Material Agreement (Form 8-K)

On May 8, 2025, Wintrust Financial Corporation (the "Company") entered into an Underwriting Agreement (the "Underwriting Agreement") with RBC Capital Markets, LLC, as representative of the several underwriters named in Schedule A thereto (the "Underwriters"), providing for the offer and sale in a firm commitment underwritten public offering (the "Offering") of 17,000,000 depositary shares (the "Depositary Shares"), each representing a 1/1,000th interest in a share of the Company's 7.875% Fixed-Rate Reset Non-Cumulative Perpetual Preferred Stock, Series F, no par value per share (the "Series F Preferred Stock"), with a liquidation preference of $25,000 per share (equivalent to $25.00 per Depositary Share).

The Underwriting Agreement includes customary representations, warranties and covenants by each of the Company and the Underwriters related to the Offering. The Company also agreed to indemnify the Underwriters against certain liabilities, including liabilities under the Securities Act of 1933, as amended, and to customary contribution provisions in respect of those liabilities.

The Offering is being conducted pursuant to the Prospectus Supplement, dated May 8, 2025 (the "Prospectus Supplement"), to the Prospectus dated May 9, 2023, forming a part of the Company's effective shelf registration statement on Form S-3 (File No. 333-271788). The Offering is expected to close on May 22, 2025, subject to customary closing conditions.

The estimated net proceeds from the Offering, after deducting the underwriting discounts and estimated offering expenses payable by the Company, will be approximately $414.7 million.

The Company intends to use the net proceeds from the Offering for general corporate purposes, which may include the redemption of all or a portion of our outstanding shares of Series D preferred stock and/or Series E preferred stock and the corresponding depositary shares representing interests in the Series E preferred stock, subject to approval from the Federal Reserve. Pending such use, the net proceeds may be invested in cash or short-term marketable securities.

Certain affiliates of the Underwriters serve as lenders and administrative agent under the Company's existing credit facilities, the terms of which are set forth in the Company's amended and restated credit agreement, dated December 12, 2022, as amended, among the Company, the lenders named therein and U.S. Bank National Association, as administrative agent. In addition, U.S. Bank Trust Company, National Association, an affiliate of one of the Underwriters, will act as the registrar and depositary for the Depositary Shares. The Underwriters and their respective affiliates also have engaged in, and may in the future engage in, commercial banking, financial advisory, investment banking and other commercial dealings in the ordinary course of business with the Company or its affiliates and have received, or may in the future receive, customary fees and commissions for those transactions, plus customary reimbursement of out-of-pocket expenses.

The foregoing description of the Underwriting Agreement is qualified in its entirety by reference to the full text of the Underwriting Agreement, a copy of which is attached hereto as Exhibit 1.1 and is incorporated herein by reference.