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UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K ☑ Annual Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the fiscal year ended December 31, 2020 ☐ Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 For the Transition Period from to Commission File Number 001-35077 Wintrust Financial Corporation (Exact name of registrant as specified in its charter) Illinois 36-3873352 (State or other jurisdiction of incorporation or organization) (I.R.S. Employer Identification No.) 9700 W. Higgins Road, Suite 800 Rosemont, Illinois 60018 (Address of principal executive offices) Registrant’s telephone number, including area code: (847) 939-9000 Securities registered pursuant to Section 12(b) of the Act: Title of Each Class Trading Symbol(s) Name of Each Exchange on Which Registered Common Stock, no par value WTFC The NASDAQ Global Select Market Series D Preferred Stock, no par value WTFCM The NASDAQ Global Select Market Depositary Shares, Each Representing a 1/1,000th Interest in a Share of WTFCP The NASDAQ Global Select Market 6.875% Fixed-Rate Non-Cumulative Perpetual Series E Preferred Stock, no par value Securities registered pursuant to Section 12(g) of the Act: None Indicate by check mark if the registrant is a well-known seasoned issuer, as defined in Rule 405 of the Securities Act. þ Yes ¨ No Indicate by check mark if the registrant is not required to file reports pursuant to Section 13 or Section 15(d) of the Act. ¨ Yes þ No Indicate by check mark whether the registrant: (1) has filed all reports required to be filed by Section 13 or 15(d) of the Securities Exchange Act of 1934 during the preceding 12 months (or for such shorter period that the registrant was required to file such reports), and (2) has been subject to such filing requirements for the past 90 days. þ Yes ¨ No Indicate by check mark whether the registrant has submitted electronically, every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S-T (§232.405 of this chapter) during the preceding 12 months (or for such shorter period that the registrant was required to submit such files). þ Yes ¨ No Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company or an emerging growth company. See the definition of “large accelerated filer,” “accelerated filer,” “smaller reporting company,” and "emerging growth company" in Rule 12b-2 of the Exchange Act. Large accelerated filer ☑ Accelerated filer ☐ Non-Accelerated filer ☐ Smaller reporting company ☐ Emerging growth company ☐ If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ¨ Indicate by check mark whether the registrant has filed a report on and attestation to its management's assessment of the effectiveness of its internal controls over financial reporting under Section 404(b) of the Sarbanes-Oxley Act (15 U.S.C. 7262(b)) by the registered public accounting firm that prepared or issued its audit report. þ Yes ¨ No Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Act). ☐ Yes ☑ No The aggregate market value of the voting and non-voting common equity held by non-affiliates of the registrant on June 30, 2020 (the last business day of the registrant’s most recently completed second quarter), determined using the closing price of the common stock on that day of $43.62, as reported by the NASDAQ Global Select Market, was $2,490,791,184. As of February 22, 2021, the registrant had 56,891,238 shares of common stock outstanding. DOCUMENTS INCORPORATED BY REFERENCE Portions of the Proxy Statement for the Company’s Annual Meeting of Shareholders to be held on May 27, 2021 are incorporated by reference into Part III. TABLE OF CONTENTS Page PART I ITEM 1 Business............................................................................................................................................ 3 ITEM 1A. Risk Factors....................................................................................................................................... 22 ITEM 1B. Unresolved Staff Comments............................................................................................................. 42 ITEM 2. Properties ......................................................................................................................................... 43 ITEM 3. Legal Proceedings ............................................................................................................................ 43 ITEM 4. Mine Safety Disclosures .................................................................................................................. 43 PART II Market for Registrant’s Common Equity, Related Stockholder Matters and Issuer Purchases of ITEM 5. Equity Securities .............................................................................................................................. 44 ITEM 6. Selected Financial Data..................................................................................................................... 47 ITEM 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations .......... 48 ITEM 7A. Quantitative and Qualitative Disclosures About Market Risk.......................................................... 98 ITEM 8. Financial Statements and Supplementary Data................................................................................. 100 ITEM 9. Changes in and Disagreements with Accountants on Accounting and Financial Disclosure .......... 180 ITEM 9A. Controls and Procedures .................................................................................................................. 181 ITEM 9B. Other Information............................................................................................................................. 184 PART III ITEM 10. Directors, Executive Officers and Corporate Governance................................................................ 184 ITEM 11. Executive Compensation................................................................................................................... 184 Security Ownership of Certain Beneficial Owners and Management and Related Stockholder ITEM 12. Matters.............................................................................................................................................. 184 ITEM 13. Certain Relationships and Related Transactions, and Director Independence................................. 185 ITEM 14. Principal Accountant Fees and Services........................................................................................... 185 PART IV ITEM 15. Exhibits, Financial Statement Schedules.......................................................................................... 186 ITEM 16. Form 10-K Summary........................................................................................................................ 192 Signatures.......................................................................................................................................... 193 PART I ITEM 1. BUSINESS Overview Wintrust Financial Corporation, an Illinois corporation (“we,” “Wintrust” or “the Company”), which was incorporated in 1992, is a financial holding company based in Rosemont, Illinois, with total assets of approximately $45.1 billion as of December 31, 2020. We provide community-oriented, personal and commercial banking services to customers located in the Chicago metropolitan area, southern Wisconsin and northwest Indiana (“our market area”) through our fifteen wholly-owned-banking subsidiaries (collectively, the “banks”), as well as the origination and purchase of residential mortgages for sale into the secondary market through Wintrust Mortgage, a division of Barrington Bank & Trust Company, N.A. (“Barrington Bank”). In addition, we provide specialty finance services, including financing for the payment of commercial insurance premiums and life insurance premiums (“premium finance receivables”) on a national basis through FIRST Insurance Funding, a division of our wholly-owned subsidiary Lake Forest Bank & Trust Company, N.A. (“Lake Forest Bank”), and Wintrust Life Finance, a division of Lake Forest Bank, and in Canada through our premium finance company, First Insurance Funding of Canada (“FIFC Canada”), lease financing and other direct leasing opportunities through our wholly-owned subsidiary, Wintrust Asset Finance, Inc. (“Wintrust Asset Finance”), and short-term accounts receivable financing and outsourced administrative services through our wholly-owned subsidiary, Tricom, Inc. of Milwaukee (“Tricom”). Further, we provide a full range of wealth management services primarily to customers in our market area through four separate subsidiaries, The Chicago Trust Company, N.A. (“CTC”), Wintrust Investments, LLC (“Wintrust Investments”), Great Lakes Advisors, LLC (“Great Lakes Advisors”) and Chicago Deferred Exchange Company, LLC (“CDEC”). Our Business and Reporting Segments As set forth in Note 24, “Segment Information,” our operations consist of three primary segments: community banking, specialty finance and wealth management. The three reportable segments are strategic

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