Exhibit 99.1 UNAUDITED PRO FORMA COMBINED CONDENSED CONSOLIDATED FINANCIAL INFORMATION The following tables show the condensed consolidated financial information for each of Chemical Financial Corporation (“Chemical”) and TCF Financial Corporation (“TCF”), as well as unaudited pro forma combined condensed financial information for Chemical and TCF reflecting the proposed merger contemplated in the Agreement and Plan of Merger by and between Chemical and TCF, dated as of January 27, 2019 and pro forma adjustments described in the accompanying notes. The unaudited pro forma combined condensed financial information should be read in conjunction with Chemical’s audited financial statements as of and for the three year period ended December 31, 2018, which is included in Chemical’s Annual Report on Form 10-K for the year ended December 31, 2018, and unaudited consolidated financial statements as of and for the three months ended March 31, 2019, which is included in Chemical’s Quarterly Report on Form 10-Q for the quarter ended March 31, 2019, and TCF’s audited financial statements as of and for the three year period ended December 31, 2018, which is included in TCF’s Annual Report on 10-K for the year ended December 31, 2018, and unaudited consolidated financial statements as of and for the three months ended March 31, 2018, which is included in TCF’s Quarterly Report on Form 10-Q for the quarter ended March 31, 2019. The unaudited pro forma combined condensed financial information assumes that the merger is accounted for as a reverse acquisition using the acquisition method of accounting, pursuant to FASB Topic 805-10, Business Combinations. Following the merger, existing shareholders of TCF will control approximately 54% of the pro forma voting interests in the combined company (based on common shares outstanding as of March 31, 2019), which is the primary reason that TCF is the accounting acquirer in the merger. Under the acquisition method of accounting, the assets and liabilities of Chemical, as the accounting acquiree, will be recorded at their respective fair values as of the date the merger is completed. The unaudited pro forma combined condensed statement of financial condition gives effect to the merger as if the transaction had occurred on March 31, 2019. The unaudited pro forma combined condensed income statement for the quarter ended March 31, 2019 gives effect to the merger as if the transaction had become effective on January 1, 2019 and the unaudited pro forma combined condensed income statement for the year ended December 31, 2018 gives effect to the merger as if the transaction had become effective on January 1, 2018. For purposes of the unaudited pro forma combined condensed financial information, the purchase consideration has been allocated to Chemical’s assets and liabilities based upon management’s preliminary estimate of their fair values as of March 31, 2019. The unaudited pro forma combined condensed financial information is presented for illustrative purposes only and does not indicate the financial results of the combined company had the companies actually been combined at the beginning of the period presented, nor the impact of possible business model changes. The unaudited pro forma combined condensed financial information, while helpful in illustrating the financial characteristics of the combined company under one set of assumptions, does not reflect the realization of potential cost savings, revenue synergies, changes in market conditions and asset dispositions, among other factors, and, accordingly, does not attempt to predict or suggest future results. Chemical and TCF expect to incur costs associated with the merger and the integration of the businesses and operations of Chemical and TCF. However, the unaudited pro forma combined condensed financial information does not include these estimated merger and integration costs (other than estimated contractually obligated after-tax merger costs). See Note 5 accompanying the unaudited pro forma combined condensed financial information for additional information regarding estimated merger and integration costs. In addition, as explained in more detail in the accompanying notes, the preliminary allocation of the pro forma purchase price reflected in the unaudited pro forma combined condensed financial information is subject to adjustment and may vary significantly from the actual purchase price allocation that will be recorded upon completion of the merger. 1
Chemical Financial Corporation and TCF Financial Corporation Unaudited Pro Forma Combined Condensed Consolidated Statements of Financial Condition As of March 31, 2019 Pro Forma Pro Forma Chemical as TCF as Pro Forma Chemical and Chemical and Reported Reported Adjustments TCF Capital Actions TCF (Amounts in thousands, except per share data) Assets Cash and cash equivalents $ 517,576 $ 463,822 $ (45,415) (1) $ 935,983 $ 71,025 (16)(17) $ 1,007,008 Investment securities 3,923,573 3,197,010 5,096 (2) 7,125,679 - 7,125,679 Loans held-for-sale 23,535 64,468 - 88,003 - 88,003 Total loans and leases 15,324,048 19,383,675 (287,260) (3) 34,420,463 - 34,420,463 Allowance for loan and lease losses (110,284) (147,972) 110,284 (4) (147,972) - (147,972) Net loans and leases 15,213,764 19,235,703 (176,976) 34,272,491 - 34,272,491 Premises and equipment, net 122,452 429,711 (6,600) (5) 545,563 - 545,563 Goodwill 1,134,568 154,757 (72,271) (6) 1,217,054 - 1,217,054 Other intangible assets 27,195 19,684 141,069 (7) 187,948 - 187,948 Interest receivable and other assets 837,650 853,560 3,558 (8) 1,694,768 975 (17) 1,695,743 Total Assets $ 21,800,313 $ 24,418,715 $ (151,539) $ 46,067,489 $ 72,000 $ 46,139,489 Liabilities and Shareholders' Equity Deposits $ 16,061,999 $ 19,024,111 $ (19,351) (9) $ 35,066,759 $ - $ 35,066,759 Collateralized customer deposits 413,199 - - 413,199 - 413,199 Interest payable and other liabilities 261,571 981,341 - 1,242,912 - 1,242,912 Short-term borrowings 1,740,000 355,992 - 2,095,992 - 2,095,992 Other borrowings 426,035 1,411,426 (1,119) (10) 1,836,342 150,000 (17) 1,986,342 Total liabilities 18,902,804 21,772,870 (20,470) 40,655,204 150,000 40,805,204 Shareholders' equity: Preferred stock - 169,302 - (11) 169,302 - 169,302 Common stock 71,551 1,733 81,571 (12) 154,855 (1,889) (16) 152,966 Additional paid-in capital 2,209,860 875,797 202,252 (13) 3,287,909 (76,111) (16) 3,211,798 Retained earnings 654,605 1,810,701 (700,020) (14) 1,765,286 - 1,765,286 Accumulated other comprehensive income (loss) (38,507) 5,481 38,507 (15) 5,481 - 5,481 Treasury stock and other - (246,621) 246,621 (13) - - - Noncontrolling interests in subsidiaries - 29,452 - 29,452 - 29,452 Total shareholders' equity 2,897,509 2,645,845 (131,069) 5,412,285 (78,000) 5,334,285 Total Liabilities and Shareholders' Equity $ 21,800,313 $ 24,418,715 $ (151,539) $ 46,067,489 $ 72,000 $ 46,139,489 Book value per common share $ 40.50 $ 14.93 $ 33.67 $ 33.57 Tangible book value per common share $ 24.39 $ 13.86 $ 24.59 $ 24.39 See accompanying notes to unaudited pro forma combined condensed consolidated financial statements. 2
Chemical Financial Corporation and TCF Financial Corporation Unaudited Pro Forma Combined Condensed Consolidated Statements of Income For the Quarter Ended March 31, 2019 Pro Forma Pro Forma Chemical as TCF as Pro Forma Chemical and Chemical and Reported Reported Adjustments TCF Capital Actions TCF (Amounts in thousands, except per share data) Interest income $ 213,981 $ 303,245 $ 9,335 (18) $ 526,561 $ - $ 526,561 Interest expense 51,157 52,338 5,778 (19) 109,273 1,875 (23) 111,148 Net interest income 162,824 250,907 3,557 417,288 (1,875) 415,413 Provision for credit losses 2,059 10,122 - 12,181 - 12,181 Noninterest income 24,857 107,026 - 131,883 - 131,883 Operating expenses 109,015 253,075 (8,499) (20) 353,591 25 (23) 353,616 Net income before income tax expenses 76,607 94,736 12,056 183,399 (1,900) 181,499 Income tax expense 13,665 21,287 2,532 (21) 37,484 (399) (21) 37,085 Net income after income tax expense 62,942 73,449 9,524 145,915 (1,501) 144,414 Income attributable to noncontrolling interest - 2,955 - 2,955 - 2,955 Net income attributable to Chemical/TCF 62,942 70,494 9,524 142,960 (1,501) 141,459 Preferred stock dividends - 2,493 - 2,493 - 2,493 Net income attributable to common shareholders $ 62,942 $ 68,001 $ 9,524 $ 140,467 $ (1,501) $ 138,966 Net income per common share Basic $ 0.88 $ 0.42 $ 0.91 $ 0.91 $ 0.87 $ 0.42 $ 0.90 $ 0.90 Diluted $ 0.34 $ 0.15 $ 0.34 $ 0.34 Dividends per share Average common shares outstanding: (22) (24) Basic 71,474 161,865 (78,561) 154,778 (1,889) 152,889 (22) (24) Diluted 72,141 162,428 (78,838) 155,731 (1,889) 153,842 See accompanying notes to unaudited pro forma combined condensed consolidated financial statements. 3
Chemical Financial Corporation and TCF Financial Corporation Unaudited Pro Forma Condensed Combined Statement of Income Year Ended December 31, 2018 Pro Forma Pro Forma Pro Forma Chemical TCF Adjustment Chemical and Capital Chemical and Historical Historical s TCF Actions TCF (Amounts in thousands, except per share data) Interest income $ 775,996 $ 1,142,264 $ 34,536 (18) $ 1,952,796 $ - $ 1,952,796 Interest expense 143,663 150,257 23,111 (19) 317,031 7,500 (23) 324,531 Net interest income 632,333 992,007 11,425 1,635,765 (7,500) 1,628,265 Provision for credit losses 30,750 46,768 - 77,518 - 77,518 Noninterest income 148,536 470,885 - 619,421 - 619,421 Operating expenses 424,198 1,014,400 25,267 (20) 1,463,865 98 (23) 1,463,963 Net income before income tax expenses 325,921 401,724 (13,842) 713,803 (7,598) 706,205 Income tax expense 41,901 86,096 (2,907) (21) 125,090 (1,596) (21) 123,494 Net income after income tax expense 284,020 315,628 (10,935) 588,713 (6,002) 582,711 Income attributable to noncontrolling interest - 11,270 - 11,270 - 11,270 Net income attributable to Chemical/TCF 284,020 304,358 (10,935) 577,443 (6,002) 571,441 Preferred stock dividends - 11,588 - 11,588 - 11,588 Impact of preferred stock redemption - 3,481 - 3,481 - 3,481 Net income attributable to common $ shareholders $ 284,020 $ 289,289 $ (10,935) $ 562,374 (6,002) $ 556,372 Net income per common share Basic $ 3.98 $ 1.75 $ 3.64 $ 3.64 Diluted $ 3.94 $ 1.74 $ 3.61 $ 3.61 Dividends per share $ 1.24 $ 0.60 $ 1.24 $ 1.24 Average common shares outstanding: Basic 71,338 165,585 (82,296) (22) 154,627 (1,783) (24) 152,844 Diluted 72,025 166,562 (82,777) (22) 155,810 (1,783) (24) 154,027 See accompanying notes to unaudited pro forma combined condensed financial statements. Note 1—Basis of Presentation The unaudited pro forma combined condensed financial information and explanatory notes have been prepared to illustrate the effects of the merger involving Chemical and TCF under the acquisition method of accounting with Chemical treated as the legal acquirer and TCF treated as the accounting acquirer. The unaudited pro forma combined condensed financial information is presented for illustrative purposes only and does not necessarily indicate the financial results of the combined companies had the companies actually been combined at the beginning of the period presented, nor does it necessarily indicate the results of operations in future periods or 4
the future financial position of the combined entities. Under the acquisition method of accounting, the assets and liabilities of Chemical (as the accounting acquiree), as of the effective date of the merger, will be recorded at their respective fair values, and the excess of the purchase price consideration over the fair value of Chemical’s net assets will be allocated to goodwill. See Note 2 to the unaudited pro forma combined condensed financial information for detailed calculations of the estimated purchase price. The merger, which is currently expected to be completed in the third or early fourth quarter of 2019, provides for TCF common shareholders to receive 0.5081 shares of Chemical common stock for each share of TCF common stock they hold immediately prior to the merger. Based on the closing trading price of shares of Chemical common stock on the NASDAQ Stock Market on June 17, 2019, the value of the merger consideration of TCF common stock would be $20.12 per share. Based on the closing trading price of shares of Chemical common stock on the NASDAQ Stock Market on January 25, 2019, the last trading day before the public announcement of the merger, the value of the merger consideration of TCF common stock would be $21.58 per share. The pro forma purchase price allocation reflected in the unaudited pro forma combined condensed financial information is subject to adjustment and may vary from the actual purchase price allocation that will be recorded at the time the merger is completed. Adjustments may include, but not be limited to, changes in (i) Chemical’s statement of financial condition and operating results through the effective time of the merger; (ii) the aggregate value of the accounting purchase price determination if the price of shares of TCF common stock varies from the assumed $19.90 per share, which represents the closing share price of TCF common stock on June 17, 2019; (iii) total merger-related expenses from amounts included herein; and (iv) the underlying values of assets and liabilities if market conditions differ from current assumptions. The accounting policies of both Chemical and TCF are in the process of being reviewed in detail. Upon completion of such review, conforming adjustments or financial statement reclassification may be made. Note 2—Purchase Price Determination The unaudited pro forma combined condensed statement of financial condition has been adjusted to reflect the preliminary calculation of the estimated purchase price to identifiable net assets acquired. Since the merger will be accounted for as a reverse acquisition, the estimated purchase price was determined in accordance with FASB ASC 805-40-30-2, which explains that the purchase price in a reverse acquisition is determined based on “the number of equity interests the legal acquiree would have had to issue to give the owners of the legal acquirer the same percentage equity interest in the combined entity that results from the reverse acquisition.” The first step in estimating the purchase price in the merger is to determine the pro forma ownership of the combined institution following the merger. The table below summarizes, for each current shareholder group, the pro forma ownership of Chemical common stock following the merger as well as the pro forma market capitalization of the combined company using shares of Chemical and TCF common stock outstanding at March 31, 2019 and Chemical’s closing price on June 17, 2019. Chemical Financial Corporation Ownership and Market Value Table (Pro Forma) Number of Chemical Market Value at Outstanding $39.59 Chemical Shares Percentage Share Price (in thousands) Ownership (in thousands) Current Chemical shareholders 71,551 46.2% $ 2,832,704 Current TCF shareholders 83,304 53.8% 3,298,005 Total 154,855 100.0% $ 6,130,709 Next, the hypothetical number of shares TCF would have to issue to give Chemical owners the same percentage ownership in the combined company is calculated in the table below (based on shares of TCF common stock outstanding at March 31, 2019): 5
Hypothetical TCF Ownership Number of TCF Outstanding Shares (in thousands) Percentage Ownership Current Chemical shareholders 140,847 46.2% Current TCF shareholders 163,951 53.8% Total 304,798 100.0% Finally, the purchase price is calculated based on the number of hypothetical shares of TCF common stock issued to Chemical shareholders multiplied by the share price as demonstrated in the table below (amounts in thousands except per share data). Number of hypothetical TCF shares issued to Chemical shareholders 140,847 TCF market price per share as of June 17, 2019 $ 19.90 Purchase price determination of hypothetical TCF shares issued to Chemical shareholders 2,802,855 Value of Chemical stock options hypothetically converted to options to acquire shares of TCF common stock 9,000 Purchase price consideration $ 2,811,855 Note 3—Preliminary Purchase Price Allocation The pro forma adjustments include the estimated acquisition accounting entries to record the completion of the merger. The excess of the purchase price over the fair value of net assets acquired, net of deferred taxes, is allocated to goodwill. Estimated fair value adjustments included in the pro forma financial statements are based upon available information and certain assumptions considered reasonable, and may be revised as additional information becomes available. Core deposit intangible assets of $168.3 million are included in the pro forma adjustments separate from goodwill and will be amortized on an accelerated method over ten years. Goodwill totaling $1.06 billion is included in the pro forma adjustments and is not subject to amortization. The purchase price is variable based on the price per share of TCF common stock at the closing date of the merger, which has not yet occurred. Accordingly, a 10% increase or decrease in the price per share of TCF common stock would result in a corresponding purchase price and goodwill adjustment of approximately $314 million. Below is a summary of the preliminary purchase price allocation used to develop the unaudited pro forma combined condensed statement of financial condition (amounts in thousands): 6
Note 4—Pro Forma Adjustments The following pro forma adjustments have been reflected in the unaudited pro forma combined condensed financial information. All taxable adjustments were calculated using a 21.0% tax rate to arrive at deferred tax asset or liability adjustments. All adjustments are based on current assumptions and valuations, which are subject to change. (1) Adjustments to reflect the estimated contractually obligated after-tax merger costs of $45.4 million. (2) Adjustment to Chemical’s held-to-maturity investment securities to reflect the estimated fair value based on estimates of expected cash flows and current interest rates. (3) Adjustment to Chemical’s total loans, net of unrecognized costs, to reflect the estimated fair value of the loan portfolio based on estimates of expected cash flows, which includes credit loss expectations and current interest rates. The net adjustment includes the elimination of net unrecognized loan costs of $22.7 million, establishment of an estimated credit mark of $189.2 million, which is partially offset by reversal of Chemical’s existing credit mark on acquired loans of $25.0 million, and recognition of an estimated interest discount of $100.4 million. (4) Elimination of Chemical’s existing allowance for loan losses. Purchased loans in a business combination are recorded at estimated fair value on the purchase date, and the carryover of the related allowance for loan losses is prohibited. (5) Adjustment to the statement of financial condition to reduce Chemical’s land and buildings to estimated fair value, with a corresponding adjustment to the income statement to reduce depreciation expense over estimated lives of 25-40 years. (6) Adjustments to goodwill to eliminate Chemical’s goodwill of $1.13 billion associated with prior acquisitions and record estimated goodwill associated with the merger of $1.06 billion. (7) Adjustments to other intangible assets to eliminate Chemical’s core deposit intangible assets of $27.2 million associated with prior acquisitions and record estimated core deposit intangible assets associated with the merger of $168.3 million, based on a value of 1.50% of Chemical’s non-time customer deposits. Core deposit intangible assets recorded as a result of the merger are expected to be amortized on an accelerated basis over a period of ten years. 7
(8) Adjustment to net deferred tax assets to reflect the effects of the acquisition accounting adjustments. (9) Adjustment to reflect the estimated fair value of Chemical’s interest-bearing time deposits based on market interest rates for similar instruments. (10) Adjustment of $4.0 million primarily related to reducing Chemical’s $410 million of long-term FHLB advances included in other borrowings to estimated fair value and adjustment of $2.8 million to increase Chemical’s $15.9 million of trust preferred securities included in other borrowings to estimated fair value. (11) No adjustment needed as each share of TCF 5.70% Series C Non-Cumulative Perpetual Preferred Stock issued and outstanding immediately prior to the merger date will be converted into one share of a newly created series of preferred stock of Chemical. (12) Adjustment to reflect the issuance of 83.3 million common shares of Chemical common stock with $1.00 par value per share in connection with the merger and eliminating 173.3 million issued common shares of TCF common stock with $0.01 par value per share. (13) Adjustments to eliminate Chemical’s additional paid in capital of $2.21 billion, record the hypothetical issuance of TCF common stock in excess of par value of $2.73 billion, which represents the purchase price consideration of $2.81 billion less $83.3 million classified as $1.00 par value common stock, and reclassify TCF’s historical equity accounts (common stock and treasury stock) into surplus due to the elimination of TCF’s common stock. (14) Adjustment to eliminate historical retained earnings of Chemical of $654.6 million and recognize contractually obligated after-tax merger costs of $45.4 million. (15) Adjustment to eliminate historical accumulated other comprehensive income of Chemical. (16) Adjustment to reflect TCF’s repurchases of $78.1 million of its common stock before the closing of the merger, representing the completion of its existing authorized share repurchase plan. Approximately 3.5 million shares are assumed to be repurchased by TCF at an average price of $22.23 per share, with the adjustment reflected in the pro forma based on the merger exchange ratio of 0.5081. (17) Adjustment to reflect issuance of $150 million of subordinated notes, net of estimated fees of $1.0 million, which subordinated notes are anticipated to be offered by TCF National Bank in June 2019. Fees associated with the issuance of such subordinated notes are capitalized and amortized over the life of the notes of ten years. (18) Net adjustment to interest income to recognize estimated discount loan accretion of $8.5 million for the three months ended March 31, 2019 and $31.6 million for the year ended December 31, 2018 attributable to recording the Chemical loans at fair value as of the transaction date. Adjustment also includes estimated interest accretion of $0.8 million for the three months ended March 31, 2019 and $2.9 million for the year ended December 31, 2018 associated with recording Chemical’s investment securities at fair value. The discount loan accretion and investment securities accretion are expected to accrete over a period of approximately seven years on an accelerated basis. (19) Net adjustment to interest expense to record estimated net amortization of premiums on Chemical’s time deposits and long-term debt of $5.8 million for the three months ended March 31, 2019 and $23.3 million for the year ended December 31, 2018 and net accretion on the net discount on Chemical’s trust preferred securities of $0.05 million for the three months ended March 31, 2019 and $0.2 million for the year ended December 31, 2018. The premium amortization on deposits and long-term debt is expected to be approximately one year for each, and the discount accretion on trust preferred securities is expected to be approximately 14 years. 8
(20) Adjustment to eliminate Chemical’s amortization of core deposit intangible asset amortization of $1.4 million for the three months ended March 31, 2019 and $5.7 million for the year ended December 31, 2018 and recognize estimated core deposit intangible asset amortization of $7.8 million for the three months ended March 31, 2019 and $31.2 million for the year ended December 31, 2018. See pro forma adjustment (7) above for information regarding Chemical’s amortization of core deposit intangible assets. Chemical is still in the process of evaluating the fair value of the intangible assets. Any resulting change in the fair value would have a direct impact on amortization expense. Amortization expense of the core deposit intangible assets for the first five years following the completion of the merger is estimated as follows: Year 1—$31.2 million; Year 2—$27.9 million; Year 3—$24.6 million; Year 4—$21.3 million; and Year 5—$18.1 million. Adjustment also includes elimination of $14.9 million of combined merger-related expenses incurred by Chemical and TCF for the three months ended March 31, 2019. (21) Adjustment to recognize the tax impact of pro forma transaction-related adjustments at 21%. (22) Adjustment to eliminate TCF’s average common shares outstanding and recognize the issuance of 83.3 million shares of Chemical common stock based on TCF’s 163.95 million common shares outstanding at March 31, 2019 and 163.9 million common shares outstanding at December 31, 2018 and the merger exchange ratio of 0.5081. Average diluted shares outstanding also include the effect of dilutive nonparticipating restricted stock outstanding during the three months ended March 31, 2019 and dilutive nonparticipating restricted stock and stock options outstanding during the year ended December 31, 2018, adjusted for the merger exchange ratio of 0.5081. (23) Adjustment to recognized interest expense associated with TCF National Bank’s issuance of $150 million of subordinated notes, which subordinated notes are anticipated to be offered by TCF National Bank in June 2019 at an assumed interest rate of 5.0%. Adjustment to operating expenses to recognize amortization of $1.0 million of expected financing costs associated with issuance over a period of ten years. A 0.125% increase or decrease in the assumed interest rate would result in a change in interest expense associated with these subordinated notes of $0.05 million for the three months ended March 31, 2019 and $0.2 million for the year ended December 31, 2018. (24) Adjustment to reduce TCF’s common shares outstanding for repurchase of 3.5 million shares of its common stock before the closing of the merger, as discussed in pro forma adjustment (16) above, adjusted for the merger exchange ratio of 0.5081. Note 5—Merger Integration Costs Merger and integration related costs are estimated to be $325 million on a combined pre-tax basis, with contractually obligated pre-tax merger costs of $53.5 million ($45.4 million net of tax) due at closing. Contractually obligated merger costs are reflected in the pro forma combined condensed statement of financial condition as part of the pro forma adjustments discussed in Note 4. Merger and integration related costs are not included in the unaudited pro forma combined condensed statement of income since they will be recorded in the combined results of income as they are incurred prior to, or after completion of, the merger and are not indicative of what the historical results of the combined company would have been had the companies been actually combined during the periods presented. 9
