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17,000,000 Depositary Shares, Each Representing a 1/1,000th Interest in a Shareof7.875% Fixed-Rate Reset Non-Cumulative Perpetual Preferred Stock, SeriesF We are offering to sell 17,000,000 depositary shares, each representing a 1/1,000th ownership interest in a share of 7.875% Fixed-RateReset Non-Cumulative Perpetual Preferred Stock, SeriesF, with a liquidation preference of $25,000 per share (equivalent to $25.00 perdepositary share) of Wintrust Financial Corporation, which we refer to as the Preferred Stock. The depositary shares are represented bydepositary receipts. As a holder of depositary shares, you will be entitled to all proportional rights and preferences of the PreferredStock (including dividend, voting, redemption and liquidation rights). You must exercise such rights through the depositary. We will pay dividends on the Preferred Stock when, as and if declared by our board of directors (the “Board”) or a duly authorizedcommittee of the Board and to the extent that we have lawfully available funds to pay dividends. Dividends will accrue on theliquidation preference of the Preferred Stock (i) from and including the original issuance date to, but excluding, July15, 2030, at afixed rate equal to 7.875% per annum, and (ii)from and including July15, 2030, during each reset period, at a rate per annum equal tothe five-year treasury rate as of the most recent reset dividend determination date (as described elsewhere in this prospectussupplement) plus 3.878%. Dividends will be payable in arrears on January15, April15, July15 and October15 of each year, beginningon October15, 2025. Dividends on the Preferred Stock will not be cumulative. If for any reason our Board or a duly authorized committee of the Board doesnot declare a dividend on the Preferred Stock in respect of a dividend period (as defined herein), then no dividend will be deemed tohave accrued for such dividend period or be payable, and we will have no obligation to pay any dividend for such dividend period tothe holder of the Preferred Stock, including the depositary, and no related distribution will be made on the depositary shares, whetheror not our Board or a duly authorized committee of the Board declares a dividend on the Preferred Stock for any future dividendperiod. Dividends on the Preferred Stock will not be declared, paid or set aside for payment to the extent such act would cause us tofail to comply with applicable laws and regulations, including applicable capital adequacy guidelines.We may, at our option, redeem the Preferred Stock, (i)in whole or in part, from time to time, on any dividend payment date on or after July15, 2030, or (ii)in whole but not in part, at any time within 90days following a “regulatory capital treatment event”(as definedherein), in each case, at a redemption price equal to $25,000 per share of Preferred Stock (equivalent to $25.00 per depositary share),plus any declared and unpaid dividends, without accumulation of any undeclared dividends to, but excluding, the redemption date. Ifwe redeem the Preferred Stock, the depositary will redeem a proportionate number of depositary shares. Neither the holders of thePreferred Stock nor holders of depositary shares will have the right to require redemption or repurchase of the Preferred Stock. ThePreferred Stock will not have any voting rights, except as set forth under “Description of Preferred Stock — Voting Rights” on pageS-25. A holder of depositary shares will be entitled to direct the depositary to vote in such circumstances. See “Description of DepositaryShares — Voting the Preferred Stock” on pageS-30. Prior to this offering, there has been no public market for the depositary shares. We intend to apply to list the depositary shares on TheNASDAQ Global Select Market under the symbol “WTFCN.” If the application is approved, we expect trading of the depositary shareson The NASDAQ Global Select Market to begin within the 30-day period after the initial delivery of the depositary shares. (1)Plus accrued dividends, if any, from May 22, 2025 to the original issuance date. (2)Reflects 14,608,000 depository shares sold to institutional investors, for which the underwriters received an underwritingdiscount of $0.5000 per depository share, and 2,392,000 depository shares sold to retail investors, for which the underwritersreceived an underwriting discount of $0.7875 per depository share. Investing in the depositary shares involves risks. See “Risk Factors” beginning on pageS-10and “Item1A. Risk Factors” in ourAnnualReport on Form10-K for the year ended December31, 2024for a discussion of certain risks that you should consider in connection with aninvestment in the depositaryshares.Neither the Securities and Exchange Commission nor any state securities commission has approved or disapproved of these securities or passed upon the accuracy or adequacy of this prospectus supplement or the accompanying prospectus. Any representation to the contrary isa criminal