Wintrust Financial Corp S-4, filed May 30, 2024

Wintrust Financial Corp (WTFC)

S-4 2024-05-30

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Added on October 19, 2026

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	Large accelerated filer ☒			Accelerated filer ☐
	Non-accelerated filer ☐			Smaller reporting company ☐
	Emerging growth company ☐

	QUESTIONS AND ANSWERS ABOUT THE MERGER					1
	SUMMARY					6
	RISK FACTORS					15
	SPECIAL NOTES CONCERNING FORWARD-LOOKING STATEMENTS					19
	THE MACATAWA PROPOSALS					22
	Approval of the Merger Agreement					22
	Macatawa Merger-Related Compensation Proposal					22
	Adjournment Proposal					22
	INFORMATION ABOUT THE SPECIAL MEETING OF MACATAWA SHAREHOLDERS					23
	THE MERGER					26
	General					26
	The companies					26
	Macatawa’s proposals					27
	Background of the merger					27
	Opinion of Macatawa’s Financial Advisor					34
	Dividend Discount Analysis					38
	Macatawa Analyst Price Targets Analysis					40
	Certain unaudited prospective financial information of Macatawa					42
	Macatawa’s reasons for the merger and recommendation of Macatawa board of directors					43
	Wintrust’s reasons for the merger					45
	Material U.S. federal income tax consequences of the merger					46
	Regulatory approvals					48
	Interests of Directors and Executive Officers in the Merger					49
	Voting agreement					53
	Restrictions on resale of Wintrust common stock					53
	Macatawa’s shareholder dissenters’ rights					53
	DESCRIPTION OF THE MERGER AGREEMENT					54
	General					54
	Closing and effective time					54
	Consideration to be received in the merger					54
	Upset Condition					55
	Fractional shares					56
	Exchange of certificates					56
	Conduct of business pending the merger and certain covenants					56
	No solicitation of or discussions relating to a Company Takeover Proposal					58
	Representations and warranties					60
	Conditions to completion of the merger					61
	Termination					62
	Termination fee					62
	Governance matters					63
	Employee benefit matters					63
	Expenses					63

	Nasdaq stock listing					63
	Amendment					64
	SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT OF MACATAWA					65
	COMPARISON OF RIGHTS OF WINTRUST SHAREHOLDERS AND MACATAWA SHAREHOLDERS					67
	DESCRIPTION OF WINTRUST CAPITAL STOCK					80
	LEGAL MATTERS					83
	EXPERTS					83
	SHAREHOLDER PROPOSALS					83
	WHERE YOU CAN FIND MORE INFORMATION					84
	Wintrust SEC Filings					84
	Macatawa SEC Filings					84
	ANNEX A: AGREEMENT AND PLAN OF MERGER					A-1
	ANNEX B: VOTING AGREEMENT					B-1
	ANNEX C: OPINION OF MACATAWA’S FINANCIAL ADVISOR					C-1

	Wintrust Common Stock			Macatawa Common Stock			Implied Per Share Value of Merger Consideration
April 12, 2024		$	97.00		$	9.59		$	14.85
[•], 2024			[•]			[•]			[•]

Acquiror / Target			Date Announced
Byline Bancorp, Inc. / Inland Bancorp, Inc.			November 30, 2022
Peoples Bancorp Inc. / Limestone Bancorp, Inc.			October 25, 2022
Southern Missouri Bancorp, Inc. / Citizens Bancshares Co.			September 20, 2022
HBT Financial, Inc. / Town and Country Financial Corporation			August 23, 2022
Bank First Corporation / Hometown Bancorp, Ltd.			July 26, 2022
Nicolet Bankshares, Inc. / Charter Bankshares, Inc.			March 30, 2022
Bank First Corporation / Denmark Bancshares, Inc.			January 19, 2022
QCR Holdings, Inc. / Guaranty Federal Bancshares, Inc.			November 9, 2021
First Merchants Corporation / Level One Bancorp, Inc.			November 4, 2021
German American Bancorp, Inc. / Citizens Union Bancorp of Shelbyville, Inc.			September 20, 2021
Arbor Bancorp, Inc. / FNBH Bancorp, Inc.			August 9, 2021
Stock Yards Bancorp, Inc. / Commonwealth Bancshares, Inc.			August 3, 2021
First Mid Bancshares, Inc. / Delta Bancshares Company			July 29, 2021
Old Second Bancorp, Inc. / West Suburban Bancorp, Inc.			July 26, 2021
Farmers National Banc Corp. / Cortland Bancorp			June 23, 2021
Nicolet Bankshares, Inc. / County Bancorp, Inc.			June 22, 2021
The Farmers & Merchants State Bank / Perpetual Federal Savings Bank			May 4, 2021
Nicolet Bankshares, Inc. / Mackinac Financial Corporation			April 12, 2021
Stock Yards Bancorp, Inc. / Kentucky Bancshares, Inc.			January 27, 2021
First Busey Corporation / Cummins-American Corp.			January 19, 2021

	Macatawa Metric			Multiple Range	Implied Value Per Share of Macatawa Common Stock
Price/Forward EPS		$	1.24	11.4x – 13.4x		$	14.14 – $16.62
Price/TBV		$	8.35	1.5x – 1.7x		$	12.53 – $14.20

Macatawa Management Projections:	2024E			2025E			2026E			2027E			2028E
Net Income ($MM)		$	44.8		$	48.8		$	51.2		$	53.9		$	56.2
Earnings per Share ($)		$	1.31		$	1.42		$	1.49		$	1.57		$	1.64
Total Assets ($MM)		$	2,778		$	2,910		$	3,005		$	3,064		$	3,171
Avg. Assets for Leverage Ratio ($MM)		$	2,772		$	2,844		$	2,958		$	3,035		$	3,118
Return on Tangible Common Equity (%)			14.8%			—			—			—			—

Named Executive Officer	Cash ($)(1)		Equity ($)(2)		Total ($)
Jon W. Swets		718,182		253,984		972,166
Craig A. Hankinson		719,053		245,076		964,129
Jill A. Walcott		350,494		157,867		508,361

Named Executive Officer	Severance Based on Average Compensation ($)		Health Coverage Payment ($)		Total ($)
Jon W. Swets		697,979		20,202		718,182
Craig A. Hankinson		692,124		26,928		719,053
Jill A. Walcott		340,413		10,081		350,494

Name of Beneficial Owner	Sole Voting Power		Sole Dispositive Power		Shared Voting or Dispositive Power		Total Beneficial Ownership		Percent of Class(1)
White Bay Capital, LLLP(2) 3133 Orchard Vista Drive, S.E. Grand Rapids, Michigan 49546		5,319,788		5,319,788		—		5,319,788		15.5%
AllianceBernstein L.P.(3) 501 Commerce Street Nashville, Tennessee 37203		2,038,609		2,038,609		—		2,038,609		5.9%

	Amount and Nature of Beneficial Ownership(1)
Name of Beneficial Owner	Sole Voting and Dispositive Power		Shared Voting or Dispositive Power(2)		Total Beneficial Ownership		Percent of Class(3)
Nicole S. Dandridge		—		—		—		*
Charles A. Geenen		123,724		—		123,724		*
Ronald L. Haan		170,039		144,048		314,087		*
Craig A. Hankinson		17,606		64,136		81,742		*
Robert L. Herr		4,767		23,310		28,077		*
Birgit M. Klohs		17,269		—		17,269		*
Michael K. Le Roy		12,702		—		12,702		*
Douglas B. Padnos		120,087		15,781		135,868		*
Richard L. Postma		1,559,639		—		1,559,639		4.5%
Thomas P. Rosenbach		75,702		—		75,702		*
Jon W. Swets		148,512		1,995		150,507		*
Jill Walcott		87,970		393,152		481,122		1.4%
All directors and executive officers as a group (12 persons)		2,338,017		642,422		2,980,439		8.7%

			Wintrust Shareholder Rights			Macatawa Shareholder Rights
Authorized Capital Stock:			Wintrust is authorized to issue 100 million shares of common stock, no par value per share, and 20 million shares of preferred stock, no par value per share, which we refer to as Wintrust preferred stock. Of the 20 million shares of Wintrust preferred stock, five million have been designated as Fixed-to-Floating Rate Non-Cumulative Perpetual Preferred Stock, Series D (“Wintrust Series D Preferred”). Another 14,000 shares of Wintrust preferred stock have been designated as Fixed-Rate Reset Non-Cumulative Perpetual Preferred Stock, Series E (“Wintrust Series E Preferred”). On March 31, 2024, Wintrust had 61,736,715 shares of common stock outstanding, 5,000,000 shares of Wintrust Series D Preferred outstanding, and 11,500 shares of Wintrust Series E Preferred outstanding. Further issuance of shares of Wintrust’s preferred stock could affect the relative rights of the holders of its common stock, depending upon the exact terms, qualifications, limitations and relative rights and preferences, if any, of the shares of the preferred stock as determined by Wintrust’s board of directors.			Macatawa is authorized to issue 200 million shares of common stock, no par value per share, and 500,000 shares of preferred stock, no par value per share. On March 31, 2024, Macatawa had 34,361,562 shares of common stock outstanding.

	Wintrust Shareholder Rights	Macatawa Shareholder Rights
Dividends:	Subject to any rights to receive dividends to which holders of Wintrust preferred stock may be entitled, Wintrust may pay dividends if, as and when declared payable from time to time by its board of directors from any funds legally available therefor.	Macatawa may pay dividends as may be declared from time to time by its board of directors upon Macatawa’s outstanding shares out of funds legally available for such purposes which may be payable in cash or other property permitted by law. Under Section 345 of the MBCA, Macatawa may not pay a dividend if, after giving it effect, Macatawa would not be able to pay its debts as the debts become due in the usual course of business, or Macatawa’s total assets would be less than the sum of its total liabilities plus the amount that would be needed, if Macatawa were to be dissolved at the time of the dividend, to satisfy the preferential rights upon dissolution of shareholders of any class having preference over the common stock as to the payment of dividends.
Voting Securities Held by the Corporation	Wintrust’s by-laws provide that voting securities belonging to the corporation shall not be voted, directly or indirectly, at any meeting and shall not be counted in determining the total number of outstanding shares at any given time, but shares of its own stock held by the corporation in a fiduciary capacity may be voted and shall be counted in determining the total number of outstanding shares at any given time.	Macatawa’s bylaws provide that voting securities of another corporation or entity standing in the name of Macatawa, which are entitled to vote may be voted, in person or by proxy, by the chairman of the board or the president of Macatawa or by other persons as may be designated by the board of directors. Macatawa’s bylaws do not explicitly provide for voting shares of its own stock held by Macatawa.
Number of Directors, Classification:	The Wintrust board of directors currently consists of 14 members. Wintrust’s by-laws provide, however, that the number may be increased or decreased (provided the number is never less than eleven or more than 14) by an amendment of the by-laws by the shareholders, or by a resolution adopted by the majority of the board of directors. Wintrust’s board of directors consists of a single class of directors.	The Macatawa Board currently consists of ten members. Macatawa’s articles of incorporation provide that the number of directors may be determined from time to time by resolution adopted by at least 80% of the board of directors and a majority of the Continuing Directors. “Continuing Director” means any member of the board of directors of Macatawa who is unaffiliated with the interested shareholder and was a member of

	Wintrust Shareholder Rights	Macatawa Shareholder Rights
		the board prior to the time that the interested shareholder became an interested shareholder, and any successor of a Continuing Director who is unaffiliated with the interested shareholder and is recommended to succeed a Continuing Director by a majority of Continuing Directors then on the board.
		The Macatawa Board is divided into three classes, with each class as equal in number as possible. Directors are elected for a three year term.
Election of Directors; Vacancies:	Each Wintrust shareholder is entitled to vote the number of shares owned by such shareholder for as many persons as there are directors to be elected. The IBCA requires that directors be elected by the affirmative vote of a majority of the shares represented at the meeting and entitled to vote thereon. The Wintrust by-laws provide that no cumulative voting is permitted. Wintrust’s by-laws provide that any vacancy on the board of directors may be filled at an annual meeting or special meeting of the shareholders called for such purpose, or if such vacancy arises between meetings of shareholders, by a majority vote of the board of directors then in office.	Each holder of Macatawa common stock is entitled to one vote for each share of stock entitled to vote. A plurality of the shares voted is required to elect a director. This means that, if there are more nominees than positions to be filled, the nominees who receive the most votes will be elected to the open director positions. The Macatawa organizational documents do not provide for cumulative voting. Macatawa’s articles of incorporation provide that any vacancy on the board of directors that arises for any reason may be filled only by the board of directors acting by an affirmative vote of a majority of the Continuing Directors and an 80% majority of all the directors then in office, even if less than a quorum.
Removal of Directors:	A Wintrust director may be removed at a shareholders’ meeting, with or without cause, by the affirmative vote of a majority of the outstanding shares entitled to vote.	Any Macatawa director may be removed at any time, with or without cause, by either (i) the affirmative vote of a majority of the Continuing Directors and at least 80% of the board of directors or (ii) the affirmative vote of the holders of at least 80% of the voting power of the outstanding shares of capital stock of Macatawa entitled to vote generally in the election directors, voting together as a single class.

	Wintrust Shareholder Rights	Macatawa Shareholder Rights
Call of Special Meeting of Directors:	Wintrust’s by-laws provide that a special meeting of the board of directors may be called by or at the request of the chairman of the board, president or a majority of then-acting directors.	Macatawa’s bylaws provide that a special meeting of the board of directors may be called by the chairman of the board or the president. The chairman of the board or the president are required to call a special meeting on the request of any two directors.
Limitation on Director Liability:	Wintrust’s articles of incorporation provide that no director will be personally liable to the corporation or any of its shareholders for monetary damages for any breach of fiduciary duty except for liability: • for any breach of the director’s duty of loyalty to the corporation or its shareholders; • for acts and omissions not in good faith or that involve intentional misconduct or a knowing violation of law; • under Section 8.65 of the IBCA (which creates liability for unlawful distributions to shareholders), as it exists or hereafter may be amended; or • for any transaction from which the director derived an improper personal benefit.	Macatawa’s articles of incorporation provide that no director will be personally liable to Macatawa or its shareholders for monetary damages for breach of fiduciary duty except for limitations on liability not permitted under the MBCA including: • for any transaction from which the director derived a financial benefit to which they were not entitled; • for intentionally inflicted harm on Macatawa or its shareholders; • for violating Section 551 of the MBCA; or • for intentionally committing a criminal act.
Indemnification:	Wintrust’s articles of incorporation and by-laws provide that Wintrust has the power to indemnify its directors, officers, employees and agents to the fullest extent authorized by the IBCA. The by-laws provide that, to the extent a present or former director, officer or employee of the corporation (or of any subsidiary, as the case may be) has been successful on the merits or otherwise in defense of any proceeding, or in connection with any claim, issue or matter therein, the corporation shall indemnify the director or officer against expenses actually and reasonably incurred by him or her in connection with such proceeding to the extent he or	Macatawa’s bylaws and articles of incorporation provide that the corporation has the power to indemnify its directors and executive officers to the fullest extent permitted by law. Macatawa’s bylaws and articles of incorporation provide that, to the extent a present or former director, officer or employee of Macatawa (or of any subsidiary, as the case may be) has been successful on the merits or otherwise in defense of any proceeding, or in connection with any claim, issue or matter therein, Macatawa shall indemnify the director or officer against expenses actually and reasonably incurred by him or her in connection with such proceeding

	Acceptable Company Confidentiality Agreement					A-33
	Acceptance Period					A-6
	Adjusted Per Share Merger Consideration					A-6
	Aggregate Share Amount					A-3
	Average Purchaser Closing Price					A-6
	Borrowing Affiliate					A-32
	Certificate of Merger					A-2
	Closing					A-1
	Closing Date					A-2
	Code					A-1
	Company					A-1
	Company Acquisition Agreement					A-34
	Company Adverse Recommendation Change					A-34
	Company Board Recommendation					A-7
	Company Common Stock					A-9
	Company Confidentiality Agreement					A-39

	Company Designated Director					A-41
	Company Disclosure Letter					A-7
	Company Financial Statements					A-9
	Company Investment Banker					A-21
	Company Lease					A-14
	Company Material Contract					A-15
	Company Real Property					A-13
	Company Retirement Plan					A-38
	Company SEC Reports					A-22
	Company Shareholder Approval					A-7
	Company Shareholder Meeting					A-35
	Company Subsidiaries					A-7
	Company Subsidiary					A-7
	Company Superior Proposal					A-35
	Company Takeover Proposal					A-34
	Company Termination Fee					A-45
	Company-Leased Real Property					A-13
	Company-Owned Intellectual Property					A-14
	Company-Related Person					A-21
	Confidentiality Agreements					A-39
	Constituent Company					A-1
	Continuing Employee					A-37
	Effective Time					A-2
	Employment-Related Payments					A-18
	End Date					A-44
	Exchange Agent					A-3
	Exchange Fund					A-4
	Excluded Shares					A-3
	Exercise Period					A-6
	Final Index Price					A-6
	Floor Purchaser Price					A-6
	Increase Notice					A-6
	Indemnified Party					A-39
	Initial Index Price					A-6
	Initial Term					A-41
	Intended Tax Treatment					A-40
	Materially Burdensome Regulatory Condition					A-37
	Maximum Amount					A-39
	MBCA					A-1
	Merger					A-1

	Per Share Merger Consideration					A-3
	Plan of Merger					A-1
	Pricing Period					A-6
	Proxy Statement					A-35
	Purchaser					A-1
	Purchaser Common Stock					A-26
	Purchaser Common Stock Price					A-3
	Purchaser Confidentiality Agreement					A-39
	Purchaser Disclosure Letter					A-24
	Purchaser Financial Statements					A-26
	Purchaser SEC Reports					A-28
	Purchaser Subsidiaries					A-25
	Purchaser Subsidiary					A-25
	Registration Statement					A-35
	Regulatory Agreement					A-11
	Requisite Regulatory Approvals					A-42
	Surviving Company					A-1
	Termination Date					A-44
	Upset Condition					A-6
	VWAP					A-3

PURCHASER:		COMPANY:
WINTRUST FINANCIAL CORPORATION		MACATAWA BANK CORPORATION
By:		By:
	Name: Timothy S. Crane		Name: Richard L. Postma
	Title: President and Chief Executive Officer		Title: Chairman of the Board of Directors

	Wintrust Shareholder Rights	Macatawa Shareholder Rights
	she was a party as a result of being a director, officer or employee, provided that such person acted in good faith and in a manner he or she reasonably believed to be in, or not opposed to, the best interests of the corporation. The board may indemnify agents of the corporation in this context. Wintrust has entered into individual indemnification agreements with each of its non-employee directors and certain of its executive officers, which we refer to as the “indemnification agreements,” which implement with more specificity the indemnification provisions provided by Wintrust’s by-laws and provide, among other things, that to the fullest extent permitted by applicable law, Wintrust will indemnify such director or officer against any and all losses, expenses and liabilities arising out of such director’s or officer’s service as a director or officer of Wintrust, as the case may be. The indemnification agreements also contain detailed provisions concerning expense advancement and reimbursement. The indemnification agreements are in addition to any other rights each non-employee director or officer may be entitled to under Wintrust’s articles of incorporation, by-laws and applicable law.	to the extent he or she was a party as a result of being a director, officer or employee, provided that such person acted in good faith and in a manner he or she reasonably believed to be in, or not opposed to, the best interests of Macatawa. The articles of incorporation provide that the right of indemnity is not exclusive and Macatawa can provide indemnification to anyone on terms that the board of directors approve and that are not inconsistent with the MBCA.
Call of Special Meetings of Shareholders:	Wintrust’s by-laws provide that a special meeting of its shareholders may be called by the board of directors, the president or the holders of not less than one-fifth of all the outstanding shares entitled to vote on the matter for which the meeting is called, for the purpose(s) stated in the call of the meeting. Written notice stating the place, date, hour and purpose(s) of the special meeting must be delivered, either personally or by mail, not	Macatawa’s bylaws provide that a special meeting of the shareholders may be called by resolution of a majority of the board of directors, by the chairman of the board, or by the president and must be held on a date fixed by the board of directors, the chairman of the board or the president. Written notice stating the time, place, if any, and purpose(s) of the special meeting must be delivered, either personally or by mail or, if permitted by the board of

	Wintrust Shareholder Rights	Macatawa Shareholder Rights
	less than ten nor more than 60 days before the date of the meeting.	directors, by a form of electronic transmission to which the shareholder has consented, not less than ten nor more than 60 days before the date of the meeting.
Quorum of Shareholders:	Wintrust’s by-laws provide that a majority of the votes of shares entitled to vote on a matter, present in person or represented by proxy, constitutes a quorum at any meeting of shareholders.	Macatawa’s bylaws provide that the number of shares entitled to cast a majority of the votes at a meeting constitute a quorum at the meeting.
Advance Notice Regarding Shareholders Proposals (other than Nomination of Candidates for Election to the Board of Directors):	Wintrust’s by-laws provide that, for a shareholder to properly bring business before an annual or special meeting of shareholders, written notice of such shareholder’s intent to make such proposal(s) must be given by personal delivery or U.S. mail postage prepaid and received by the secretary of the corporation no later than the following dates: (i) with respect to an annual meeting of shareholders, not less than 90 days nor more than 120 days prior to the anniversary date of the immediately preceding annual meeting of shareholders (provided, however, that in the event that the annual meeting is called for a date that is not within 30 days before or after such anniversary date, notice by the shareholder to be timely must be so delivered or received not later than the close of business on the tenth day following the earlier of the date on which such notice or public disclosure of the date of the meeting was given or made); and (ii) with respect to any special meeting of shareholders, the close of business on the tenth day following the date of public disclosure of the date of such meeting. A shareholder’s notice to the secretary shall set forth as to each item of business the shareholder proposes to bring before such meeting: (a) a brief description of the business desired to be brought	Macatawa’s articles of incorporation provide that, in order for a shareholder to properly bring business before an annual or special meeting of shareholders, a notice of proposal must be given, either by personal delivery or by U.S. mail, postage prepaid, and received by Macatawa no later than the following dates: (i) with respect to an annual meeting of shareholders, not later than 60 days nor more than 90 days prior to the first anniversary of the preceding year’s annual meeting (or, if the date of the annual meeting is changed by more than 20 days from such anniversary date, within ten days after the date Macatawa mails or otherwise gives notice of the date of such meeting); and (ii) with respect to any special meeting of shareholders, not later than the close of business on the tenth day following the date on which notice of the special meeting was first mailed to the shareholders by Macatawa. A shareholder’s notice of proposal must set forth: (a) the name and address of the shareholder submitting the proposal, as they appear on Macatawa’s books and records; (b) a representation that the shareholder (i) is a holder of record of stock of Macatawa entitled to vote at such meeting, (ii) will continue to hold such stock through the date on which the meeting is held, and (iii) intends to

			Wintrust Shareholder Rights			Macatawa Shareholder Rights
			before the meeting and the reasons for conducting the business at the meeting; (b) the name and record address of the shareholder who proposes such business; (c) the number and class of shares of stock of the corporation beneficially owned by such shareholder; (d) whether and the extent to which any derivative instrument, hedging or other transaction or series of transactions has been entered into by or on behalf of, or any other agreement, arrangement or understanding (including any short position or any borrowing or lending of shares) has been made the effect or intent of any of which is to increase or decrease economic interest in the corporation’s stock or manage the risk or benefit of share price changes for, or to increase or decrease the voting power of, such shareholder with respect to the corporation’s stock (which information shall be updated by such shareholder as of the record date for the meeting, such update to be provided not later than ten days after the record date for the meeting); (e) a representation that the shareholder intends to appear in person or by proxy at the meeting to introduce the item of business proposed to be brought before the meeting; (f) a description of all arrangements or understandings between the shareholder and any other person(s) pursuant to which the proposal or proposals are to be made by the shareholder and any material interest of the shareholder in the business being proposed; and (g) all other information which would be required to be included in a proxy statement filed with the SEC if, with respect to any such item of business or nomination, such shareholder were a participant in a solicitation subject to Section 14 of the Exchange Act.			appear in person or by proxy at the meeting to submit the proposal for shareholder vote; (c) a brief description of the proposal desired to be submitted to the meeting for shareholder vote and the reasons for conducting such business at the meeting; and (d) a description of any financial or other interest of such shareholder in the proposal.

	Wintrust Shareholder Rights	Macatawa Shareholder Rights
Advance Notice Regarding Shareholders Nomination of Candidates for Election to the Board of Directors:	Wintrust’s by-laws provide that nominations of persons for election to the board of directors may be made at an annual or special meeting of shareholders by a shareholder of Wintrust.	Macatawa’s articles of incorporation provide that nominations of person for election to the board of directors may be made by any shareholder of record entitled to vote in the election of directors.
	For nominations for election to the board of directors of Wintrust to be properly brought before an annual or special meeting, written notice of such shareholder’s intent to make such proposal(s) must be given by personal delivery or U.S. mail postage prepaid and received by the secretary of the corporation no later than the following dates: (i) with respect to an election to be held at an annual meeting of shareholders, not less than 90 days nor more than 120 days prior to the anniversary date of the immediately preceding annual meeting of shareholders (provided, however, that in the event that the annual meeting is called for a date that is not within 30 days before or after such anniversary date, notice by the shareholder to be timely must be so delivered or received not later than the close of business on the tenth day following the earlier of the date on which such notice or public disclosure of the date of the meeting was given or made); and (ii) with respect to an election to be held at any special meeting of shareholders called for the purpose of electing directors, the close of business on the tenth day following the date of public disclosure of the date of such meeting. A shareholder’s notice to the secretary shall set forth each item described above under “Advance Notice Regarding Shareholders Proposals (other than Nomination of Candidates for Election to the Board of Directors)” as well as (a) the nominee’s name, age, principal occupation and	For a shareholder’s nomination for election to the board of directors of Macatawa to be properly brought before an annual or special meeting, written notice must be given by personal delivery or U.S. mail, postage prepaid and received by the corporation no later than the following dates: (i) with respect to an election to be held at an annual meeting of shareholders, not later than 60 days nor more than 90 days prior to the first anniversary of the preceding year’s annual meeting (or, if the date of the annual meeting is changed by more than 20 days from such anniversary date, within ten days after the date Macatawa mails or otherwise gives notice of the date of such meeting); and (b) with respect to an election to be held at a special meeting of shareholders called for that purpose, not later than the close of business on the tenth day following the date on which notice of the special meeting was first mailed to the shareholders by Macatawa. A shareholder’s notice of intent to make a nomination shall set forth: (i) the name(s) and address(es) of the shareholder who intends to make the nomination and of the person or persons to be nominated; (ii) a representation that the shareholder (a) is a holder of record of stock of Macatawa entitled to vote at such meeting, (b) will continue to hold such stock through the date on which the meeting is held, and (c) intends to appear in person or by proxy at the meeting to nominate the person or persons specified in the notice;

	Wintrust Shareholder Rights	Macatawa Shareholder Rights
	employment, business and residence addresses and qualifications, (b) a description of all arrangements or understandings between the shareholder and each nominee of the shareholder and any other person or persons (naming such person or persons) pursuant to which the nominations are to be made by the shareholder and (c) the consent of each nominee to be named in any proxy statement and to serve as a director of Wintrust if so elected.	(iii) a description of all arrangements or understandings between the shareholder and each nominee and any other person or persons (naming such person or persons) pursuant to which the nomination is to be made by the shareholder; (iv) such other information regarding each nominee proposed by such shareholder as would be required to be included in a proxy statement filed pursuant to Regulation 14A promulgated under Section 14 of the Exchange Act, as amended, as now in effect or hereafter modified; and (v) the consent of each nominee to serve as a director of Macatawa if so elected.
Shareholder Action by Written Consent:	Wintrust’s articles of incorporation and by-laws provide that its shareholders are not permitted to act by written consent. Any action required or permitted to be taken at a meeting of the shareholders must be effected at a duly called annual or special meeting.	Macatawa’s articles of incorporation do not permit shareholders to act by written consent. Any action required or permitted to be taken at a meeting of the shareholders must be effected at a duly called annual or special meeting
Appointment and Removal of Officers:	Wintrust’s by-laws provide that the officers shall be elected annually by the board of directors at the first meeting of the board of directors held after each annual meeting of the shareholders. Each officer will hold office until his successor is duly elected and qualified or until his prior death, resignation or removal. Any officer may be removed by the board of directors whenever in its judgment the best interests of the corporation will be served thereby.	Macatawa’s bylaws provide that the board of directors shall appoint officers of Macatawa. Each officer will hold office for an indefinite term at the pleasure of the board. Any officer may be removed by the board of directors at any time and for any reason.
Required Vote for Certain Transactions:	The Wintrust articles of incorporation do not specifically discuss the required vote for transactions involving merger, consolidation, or sale, lease or exchange of all or substantially all of the property or assets of the corporation. However, the applicable IBCA provisions state that such a transaction must be approved by two-thirds of the	The Macatawa bylaws specify that any action to be taken by vote of the shareholders, other than the election of directors, shall be authorized by a majority of the votes cast by the holders of shares entitled to vote thereon unless a greater plurality is required by the express provisions of the MBCA. The MBCA provides that a transaction, such as the merger,

	Wintrust Shareholder Rights	Macatawa Shareholder Rights
	outstanding shares of stock entitled to vote on the matter. The corporation may, however, without approval by a vote of shareholders, merge into itself any corporation of which at least 90% of the outstanding shares of each class is owned by the corporation.	must be recommended by the board of directors to the shareholders and receive an affirmative vote of the holders of a majority of the outstanding shares of Macatawa unless a greater vote is required in the articles of incorporation.
Amendment to Charter and By-laws:	An amendment to the articles of incorporation that relates to certain provisions, including, the prohibition of cumulative voting, shareholder purchase rights, the prohibition of shareholder action by written consent, director liability, indemnification and insurance, number, tenure and qualification of directors or the amendment process, must be approved by the affirmative vote of the holders of 85% or more of the voting power of the then-outstanding shares of stock entitled to vote generally in the election of directors, voting together as a single class. Otherwise, as provided by the IBCA, the articles of incorporation may be amended by the affirmative vote of at least two-thirds of the shares entitled to vote on the proposal after the board of directors has passed a resolution by majority vote setting forth the proposed amendment and directing that it be submitted to a vote at a shareholders’ meeting. The power to make, alter, amend or repeal the by-laws of the corporation is vested in the shareholders or the board of directors by a resolution adopted by a majority of the board of directors.	An amendment to or repeal of Article VIII, Article IX, Article X, Article XI or XII of the articles of incorporation requires the affirmative vote of the holders of 80% or more of the outstanding shares of capital stock entitled to vote for the election of directors, voting together as a single class unless such amendment or repeal has been recommended for approval by at least 80% of all directors then holding office and by a majority of the Continuing Directors. Otherwise, the MBCA provides that amendments to the Macatawa articles of incorporation generally may be proposed by the Macatawa board of directors and approved by the affirmative vote of a majority of the outstanding shares entitled to vote on the proposed amendment. Macatawa’s bylaws may be amended by a majority vote of the board of directors at any regular or special meeting, without prior notice of intent to do so, or by vote of the holders of a majority of the outstanding voting shares of Macatawa at any annual or special meeting if notice of the proposed amendment is contained in the notice of the meeting.

	ARTICLE I THE MERGER					A-1
	1.1 Merger					A-1
	1.2 The Closing					A-1
	1.3 Effective Time of Merger					A-2
	1.4 Additional Actions					A-2
	1.5 Surviving Company					A-2
	1.6 Reservation of Right to Revise Structure					A-2
	ARTICLE II EFFECT OF MERGER ON CAPITAL STOCK					A-2
	2.1 Conversion of Securities					A-2
	2.2 Exchange Procedure					A-3
	2.3 Distributions with Respect to Unexchanged Shares					A-4
	2.4 No Further Ownership Rights in Company Common Stock					A-5
	2.5 No Liability					A-5
	2.6 Lost, Stolen or Destroyed Certificates					A-5
	2.7 Withholding Rights					A-5
	2.8 No Fractional Shares					A-5
	2.9 Adjustments					A-5
	2.10 Upset Condition					A-6
	ARTICLE III COMPANY’S REPRESENTATIONS AND WARRANTIES					A-7
	3.1 Authorization, No Conflicts, Etc.					A-7
	3.2 Organization and Good Standing					A-8
	3.3 Subsidiaries					A-8
	3.4 Capital Stock					A-9
	3.5 Financial Statements					A-9
	3.6 Absence of Certain Changes or Events					A-10
	3.7 Legal Proceedings					A-10
	3.8 Regulatory Filings					A-10
	3.9 No Indemnification Claims					A-10
	3.10 Conduct of Business; Compliance with Law					A-10
	3.11 Transaction Documents					A-11
	3.12 Agreements With Bank Regulators					A-11
	3.13 Tax Matters					A-11
	3.14 Properties					A-13
	3.15 Intellectual Property					A-14
	3.16 Required Licenses, Permits, Etc.					A-14
	3.17 Material Contracts and Change of Control					A-15
	3.18 Labor and Employment Matters					A-16
	3.19 Employee Benefits					A-18
	3.20 Environmental Matters					A-20
	3.21 Duties as Fiduciary					A-20
	3.22 Investment Bankers and Brokers					A-21

	3.23 Company-Related Persons					A-21
	3.24 Change in Business Relationships					A-21
	3.25 Insurance					A-21
	3.26 Allowance for Credit Losses					A-22
	3.27 Loan Origination and Servicing					A-22
	3.28 Data Security and Customer Privacy					A-22
	3.29 Loans and Investments					A-22
	3.30 Securities Laws Matters					A-22
	3.31 Investment Securities					A-23
	3.32 Books and Records					A-23
	3.33 Community Reinvestment Act					A-24
	3.34 Bank Secrecy Act					A-24
	3.35 Takeover Statutes					A-24
	3.36 No Undisclosed Liabilities					A-24
	3.37 No Other Representations or Warranties					A-24
	ARTICLE IV PURCHASER’S AND MERGER SUB’S REPRESENTATIONS AND WARRANTIES					A-24
	4.1 Authorization, No Conflicts, Etc.					A-24
	4.2 Organization and Good Standing					A-25
	4.3 Subsidiaries					A-26
	4.4 Capital Stock					A-26
	4.5 Financial Statements					A-26
	4.6 Absence of Certain Changes or Events					A-27
	4.7 Legal Proceedings					A-27
	4.8 Regulatory Filings					A-27
	4.9 Conduct of Business					A-27
	4.10 Transaction Documents					A-27
	4.11 Agreements With Bank Regulators					A-28
	4.12 Investment Bankers and Brokers					A-28
	4.13 Allowance for Credit Losses					A-28
	4.14 Securities Laws Matters					A-28
	4.15 Community Reinvestment Act					A-28
	4.16 Bank Secrecy Act					A-29
	4.17 No Other Representations or Warranties					A-29
	ARTICLE V COVENANTS					A-29
	5.1 Conduct of Business by Company					A-29
	5.2 Conduct of Business by Purchaser					A-32
	5.3 No Solicitation by Company					A-32
	5.4 Preparation of the Registration Statement; Shareholder Meeting					A-35
	5.5 Stock Exchange Listing					A-36
	5.6 Regulatory Matters and Approvals					A-36
	5.7 Employee Matters					A-37
	5.8 Press Releases and Public Announcement					A-38

	5.9 Access to Information					A-38
	5.10 Indemnification and Insurance					A-39
	5.11 Takeover Laws					A-40
	5.12 Securityholder Litigation					A-40
	5.13 Tax-Free Reorganization Treatment					A-40
	5.14 Expenses					A-40
	5.15 Miscellaneous Agreements and Consents					A-41
	5.16 Advice of Changes					A-41
	5.17 280G Matters					A-41
	5.18 Section 16 Matters					A-41
	5.19 Dividends					A-41
	5.20 Governance Matters					A-41
	5.21 Post-Signing Deliveries					A-42
	ARTICLE VI CLOSING CONDITIONS					A-42
	6.1 Conditions to Each Party’s Obligation to Effect the Merger					A-42
	6.2 Conditions to Company’s Obligation to Effect the Merger					A-42
	6.3 Conditions to Purchaser’s Obligation to Effect the Merger					A-43
	ARTICLE VII TERMINATION					A-44
	7.1 Termination of Plan of Merger					A-44
	7.2 Effect of Termination					A-45
	ARTICLE VIII CERTAIN DEFINITIONS					A-46
	ARTICLE IX MISCELLANEOUS					A-53
	9.1 No Third-Party Beneficiaries					A-53
	9.2 Specific Performance					A-53
	9.3 Entire Agreement					A-54
	9.4 Succession and Assignment					A-54
	9.5 Construction					A-54
	9.6 Exclusive Jurisdiction					A-54
	9.7 Waiver of Jury Trial					A-54
	9.8 Notices					A-54
	9.9 Governing Law					A-55
	9.10 Counterparts					A-55
	9.11 Headings					A-55
	9.12 Calculation of Dates and Deadlines					A-55
	9.13 Severability					A-55
	9.14 Non-Survival of Representations, Warranties and Agreements					A-55
	9.15 Amendments					A-55

	Principal Shareholders			Shares Owned
	Name:
	Name:
	Name:
	Name:
	Name:
	Name:
	Name:

	Exhibit Number			Description of Exhibit
	2.1**			Agreement and Plan of Merger, by and among Wintrust Financial Corporation, Leo Subsidiary LLC and Macatawa Bank Corporation, dated April 15, 2024 (included as Annex A to this proxy statement/prospectus).*
	3.1			Amended and Restated Articles of Incorporation of Wintrust Financial Corporation, as amended (incorporated by reference to Exhibit 3.1 of Wintrust’s Quarterly Report on Form 10-Q for the quarter ended June 30, 2006, Exhibits 3.1 and 3.2 of Wintrust’s Current Report on Form 8-K filed with the SEC on July 29, 2011 and Exhibit 3.1 of Wintrust’s Quarterly Report on Form 10-Q for the quarter ended June 30, 2012).
	3.2			Restated Certificate of Designations of Wintrust filed on May 5, 2023 with the Secretary of State of the State of Illinois designating the preferences, limitations, voting powers and relative rights of the Series D Preferred Stock (incorporated by reference to Exhibit 3.2 of Wintrust’s Quarterly Report on Form 10-Q for the quarter ended March 31, 2023).
	3.3			Certificate of Designations of Wintrust filed on May 7, 2020 with the Secretary of State of the State of Illinois designating the preferences, limitations, voting powers and relative rights of the Series E Preferred Stock (incorporated by reference to Exhibit 3.1 of Wintrust’s Current Report on Form 8-K filed with the Securities and Exchange Commission on May 8, 2020).
	3.4			Amended and Restated By-laws of Wintrust, as amended (incorporated by reference to Exhibit 3.2 of Wintrust’s Current Report on Form 8-K filed with the Securities and Exchange Commission on August 1, 2023).
	5.1**			Opinion of Kathleen M. Boege.
	8.1#			Tax Opinion of ArentFox Schiff LLP.
	8.2#			Tax Opinion of Warner Norcross + Judd LLP.
	9.1**			Form of Voting and Support Agreement (included as Annex B to this proxy statement/prospectus).
	23.1**			Consent of Ernst & Young LLP.
	23.2**			Consent of BDO USA, P.C.
	23.3**			Consent of Morgan Stanley & Co. LLC.
	23.4**			Consent of Kathleen M. Boege (included in Exhibit 5.1).
	23.5#			Consent of ArentFox Schiff LLP (included in Exhibit 8.1).
	23.6#			Consent of Warner Norcross + Judd LLP (included in Exhibit 8.2).
	24.1**			Power of Attorney (contained in signature page to this Registration Statement).
	99.1#			Form of proxy card.
	107**			Filing Fee Table.

Name	Title	Date
/s/ TIMOTHY S. CRANE Timothy S. Crane	President, Chief Executive Officer and Director (Principal Executive Officer)	May 30, 2024
/s/ DAVID L. STOEHR David L. Stoehr	Executive Vice President and Chief Financial Officer (Principal Financial Officer)	May 30, 2024
/s/ JEFFREY D. HAHNFELD Jeffrey D. Hahnfeld	Executive Vice President, Controller and Chief Accounting Officer (Principal Accounting Officer)	May 30, 2024
/s/ H. PATRICK HACKETT, JR. H. Patrick Hackett, Jr.	Director and Chairman of the Board	May 30, 2024
/s/ EDWARD J. WEHMER Edward J. Wehmer	Founder and Senior Advisor and Director	May 30, 2024
/s/ PETER D. CRIST Peter D. Crist	Director	May 30, 2024

	/s/ Kathleen Boege
	Kathleen M. Boege
	Executive Vice President, General Counsel, and Corporate Secretary

MORGAN STANLEY & CO. LLC

By:	/s/ Elizabeth Jacobs Kapp
Name:	Elizabeth Jacobs Kapp
Title:	Managing Director