’s personal injury protection insurance statute contains provisions that favor claimants, causing us to experience a higher frequency of claims than might otherwise be the case if we operated only outside of Florida.

Florida’s personal injury protection insurance statute limits an insurer’s ability to deny benefits for medical treatment that is unrelated to the accident, that is unnecessary, or that is fraudulent. In addition, the statute allows claimants to obtain awards for attorney’s fees. Although this statute has been amended several times in recent years, primarily to address concerns over fraud, the Florida legislature has been only marginally successful in implementing effective mechanisms that allow insurers to combat fraud and other abuses. We believe that this statute contributes to a higher frequency of claims under nonstandard automobile insurance policies in Florida, as compared to claims under standard automobile insurance policies in Florida and nonstandard and standard automobile insurance polices in other states. Although we believe that we have successfully offset these higher costs with premium increases, because of competition, we may not be able to do so with as much success in the future.

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Our business strategy is to avoid competition in our automobile insurance products based on price to the extent possible. This strategy, however, may result in the loss of business in the short term.

Although our pricing of our automobile insurance products is inevitably influenced to some degree by that of our competitors, we believe that it is generally not in our best interest to compete solely on price, choosing instead to compete on the basis of underwriting criteria, our distribution network, and our superior service to our agents and insureds. We compete with respect to automobile insurance with more than 100 companies, including companies of comparable or smaller size, such as U.S. Security Insurance Company, United Automobile Insurance Company, Direct General Insurance Company and Security National, as well as major insurers such as Progressive Casualty Insurance Company.  If we do not meet the prices offered by our competitors, we may lose business in the short term, which could also result in reduced revenues.

With operations concentrated in Florida, we could be adversely affected by unpredictable catastrophic events such as hurricanes and tropical storms.

We write insurance policies that cover automobile owners, homeowners and business owners for losses that result from catastrophes. Catastrophic losses can be caused by hurricanes, tropical storms, tornadoes, wind, hail, fires, riots and explosions, and their incidence and severity are inherently unpredictable. The extent of losses from a catastrophe is a function of two factors: the total amount of the insurance company’s exposure in the area affected by the event and the severity of the event. Our policyholders are currently concentrated in South and Central Florida, which is especially subject to adverse weather conditions such as hurricanes and tropical storms. Although we have not experienced significant claims as a result of a recent hurricane or other weather events, the occurrence of a catastrophe in South Florida could substantially harm u s by causing claims to exceed our anticipated reserve for losses.

Our president and chief executive officer are key to the strategic direction of our company. If we were to lose the services of either of them, our business could be harmed.

We depend, and will continue to depend, on the services of one of our founders and principal shareholders, Edward J. Lawson, who is also our president and chairman of the board, as well as Richard Widdicombe, who is our chief executive officer. We have entered into an employment agreement with each of them and we maintain $3 million and $1 million in keyman life insurance on the lives of Mr. Lawson and Mr. Widdicombe, respectively. Nevertheless, because of Mr. Lawson’s and Mr. Widdicombe’s role and involvement in developing and implementing our current business strategy, the loss of either of their services could substantially harm our business.

Risks Related to an Investment in Our Shares

The trading of our warrants may negatively affect the trading prices of our common stock if investors purchase and exercise the warrants to facilitate other trading strategies, such as short selling.

We intend to list the 816,100 warrants we issued in a recently completed private offering for trading on the Nasdaq National Market. Each of the warrants entitles the holder to purchase

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one-half of one share of our common stock at an exercise price per share of $19.1153. Investors may purchase and exercise warrants to facilitate trading strategies such as short selling, which involves the sale of securities not yet owned by the seller.  In a short sale, the seller must either purchase or borrow the security in order to complete the sale.  If shares of our common stock received upon the exercise of warrants are used to complete short sales, this may have the effect of reducing the trading price of our common stock.

Our largest shareholders control approximately 32% of the voting power of our outstanding common stock, which could discourage potential acquirors and prevent changes in management.

Edward J. Lawson and Michele V. Lawson beneficially own approximately 32% of our outstanding common stock. As our largest shareholders, and our only shareholders owning more than 10% of our common stock, the Lawsons have significant influence over the outcome of any shareholder vote. This voting power may discourage takeover attempts, changes in our officers and directors or other changes in our corporate governance that other shareholders may desire.

We have authorized but unissued preferred stock, which could affect rights of holders of common stock.

Our articles of incorporation authorize the issuance of preferred stock with designations, rights and preferences determined from time to time by our board of directors. Accordingly, our board of directors is empowered, without shareholder approval, to issue preferred stock with dividends, liquidation, conversion, voting or other rights that could adversely affect the voting power or other rights of the holders of common stock. In addition, the preferred stock could be issued as a method of discouraging a takeover attempt. Although we do not intend to issue any preferred stock at this time, we may do so in the future.

Our articles of incorporation and bylaws and Florida law may discourage takeover attempts and may result in entrenchment of management.

Our articles of incorporation and bylaws contain provisions that may discourage takeover attempts and may result in entrenchment of management.

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Our board of directors is elected in classes, with only two or three of the directors elected each year. As a result, shareholders would not be able to change the membership of the board in its entirety in any one year. Shareholders would also be unable to bring about, through the election of a new board of directors, changes in our officers.

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Our articles of incorporation prohibit shareholders from acting by written consent, meaning that shareholders will be required to conduct a meeting in order to vote on any proposals or take any action.

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Our bylaws require at least 60 days’ notice if a shareholder desires to submit a proposal for a shareholder vote or to nominate a person for election to our board of directors.

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In addition, Florida has enacted legislation that may deter or frustrate takeovers of Florida corporations, such as our company.

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The Florida Control Share Act provides that shares acquired in a “control share acquisition” will not have voting rights unless the voting rights are approved by a majority of the corporation’s disinterested shareholders. A “control share acquisition” is an acquisition, in whatever form, of voting power in any of the following ranges: (a) at least 20% but less than 33-1/3% of all voting power, (b) at least 33-1/3% but less than a majority of all voting power; or (c) a majority or more of all voting power.

•

The Florida Affiliated Transactions Act requires supermajority approval by disinterested shareholders of certain specified transactions between a public corporation and holders of more than 10% of the outstanding voting shares of the corporation (or their affiliates).

As a holding company, we depend on the earnings of our subsidiaries and their ability to pay dividends to the holding company as the primary source of our income.

We are an insurance holding company whose primary assets are the stock of our subsidiaries. Our operations, and our ability to service our debt, are limited by the earnings of our subsidiaries and their payment of their earnings to us in the form of management fees, dividends, loans, advances or the reimbursement of expenses. These payments can be made only when our subsidiaries have adequate earnings. In addition, these payments made to us by our insurance subsidiaries are restricted by Florida law governing the insurance industry. Generally, Florida law limits the dividends payable by insurance companies under complicated formulas based on the subsidiary’s available capital and earnings. Under these formulas, Federated National would be able to pay approximately $200,000 in dividends in 2004 and American Vehicle would be able to pay approximate ly $70,000 in dividends in 2004. Florida law does authorize the Florida Office of Insurance Regulation to approve dividends that exceed the formula amounts.

No dividends were declared or paid by our subsidiaries in 2002, 2001 or 2000 and we do not anticipate any dividends to be paid in 2003. Whether our subsidiaries will be able to pay dividends in 2004 depends on the results of their operations and their expected needs for capital. If our subsidiaries continue to achieve net income at current levels and conditions in the insurance markets remain relatively consistent, then we currently anticipate that our subsidiaries should begin to pay dividends to the parent company in 2004.

Historically, the operations and financing obligations of 21^st Century as the parent company have required approximately $1.3 million per year. We anticipate that some of our obligations will be met through future dividends from our subsidiaries and the remainder from our existing sources of capital, such as our revolving loan. The most likely reason why we would not be able to meet our obligations is if a catastrophic event expected to occur no more often than once in every 100 years were actually to occur and simultaneously, our reinsurance arrangements were to fail. If we need additional sources of capital, we currently expect that we would offer our securities to investors or obtain financing secured by our assets.

10

NOTE REGARDING FORWARD LOOKING STATEMENTS

Statements in this prospectus or in documents incorporated by reference that are not historical fact are forward-looking statements.  Forward-looking statements are subject to certain risks and uncertainties that could cause actual events and results to differ materially from those discussed herein. Without limiting the generality of the foregoing, words such as "may," "will," "expect," "believe," "anticipate," "intend," "could," "would," "estimate," or "continue" or the negative other variations thereof or comparable terminology are intended to identify forward-looking statements. The risks and uncertainties include, but are not limited to, the risks and uncertainties described in this prospectus or from time to time in our filings with the SEC.

USE OF PROCEEDS

We will not receive any proceeds from the resale of the common stock by the selling shareholders.

SELLING SHAREHOLDERS

The following table shows certain information as of the date of this prospectus regarding the number of shares of common stock owned by the selling shareholders and that are included for sale in this prospectus.  The table assumes that all shares offered for sale in the prospectus are sold.

No selling shareholder has been within the last three years, or is currently, affiliated with us.

Selling Shareholder	Ownership of Common Stock Before Offering		Number Offered By Selling Shareholder	Ownership of Common Stock After Offering
	Number	Percent		Number	Percent
Coastal Convertibles LTD	43,090	1.31%	3,854	39,236	1.19%
Omicron Master Trust	28,727	*	2,570	26,157	*
OTAPE Investments LLC	14,364	*	1,285	13,079	*
Newport Alternative Income Fund	5,745	*	514	5,231	*
Pandora Select Advisors, LLC	57,453	1.74%	5,139	52,314	1.58%
SilverCreek II Limited	16,087	*	1,439	14,648	*
SilverCreek Limited Partnership	35,621	1.09%	3,186	32,435	*
Whitebox Convertible  Arbitrage Partners, LP	114,906	3.43%	10,278	104,628	3.12%
Whitebox Hedged High  Yield Partners, LP	114,906	3.43%	10,278	104,638	3.12%

————————

*

Less than 1%.

The selling shareholders listed above have provided us with additional information regarding the individuals or entities that exercise control over the selling shareholder.  The proceeds of any sale of shares pursuant to this prospectus will be for the benefit of the individuals that control the selling entity. The following is a list of the selling shareholders and the entities that may exercise the right to vote or dispose of the shares owned by each selling shareholder:

•

Coastal Convertibles LTD is managed by Tradewinds.

11

•

J. Giordano Securities, LLC is controlled by James Giordano.

•

Omicron Master Trust is managed by Omicron.

•

OTAPE Investments, LLC is managed by OTA.

•

Each of Newport Alternative Income Fund, SilverCreek II Limited and SilverCreek Limited Partnership is managed by SilverCreek.

•

Each of Pandora Select Partners, LP, Whitebox Convertible Arbitrage Partners, LP and Whitebox Hedged High Yield Partners, LP is managed by Whitebox Advisors, LLC.

HOW THE SHARES MAY BE DISTRIBUTED

The selling shareholders may sell shares of common stock in various ways and at various prices.  Some of the methods by which the selling shareholders may sell shares include:

•

ordinary brokerage transactions and transactions in which the broker solicits purchasers or makes arrangements for other brokers to participate in soliciting purchasers;

•

privately negotiated transactions;

•

block trades in which the broker or dealer will attempt to sell the shares as agent but may position and resell a portion of the block as principal to facilitate the transaction;

•

purchases by a broker or dealer as principal and resale by that broker or dealer for the selling shareholder’s account under this prospectus on the Nasdaq National Market at prices and on terms then-prevailing in the market;

•

sales under Rule 144, if available, rather than using this prospectus;

•

a combination of any of these methods of sale; and

•

any other legally permitted method.

The applicable sales price may be affected by the type of transaction.

The selling shareholders may also pledge shares as collateral for margin loans under their customer agreements with their brokers.  If there is a default by a selling shareholder, the broker may offer and sell the pledged shares.  When selling shares, the selling shareholders intend to comply with the prospectus delivery requirements under the Securities Act, by delivering a prospectus to each purchaser.  We may file any supplements, amendments or other necessary documents in compliance with the Securities Act that may be required in the event a selling shareholder defaults under any customer agreement with brokers.

Brokers and dealers may receive commissions or discounts from the selling shareholders or, in the event the broker-dealer acts as agent for the purchaser of the shares, from that purchaser, in amounts to be negotiated.  These commissions are not expected to exceed those customary in the types of transactions involved.

We cannot estimate at the present time the amount of commissions or discounts, if any, that will be paid by the selling shareholders in connection with the sales of the shares.

12

The selling shareholders and any broker-dealers or agents that participate with a selling shareholder in sales of the shares may be deemed to be “underwriters” within the meaning of the Securities Act in connection with such sales.  In that event, any commissions received by the broker-dealers or agents and any profit on the resale of the shares purchased by them may be deemed to be underwriting commissions or discounts under the Securities Act.

Under the securities laws of certain states, the shares may be sold in those states only through registered or licensed broker-dealers.  In addition, the shares may not be sold unless the shares have been registered or qualified for sale in the relevant state or unless the shares qualify for an exemption from registration or qualification.

We have agreed to pay all of our out-of-pocket expenses and our professional fees and expenses incident to the registration of the shares.

The selling shareholders and other persons participating in the distribution of the shares offered under this prospectus are subject to the applicable requirements of Regulation M promulgated under the Exchange Act in connection with sales of the shares.

LEGAL MATTERS

Broad and Cassel, a partnership including professional associations, Miami, Florida, is giving an opinion regarding the validity of the offered shares of common stock.

EXPERTS

The financial statements of 21st Century Holding Company for the year ended December 31, 2002, incorporated by reference in this prospectus, have been audited by De Meo, Young, McGrath, independent certified public accountants, to the extent and for the periods set forth in their report incorporated herein by reference, and are incorporated herein in reliance upon such reports given upon the authority of said firm as experts in auditing and accounting.

The financial statements of 21st Century Holding Company for the years ended December 31, 2001 and 2000, incorporated by reference in this prospectus, have been audited by McKean, Paul, Chrycy, Fletcher & Co., independent certified public accountants, to the extent and for the periods set forth in their report incorporated herein by reference, and are incorporated herein in reliance upon such reports given upon the authority of said firm as experts in auditing and accounting.

WHERE YOU CAN FIND MORE INFORMATION

We have filed a registration statement on Form S-3 with the SEC in connection with this offering. This prospectus does not contain all of the information set forth in the registration statement, as permitted by the rules and regulations of the SEC. This prospectus may include references to material contracts or other material documents of ours; any summaries of these material contracts or documents are complete and are either included in this prospectus or incorporated by reference into this prospectus. You may refer to the exhibits that are part of the registration statement for a copy of the contract or document.

13

We also file annual, quarterly and current reports and other information with the SEC. You may read and copy any report or document we file, and the registration statement, including the exhibits, may be inspected at the SEC's public reference room located at 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 rooms. Our SEC filings are also available to the public from the SEC's website at http://www.sec.gov.

Quotations for the prices of our common stock appear on the Nasdaq National Market, and reports, proxy statements and other information about us can also be inspected at the offices of the National Association of Securities Dealers, Inc., 1735 K Street, N.W., Washington, D.C. 20006.

INCORPORATION OF CERTAIN INFORMATION BY REFERENCE

The following documents are incorporated by reference into this prospectus:

•

Our Annual Report on Form 10-K for the year ended December 31, 2002, filed with the SEC on April 11, 2003,

•

Our proxy statement for our 2003 Annual Meeting of Shareholders filed with the SEC on April 16, 2003,

•

Our Quarterly Report on Form 10-Q for the quarter ended March 31, 2003, filed with the SEC on May 15, 2003,

•

Our Quarterly Report on Form 10-Q for the quarter ended June 30, 2003, filed with the SEC on August 14, 2003,

•

Amendment No. 1 to our Quarterly Report on Form 10-Q for the quarter ended March 31, 2003, filed with the SEC on August 28, 2003,

•

Amendment No. 1 to our Annual Report on Form 10-K for the year ended December 31, 2002, filed with the SEC on September 3, 2003,

•

Amendment No. 2 to our Annual Report on Form 10-K for the year ended December 31, 2002, filed with the SEC on October 24,  2003, and

•

The description of our common stock contained in our registration statement on Form 8-A filed with the SEC on October 28, 1998, as this description may be updated in any amendment to the Form 8-A.

In addition, all documents filed by us pursuant to Sections 13(a), 13(c), 14 or 15(d) of the Securities Exchange Act of 1934, other than information furnished pursuant to Items 9 or 12 of Form 8-K, after the date of this prospectus and prior to the filing of a post-effective amendment that indicates that all securities registered hereby have been sold or that deregisters all securities then remaining unsold, shall be deemed to be incorporated by reference into this prospectus and to be a part hereof from the date of filing of such documents with the SEC. Any statement contained in a document incorporated by reference herein shall be deemed to be modified or superseded for purposes of this prospectus to the extent that a statement contained herein, or in a

14

subsequently filed document incorporated by reference herein, modifies or supersedes that statement. Any statement so modified or superseded shall not be deemed, except as so modified or superseded, to constitute part of this prospectus.

You may obtain a copy of these filings, excluding all exhibits unless we have specifically incorporated by reference an exhibit in this prospectus or in a document incorporated by reference herein, at no cost, by writing or telephoning:

21st Century Holding Company

4161 N.W. 5th Street

Plantation, Florida 33317

Attention: James A. Epstein, General Counsel

Telephone: (954) 581-9993

Our file number under the Securities Exchange Act of 1934 is 0-2500111.

INDEMNIFICATION OF DIRECTORS AND OFFICERS

We have authority under Section 607.0850 of the Florida Business Corporation Act to indemnify our directors and officers to the extent provided for in that law. Our articles of incorporation provide that we may insure, shall indemnify and shall advance expenses on behalf of our officers and directors to the fullest extent not prohibited by law. We also are a party to indemnification agreements with each of our directors and officers.

The SEC is of the opinion that indemnification of directors, officers and controlling persons for liabilities arising under the Securities Act is against public policy and is, therefore, unenforceable.

15

PART II

INFORMATION REQUIRED IN PROSPECTUS

ITEM 14.  OTHER EXPENSES OF ISSUANCE AND DISTRIBUTION.

The Registrant estimates that its expenses in connection with this registration statement will be as follows:

SEC registration fee.	$	58.74
Accounting fees and expenses.		10,000.00
Legal fees and expenses		15,000.00
Miscellaneous		9,941.26
Total	$	35,000.00

ITEM 15.  INDEMNIFICATION OF DIRECTORS AND OFFICERS.

The Registrant has authority under Section 607.0850 of the Florida Business Corporation Act to indemnify its directors and officers to the extent provided for in such law. The Registrant's Amended and Restated Articles of Incorporation provide that the Registrant may insure, shall indemnify and shall advance expenses on behalf of its officers and directors to the fullest extent not prohibited by law. The Registrant is also a party to indemnification agreements with each of its directors and officers.

ITEM 16.  EXHIBITS.

4.1

Specimen of Common Stock Certificate(1)

4.2

Revised Representative's Warrant Agreement including form of

Representative's Warrant(1)

4.3

Amendment dated October 1, 2003 to Warrant Agreement(2)

4.4

Form of 6% Senior Subordinated Note due July 31, 2006(3)

4.5

Form of Redeemable Warrant dated July 31, 2003(3)

4.6

Unit Purchase Agreement dated July 31, 2003 between the Company and the Purchasers of the 6% Senior Subordinated Notes(4)

4.7

Amendment to Unit Purchase Agreement and Registration Rights Agreement dated October 15, 2003 between the Company and the Purchasers of the 6% Senior Subordinated Notes(5)

5.1

Opinion of Broad and Cassel(5)

23.1

Consent of Broad and Cassel (included in its opinion filed as Exhibit 5.1)(5)

23.2

Consent of McKean, Paul, Chrycy, Fletcher & Co.(5)

23.3

Consent of De Meo, Young, McGrath(5)

25.1

Power of Attorney(4)

____________

(1)

Previously filed as an exhibit of the same number to the Registrant's Registration Statement on Form SB-2 (File No. 333-63623) and incorporated herein by reference.

II-1

(2)

Previously filed as an exhibit of the same number to the Registrant’s Registration Statement on Form S-3 (File No. 333-105221) and incorporated herein by reference.

(3)

Previously filed as Exhibits 4.1 and 4.2, respectively, to the Quarterly Report on Form
10-Q for the quarter ended June 30, 2003 and incorporated herein by reference.

(4)

Previously filed as Exhibit 4.5 to the Registrant’s Registration Statement on Form S-3 (333-109313) and incorporated herein by reference.

(5)

Filed herewith.

(6)

Filed with this Registration Statement, File Number 333-108739, as originally filed.

Item 17.  Undertakings.

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:

(a)

To include any prospectus required by section 10(a)(3) of the Securities Act of 1933, as amended;

(b)

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; and

(c)

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.

(2)

That, for the purpose of determining any liability under the Securities Act of 1933, 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.

The undersigned Registrant hereby undertakes that, for purposes of determining any liability under the Securities Act of 1933, each filing of the Registrant’s annual report pursuant to Section 13(a) or Section 15(d) of the Securities Exchange Act of 1934 (and, where applicable, each filing of an employee benefit plan’s annual report pursuant to 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.

II-2

Insofar as indemnification for liabilities arising under the Securities Act of 1933 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 SEC such indemnification is against public policy as expressed in the Securities Act of 1933 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 set tled 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 of 1933 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 Amendment No. 1 to the Registration Statement to be signed on its behalf by the undersigned, thereunto duly authorized, in the City of Plantation, State of Florida on this 4^th day of November, 2003.

21^st CENTURY HOLDING COMPANY

By: /s/ Edward J. Lawson

Edward J. Lawson,

Chairman of the Board and President

Pursuant to the requirements of the Securities Act of 1933, this registration statement has been signed by the following persons in the capacities and on the date indicated.

Signatures	Title	Date
/s/ Edward J. Lawson Edward J. Lawson	Chairman of the Board of Directors and President	November 4, 2003
* Richard A. Widdicombe	Chief Executive Officer and Director  (Principal Executive Officer)	November 4, 2003
* James G. Jennings, III	Chief Financial Officer (Principal Financial and Accounting Officer)	November 4, 2003
* Carl Dorf	Director	November 4, 2003
* Charles B. Hart, Jr.	Director	November 4, 2003
* Bruce Simberg	Director	November 4, 2003
* James DePelisi	Director	November 4, 2003
* Richard W. Wilcox, Jr.	Director	November 4, 2003
*  By: /s/ Edward J. Lawson Attorney-in-fact

II-4

EXHIBIT INDEX

EXHIBIT

DESCRIPTION

4.7

Amendment to Unit Purchase Agreement and Registration Rights Agreement dated October 15, 2003 between the Company and the purchasers of the 6% Senior Subordinated Notes

5.1

Opinion of Broad and Cassel

23.2

Consent of McKean, Paul, Chrycy, Fletcher & Co.

23.3

Consent of De Meo, Young, McGrath

EX-4.7

EXHIBIT 4.7

AMENDMENT

TO

UNIT PURCHASE AGREEMENT

AND

REGISTRATION RIGHTS AGREEMENT

THIS AMENDMENT TO UNIT PURCHASE AGREEMENT AND REGISTRATION RIGHTS AGREEMENT (the “Amendment”) is dated effective as of October 15, 2003 by and among 21^st Century Holding Company, a Florida corporation (the “Company”), J. Giordano Securities, LLC (the “Placement Agent”), and the holders of the Company’s 6% Senior Subordinated Notes due July 31, 2006 (the “Notes”) as set forth on Schedule A hereto (collectively, the “Investors”).

RECITALS:

A.

The Company and the Investors entered into that certain Unit Purchase Agreement dated July 31, 2003 (the “Unit Purchase Agreement”) pursuant to which the Investors purchased the Notes and, in connection therewith, the Company, the Placement Agent and the Investors also entered into a Registration Rights Agreement of even date therewith (the “Registration Rights Agreement”).

B.

The parties now desire to modify and amend certain rights and obligations of the parties under the Unit Purchase Agreement and the Registration Rights Agreement.

AGREEMENT:

NOW, THEREFORE, in consideration of the terms and conditions hereof, and other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the parties agree as follows:

1.

Capitalized Terms.  Capitalized terms used but not defined in this Amendment shall have the meanings as set forth in the Unit Purchase Agreement and the Registration Rights Agreement, as applicable.

2.

Amendments to Unit Purchase Agreement.  

(a)  Section 7.1 of the Unit Purchase Agreement is hereby amended and restated in its entirety as follows:

“7.1 Required Payments.

(a) Principal.  The principal amount of the Notes shall be due and payable in equal quarterly installments commencing on October 31, 2003 with the last installment due on July 31, 2006 (the date due of each quarterly installment is referred to herein as a “Quarterly Payment Date” and the last Quarterly Payment

1

Date on July 31, 2006 is referred to as the “Maturity Date”).  Each principal payment shall be paid in United States dollars or, to the extent legally permitted, in shares of Common Stock (the “Principal Shares”), at the Company’s option; provided, however, that the Company shall make principal payments in Principal Shares only to the extent provided in Section 12 hereof.  If such principal payment is paid in Principal Shares, then the number of Principal Shares to be issued on account of the principal payment shall be equal to (i) the amount of the principal payment due divided by (ii) 95% of the weighted-average volume price for the Common Stock on Nasdaq as reported by Bloomberg Financial Markets (“Bloomberg”) for the 20 consecutive trading days prior to the Quarterly Payment Date (the
47;Calculation Price”).  In the event the Company elects to pay the principal amount due in Principal Shares, (a) it shall notify the Holder of its election no later than 15 days prior to the commencement of the 20 consecutive trading day period referenced above, (b) it shall issue the applicable Principal Shares on the Quarterly Payment Date, and (c) it shall file a registration statement covering resale of the applicable Principal Shares (the “Registration Statement”) no later than two Business Days following the Quarterly Payment Date.

(b)  Compensatory Payment.  If a principal payment is made in Principal Shares and the weighted-average volume price for the Common Stock on Nasdaq as reported by Bloomberg for the three Business Day period ending on (and including) the date of effectiveness (the “Effective Date”) of the applicable Registration Statement (the “Post-Issuance Average Price”) is less than the Calculation Price, then the Company shall pay to each holder of the Notes an amount equal to (i) the difference between the Calculation Price and the Post-Issuance Average Price, multiplied by (ii) the number of Principal Shares issued on the applicable Quarterly Payment Date.  Such amount shall be paid to each holder of the Notes in cash not later than 10 Business Days following the Effective Date of the app licable Registration Statement.”

(b)  Section 9.1 of the Unit Purchase Agreement is hereby amended and restated in its entirety as follows:

“9.1  Required Payments.

(a)  Interest.  The principal amount of the Notes outstanding shall bear interest at the rate of 6% per annum beginning on the date of issuance.  Interest shall be payable quarterly beginning on October 31, 2003.  Each interest payment shall be paid in United States dollars or, to the extent legally permitted, in shares of Common Stock (the “Interest Shares”), at the Company’s option; provided, however, that the Company shall make interest payments in Interest Shares only to the extent provided in Section 12 hereof.  If such interest payment is paid in Interest Shares, then the number of Interest Shares to be issued on account of the interest payment shall be equal to (i) the amount of the interest payment due divided by (ii) the Calculation Price.  In the even t the Company elects to pay the interest amount due in Interest Shares, (a) it shall notify the Holder of its election no later than 15 days prior to the commencement of the 20 consecutive trading

2

day period referenced in Section 7.1 above, (b) it shall issue the applicable Interest Shares on the Quarterly Payment Date, and (c) it shall file the Registration Statement covering resale of the applicable Interest Shares no later than two Business Days following the Quarterly Payment Date.

(b)  Compensatory Payment.  If an interest payment is made in Interest Shares and the Post-Issuance Average Price of the applicable Interest Shares is less than the Calculation Price, then the Company shall pay to each holder of the Notes an amount equal to (i) the difference between the Calculation Price and the Post-Issuance Average Price, multiplied by (ii) the number of Interest Shares issued on the applicable Quarterly Payment Date.  Such amount shall be paid to each holder of the Notes in cash not later than 10 Business Days following the Effective Date of the applicable Registration Statement.”

3.

Amendments to Registration Rights Agreement.

(a)

Section 4(a) of the Registration Rights Agreement shall be amended and restated in its entirety as follows:

“(a)

The parties acknowledge that as of the date of this Amendment, the Company has filed a Registration Statement on Form S-3 covering the resale of the Warrants and the Warrant Shares and a Registration Statement on Form S-1 relating to the Principal Shares and Interest Shares.  The parties agree that on or before the date specified in clause (c) of Sections 7.1 and 9.1 of the Unit Purchase Agreement, as amended, the Company will file an amendment to its Registration Statement on Form S-1 to cover the resale of the Principal Shares and Interest Shares to be issued by the Company in payment of the October 31, 2003 quarterly payment due on the Notes, and that thereafter, the Company shall file in subsequent quarters such additional registration statements (individually, a “Registration Statement,” and collect ively, the “Registration Statements”) as provided in Sections 7.1 and 9.1 of the Unit Purchase Agreement.  No later than five Trading Days prior to the anticipated effective date of each such Registration Statement, the Company shall provide copies of same to the Holders or their counsel, and shall provide the Holders with copies of any comment letters received from the Commission with respect thereto within five Trading Days of receipt thereof.  

“The Company shall use diligent best efforts to cause each Registration Statement to become effective within 60 days from the date of filing thereof.  Each such Registration Statement shall include all of the Registrable Securities then issued and not covered by a previously filed Registration Statement, to the extent permitted by the rules and interpretations of the Commission as then in effect, and shall include appropriate language regarding reliance upon Rule 416 to the extent permitted by the Commission.  The Company will notify the Holders and its transfer agent of the effectiveness of a Registration Statement within five Trading Days of such event.”

3

(b)

Section 4(c) of the Registration Rights Agreement shall be amended by deleting the third sentence thereof.

4.

Governing Law.  This Amendment shall be interpreted in accordance with the laws of the State of Florida.

5.

Effect of Amendment.  Except as expressly set forth herein, the Unit Purchase Agreement and Registration Rights Agreement shall remain unmodified and in full force and effect pursuant to their respective terms and conditions.

6.

Counterparts.  This Amendment may be executed in two or more counterparts, each of which shall be deemed an original, but all of which together shall constitute one and the same instrument.

[SIGNATURES ON FOLLOWING PAGE]

4

The parties have caused this Amendment to be executed and delivered on behalf of each such party, effective as of the date set forth above.

COMPANY:

21st CENTURY HOLDING COMPANY,

a Florida corporation

By: //s// Edward J. Lawson

Name: Edward J. Lawson

Title:  Chairman

PLACEMENT AGENT:

J. GIORDANO SECURITIES, LLC,

a _____________ limited liability

company*

By:  //s// James Giordano

Name:

James Giordano

Title:    President

*Only as to Registration Rights

  Agreement

INVESTOR:

Pandora Select Partners, LP

(Printed Name of Investor)

By:  //s// Andrew Redleaf

Name:

Andrew Redleaf

Title:

Managing Member

5

INVESTOR:

Whitebox Hedged High Yield Partners, LP

(Printed Name of Investor)

By:  //s// Andrew Redleaf

Name:

 Andrew Redleaf

Title:

Managing Member

INVESTOR:

Whitebox Convertible Arbitrage Partners, LP

(Printed Name of Investor)

By:  //s// Andrew Redleaf

Name:

 Andrew Redleaf

Title:

Managing Member

INVESTOR:

SilverCreek Limited Partnership

(Printed Name of Investor)

By:  //s// Bryn Joynt

Name:

 Bryn Joynt

Title:

VP of Manager

INVESTOR:

Newport Alternative Income Fund

(Printed Name of Investor)

By:  //s// Bryn Joynt

Name:

 Bryn Joynt

Title:

VP of Manager

6

INVESTOR:

SilverCreek II Limited

(Printed Name of Investor)

By:  //s// Bryn Joynt

Name:

 Bryn Joynt

Title:

VP of Manager

INVESTOR:

Coastal Convertibles LTD

(Printed Name of Investor)

By:  //s// J. Lurie

Name:

 J. Lurie

Title:

Director / Member

INVESTOR:

OTAPE Investments LLC

(Printed Name of Investor)

By:  //s// Richard Cayne

Name:

 Richard Cayne

Title:

General Counsel

INVESTOR:

Omicron Master Trust

(Printed Name of Investor)

By:  //s// Bruce Bernstein

Name:

 Bruce Bernstein

Title:

Managing Member

7

Schedule A

Manager	Purchaser (LEGAL NAME TO BE PUT NOTE)	Number of Units
Whitebox Advisors	Pandora Select Partners, LP Whitebox Hedged High Yield Partners, LP Whitebox Convertible Arbitrage Partners, LP	1,000 2,000 2,000
SilverCreek	SilverCreek Limited Partnership Newport Alternative Income Fund SilverCreek II Limited	620 100 280
Tradewinds	Coastal Convertibles LTD	750
OTA	OTAPE Investments LLC	250
Omicron	Omicron Master Trust	500

A-1

EX-5.1

7777 GLADES ROAD SUITE 300 BOCA RATON, FLORIDA 33434 TELEPHONE: 561.483.7000 FACSIMILE: 561.483.7321 www.broadandcassel.com                                                                                                                                             

November 4, 2003

21st Century Holding Company

4161 N.W. 5th Street

Plantation, FL 33317

Re:     21st Century Holding Company (the "Company") Amendment No. 1 to Registration Statement on Form S-1 on Form S-3   

Ladies and Gentlemen:

We have acted as counsel for the Company with respect to the preparation and filing with the U.S. Securities and Exchange Commission of Amendment No. 1 to the Registration Statement on Form S-1 on Form S-3 (the “Form S-3”) pursuant to the Securities Act of 1933, as amended (the “Securities Act”).You have requested our opinion with respect to the issuance of 38,543 shares (the “Shares”) of the Company’s common stock, par value $.01 per share, by the Company on October 31, 2003 in payment of the principal and interest due on the Company’s 6% Senior Subordinated Notes due 2006.

As counsel to the Company, we have examined the original or certified copies of such records of the Company, and such agreements, certificates of public officials, certificates of officers and representatives of the Company and others, and such other documents as we deemed relevant and necessary for the opinion expressed in this opinion letter. In such examination, we have assumed the genuineness of all signatures on original documents, and the conformity to original documents of all copies submitted to us as conformed or photostatic copies. As to various questions of fact material to such opinion, we have relied upon statements or certificates of officials and representatives of the Company and others.

Based on, and subject to the foregoing, we are of the opinion that the Shares have been legally issued, fully paid and nonassessable.

The opinion expressed herein is based on Florida law, including the statutes and constitution of the State of Florida as in existence on the date hereof and the reported judicial decisions interpreting such statutes and constitution.

In rendering this opinion, we advise you that members of this Firm are members of The Bar of the State of Florida, and we express no opinion herein concerning the applicability or effect of any laws of any other jurisdiction, except the securities laws of the United States of American referred to herein.

BOCA RATON   ·   FT. LAUDERDALE   ·   MIAMI   ·   ORLANDO   ·   TALLAHASSEE   ·   TAMPA   ·   WEST PALM BEACH

21st Century Holding Company

November 4, 2003

Page 2

We hereby consent to the filing of this opinion letter as an exhibit to the Form S-3. We also consent to the use of our name under the caption “Legal Matters” in the prospectus constituting part of the Form S-3. In giving such consent, we do not thereby admit that we are included within the category of persons whose consent is required under Section 7 of the Securities Act, or the rules and regulations promulgated thereunder.

Very truly yours,

/s/ Broad and Cassel

BROAD AND CASSEL

BOCA RATON   ·   FT. LAUDERDALE   ·   MIAMI   ·   ORLANDO   ·   TALLAHASSEE   ·   TAMPA   ·   WEST PALM BEACH

EX-23.2

Exhibit 23.2

CONSENT OF INDEPENDENT CERTIFIED PUBLIC ACCOUNTANTS

As independent certified public accountants, we hereby consent to the incorporation by reference in this Form S-1/A No. 1 on Form S-3 registration statement covering the registration of up to 38,543 shares of common stock, of our report dated March 29, 2002 included in 21^st Century Holding Company's Form 10-K/A No. 1 for the year ended December 31, 2002 and to all references to our Firm included in this registration statement.

McKEAN, PAUL, CHRYCY, FLETCHER & CO.

Miami, Florida,

  October 31, 2003.

EX-23.3

Exhibit 23.3

CONSENT OF INDEPENDENT CERTIFIED PUBLIC ACCOUNTANTS

We consent to the inclusion by reference in this Amendment No.1 to Form S-1 on Form S-3 of our report dated March 30, 2002, which appears on page 29 of the annual report on Form 10-K of 21st Century Holding Company for the year ended December 31, 2002, as amended, and to the reference to our firm under the caption “Experts” in the prospectus.

De MEO, YOUNG, McGRATH

Miami, Florida,

November 4, 2003.