0000950123-10-112849 Sample Contracts

WINTRUST FINANCIAL CORPORATION (an Illinois corporation) 3,205,128 Shares of Common Stock PURCHASE AGREEMENT
Purchase Agreement • December 10th, 2010 • Wintrust Financial Corp • State commercial banks • New York

Merrill Lynch, Pierce, Fenner & Smith Incorporated Sandler O’Neill & Partners, L.P. as Representatives of the several Underwriters

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WINTRUST FINANCIAL CORPORATION, U.S. BANK NATIONAL ASSOCIATION, as Purchase Contract Agent and U.S. NATIONAL BANK ASSOCIATION, as Trustee under the Indenture referred to herein PURCHASE CONTRACT AGREEMENT Dated as of December 10, 2010
Purchase Contract Agreement • December 10th, 2010 • Wintrust Financial Corp • State commercial banks • New York

PURCHASE CONTRACT AGREEMENT, dated as of December 10, 2010, among WINTRUST FINANCIAL CORPORATION, an Illinois corporation (the “Company”), U.S. BANK NATIONAL ASSOCIATION, a national banking association, acting as purchase contract agent and attorney-in-fact for the Holders of Purchase Contracts (as defined herein) from time to time (the “Purchase Contract Agent”), and U.S. BANK NATIONAL ASSOCIATION, acting as Trustee under the Indenture (as defined herein).

WINTRUST FINANCIAL CORPORATION, as Issuer and U.S. BANK NATIONAL ASSOCIATION, as Trustee First Supplemental Indenture Dated as of December 10, 2010 Supplement to Junior Subordinated Indenture of Wintrust Financial Corporation dated as of December 10, 2010
Wintrust Financial Corp • December 10th, 2010 • State commercial banks • New York

FIRST SUPPLEMENTAL INDENTURE, dated as of December 10, 2010 (this “First Supplemental Indenture”), between WINTRUST FINANCIAL CORP., an Illinois corporation (the “Company,” which term includes any successor as permitted in accordance with the terms of the Indenture hereafter referred to), and U.S. BANK NATIONAL ASSOCIATION, not in its individual capacity but solely as trustee (the “Trustee”) under the Junior Subordinated Indenture, dated as of December 10, 2010, between the Company and the Trustee (the “Base Indenture,” and the Base Indenture, as supplemented by this First Supplemental Indenture, the “Indenture”).

WINTRUST FINANCIAL CORPORATION (an Illinois corporation) 4,000,000 Tangible Equity Units PURCHASE AGREEMENT
Purchase Agreement • December 10th, 2010 • Wintrust Financial Corp • State commercial banks • New York

Wintrust Financial Corporation, an Illinois corporation (the “Company”) confirms its agreement with Merrill Lynch, Pierce, Fenner & Smith Incorporated (“Merrill Lynch”) and each of the other Underwriters named in Schedule A hereto (collectively, the “Underwriters,” which term shall also include any underwriter substituted as hereinafter provided in Section 10 hereof), for whom Merrill Lynch is acting as representative (in such capacity, the “Representative”), with respect to (i) the sale by the Company and the purchase by the Underwriters, acting severally and not jointly, of the respective numbers of tangible equity units of the Company (“Tangible Equity Units”) set forth in Schedule A hereto and (ii) the grant by the Company to the Underwriters , acting severally and not jointly, of the option described in Section 2(b) hereof to purchase all or any part of 600,000 additional Tangible Equity Units to cover overallotments, if any. The aforesaid 4,000,000 Tangible Equity Units (the “Ini

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