DEF 14A of Wintrust Financial Corp, Apr 9, 2026

DEF 14A of Wintrust Financial Corp

Filed Apr 9, 2026 · FY20250001104659-26-041498

Open on EDGAR

  1. WINTRUST FINANCIAL CORPORATION NOTICE OF ANNUAL MEETING OF SHAREHOLDERS TO BE HELD ON MAY 28, 2026

    | About the Meeting | 1 | | Board of Directors, Committees and Governance | 4 | | Director Compensation | 16 | | Security Ownership of Certain Beneficial Owners, Directors and Management | 20 | | Delinquent Section 16(a) Reports | 21 | | Related Person Transactions | 22 | | Corporate Social Responsibility | 22 | | Proposal No. 1 — Election of Directors | 25 | | Executive Officers of the Company | 33 | | Executive Compensation — Compensation Discussion & Analysis | 35 | | 2025 Summary Compensation Table | 52 | | 2025 Grants of Plan-Based Awards Table | 53 | | 2025 Outstanding Equity Awards at Fiscal Year-End Table | 54 | | 2025 Option Exercises and Stock Vested Table | 56 | | 2025 Nonqualified Deferred Compensation Table | 56 | | Potential Payments Upon Termination or Change in Control | 57 | | Compensation Committee Report | 62 | | CEO Pay Ratio Disclosure | 62 | | Pay Versus Performance | 63 | | Equity Compensation Plan Information | 67 | | Proposal No. 2 — Approval of, on an Advisory (Non-Binding) Basis, the Company’s Executive Compensation as described in this Proxy Statement | 67 | | Report of the Audit Committee | 68 | | Proposal No. 3 — Ratification of Ernst & Young LLP to Serve as the Company’s Independent Registered Public Accounting Firm for Fiscal Year 2026 | 69 | | Audit and Non-Audit Fees Paid | 69 | | Shareholder Proposals for the 2027 Annual Meeting | 70 | | Other Business | 71 |

  2. Board of Directors

    Board of Directors

  3. DIRECTOR COMPENSATION

    DIRECTOR COMPENSATION The Company seeks to compensate its non-employee Directors in a manner that attracts and retains qualified candidates to serve on the Board and to compensate such Directors for their service on the Board in an amount that is commensurate with their role and involvement. In setting non-employee Director compensation, the Nominating Committee and the Board consider the significant amount of time the Directors expend in fulfilling their duties as well as the skill level required.

  4. 2025 Director Compensation Table

    2025 Director Compensation Table The table below summarizes the compensation paid by the Company to non-employee Directors for the fiscal year ended December 31, 2025.

  5. 2025 Director Compensation Table

    | Name | (b) Fees Earned or Paid in Cash ($)(1) | (c) Stock Awards ($) | (d) Option Awards ($) | (e) Change in Pension Value and Nonqualified Deferred Compensation Earnings ($) | (f) All Other Compensation ($)(2) | (g) Total ($) | | Elizabeth H. Connelly | 206,500 | — | — | — | 13,792 | 220,292 | | Peter D. Crist | 216,500 | — | — | — | 146,447 | 362,947 | | William J. Doyle | 180,000 | — | — | — | 34,538 | 214,538 | | Marla F. Glabe | 180,000 | — | — | — | 11,793 | 191,793 | | H. Patrick Hackett, Jr. | 220,000 | — | — | — | 6,253 | 226,253 | | Scott K. Heitmann(3) | 85,417 | — | — | — | 48,341 | 133,758 | | Brian A. Kenney | 194,583 | — | — | — | 1,170 | 195,753 | | Laura A. Kohl(4) | 45,000 | — | — | — | — | 45,000 | | Deborah L. Hall Lefevre | 205,000 | — | — | — | 29,204 | 234,204 | | Suzet M. McKinney | 181,500 | — | — | — | 5,646 | 187,146 | | Richard L. Postma(5) | 90,000 | — | — | — | 945 | 90,945 | | David S. Richter(4) | 45,000 | — | — | — | 6,641 | 51,641 | | Gregory A. Smith | 180,000 | — | — | — | 1,127 | 181,127 | | Karin Gustafson Teglia | 206,500 | — | — | — | 22,143 | 228,643 | | Alex E. Washington, III | 206,500 | — | — | — | 33,047 | 239,547 |

  6. 2025 Director Compensation Table

    (1) Represents fees for services as non-employee Directors of the Company. During 2025, certain Directors elected to receive fees in Common Stock, in lieu of cash payments, as follows:

  7. 2025 Director Compensation Table

    | Name | Fees Earned in Common Stock ($) | | Elizabeth H. Connelly | 206,500 | | Peter D. Crist | 216,500 | | William J. Doyle | 180,000 | | Marla F. Glabe | 180,000 | | Scott K. Heitmann | 34,167 | | Brian A. Kenney | 194,583 | | Laura A. Kohl | 45,000 | | Deborah L. Hall Lefevre | 205,000 | | Suzet M. McKinney | 181,500 | | Richard L. Postma | 90,000 | | David S. Richter | 45,000 | | Gregory A. Smith | 180,000 | | Karin Gustafson Teglia | 206,500 | | Alex E. Washington, III | 206,500 |

  8. 2025 Director Compensation Table

    As of December 31, 2025, Directors held unissued Units under the Director Plan as follows: Ms. Connelly: 8,006 Units; Mr. Crist: 74,224 Units; Mr. Doyle: 18,347 Units; Ms. Glabe: 1,560 Units; Mr. Hackett: 3,158 Units; Mr. Heitmann: 16,309 Units; Mr. Kenney: 1,589 Units; Ms. Kohl: 340 Units; Ms. Lefevre: 15,778 Units; Ms. McKinney: 1,521 Units; Mr. Postma: 769 Units; Mr. Richter: 393 Units; Mr. Smith: 1,473 Units; Ms. Teglia: 12,224 Units and Mr. Washington: 14,281 Units. Includes fees paid in cash and stock, both currently paid and deferred, for services as directors of the Company’s subsidiaries. Also includes dividends earned on fees deferred as described above. Directors with $10,000 or more in “All Other Compensation” for the fiscal year ended December 31, 2025 were: Ms. Connelly ($13,792 in dividends earned); Mr. Crist ($144,797 in dividends earned and $1,650 in fees for service as a director of one of the Company’s subsidiaries); Mr. Doyle ($34,538 in dividends earned); Ms. Glabe ($1,193 in dividends earned and $10,600 in fees for service as a director or member of the executive advisory committee of five of the Company’s subsidiaries or divisions); Mr. Heitmann ($32,091 in dividends earned and $16,250 in fees for service as a director of four of the Company’s subsidiaries); Ms. Lefevre ($29,204 in dividends earned); Ms. Teglia ($22,143 in dividends earned); and Mr. Washington ($26,147 in dividends earned and $6,900 in fees for service as a director of one of the Company’s subsidiaries). (3) Mr. Heitmann retired from the Board on May 22, 2025. (4) Ms. Kohl and Mr. Richter were appointed to the Board on October 1, 2025. Mr. Postma resigned from the Board on June 11, 2025.

  9. PROPOSAL NO. 1 — ELECTION OF DIRECTORS

    PROPOSAL NO. 1 — ELECTION OF DIRECTORS The Company’s Board is currently comprised of 14 Directors, each serving a term that will expire at this year’s Annual Meeting or until a successor has been elected and qualified. Immediately following the Annual Meeting, the size of the Board will be set at 12 Directors. The Board, acting pursuant to the recommendation of the Nominating Committee, has nominated each of the incumbent Directors for re-election, other than Messrs. Doyle and Hackett, who are not standing for re-election. Each nominee has indicated a willingness to serve, and the Board has no reason to believe that any of the nominees will not be available for election. However, if any of the nominees is not available for election, proxies may be voted for the election of other persons selected by the Board. Proxies cannot, however, be voted for a greater number of persons than the number of nominees named. Shareholders of the Company have no cumulative voting rights with respect to the election of Directors. It is expected that, pending election at the Annual Meeting, Brian A. Kenney will serve as non-executive Chairman of the Board following the Annual Meeting. Assuming each Director nominee is elected to serve on the Board until the next Annual Meeting, the membership of the Board and each of its committees following the Annual Meeting, is expected to be as reflected in the following chart.

  10. PROPOSAL NO. 1 — ELECTION OF DIRECTORS

    | Name | Age At Annual Meeting | Director Since | Committees | Subsidiaries/Divisions | | Elizabeth H. Connelly | 61 | 2022 | Compensation (Chair) Risk Management Executive | — | | Timothy S. Crane | 64 | 2023 | Executive | Shared officer and advisory director of each subsidiary | | Peter D. Crist | 74 | 1996 | Compensation Finance Nominating | — | | Marla F. Glabe | 72 | 2015 | Audit IT/IS | Great Lakes Advisors Wintrust Investments Wintrust Private Trust Company FIRST Insurance Funding Wintrust Life Finance | | Brian A. Kenney | 66 | 2023 | Executive (Chair) | — | | Laura A. Kohl | 57 | 2025 | IT/IS Risk Management | — | | Deborah L. Hall Lefevre | 58 | 2019 | IT/IS (Chair) Nominating Executive | — | | Suzet M. McKinney | 53 | 2021 | Audit Compensation | Great Lakes Advisors Wintrust Investments Wintrust Private Trust Company | | David S. Richter | 64 | 2025 | Risk Management (Chair) Finance Executive | Wintrust Bank | | Gregory A. Smith | 62 | 2024 | Finance (Chair) Audit Executive | — | | Karin Gustafson Teglia | 58 | 2019 | Audit (Chair) Compensation Executive | — | | Alex E. Washington, III | 52 | 2020 | Nominating (Chair) Finance Executive | Wintrust Bank |

  11. Nominees for Election at the 2026 Annual Meeting of Shareholders

    Nominees for Election at the 2026 Annual Meeting of Shareholders Elizabeth H. Connelly (61), Director since 2022. Ms. Connelly is chief commercial officer for CDW Corporation (Nasdaq: CDW) (“CDW”), a leading multi-brand technology solutions provider to business, government, education, and healthcare organizations in the United States, the United Kingdom, and Canada. She is responsible for managing all global sales, sales enablement and Marketing including short- and long-term performance goals, strategic direction, business initiatives, talent development, and the deepening of CDW’s relationships with, and relevance to, customers. She is also responsible for international operations. She has more than 30 years of experience in managing a spectrum of complex businesses, including human resources, commercial banking with a focus in the healthcare, higher education and not-for-profit sectors, and private wealth management. Ms. Connelly possesses a keen ability for building high-performing teams, fostering best-in-class culture, and delivering strong results. Before assuming her current CDW role in October 2024, Ms. Connelly also served as senior vice president of vertical markets and senior vice president of healthcare. She previously also served as chief human resources officer and senior vice president of coworker services for CDW, where she was responsible for the company’s coworker services strategy and all aspects of its human capital plan, including talent acquisition and employment branding, organizational and leadership development, sales training, compensation, benefits, performance management and succession planning. Prior to joining CDW in 2018, Ms. Connelly served as the head of the Healthcare, Higher Ed. and Not-for-Profit Commercial Banking business unit at J.P. Morgan Chase, a leading global financial services firm, where she led business groups that were national in scope and provided treasury, credit and specialized industry solutions to more than 3,000 clients. Previously, she served as the firm’s Midwest Region Head for the Private Wealth Management business unit, where she delivered investment, banking and trust services to high-net-worth individuals, families and foundations. Prior to joining J.P. Morgan Chase, Ms. Connelly held a series of roles with increasing responsibility at Bank One. Ms. Connelly earned a bachelor’s degree in foreign service from Georgetown University and a master’s degree in business administration from the Kellogg School of Management at Northwestern University. She serves on the board of directors for the Catholic Extension, the Polk Bros. Foundation, and the Shedd Aquarium. Additionally, Ms. Connelly is a member of the Georgetown University Board of Regents, the Healthcare at Kellogg Advisory Council, and the National Association of Corporate Directors. Ms. Connelly’s experience in the banking industry, including service in several leadership roles at J.P. Morgan Chase and Bank One, provide her with knowledge of the financial services business, generally, and the business of community banking in particular. Her experience in human resources and commercial leadership at CDW provides her with insight into executive compensation, attraction, and retention of talent, and the management of the commercial activities of a large public company. Timothy S. Crane (64), Director since 2023. Mr. Crane was appointed to serve as a Director of the Company in January 2023. He joined the Company in August 2008 and has held a series of executive management roles. Mr. Crane currently serves as President and Chief Executive Officer of the Company. Additionally, he currently serves as an Advisory Director for each of the Company’s main operating subsidiaries. Prior to the transition to his current role on May 1, 2023, Mr. Crane served as President of the Company since February 2020, after previously holding the title of Executive Vice President, Senior Market Head and Treasurer since February 2017, during which time he was responsible for oversight of Wintrust’s subsidiary banks, banking operations and treasury business. Previously, in January 2016, Mr. Crane was appointed to serve as Corporate Treasurer of the Company. Before joining the Company, Mr. Crane served as President of Harris Bankcorp (Harris Bank, Bank of Montreal) in Chicago, where he was employed for 24 years. He also serves on the boards of the Metropolitan Family Services, Millennium Park Foundation, and ProSight, and serves as a Trustee of DePaul University. Mr. Crane brings a wealth of knowledge to the Board of Directors relating to banking operations, regulations, financial management, and mergers and acquisitions. He is the only member of the Board who is also an executive officer of the Company. As such, he provides views of the management of the Company and substantial insight into the operations of the Company. Peter D. Crist (74), Director since 1996. Mr. Crist served as the Company’s Chairman from 2008 to 2017 and has served as the Chair of the Nominating Committee from 2017 to 2025. Mr. Crist founded Crist/ Kolder Associates, an executive recruitment firm, which focuses on chief executive officer and director searches, in 2003 and has served since inception as its Chairman and Chief Executive Officer. From December 1999 to January 2003, Mr. Crist served as Vice Chairman of Korn/Ferry International (NYSE: KFY), the largest executive search firm in the world. Previously, he was President of Crist Partners, Ltd., an executive search firm he founded in 1995 and sold to Korn/Ferry International in 1999. Immediately prior thereto he was Co-Head of North America and the Managing Director of the Chicago office of Russell Reynolds Associates, Inc., the largest executive search firm in the Midwest, where he was employed for more than 18 years. He currently serves as a director of Northwestern Memorial Hospital, where he is Chair of the Nominating and Corporate Governance Committee. Mr. Crist’s experience assisting companies with executive searches provides him with insight into the attraction and retention of Company personnel, an important concern of the Company. In addition, Mr. Crist’s experience as an executive of several large, Chicago-based businesses provides him with insight into the management and operational challenges and opportunities facing the Company in its markets. He also brings experience as the previous Chair of the Compensation Committee of Northwestern Memorial Hospital. Additionally, Mr. Crist’s past experience as a director of Hinsdale Bank gave him valuable insight into the Company’s banking operations. Marla F. Glabe (72), Director since 2015. Ms. Glabe has over 40 years of experience in the financial services industry including her service as a senior executive with Allstate Insurance Company (“Allstate”) and as a member of the board of directors of Allstate Life Insurance Company. From 1974 to 2009, she held various executive positions at Allstate and its affiliates. Subsequently, Ms. Glabe served as the Lead Managing Director for MasterMind Advisory Board, a corporation offering advisory services to CEOs and business entrepreneurs and as a member of the Board of Directors for Royal Neighbors of America, a fraternal life insurance company. Ms. Glabe is Senior Advisor for Management Control International, Inc., a privately owned family asset management firm, serves on the Northwest Community Hospital Foundation Board, and is a member of the Society of Actuaries. Ms. Glabe is a director of Great Lakes Advisors, Wintrust Investments, and Wintrust Private Trust Company and serves on the Executive Advisory Committee for First Insurance Funding and Wintrust Life Finance.

  12. Nominees for Election at the 2026 Annual Meeting of Shareholders

    Ms. Glabe’s business experience gives her in-depth knowledge of managing and providing leadership at sophisticated nationwide organizations in highly regulated businesses. Her knowledge of the insurance industry gives her insight into an area, which, through the Company’s insurance premium financing business, impacts a substantial portion of the Company’s business. In addition, her experience in leadership provides Ms. Glabe with knowledge of the issues faced by large and complex businesses in the financial services industry. As a result of her financial experience, Ms. Glabe qualifies as a financial expert for purposes of rules governing audit committees. Ms. Glabe’s experience on the Executive Advisory Committee for First Insurance Funding and Wintrust Life Finance and as a current director of the boards associated with Wintrust Wealth Management gives her valuable insight into the Company’s non-banking operations. Brian A. Kenney (66), Director since 2023. Mr. Kenney currently serves as an Industry Advisor to Kohlberg Kravis Roberts & Co. L.P. (“KKR”). Previously, Mr. Kenney served as the Chairman, President and Chief Executive Officer of GATX Corporation (NYSE: GATX) (“GATX”), a global railcar lessor, from April 2005 until his retirement in April 2022. He held positions at GATX as President from 2004 to 2005, Senior Vice President, Finance and Chief Financial Officer from 2002 to 2004, Vice President, Finance and Chief Financial Officer from 1999 to 2002, and Vice President — Finance from 1998 to 1999. He first joined GATX in 1995 as Treasurer. Before his career at GATX, Mr. Kenney held various financial positions at AMR Corporation, United Airlines, and Morton International, Inc. He currently serves as Chairman of the Board of Depot Connect International, a KKR portfolio company and a global leader in tank container services. He also serves on the Board of Trustees of the Shedd Aquarium in Chicago, where he was Chairman from 2018 to 2022, and on the board of directors of the Big Shoulders Fund in Chicago. Mr. Kenney also served as a member of the board of directors of USG Corporation, a publicly-held manufacturer and supplier of building supply products, from 2011 until its acquisition in April 2019. Mr. Kenney’s experience as Chairman, President and Chief Executive Officer of GATX provides him with the unique perspective that comes from leading a large, publicly-traded global business. In addition, his extensive financial and capital markets expertise gives him valuable insight into key functions of the Company. Laura A. Kohl (57), Director since 2025. Ms. Kohl currently serves as Chief Information Officer of Morningstar, Inc. (Nasdaq: MORN) (“Morningstar”), a global financial services firm providing independent investment research and data platforms. She has served in this role since April 2021. In her role at Morningstar, she leads the company’s global technology strategy and continues to create efficiencies with artificial intelligence and other corporate systems to drive growth, product and service excellence, security and operational productivity. From September 2019 until joining Morningstar, she served as Senior Vice President, Enterprise Applications at Ulta Beauty Inc. (Nasdaq: ULTA) (“Ulta Beauty”), where Ms. Kohl was responsible for the enterprise application development, including eCommerce, enterprise and guest mobility, data analytics, cloud migration, integrations, loyalty, marketing, merchandising, finance, HR, supply chain, store and distribution center technology. Before she joined Ulta Beauty in 2019, Ms. Kohl served in management level roles within the information technology department of United Airlines, Inc. (Nasdaq: UAL) (“United”), including Managing Director, Field Service Delivery & End User Engineering and Support (June 2016 – September 2019) and Managing Director, Infrastructure/Platform Engineering (January 2015 – June 2016). At United, she was responsible for successfully leading global infrastructure, field support services and end user engineering with an organization of more than 550 team members. She upgraded technical infrastructure, support and deployment with updated technologies and services for premium customer and employee user experience at United at over 360 airport locations and 90,000 employees. Prior to joining United, Ms. Kohl also served in two key management positions as VP, Global Market & Supply Chain Business Integration, International CIO (September 2013 – December 2014) and as VP, Global Enterprise & Architecture (May 2012 – August 2013) at W.W. Grainger, Inc. (NYSE: GWW) (“Grainger”). At Grainger, she was responsible for international and global supply chain delivery and strategy including working closely with the distribution centers. Ms. Kohl also held various roles for McDonald’s Corporation, including the Regional Chief Information Officer for the U.S., Latin America and Canada, providing direct support for more than 14,000 store locations and 22 regional offices with 3,000 employees. She implemented the first Enterprise Resource Planning system and next generation store systems to be adopted globally. Ms. Kohl’s extensive knowledge of information technology systems, infrastructure, security and artificial intelligence, M&A and risk management provides the Company with sophisticated guidance regarding the Company’s technology and information security strategy and artificial intelligence objectives. In addition, her experience as a senior executive of large, public companies provides her with comprehensive knowledge of the technical issues, particularly relating to artificial intelligence, faced by highly complex businesses. Deborah L. Hall Lefevre (58), Director since 2019. Ms. Lefevre served as Executive Vice President, Chief Technology Officer of Starbucks Corporation (Nasdaq: SBUX) (“Starbucks”), which is an American multinational chain of coffeehouses and roaster, from May 2022 to September 2025. In her role, she was responsible for the company’s global technology strategy and execution for 40,000+ locations in 80+ countries. From 2017 until joining Starbucks, she served as Executive Vice President, Chief Technology Officer of Couche-Tard/ Circle K (“Circle K”), where she was responsible for global technology and digital strategy and execution across a network of approximately 15,500 convenience and fuel retail locations. Prior to 2017, Ms. Lefevre served in several senior level management roles within the Information Technology department of McDonald’s Corporation, including Corporate Vice President, Global Enterprise Solutions and Business Transformation (2015 – 2017); Chief Information Officer, U.S. Segment (2013 – 2015); and Vice President, IT Enterprise (2008 – 2013). Ms. Lefevre’s extensive knowledge of information technology systems and cybersecurity risk management provides the Company with sophisticated guidance regarding the Company’s technology, digital and information security strategy and tactical objectives. In addition, her experience as a senior executive of large, public companies provides her with comprehensive knowledge of the issues faced by highly complex businesses.

  13. Nominees for Election at the 2026 Annual Meeting of Shareholders

    Suzet M. McKinney DrPH, MPH (53), Director since 2021. Dr. McKinney is the former Principal & Director of Life Sciences at Sterling Bay Company, LLC, a real estate development company, where she was responsible for relationships with the scientific, academic, corporate, tech and governmental sectors involved in the life science ecosystem, as well as managing the experience and facilitating the growth of life science tenants in Sterling Bay developments. Prior to joining Sterling Bay in February 2021, she served since September 2015 as CEO and executive director of the Illinois Medical District, which includes 560 acres of medical research facilities, labs, a biotech business incubator, universities, raw land development areas, four hospitals, and more than 40 healthcare-related facilities. It is one of the largest urban medical districts in the United States. Dr. McKinney currently serves as a director of the Company’s wealth management subsidiaries: Great Lakes Advisors, Wintrust Investments, and Wintrust Private Trust Company. Dr. McKinney has served as a member of the Board of Directors of Kemper Corporation (NYSE: KMPR), one of the nation’s leading specialized insurers, since February 7, 2024. She also currently serves as a board member of Thresholds, as well as the Ann & Robert Lurie Children’s Hospital of Chicago. Dr. McKinney holds her doctorate from the University of Illinois at Chicago School of Public Health. She received her bachelor’s degree in biology from Brandeis University, where she was also a Howard Hughes Fellow. Additionally, she received her master of public health degree, in health care administration, and certificates in managed care and health care administration, from Benedictine University. Dr. McKinney’s professional experience includes managing large and complex organizations, as well as extensive familiarity with the Chicago business community. Dr. McKinney’s experience as a director of Wintrust Investments, Great Lakes Advisors, and Wintrust Private Trust Company gives her valuable insight into the Company’s non-banking operations. David S. Richter (64), Director since 2025. Mr. Richter serves as Managing Director — Absolute Return Strategies at GCM Grosvenor (“GCM”), which is an alternative investment strategies firm located in the Chicago area. He has served in this capacity since 2002. At GCM, he also serves in the capacity of Chair of the Absolute Return Strategies Investment Committee, Co-Head of Absolute Return Strategies Research, and sits on the Investment Committee for GCM Grosvenor’s Belmont Harbor Strategy as well as several other key committees. Mr. Richter is responsible for approving portfolio allocations prior to implementation and shares responsibility for the evaluation, selection and monitoring of absolute return investment strategies and investment managers. From February 1994 to the time Mr. Richter joined GCM, he served as Founder and Managing Partner of Waveland Capital Management, L.P., a U.S. long/short equity hedge fund affiliated with GCM. Previously, he was a Manager with KPMG Peat Marwick (September 1983 – August 1988), and then a Vice President of JMB Realty Corporation in the Corporate Acquisitions Group (August 1988 – February 1994). He has a high-level of understanding complex transactions and financials with multiple companies. Mr. Richter graduated summa cum laude with his Bachelor of Science in Accountancy from the University of Illinois at Urbana-Champaign. He is a Certified Public Accountant and received the national AICPA Elijah Watt Sells Award from the American Institute of CPAs for his scores on the Uniform CPA Examination. Mr. Richter currently serves as a director of Wintrust Bank. His business and education backgrounds provide him familiarity with financial models and valuation of corporations and banks, as well as of high level investment- and alternative-opportunities, which serves the Company’s complexity in structure and products. Additionally, his experience as a director of Wintrust Bank gives him valuable insight into the Company’s banking operations. Gregory A. Smith (62), Director since 2024. Mr. Smith currently serves as an Executive-in-Residence and Professor of Practice at the University of Wisconsin-Milwaukee’s Lubar School of Business, a position he has held since 2012. He also serves as the Curriculum Director for the American Bankers Association’s Stonier Graduate School of Banking. Additionally, Mr. Smith serves as a Director of Church Mutual Holding Company, Inc. (since 2014). Mr. Smith was a Director of Envestment, Inc. (NYSE: ENV) from 2015 until its sale in 2024. Prior to joining the University of Wisconsin-Milwaukee, Mr. Smith served as Senior Vice President and Chief Financial Officer of the Marshall & Ilsley Corporation and its subsidiary M&I Bank from 2006 until Marshall & Ilsley’s sale to BMO Harris Bank in 2011. Before working at Marshall & Ilsley, Mr. Smith worked in the investment banking industry with a focus on the financial services sector. Mr. Smith is an honors graduate of both Princeton University, where he received an undergraduate degree, and The University of Chicago, where he received an MBA. More recently, he has been recognized as a Board Leadership Fellow by the National Association of Corporate Directors. Mr. Smith’s experience in the banking and investment banking industries provide him with knowledge of the financial services business and capital raising and investment processes. Mr. Smith’s banking industry experience is expected to provide sophisticated insight with respect to the Company’s banking operations and his professional experience in Wisconsin provides valuable familiarity with one of the Company’s core banking markets. His experience also includes the management of liquidity, financial reporting and risk management of a multitude of large and complex organizations. As a result of his financial experience, Mr. Smith qualifies as a financial expert for purposes of rules governing audit committees. Karin Gustafson Teglia (58), Director since 2019. Ms. Teglia is President and Manager of DEKK Enterprises, LLC, an incubator that develops innovative concepts and go-to-market strategies for consumer products and services, and DEKK Investments, LLC. Ms. Teglia also has served since 2009 as an advisor to TRP Investments, LLC, a commercial real estate investor. Prior to this role, Ms. Teglia served in various corporate finance management and international tax roles within McDonald’s Corporation, including Corporate Senior Vice President, Finance (2007 – 2008); Corporate Vice President, Finance (2005 – 2007); and Corporate Vice President of Tax (2001 – 2005). Prior to joining McDonald’s Corporation in 1995, Ms. Teglia began her career as an international tax consultant with PricewaterhouseCoopers LLP. Ms. Teglia is a certified public accountant and an attorney licensed to practice in Illinois. Ms. Teglia served as a director of Hinsdale Bank, chairing its Audit Committee and also serving on its Risk Committee. She also served on an Advisory Panel of the National Academy of Sciences, focusing on food allergy research, and served on the Food Allergy Research and Education Board of National Ambassadors. Ms. Teglia’s management experience at McDonald’s Corporation provides experience with the management of the liquidity, financial reporting, risk and audit management of a large organization. As a result of her financial experience, Ms. Teglia qualifies as a financial expert for purposes of rules governing audit committees. Additionally, Ms. Teglia’s experience as a past director of Hinsdale Bank gives her valuable insight into the Company’s banking operations, as well as experience as an audit committee member and chair.

  14. Nominees for Election at the 2026 Annual Meeting of Shareholders

    Alex E. Washington, III (52), Director since 2020. Mr. Washington serves as a Managing Director of Wind Point Partners, a middle market private equity firm based in Chicago. Wind Point Partners has approximately $8.0 billion in assets under management and focuses on acquisition of middle-market companies in the industrial products, consumer products and business services sectors. Mr. Washington joined Wind Point Partners in 2002 and is a member of the firm’s management company and investment committee. He currently serves on the boards of several Wind Point portfolio companies, including Ascensus Specialties, Envera Systems, HASA, Turf Masters Brands and Quantix. Past boards where Mr. Washington served as lead Wind Point director include Arr-Maz Custom Chemicals, Critica Infrastructure, Novolex and Paragon Films. Prior to Wind Point Partners, he held professional roles with J.H. Whitney, Donaldson Lufkin & Jenrette, and McKinsey & Company. Mr. Washington received a Bachelor of Arts in Finance from Morehouse College and a Master of Business Administration from Harvard Business School. Mr. Washington was a Class VI recipient of the Ewing Marion Kauffman Fellowship in venture capital. He currently serves as a director of Wintrust Bank, serving on the Audit Committee. His civic activities include serving as a board member of the Art Institute of Chicago, board member of the University of Chicago Laboratory Schools, and member of both the Chicago Club and the Commercial Club of Chicago. Mr. Washington’s extensive private equity experience provides him with comprehensive knowledge of mergers and acquisitions, capital raising and the investment process, each of which are key functions of the Company. The Board believes that his knowledge of underwriting approaches and valuation methodologies is extremely valuable in evaluation of proposed transactions. Mr. Washington’s significant experience on the board of directors of other companies also provides him with familiarity with the management of the liquidity, financial reporting, risk and audit management of complex organizations. Additionally, Mr. Washington’s experience as a director of Wintrust Bank gives him valuable insight into the Company’s banking operations, as well as experience as a board committee member and chair within the Wintrust enterprise. Election as a Director of the Company requires that a nominee receive the affirmative vote of a majority of the shares of Common Stock represented at the Annual Meeting, online or by proxy, and entitled to vote thereon. Accordingly, instructions to abstain will have the same effect as a vote against such nominee. Broker non-votes will have no impact on the election of Directors. THE BOARD OF DIRECTORS RECOMMENDS THAT YOU VOTE “FOR” THE ELECTION OF EACH OF THE NOMINEES FOR DIRECTOR NAMED ABOVE.

  15. Our Executive Compensation Practices

    | What We Do | What We Don’t Do | | ☑ We Pay for Performance: The majority of executive pay is not guaranteed. Our CEO and our other NEOs (excluding Mr. Wehmer) on average have approximately 81% and 64%, respectively, of their target total compensation tied to Company performance through achievement of performance goals and/or our Common Stock price. | ☒ No Hedging or Short Selling: Our NEOs are prohibited from engaging in short selling of our Common Stock or engaging in hedging or offsetting transactions regarding our Common Stock. | | ☑ We Align Our Long-Term Incentives With Performance: The majority of our long-term incentive awards are performance-based. | ☒ No Pledging: Our NEOs are prohibited from pledging our securities. | | ☑ We Set Stretch Goals: Our performance hurdles are designed to require stretch individual and Company performance along with superior returns in order to receive commensurate payout. | ☒ No Excessive Expenditures or Perquisites: We have adopted a policy designed to prevent any excessive expenditures and maintain modest perquisites. | | ☑ We Have an SEC/Nasdaq Compliant Clawback Policy: In the event of a financial restatement, we are required to claw back payments made which were predicated on achieving certain financial results. | ☒ No Undue Risk: We discourage excessive risk taking by having a balanced portfolio of short- and long-term incentive performance measures and a cap on final payouts. | | ☑ We Require Stock Ownership: We have robust stock ownership guidelines. Our CEO is required to hold Common Stock with a value equal to a multiple of six times base salary. Our other NEOs are required to hold between one and three times base salary. | ☒ No Repricing Underwater Options: Our stock incentive plan does not permit repricing or the exchange of underwater stock options without shareholder approval. | | ☑ We Utilize Independent Compensation Expertise: The Committee has retained Meridian, an independent compensation consultant, to advise on the executive compensation program and practices, including annual assessments of the Company’s peer group. | ☒ No CIC Payment Absent a Double Trigger: Payments under our employment agreements and our long-term incentive programs require two events for vesting in connection with a change in control — both a change in control and a qualifying termination of employment. |

  16. Compensation Philosophy and Objectives

    Compensation Philosophy and Objectives The philosophy underlying our executive compensation program is to promote a pay-for-performance environment and remain competitive with market practices in order to attract and retain key talent, which we believe will support the long-term success of the Company and build value for our shareholders. The compensation elements included in the pay of our NEOs are reflective of different pay objectives. Base salaries are intended to pay executives competitively relative to market peers and individual performance. Relevant performance factors that influence base pay include leadership, innovation, employee development initiatives, strategic contributions, maintaining effective company systems and infrastructure, customer service and talent management. Variable compensation (short-term and long-term incentives) is tied to financial measures (such as pre-tax net income, net interest margin, net overhead ratio, core loan and deposit growth, credit quality, and earnings per share) as well as the achievement of specific business objectives (including satisfactory regulatory exams), employee retention, and increased shareholder value. It is also the Committee’s philosophy to provide retirement and health and welfare benefits to all employees on a non- discriminatory basis. We do not provide supplemental retirement benefits to our executives. The Committee has set forth the following objectives for its executive compensation program: • Attract first-rate entrepreneurial talent that reflects our structure. We believe that our unique organizational design and structure are a significant part of our value proposition. Consequently, we need to hire leaders who will thrive within our matrixed organizational structure which allows the capacity to act in equal measure autonomously at times and in collaboration at times, while driving growth and managing risk. • Focus on performance-based compensation. Our compensation program is designed to support performance and achievement at every level of the organization, from the individual to the bank, subsidiary and Company. It is also designed to drive performance across both short-term and long-term horizons. • A significant portion of total compensation should be in the form of long-term incentives. Our compensation program includes incentives designed to align management and shareholder interests over a multi-year performance and vesting period. This longer-term horizon also helps promote retention and therefore business continuity. • Long-term incentive compensation should balance growth and risk. Our longer-term rewards are structured to help mitigate excessive risk-taking since leaders are rewarded for creating sustained value for the Company and its shareholders. • Long-term incentive compensation should be highly correlated with returns. The prescribed performance goals under our long-term incentive compensation program are designed to be challenging, and at or above target payouts should be achievable only with above target, superior organizational performance. Further, the use of total shareholder return as a long-term incentive metric is intended to directly link NEO and shareholder interests. • Compensation levels should be competitive to enable us to attract and retain a highly qualified management team to lead and grow our Company. The successful operation of our Company requires an experienced and talented management team. We hire for both the current and anticipated future needs of the organization, so executives must be able to effectively lead the organization now and also meet future needs of a growing organization. To do this, our compensation program must be competitive with those of our peer firms to attract and retain talent that is capable of scaling for the future. • Compensation opportunities should be commensurate with an executive’s roles and responsibilities. Our organization values talented executives who perform comprehensively, both within their specific roles as well as taking on more leadership responsibilities. Consequently, our compensation program seeks to recognize and reward our executives who are most responsible for the performance of the Company and who engage in broader duties than their job titles may imply. • Compensation for NEOs should be fair and perceived as such, both internally and externally. We measure the appropriateness of our compensation offerings by comparing them both internally and externally to peer group benchmarks. Shareholders are best served when we can attract and retain talented executives with compensation packages that are competitive with organizations similar in size, scope and complexity to Wintrust.

  17. Peer Group Benchmarking

    Peer Group Benchmarking On an annual basis, the Committee’s independent compensation consultant, Meridian Compensation Partners, LLC (“Meridian”), provides the Committee with assessments of the competitive market and best practices relating to executive compensation practices, including peer group development, executive and board compensation benchmarking, executive pay-for-performance analysis, research on regulatory and industry trends, and overall program design. The Committee utilizes these assessments and references when considering compensation program design and other decisions. Peer Group Analysis On an annual basis, the Committee engages Meridian to review the peer group to evaluate whether it reflects the appropriate population of banks both regionally and nationally similar to Wintrust in size, scope and complexity. When identifying and constructing the competitive peer group, the Committee took into consideration which companies compete for customers, executive talent and/or investors, as well as other factors including the amount of commercial and industrial loans, level of non-interest revenue, and comparability in business models. These factors were considered as the Committee sought to develop a peer group that approximated the size and the structure of the Company. The following peer group, developed in 2024 and used by the Committee to help guide 2025 compensation decisions, was comprised of 18 banks, including 14 similarly-sized national banks and four Midwestern banks. This reference group of banks had assets between $30 billion and $87 billion as of March 31, 2024 (reflecting the available information at time of review), with Wintrust’s assets then positioned at the sixty-first percentile.

  18. Peer Group Benchmarking

    | National Holding Company Peer Group* | | | | BOK Financial Corporation | First Horizon Corporation | Western Alliance Bancorporation | | Cadence Bank | Hancock Whitney Corporation | Zions Bancorporation, N.A. | | Columbia Banking System, Inc. | Pinnacle Financial Partners, Inc. | | | Comerica Incorporated | Synovus Financial Corp. | | | Cullen/Frost Bankers, Inc. | Valley National Bancorp | | | F.N.B. Corporation | Webster Financial Corporation | | | Midwestern Holding Company Peer Group | | | | Associated Banc-Corp | Old National Bancorp | | | Commerce Bancshares, Inc. | UMB Financial Corporation | |

  19. Peer Group Benchmarking

    * The peer group used for purposes of 2025 compensation decisions was unchanged from the peer group used for 2024 compensation decisions. When making compensation decisions, the Committee generally reviews the compensation paid to our CEO and other NEOs relative to the compensation paid to similarly-situated executives, to the extent available, at our peer companies based on publicly available information reported in our peers’ proxy statements. Benchmark Analysis In November 2024, Meridian provided the Committee with background information regarding the Company’s compensation structure as compared to the peer group and market practices. Meridian provided the Committee with an analysis undertaken with respect to each of the NEO’s positions, including a comparison of target total compensation, target total direct compensation as well as each component of compensation (e.g., base salary, short-term incentives, long-term incentives, benefits) on a comparative basis with the Company’s peer group. In addition, the Committee reviewed NEO compensation in the aggregate to that of our peer group. The Committee believes that reviewing compensation across both dimensions of their role and in aggregate provides the Committee with the most well-rounded view of the appropriateness of NEO compensation levels relative to peers. Pay-for-Performance Analysis Each year, Meridian conducts a pay-for-performance analysis which compares realized and realizable pay for the CEO as compared to the chief executive officers in our peer group. This analysis provides a retrospective look which evaluates the historical relationship between pay and performance, the effectiveness of the Company’s pay structures and performance goals and whether pay was aligned with performance. The 2025 study reviewed pay and performance over the prior three-year period (2022 – 2024) and found that the Company’s historical performance and the CEO’s actual pay results were reasonably aligned. The Committee intends to continue to monitor the effectiveness of the Company’s executive pay program and alignment of pay with performance. Amended and Restated Employment Agreement with Mr. Wehmer As previously disclosed, in early 2023, the Board appointed Mr. Crane to succeed Mr. Wehmer, the Company’s founder, as Chief Executive Officer. In negotiating the terms of continued employment and engagement with Mr. Wehmer for recommendation to the Board, the Committee took into account factors including the need to provide for a smooth and orderly leadership transition, and valuable continuity, that would benefit all of the Company’s stakeholders. The Committee considered it essential to provide for Mr. Wehmer’s continued engagement during a transition period that extends through December 31, 2026, given Mr. Wehmer’s unique role as the Founder of Wintrust, which during Mr. Wehmer’s tenure of over 30 years grew from one bank location with 12 employees and zero assets to a diversified banking and financial services enterprise with approximately 5,200 employees, over 170 banking locations and $52 billion in assets in early 2023, representing an unprecedented success story that would not have taken place absent Mr. Wehmer’s extraordinary leadership. The Committee also took into account benchmarking data provided by Meridian, as well as existing contractual obligations to Mr. Wehmer and the value to the Company and its stakeholders of Mr. Wehmer’s continued compliance with certain restrictive covenants. On January 26, 2023, the Company and Mr. Wehmer entered into an agreement (the “Wehmer Agreement”), which provided that, as of May 1, 2023 (the “Effective Date”), Mr. Wehmer would assume the position of Founder and Senior Advisor and Executive Chairman of the Board and cease his service as Chief Executive Officer of the Company. Mr. Wehmer’s employment as Executive Chairman continued until May 23, 2024, after which Mr. Wehmer continued to serve as a Director of the Company until the annual meeting in 2025. Mr. Wehmer is expected to continue to serve in the position of Founder and Senior Advisor and Chairman Emeritus of the Company until December 31, 2026 or any later date agreed to between the parties by mutual written consent (the “Employment Period”), subject to earlier termination by either party. During the Employment Period, Mr. Wehmer’s annual base salary is $450,000, and he is eligible for the perquisites specified in the Wehmer Agreement. However, he is not eligible to participate in the STIP or the LTIP or any successor plan after April 30, 2023. In addition, Mr. Wehmer’s outstanding equity awards continue to vest in accordance with their terms. Under the Wehmer Agreement, Mr. Wehmer is entitled to receive a one-time cash award of $12,000,000 (the “Transition Award”), payable in equal monthly installments over the 36-month period commencing on the Effective Date (subject to delayed payment required by tax law) and generally subject to Mr. Wehmer’s continued employment through each applicable payment date. However, if the Company terminates Mr. Wehmer’s employment without cause or due to his permanent disability, or Mr. Wehmer’s employment terminates due to his death or a constructive termination, then Mr. Wehmer will receive the unpaid portion of the Transition Award, payable in installments in accordance with its original payment schedule (or in the case of his death, within 30 days thereafter). The continued payment of the Transition Award following Mr. Wehmer’s qualifying termination is subject to Mr. Wehmer’s continued compliance with ongoing obligations under the Wehmer Agreement, including the restrictive covenants contained in the Wehmer Agreement which are of significant value to the Company. In addition, the Wehmer Agreement provides that Mr. Wehmer’s 2023 transition did not constitute a constructive termination for purposes of the Wehmer Agreement.

  20. 2025 Compensation Elements and Decisions

    | Element | Key Characteristics | Why We Pay this Element | How We Determine the Amount | 2025 Decisions | | Base Salary | Fixed compensation component payable in cash. Reviewed annually and adjusted when appropriate. | Provide a base level of competitive cash compensation for executive talent. | Experience, job scope, market data, and individual performance. | Annual base salary increases were approved for the NEOs (other than Mr. Wehmer) in 2025, ranging between 2.1% and 9.1%. | | Annual Short-Term Incentive | Variable compensation component payable in cash or stock. Performance is 100% allocated to financial measures and modified by achievement of individual performance goals. Payment is capped at 150% of target. | Motivate and reward executives for performance on key operational, financial and individual objectives met during the course of the performance year. | Market practices and individual performance with actual payouts based on the extent to which performance goals are achieved. | Annual 2025 short-term incentive payouts ranged from 120.7% to 120.8% of target, based on a combination of Company and individual performance, excluding Mr. Wehmer who did not participate in the annual short-term incentive program pursuant to the Wehmer Agreement. | | Long-Term Incentives | Variable compensation component payable in performance- based restricted stock units and time-vested restricted stock units. Payments of performance-based restricted stock units are capped at 150% of target. | Align long-term interests of management and shareholders. Retain executive talent. | Market practices and individual performance, with actual value of the award impacted by our stock price performance and, in the case of performance- based restricted stock units, achievement of the underlying performance goals. | The 2025 LTIP consisted of a mix of awards (60% performance-based restricted stock units and 40% time-based restricted stock units). Vesting of the performance-based restricted stock units is determined after the 3-year performance period (2025 – 2027), with half vesting based upon Adjusted EPS (as defined below) (30% of LTIP award) and half vesting based upon Relative TSR (as defined below) (30% of LTIP award). The time-based restricted stock units cliff vest at the conclusion of the three-year vesting period. Mr. Wehmer did not receive grants under the LTIP in 2025 pursuant to the Wehmer Agreement. For a discussion of performance results and Committee decisions relative to the 2023 – 2025 LTIP performance period, please see “2023 – 2025 LTIP Results and Payments” on page 47. | | Perquisites and Other Personal Benefits | Compensation component to provide basic competitive benefits. | Provide a base level of competitive compensation for executive talent. | Periodic assessment of competitive offerings. | The perquisites and other personal benefits range from approximately 1% to 4% of the total 2025 target compensation for each NEO other than Mr. Wehmer. |

  21. 2025 Compensation Elements and Decisions

    Annual Short-Term Incentive The Company’s performance-based annual short-term incentives are based on each NEO’s overall performance and the achievement of Company performance goals subject to the discretion and adjustment by the Committee. Annual short-term incentives are intended to provide officers across the Company with an opportunity to receive cash compensation (which may be paid in equity at the discretion of the Committee), based on consideration of the Company, subsidiary and individual performance goals. Performance-based incentives are a key component of our total compensation package because they reward our executives for pursuing objectives that the Committee believes are consistent with the overall goals and strategic direction that the Board has set for the Company. NEO short-term incentive target opportunities are reviewed by the Committee annually to evaluate appropriateness to the current business cycle and competitiveness relative to the market. In determining the target annual short-term incentives, the Committee considers several factors, including: • market practices; • the target annual incentive set and achieved in recent years; • the desire to provide, as described above, a substantial portion of total compensation as performance based; and • the relative importance and degree of difficulty of the short-term and long-term performance goals of the Company. The Committee establishes target opportunities for each participant based on their role and competitive market data. Based on a review of competitive market data, the 2025 target opportunity for the CEO was adjusted to 135%, while the target opportunities for the other NEOs did not change as compared to the 2024 target opportunities. Mr. Wehmer did not participate in the annual short-term incentive program pursuant to the Wehmer Agreement. Based on the Committee’s assessment of Corporate and individual performance, actual awards can vary from 0% to 150% of the target opportunities.

  22. 2025 Compensation Elements and Decisions

    In comparison to the 2024 target annual short-term incentive program, pursuant to which payment was determined 75% based on Company performance associated with consolidated pre-tax net income and 25% based upon individual goals and objectives, performance under the 2025 target annual short-term incentive program was determined based 100% on the Company’s consolidated pre-tax net income, subject to a performance modifier based upon the achievement of individual performance objectives. The Committee made this modification to the annual short-term incentive program based on competitive market data. Development of Company Performance Objectives The Committee considers a number of performance factors in determining short-term incentive awards, including key performance indicators such as net interest margin, net overhead ratio, loan, asset and deposit growth and credit quality, as well as qualitative factors including advances in the Company’s efforts to maintain an inclusive corporate culture, development of enterprise infrastructure that will support future growth, and continued business line diversification. One of the key Company-level objectives for 2025 was to achieve consolidated pre-tax net income of $1,037.8 million, consistent with the Board-approved 2025 budget. The Committee used the following guidelines to set the maximum, target, and threshold portion of the annual short-term incentive award opportunity allocated to the Company-level objective:

  23. 2025 Compensation Elements and Decisions

    | Wintrust 2025 Consolidated Pre-Tax Net Income | Performance Measurement of Company- Level Annual Short-Term Incentive Award | | $1,193.5 million or greater | Maximum | | $1,037.8 million | Target | | $726.5 million | Threshold |

  24. David L. Stoehr

    David L. Stoehr • Ensure that the Company’s internal controls over financial reporting are designed to provide reasonable assurance that the Company’s financial statements are reliable and prepared in accordance with generally accepted accounting principles. • Oversee the annual budgeting and regular forecasting processes. • Provide effective analytics, metrics and reporting to measure contributions of business lines and products. • Oversee the Company’s allowance for credit losses process and ensure integration with portfolio level credit loss stress testing and capital stress testing. • Maintain appropriate capital levels and oversee the capital stress testing process. • Oversee execution of five-year technology roadmap for Finance group. • Continue to make progress on the development of incoming personnel and emerging leaders. Collaborate with emerging leaders on professional development plans. Performance Results and Payouts As noted above under “2025 Business Highlights,” the Committee considered the Company’s strong performance during a year of challenges including a changing interest rate environment, reflecting the benefit of the skill and guidance provided by the Company’s executive leadership team. Company Performance Results: The Company’s consolidated pre-tax net income for the year ended December 31, 2025 was $1,118.4 million. In determining the actual annual short-term incentive for each NEO associated with the achievement of Company-level objectives, the Committee considered a number of factors, including the following achievements: the Company achieved 107.8% of the consolidated pre-tax net income objective; • strong achievement measured against our key performance indicators, including net interest margin, net overhead ratio, loan, asset and deposit growth and credit quality; • continued progress on diversification strategy via expanded lines of business; and • continued build out of enterprise infrastructure to support future success of the organization. The Committee, taking into account the Company’s actual consolidated pre-tax net income performance along with all of the other above-referenced positive key performance indicators, determined to pay out the portion of annual short-term incentives associated with the Company-level results at 105% of target. Individual Performance Objectives: The Committee reviewed each executive’s performance relative to individual goals, determined that each of the NEOs generally achieved or exceeded all of their individual performance objectives, and applied a 115% performance modifier as a result of such performance. Total Annual Short-Term Incentive Payout: Consistent with the approach taken in prior years, the final determination of an NEO’s actual short-term incentive payment was based on the Committee’s holistic evaluation of Company and individual performance metrics including consolidated pre-tax net income, individual performance objectives, and discretionary factors. The Committee retains the discretion to determine the amount of any annual short-term incentive awarded to an NEO. The final determination of the Committee could result in no short-term incentive being paid or a short-term incentive amount above or below a strictly formulaic view of performance. Based on their analysis, the Committee approved the annual short-term incentive award for each participating NEO. The extent of achievement of Mr. Crane and the other participating NEOs relative to the accomplishment of the Company’s financial objectives was taken into account. The Committee’s analysis ultimately resulted in short-term incentive payouts to NEOs other than Mr. Wehmer ranging from 120.7% to 120.8% of target. Additionally, short-term incentives were informed by the Committee’s intention to ensure that total cash compensation was at an appropriate competitive position relative to the Company’s performance. The following table sets forth the total eligible annual short-term incentive amounts at target and annual short-term incentives actually paid to each of our participating NEOs under the short-term incentive program.

  25. David L. Stoehr

    | Named Executive Officer | Total Annual Short-Term Incentive at Target | Total Annual Short-Term Incentive Paid | % Annual Short-Term Incentive Paid vs. Target | | Timothy S. Crane | $1,620,000 | $1,956,150 | 120.8% | | David A. Dykstra | $720,000 | $869,400 | 120.8% | | Richard B. Murphy | $552,000 | $666,540 | 120.8% | | David L. Stoehr | $427,000 | $515,600 | 120.7% | | Edward J. Wehmer | — | — | — |

  26. David L. Stoehr

    Our annual short-term incentive may be paid in cash and/or equity at the discretion of the Committee. With regard to 2025 performance, annual short-term incentives awarded by the Committee to the NEOs were paid in cash and are reported in the “Bonus” column in the 2025 Summary Compensation Table. Long-Term Incentive Plan (LTIP) The Committee believes that a substantial portion of each NEO’s compensation should be in the form of long-term incentive compensation in order to further align the interests of our NEOs and shareholders. The framework is also designed to: • provide a competitive compensation opportunity; • foster retention; allow the Company to compete effectively for talent; incorporate leading practices; • provide transparency; • support the Company’s long-term strategy and growth objectives; • align management’s long-term compensation with shareholder returns; • link pay and performance; • create a long-term focus based on sustainable results; and • promote long-term NEO stock ownership. Award Mix The Committee administers the LTIP and can determine on an annual basis the mix of awards included in the annual grant. As awarded in 2025, the LTIP mix consists of 100% equity, comprised of 60% performance-based restricted stock units and 40% time-based restricted stock units as indicated below:

  27. David L. Stoehr

    | Award Vehicle Mix | % of Award | | Performance-Based Restricted Stock Units | 60% | | Time-Based Restricted Stock Units | 40% |

  28. David L. Stoehr

    Performance-based restricted stock units and time-based restricted stock units are designed to promote pay for performance since the awards vest after three years and the performance-based restricted stock unit awards vest based on the achievement of pre-established long-term goals set in advance by the Committee with results measured over a multi-year performance period (i.e., three years). Each year, the Committee sets three-year performance goals for the LTIP, which results in overlapping performance cycles. Performance-based restricted stock units are earned only at the end of the performance period based on the Company’s actual performance against pre-established goals certified by the Committee, subject to negative discretionary adjustments. In 2025, the Committee selected the following award mix for the 2025 – 2027 LTIP performance period: • 30% in performance-based restricted stock units, with vesting based on a measurement of earnings per share, as adjusted to exclude income taxes, acquisition-related charges and the provision for credit losses, with such amount being further reduced by actual net charge-offs of loans, over the performance period (“Adjusted EPS”); • 30% in performance-based restricted stock units, with vesting based on the Company’s Total Shareholder Return relative to the KBW Regional Bank Index (“KRX Index”) over the performance period (“Relative TSR”); and. • 40% in time-based restricted stock units with vesting three years from the grant date (i.e., cliff vest on the third anniversary of the grant date). When it determined stock-based compensation LTIP awards for the 2025 – 2027 performance period in January 2025, the Committee believed that the targets established for these performance metrics were reasonably achievable with strong executive management performance. Actual performance will be measured against the Adjusted EPS metric, with 50% vesting at the end of the performance period for achievement of threshold Adjusted EPS, 100% for achievement of target Adjusted EPS and 150% for achievement of maximum Adjusted EPS levels (with linear interpolation in the payout between performance levels). Adjusted EPS threshold, target and maximum performance measures have been designed to be challenging but achievable through strong management performance and successful execution of our operating plan. Relative TSR will measure our performance compared to the KRX Index with 50% vesting at the end of the performance period for achievement of the 25th percentile, 100% vesting for median percentile performance and 150% vesting for 75th percentile performance (with linear interpolation in the payout between performance levels; payout is capped at target in the event our absolute TSR is negative at the conclusion of the performance period). In 2025, the Committee also selected a time-based restricted stock unit award to comprise the remaining 40% of the overall LTIP award mix. The time-based restricted stock unit award has a three-year cliff vesting period. The Committee believed that an element of the overall stock-based awards should have a time-based component to create a balance between risk and executive management’s long-term focus on the Company’s overall achievement over the three years reflected in the appreciation of the Company’s stock price. 2025 LTIP Target and Grants: The Committee provided a 2025 LTIP grant for the performance period from January 1, 2025 through December 31, 2027, based on a target opportunity developed based on market practice, input from Meridian and our desire to provide a significant portion of compensation in long-term equity-based incentives. Total target award opportunities are defined as a percentage of base salary and summarized in the table below, with 60% of the grant value provided as performance-based restricted stock units and 40% of the grant value provided as time-based restricted stock units. The ultimate value of the performance-based awards will depend on the Company’s performance relative to three-year goals and, in the case of both the performance-based and the time-based restricted stock units, the Company’s stock price at vesting. Each participating NEO’s long-term incentive target, as a percentage of base salary, is outlined below. Mr. Crane’s target LTIP opportunity was increased as compared to 2024 based on benchmarking data provided by Meridian and the Committee’s assessment of his and the Company’s performance.

  29. David L. Stoehr

    * Pursuant to the Wehmer Agreement, Mr. Wehmer was not eligible for a 2025 LTIP grant. Performance-Based Restricted Stock Unit Awards and Time-Based Restricted Stock Unit Awards: The performance-based restricted stock unit awards (60% of incentive target opportunity) will each be measured and vest following the end of the performance period ending December 31, 2027, and time-based restricted stock unit awards (40% of target incentive opportunity) will vest three years from the date of the award. The threshold, target and maximum award opportunities for each participating NEO for the performance- based restricted stock unit awards, and the number of time-based restricted stock units awarded to each participating NEO, are set forth in the following two tables: Performance-Based Restricted Stock Unit Awards

  30. David L. Stoehr

    2023 – 2025 LTIP Results and Payment: The 2023 – 2025 LTIP award consisted of three different payment vehicles: • 30% of the award in performance-based restricted stock units, with vesting based on Adjusted EPS 30% of the award in performance-based restricted stock units, with vesting based on Relative TSR 40% of the award in time-based vested restricted stock units The following tables outline the payout matrix adopted in conjunction with the 2023 – 2025 LTIP for the three-year Adjusted EPS and Relative TSR through December 31, 2025:

  31. David L. Stoehr

    | | Adjusted EPS over 3 year Performance Period | | Payout% of Target Award** | | Maximum | | 73.02 | 150% | | Target | | 58.42 | 100% | | Threshold | | 43.81 | 50% | | <Threshold | <$ | 43.81 | 0% |

  32. David L. Stoehr

    | | Relative TSR Percentile* | Payout% of Target Award** | | Maximum | 75th | 150% | | Target | 50th | 100% | | Threshold | 25th | 50% | | <Threshold | <25th | 0% |

  33. David L. Stoehr

    * Wintrust included within the peer group for purposes of determining relative ranking. ** Linear increase in payout between the performance levels if Threshold performance is achieved. For the 2023 – 2025 performance period the Adjusted EPS performance measure was achieved below target but above threshold, with Adjusted EPS of $46.50, and the result of the Relative TSR performance measure was at the 93rd percentile. Based on these levels of achievement, the Committee certified vesting of the performance-based restricted stock units at 59% of target for the Adjusted EPS performance measurement and 150% of target for the Relative TSR performance measurement, which performance-based restricted stock units vested on February 25, 2026. Based upon the weighting outlined above of the 30/30/40 allocation of the long-term incentive, the table below reflects the value of each NEO’s vested performance-based and time-based restricted stock units for the 2023 – 2025 performance period.

  34. David L. Stoehr

    | Named Executive Officer | Value of Performance-Based Restricted Stock Unit Settlement(1) | Value of Time-Based Restricted Stock Unit Settlement(2) | Total Value Delivered | | Timothy S. Crane | $2,876,436 | $1,790,658 | $4,667,094 | | David A. Dykstra | $1,410,500 | $878,223 | $2,288,723 | | Richard B. Murphy | $1,070,535 | $666,526 | $1,737,061 | | David L. Stoehr | $812,828 | $506,144 | $1,318,972 | | Edward J. Wehmer | — | — | — |

  35. David L. Stoehr

    (1) Performance-based restricted stock units: The NEOs received shares as follows: Mr. Crane 19,198; Mr. Dykstra 9,414; Mr. Murphy 7,145; and Mr. Stoehr 5,425. The value ascribed in the table above was derived based on the $149.83 fair market value of a share Common Stock on February 25, 2026, the date these awards were settled (calculated based upon the average of the highest and lowest stock price on this date). (2) Time-based restricted stock units: The NEOs received shares as follows: Mr. Crane 12,248; Mr. Dykstra 6,007; Mr. Murphy 4,559; and Mr. Stoehr 3,462. The value ascribed in the table above was derived based on the $146.20 fair market value of a share of Common Stock on January 26, 2026, the date these awards were settled (calculated based upon the average of the highest and lowest stock price on this date).

  36. Post-Termination Compensation

    Post-Termination Compensation We have entered into employment agreements with each of our NEOs that provide for post- termination compensation. These agreements provide for payments and other benefits if the NEO’s employment terminates for a qualifying event or circumstance, such as being terminated without “Cause” or leaving employment for “Constructive Termination,” as these terms are defined in the employment agreements. Additionally, the employment agreements provide for the payment of enhanced severance benefits if the NEO’s employment is terminated within eighteen months of a “Change-in-Control” (as defined in the agreements). Additional information regarding the employment agreements, including a definition of key terms and a quantification of benefits that would have been received by our NEOs had termination occurred on December 31, 2025, is found under the heading “Potential Payments upon Termination or Change in Control” on page 57 of this Proxy Statement. The Committee believes that these employment arrangements are an important part of overall compensation for our NEOs and will help to secure the continued employment and dedication of our NEOs, prior to or following a change in control, notwithstanding any concern that they might have at such time regarding their own continued employment. These agreements also contain restrictive covenants, including non-compete and non-solicitation provisions, which protect the Company’s interests in its client and employee relationships. The Committee also believes that these agreements are important as a recruitment and retention device, as nearly all of the companies with which we compete for executive talent have similar agreements in place for their senior employees.

  37. Additional Information Regarding Compensation Policies

    Additional Information Regarding Compensation Policies We have additional compensation policies that support our practices. These policies serve to further illustrate and provide context around our approaches to compensation. Clawback Policy. Our clawback policy provides that the Company will recover any payment or equity awards made to a current or former executive officer, if the payment was predicated upon achieving certain financial results that were subsequently the subject of a restatement. In such event, the Company will recover the amount by which any annual or long-term payments or awards made or granted exceeded what would have been awarded or granted based on restated financials. In addition, the Company may recover any profits realized on the sales of securities received by such executive officer pursuant to such awards. Our clawback policy is designed to comply with the requirements of U.S. Securities and Exchange Commission rules and Nasdaq Stock Market listing standards implementing Section 954 of the Dodd-Frank Wall Street Reform and Consumer Protection Act of 2010. In addition, the clawback provision of the Sarbanes-Oxley Act of 2002 also applies to Messrs. Wehmer, Crane and Stoehr. This provision provides that if the Company is required to restate its financial statements as a result of misconduct, Messrs. Wehmer, Crane and Stoehr are required to reimburse the Company for short-term incentives or other incentive-based or equity-based compensation and profits realized in the 12 months after the financial information was first publicly issued or filed with the SEC. Policy Regarding Excessive or Luxury Expenditures. Our Board adopted a policy designed to eliminate or prevent any excessive or luxury expenditures, including excessive expenditures on entertainment or events, office and facility renovations, aviation or other transportation services. A copy of this policy is available on our website, www.wintrust.com. Tax Gross-Up Provisions. Effective May 20, 2009, the Company adopted a policy that it will not enter into any new or materially amended agreements with NEOs that include any excise tax gross-up provisions with respect to payments contingent upon a change in control. In connection with the CEO transition, Mr. Wehmer’s employment agreement was amended and restated to eliminate Mr. Wehmer’s contractual right to an excise tax gross-up with respect to change in control payments. Prohibition on Hedging and Short Selling. The Company’s employees, including its executive officers and Directors, are prohibited from engaging in short selling of the Common Stock or engaging in hedging or offsetting transactions regarding the Common Stock. Prohibition on Pledging Stock. In April 2013, the Company adopted a policy prohibiting executive officers and Directors from pledging any of the Company’s securities. Stock Ownership Guidelines. The Company has adopted stock ownership guidelines for our executive officers as part of our commitment to corporate governance and to strengthen the alignment of interests between our executive officers and shareholders. Under the guidelines, our CEO and other NEOs are expected to accumulate shares of Common Stock to meet the applicable ownership level within five years of their election or appointment. For purposes of the guidelines, “shares” include shares owned by the executive or the executive’s immediate family members residing in the same household, including shares held in the Company’s 401(k) plan or employee stock purchase plan, shares held in trust for the benefit of the executive or the executive’s family, shares obtained through stock option exercises, deferred shares, shares of time-based restricted stock and restricted stock units granted under the Company’s equity plans. Unvested performance-based restricted stock units and unexercised stock options are not counted as “shares” under the guidelines.

  38. Compensation Process and Roles

    Compensation Process and Roles Role of Management. The Committee made all 2025 compensation decisions for our NEOs. Mr. Crane annually reviews the performance of each of the Company’s and its subsidiaries’ officers (other than Mr. Crane whose performance is reviewed by the Committee). The conclusions reached and the compensation recommendations based on these reviews, including with respect to salary adjustments and incentive award amounts, were presented to the Committee. The Committee exercised its discretion in modifying any recommended adjustment or award. Committee Process. During 2025, the Committee reviewed both the Company’s compensation philosophy and the actual compensation being paid by the Company. The Committee met, including in executive sessions without any members of management present, to discuss, evaluate and set executive officer compensation. In determining compensation for each of the NEOs, the Committee focused on the total compensation received by each NEO, as well as the allocation of each element of compensation in relation to those provided by the peer companies identified above. The Committee acted pursuant to a written charter that had been approved by our Board. Compensation Consultant. The Committee has the sole authority to retain and dismiss its own outside compensation consultants and any other advisors it deems necessary. The role of a compensation consultant is to assist the Committee in analyzing executive compensation packages and to provide the Committee with information regarding market compensation levels, general compensation trends and best practices. The consultant also provides advice regarding the competitiveness of specific pay decisions and actions for the NEOs, as well as the appropriateness of the design of the Company’s executive compensation program. In 2025, the Committee again engaged Meridian to advise it on executive compensation-related issues, conduct benchmarking and pay-for-performance analyses and to provide advice relating to establishing bonus opportunities and target incentives for 2025. In addition, Meridian provides guidance on leading practices on compensation as well as an analysis of director compensation. Meridian attended meetings of the Committee, including executive sessions, upon invitation. Meridian did not provide any other services to the Company. The Committee has assessed the independence of Meridian pursuant to the rules of the SEC and concluded that Meridian’s work for the Committee does not raise any conflicts of interest.

  39. 2025 Summary Compensation Table

    2025 Summary Compensation Table The following table summarizes compensation awarded to, earned by or paid to our NEOs for 2025, 2024, and 2023. The section of this Proxy Statement entitled “Compensation Discussion & Analysis” describes in greater detail the information reported in this table and the objectives and factors considered in setting NEO compensation.

  40. 2025 Summary Compensation Table

    | Name and Principal Position (a) | Year (b) | Salary ($) (c) | Bonus ($)(1) (d) | Stock Awards ($)(2) (e) | Option Awards ($) (f) | Non-Equity Incentive Plan Compensation ($) (g) | Change in Pension Value and Nonqualified Deferred Compensation Earnings ($) (h) | All Other Compensation ($)(3) (i) | Total ($) (j) | | Timothy S. Crane President and Chief Executive Officer | 2025 | 1,188,462 | 1,956,150 | 3,850,000 | — | — | — | 43,307 | 7,037,919 | | | 2024 | 1,089,231 | 1,380,500 | 3,575,000 | — | — | — | 38,220 | 6,082,951 | | | 2023 | 965,533 | 1,144,094 | 2,750,000 | — | — | — | 33,853 | 4,893,480 | | David A. Dykstra Vice Chairman and Chief Operating Officer | 2025 | 897,909 | 869,400 | 1,102,344 | — | — | — | 59,221 | 2,928,874 | | | 2024 | 878,442 | 705,000 | 1,062,500 | — | — | — | 49,508 | 2,695,450 | | | 2023 | 847,923 | 625,000 | 1,348,750 | — | — | — | 38,393 | 2,860,066 | | Richard B. Murphy Vice Chairman and Chief Lending Officer | 2025 | 688,197 | 666,540 | 842,969 | — | — | — | 76,104 | 2,273,810 | | | 2024 | 671,750 | 540,000 | 812,500 | — | — | — | 47,095 | 2,071,345 | | | 2023 | 647,923 | 480,000 | 1,023,750 | — | — | — | 33,580 | 2,185,253 | | David L. Stoehr Executive Vice President and Chief Financial Officer | 2025 | 607,693 | 515,600 | 678,500 | — | — | — | 38,888 | 1,840,681 | | | 2024 | 584,616 | 414,652 | 621,000 | — | — | — | 29,526 | 1,649,794 | | | 2023 | 537,923 | 355,974 | 777,400 | — | — | — | 29,209 | 1,700,506 | | Edward J. Wehmer Founder, Senior Advisor, and Chairman Emeritus | 2025 | 450,000 | — | — | — | — | — | 4,040,514 | 4,490,514 | | | 2024 | 450,000 | — | — | — | — | — | 4,068,810 | 4,518,810 | | | 2023 | 700,962 | 490,000 | — | — | — | — | 2,409,840 | 3,600,802 |

  41. 2025 Summary Compensation Table

    (1) The amounts shown in this column for 2025 consists of, for each of the NEOs, the annual cash bonus paid in 2026 with respect to 2025 performance. (2) The amounts shown in this column for 2025 represent performance-based restricted stock unit and time-based restricted stock unit awards granted under the Company’s LTIP. These awards are valued based on the aggregate grant date fair value computed in accordance with Financial Accounting Standards Board Accounting Standards Codification Topic 718, Compensation — Stock Compensation (“FASB ASC Topic 718”) and, in the case of performance-based restricted stock units, are reported based on the probable achievement of the performance-based vesting conditions at the time of grant. The grant date fair value of the awards represents the average of the high and low sale prices of the Common Stock on the date of grant, as reported by Nasdaq, multiplied by the number of shares subject to the award at target level. Under the LTIP, if the highest achievement level is attained for the 2025 performance-based restricted stock unit awards, the maximum grant date fair value for the performance-based and time-based awards is as follows: Mr. Crane $5,005,000; Mr. Dykstra $1,433,047; Mr. Murphy $1,095,859; and Mr. Stoehr $882,050. See Note 18 to the Audited Financial Statements included in the Company’s Form 10-K for the fiscal year ended December 31, 2025 for a discussion of the relevant assumptions used in calculating these amounts. (3) Amounts in this column include the value of all other compensation paid to or received by the NEOs in 2025. Please see the “All Other Compensation” table below for further information regarding these amounts. All Other Compensation for Mr. Wehmer includes the total of the monthly installments of the CEO Transition Award that were paid to Mr. Wehmer in 2025 pursuant to the Wehmer Agreement. Under the Wehmer Agreement (as defined above), Mr. Wehmer was awarded a one-time cash Transition Award of $12,000,000, payable in equal monthly installments over the 36-month period commencing on May 1, 2023 (subject to delayed payment required by tax law) and generally subject to Mr. Wehmer’s continued employment through each applicable payment date and his compliance with the restrictive covenants set forth in the Wehmer Agreement. See “Amended and Restated Employment Agreement with Mr. Wehmer” on page 40. Perquisites are valued at actual amounts paid for such perquisites and other compensation. Anniversary Gift reflects the gift value presented to Mr. Dykstra for thirty years of service. Executive Physical reflects the amount paid directly to the third-party vendor. Corporate Automobile Usage for Messrs. Dykstra, Murphy and Wehmer is calculated based on the IRS Annual Lease Value Table. Corporate Automobile Usage for Messrs. Crane and Stoehr is a cash automobile allowance. All Other Compensation*

  42. 2025 Summary Compensation Table

    | Named Executive Officer | Anniversary Gift ($) | Executive Physical ($) | Corporate Automobile Usage ($) | Club Memberships Not Exclusively For Business Use ($) | Life Insurance Premiums ($) | 401(k) Plan Matching Contribution ($) | CEO Transition Award ($) | Total ($) | | Timothy S. Crane | — | 9,075 | 18,000 | 1,624 | 9,108 | 5,500 | — | 43,307 | | David A. Dykstra | 1,667 | — | 30,787 | — | 21,267 | 5,500 | — | 59,221 | | Richard B. Murphy | — | — | 32,548 | 16,382 | 21,674 | 5,500 | — | 76,104 | | David L. Stoehr | — | — | 12,000 | 121 | 21,267 | 5,500 | — | 38,888 | | Edward J. Wehmer | — | — | 11,982 | 15,080 | 7,952 | 5,500 | 4,000,000 | 4,040,514 |

  43. 2025 Summary Compensation Table

    * See Note 3 to the “2025 Summary Compensation Table” above.

  44. 2025 Grants of Plan-Based Awards Table

    2025 Grants of Plan-Based Awards Table

  45. 2025 Grants of Plan-Based Awards Table

    | | | Estimated Future Payouts Under Non-Equity Incentive Plan Awards | | | Estimated Future Payouts Under Equity Incentive Plan Awards(1) | | | All Other Stock Awards: Number of Shares of Stock or Units(2) (#) (i) | All Other Option Awards: Number of Securities Underlying Options (#) (j) | Exercise or Base Price of Option Awards ($/Sh) (k) | Grant Date Fair Value of Stock and Option Awards(3) ($) (l) | | Name (a) | Grant Date (b) | Threshold ($) (c) | Target ($) (d) | Maximum ($) (e) | Threshold (#) (f) | Target (#) (g) | Maximum (#) (h) | | | | | | Timothy S. Crane | 1/23/2025 | — | — | — | — | — | — | 11,525 | — | — | 1,540,000 | | | 1/23/2025 | — | — | — | 8,644 | 17,288 | 25,932 | — | — | — | 2,310,000 | | David A. Dykstra | 1/23/2025 | — | — | — | — | — | — | 3,300 | — | — | 440,938 | | | 1/23/2025 | — | — | — | 2,475 | 4,950 | 7,425 | — | — | — | 661,406 | | Richard B. Murphy | 1/23/2025 | — | — | — | — | — | — | 2,523 | — | — | 337,188 | | | 1/23/2025 | — | — | — | 1,892 | 3,784 | 5,676 | — | — | — | 505,781 | | David L. Stoehr | 1/23/2025 | — | — | — | — | — | — | 2,031 | — | — | 271,400 | | | 1/23/2025 | — | — | — | 1,523 | 3,046 | 4,569 | — | — | — | 407,100 |

  46. 2025 Grants of Plan-Based Awards Table

    (1) The amounts in this column represent performance-based restricted stock unit awards granted to the NEOs pursuant to the 2025 LTIP and granted under the Wintrust Financial Corporation 2022 Stock Incentive Plan (the “2022 Plan”) that will be earned at the end of the performance period ending December 31, 2027 based on the Company’s achievement of performance objectives relating to the Company’s Adjusted EPS and Relative TSR. Subject to certain qualifying termination events, the participant is required to be employed on the award settlement date in order to vest in the award. (2) The amounts in this column represent time-based restricted stock unit awards granted to the NEOs pursuant to the 2025 LTIP and granted under the 2022 Plan that will be earned at the end of the vesting period ending January 23, 2028, subject to continued service through such date and certain qualifying termination events. The amounts in this column are valued based on the grant date fair value of the award calculated in accordance with FASB ASC Topic 718 based on the probable outcome of the applicable performance conditions. See Note 2 to the 2025 Summary Compensation Table for a discussion of the relevant assumptions used in calculating the grant date fair value. Narrative to the Summary Compensation Table and Grants of Plan-Based Awards Table As of December 31, 2025, each of our current NEOs was subject to an employment agreement with the Company. In the case of Messrs. Wehmer and Crane, their previous employment agreements were modified by the terms of their respective amended and restated employment agreements dated as of January 26, 2023, which were executed in connection with the transition of the CEO role from Mr. Wehmer to Mr. Crane, which occurred effective May 1, 2023, as discussed above. For Messrs. Dykstra and Murphy, the initial terms of their employment agreements expired in 2011 and the initial term of Mr. Stoehr’s employment agreement expired in 2009. However, each NEO’s agreement automatically renews for successive three-year terms, in the case of Messrs. Crane, Dykstra and Murphy, and one-year term in the case of Mr. Stoehr, unless either the NEO or the Company provides notice of non- renewal at least 60 days prior to the expiration of the then-current term. For Mr. Wehmer, the initial term of the Wehmer Agreement ends on December 31, 2026, and the Wehmer Agreement is renewable beyond such initial term by the mutual written agreement of Mr. Wehmer and the Company not less than 90 days prior to expiration of the initial term (or any subsequent term). If a change in control occurs, the then-current term of each NEO’s employment agreement, other than Mr. Wehmer, automatically extends for two years from the date of the change in control. If the term is extended due to a change in control, such extension will be further extended automatically for successive three-year terms, in the case of Messrs. Crane, Dykstra and Murphy, and one-year term in the case of Mr. Stoehr, unless either the NEO or the Company provides notice of non-renewal at least 60 days prior to the expiration of the then-current term.

  47. 2025 Outstanding Equity Awards at Fiscal Year-End Table

    2025 Outstanding Equity Awards at Fiscal Year-End Table The following table sets forth information for each NEO with respect to each award of restricted stock units that has not vested and remained outstanding at December 31, 2025. The market value as of December 31, 2025 has been calculated using the closing price of the Company’s Common Stock on December 31, 2025 of $139.82, as reported on Nasdaq. As of December 31, 2025, none of our NEOs held any outstanding stock options.

  48. 2025 Outstanding Equity Awards at Fiscal Year-End Table

    | | Options Awards | | | | | Stock Awards | | | | | Name (a) | Number of Securities Underlying Unexercised Options (#) Exercisable (b) | Number of Securities Underlying Unexercised Options Unexercisable (#) (c) | Equity Incentive Plan Awards: Number of Securities Underlying Unexercised Unearned Options (#) (d) | Option Exercise Price ($) (e) | Option Expiration Date (f) | Number of Shares or Units of Stock That Have Not Vested (#) (g) | Market Value of Shares or Units of Stock That Have Not Vested ($) (h) | Equity Incentive Plan Awards: Number of Unearned Shares, Units or Other Rights that Have Not Vested (#)(1) (i) | Equity Incentive Plan Awards: Market or Payout Value of Unearned Shares, Units or Other Rights That Have Not Vested ($) (j) | | Timothy S. Crane | — | — | — | — | — | 12,248(2) | 1,712,515 | — | — | | | — | — | — | — | — | 14,456(4) | 2,021,238 | 21,684(5) | 3,031,857 | | | — | — | — | — | — | 11,525(6) | 1,611,426 | 17,288(7) | 2,417,208 | | | — | — | — | — | — | 19,198(3) | 2,684,264 | — | — | | David A. Dykstra | — | — | — | — | — | 6,007(2) | 839,899 | — | — | | | — | — | — | — | — | 4,296(4) | 600,667 | 6,444(5) | 901,000 | | | — | — | — | — | — | 3,300(6) | 461,406 | 4,950(7) | 692,109 | | | — | — | — | — | — | 9,414(3) | 1,316,265 | — | — |

  49. 2025 Outstanding Equity Awards at Fiscal Year-End Table

    | | Options Awards | | | | | Stock Awards | | | | | Name (a) | Number of Securities Underlying Unexercised Options (#) Exercisable (b) | Number of Securities Underlying Unexercised Options Unexercisable (#) (c) | Equity Incentive Plan Awards: Number of Securities Underlying Unexercised Unearned Options (#) (d) | Option Exercise Price ($) (e) | Option Expiration Date (f) | Number of Shares or Units of Stock That Have Not Vested (#) (g) | Market Value of Shares or Units of Stock That Have Not Vested ($) (h) | Equity Incentive Plan Awards: Number of Unearned Shares, Units or Other Rights that Have Not Vested (#)(1) (i) | Equity Incentive Plan Awards: Market or Payout Value of Unearned Shares, Units or Other Rights That Have Not Vested ($) (j) | | Richard B. Murphy | — | — | — | — | — | 4,559(2) | 637,439 | — | — | | | — | — | — | — | — | 3,285(4) | 459,309 | 4,928(5) | 689,033 | | | — | — | — | — | — | 2,523(6) | 352,766 | 3,784(7) | 529,079 | | | — | — | — | — | — | 7,145(3) | 999,014 | — | — | | David L. Stoehr | — | — | — | — | — | 3,462(2) | 484,057 | — | — | | | — | — | — | — | — | 2,511(4) | 351,088 | 3,766(5) | 526,562 | | | — | — | — | — | — | 2,031(6) | 283,974 | 3,046(7) | 425,892 | | | — | — | — | — | — | 5,425(3) | 758,524 | — | — | | Edward J. Wehmer | — | — | — | — | — | — | — | — | — |

  50. 2025 Outstanding Equity Awards at Fiscal Year-End Table

    The amounts in this column represent restricted stock unit awards that remained subject to performance- based vesting conditions as of December 31, 2025. (2) Represents time-based restricted stock unit awards that vested on January 26, 2026. (3) Represents awards that vested and were settled on February 25, 2026, based on performance during the period from January 1, 2023 through December 31, 2025. The awards are reported at the actual vesting level, which was determined based on the Company’s achievement of Adjusted EPS and Relative TSR over the three-year performance period. (4) Represents time-based restricted stock unit awards that are scheduled to vest on January 25, 2027. (5) Represents performance-based restricted stock unit awards that are scheduled to be earned at the end of the January 1, 2024 through December 31, 2026 performance period based on the Company’s achievement of performance objectives relating to the Company’s Adjusted EPS and Relative TSR. These restricted stock unit awards are reported in this table assuming target achievement. (6) Represents time-based restricted stock unit awards that are scheduled to vest on January 23, 2028. Represents performance-based restricted stock unit awards that are scheduled to be earned at the end of the January 1, 2025 through December 31, 2027 performance period based on the Company’s achievement of performance objectives relating to the Company’s Adjusted EPS and Relative TSR. These restricted stock unit awards are reported in this table assuming target achievement.

  51. 2025 Option Exercises and Stock Vested Table

    2025 Option Exercises and Stock Vested Table The following table sets forth information for each NEO with respect to the vesting of stock awards during 2025, and the value realized upon such vesting. No options were held or exercised by the NEOs during 2025.

  52. 2025 Option Exercises and Stock Vested Table

    | | Option Awards | | Stock Awards | | | Name (a) | Number of Shares Acquired on Exercise (#) (b) | Value Realized on Exercise ($) (c) | Number of Shares Acquired on Vesting (#)(1) (d) | Value Realized on Vesting ($)(2) (e) | | Timothy S. Crane | — | — | 9,517 | 1,198,518 | | David A. Dykstra | — | — | 13,693 | 1,724,410 | | Richard B. Murphy | — | — | 10,352 | 1,303,673 | | David L. Stoehr | — | — | 7,679 | 967,048 | | Edward J. Wehmer | — | — | 38,458 | 4,843,170 |

  53. 2025 Option Exercises and Stock Vested Table

    (1) Represents the vesting of time-based restricted stock unit awards and performance-based restricted stock unit awards granted under the Company’s 2015 Stock Incentive Plan. (2) The value realized on the vesting of time-based restricted stock unit awards and performance-based restricted stock unit awards represents the average of the high and low market price of the Common Stock on the date of vesting multiplied by the number of time-based restricted stock unit awards and performance-based restricted stock unit awards that vested.

  54. 2025 Nonqualified Deferred Compensation Table

    2025 Nonqualified Deferred Compensation Table

  55. 2025 Nonqualified Deferred Compensation Table

    | Name (a) | Executive Contributions in Last Fiscal Year ($) (b) | Registrant Contributions in Last Fiscal Year ($) (c) | Aggregate Earnings in Last Fiscal Year ($) (d) | Aggregate Withdrawals/ Distributions ($) (e) | Aggregate Balance at Last Fiscal Year End ($) (f) | | Edward J. Wehmer | — | — | 90,159(1) | 1,097,587(4) | 10,470,289(2) | | Timothy S. Crane | — | — | — | — | — | | David A. Dykstra | — | — | 719,549(1) | — | 5,893,206(3) | | Richard B. Murphy | — | — | — | — | — | | David L. Stoehr | — | — | — | — | — |

  56. 2025 Nonqualified Deferred Compensation Table

    (1) The amounts reported in the column entitled “Aggregate Earnings in Last Fiscal Year” represent the change in the value of the shares subject to the deferred LTIP and restricted stock unit awards from December 31, 2024 to December 31, 2025, net of distributions. (2) This amount represents the value of Mr. Wehmer’s deferred LTIP award settled in 2019 and his restricted stock unit award which have vested but are not issuable until the earlier to occur of (i) the January 15th after the executive’s termination of employment and (ii) the time at which the award is no longer subject to the deduction limits under Section 162(m) of the Internal Revenue Code (the “Code”). (3) This amount represents the value of Mr. Dykstra’s restricted stock unit awards which have vested but are not issuable until the earlier to occur of (i) the January 15th after the executive’s termination of employment and (ii) the time at which the award is no longer subject to the deduction limits under Section 162(m) of the Code. This amount represents the value of Mr. Wehmer’s deferred LTIP awards settled in 2018 that were distributed in 2025 in accordance with the deferral terms of his LTIP award agreement.

  57. POTENTIAL PAYMENTS UPON TERMINATION OR CHANGE IN CONTROL

    POTENTIAL PAYMENTS UPON TERMINATION OR CHANGE IN CONTROL As noted under “Compensation Discussion & Analysis — Post-Termination Compensation” on page 49 of this Proxy Statement, we have entered into employment agreements with each of our NEOs that provide for payments in connection with such NEO’s termination, whether in connection with a change in control or otherwise. The benefits to be provided to the current NEOs under the employment agreements upon various termination situations are described below, including a summary of payments that would have been required had a termination taken place on December 31, 2025.

  58. CEO PAY RATIO DISCLOSURE

    CEO PAY RATIO DISCLOSURE As required by Section 953(b) of the Dodd-Frank Wall Street Reform and Consumer Protection Act, the Company is providing the following disclosure about the relationship of the annual total compensation of our employees to the annual total compensation of Mr. Crane, our President and Chief Executive Officer as of December 31, 2025. We believe that the pay ratio disclosed below is a reasonable estimate calculated in a manner consistent with Item 402(u) of Regulation S-K. For 2025, • The median of the annual total compensation of all of our employees, other than Mr. Crane, was $81,448. • Mr. Crane’s annual total compensation, as reported in the Total column of the 2025 Summary Compensation Table was $7,037,919. • Based on this information, the ratio of the annual total compensation of Mr. Crane to the median of the annual total compensation of all employees is estimated to be 86.4 to 1. We selected October 1, 2025 as the date on which to determine our median employee. As of that date, we had had approximately 5,883 employees. The pay ratio disclosure rules provide an exemption for companies to exclude non-U.S. employees from the median employee calculation if non-U.S. employees in a particular jurisdiction account for five percent (5%) or less of the Company’s total number of employees. We applied this de minimis exemption when identifying the median employee by excluding 156 employees in Canada and one employee in Puerto Rico. After taking into account the de minimis exemption, 5,726 employees in the United States and zero employees located outside of the United States were considered for identifying the median employee. For purposes of identifying the median employee from the employee population base, other than Mr. Crane, we considered W-2 gross taxable wages for calendar year 2025. In addition, we annualized compensation for employees who commenced employment with the Company after January 1, 2025 or who terminated prior to December 31, 2025. In determining the annual total compensation of the median employee, such employee’s compensation was calculated in accordance with Item 402(c)(2)(x) of Regulation S-K, as required pursuant to the SEC executive compensation disclosure rules. This calculation is the same calculation used to determine total compensation for purposes of the 2025 Summary Compensation Table with respect to each of the NEOs.

  59. PAY VERSUS PERFORMANCE

    PAY VERSUS PERFORMANCE As required by Section 953(b) of the Dodd-Frank Wall Street Reform and Consumer Protection Act, and Item 402(v) of Regulation S-K, the Company is providing the following information for “Compensation Actually Paid,” as calculated per SEC disclosure rules, and the Company’s financial performance against specific performance metrics for each of the last five completed calendar years. The table below summarizes “Compensation Actually Paid” to Mr. Wehmer, the Company’s former Principal Executive Officer (“PEO”), “Compensation Actually Paid” to Mr. Crane, the Company’s current PEO, and the average “Compensation Actually Paid” to our NEOs other than Mr. Wehmer and Mr. Crane. In determining the “Compensation Actually Paid,” we are required to make various adjustments to amounts that have been reported in the Summary Compensation Table in previous years as the valuations methods for this section differ from those required in the Summary Compensation Table, primarily as it relates to equity valuations. Under the Summary Compensation Table rules, equity awards are reflected as compensation in the year of grant based on the full grant date fair value, whereas equity awards are reported as “Compensation Actually Paid” during the vesting period and are impacted by changes in the Company’s stock price through the vesting date. Similar to the Summary Compensation Table, “Compensation Actually Paid” includes the value of equity awards as compensation prior to vesting and, thus, such compensation may never be realized by the NEOs if the underlying vesting conditions are not satisfied.

  60. PAY VERSUS PERFORMANCE

    | Year(1) | Summary Compensation Table Total PEO — Mr. Crane(2) ($) | Compensation Actually Paid to PEO — Mr. Crane(3) ($) | Summary Compensation Table Total PEO — Mr. Wehmer(2) ($) | Compensation Actually Paid to PEO — Mr. Wehmer(3) ($) | Average Summary Compensation Table Total for Non-PEO NEOs(2) ($) | Average Compensation Actually Paid to Non-PEO NEOs(3) ($) | Value of Initial Fixed $100 Investment Based On(4): | | Net Income ($ in millions) | Adjusted EPS(6) ($) | | | | | | | | | Wintrust TSR ($) | Peer Group TSR(5) ($) | | | | 2025 | 7,037,919 | 9,079,415 | | | 2,883,470 | 3,320,115 | 249.22 | 216.97 | 824 | 16.92 | | 2024 | 6,082,951 | 9,039,311 | | | 2,733,850 | 4,106,924 | 218.75 | 168.35 | 695 | 14.81 | | 2023 | 4,893,480 | 4,980,483 | 3,600,802 | 4,822,614 | 2,058,687 | 2,257,999 | 159.87 | 125.02 | 623 | 14.78 | | 2022 | | | 7,542,089 | 8,359,216 | 2,350,417 | 2,507,670 | 142.73 | 113.60 | 510 | 12.63 | | 2021 | | | 7,140,312 | 9,915,585 | 2,066,281 | 2,621,076 | 151.10 | 137.31 | 466 | 9.64 |

  61. PAY VERSUS PERFORMANCE

    (1) Mr. Wehmer served as the Company’s sole PEO in years 2021 – 2022 and the Company’s other NEOs for years 2021 – 2022 are Messrs. Dykstra, Murphy, Crane and Stoehr. Mr. Wehmer and Mr. Crane each served as the Company’s PEO in 2023 for the time periods as reported above, and the Company’s other NEOs for 2023 are Messrs. Dykstra, Murphy, Stoehr and Ms. Boege. Mr. Crane served as the Company’s sole PEO in 2024 and 2025, and the Company’s other NEOs for 2024 and 2025 are Messrs. Wehmer, Dykstra, Murphy and Stoehr. (2) Amounts reported in this column represent (i) the total compensation reported in the Summary Compensation Table for the applicable years for Mr. Crane and Mr. Wehmer and (ii) the average of the total compensation reported in the Summary Compensation Table for the Company’s other NEOs for the applicable years, as described in (1) above. SEC rules require certain adjustments be made to the Summary Compensation Table totals to determine “Compensation Actually Paid” as reported in the Pay-versus-Performance Table. “Compensation Actually Paid” does not necessarily represent cash and/or equity value transferred to the applicable NEO without restriction, but rather is a value calculated under applicable SEC rules. In general, “Compensation Actually Paid” is calculated as the total compensation reported in the Summary Compensation Table adjusted to include the fair market value of equity awards as of December 31 of the applicable year or, if earlier, the vesting date. The Company does not provide a defined benefit plan so no adjustment for pension benefits is included. The following table details these adjustments:

  62. PAY VERSUS PERFORMANCE

    | Year | Summary Compensation Table Total ($)(a) | (Minus) Grant Date Fair Value of Stock Awards Granted in Fiscal Year ($)(b) | Plus Fair Value at Fiscal Year-End of Outstanding and Unvested Stock Awards Granted in Fiscal Year ($)(c) | Plus/(Minus) Change in Fair Value of Outstanding and Unvested Stock Awards Granted in Prior Fiscal Years ($)(d) | Plus Fair Value at Vesting of Stock Awards Granted in Fiscal Year that Vested During Fiscal Year ($)(e) | Plus/(Minus) Change in Fair Value as of Vesting Date of Stock Awards Granted in Prior Years for which Applicable Vesting Conditions Were Satisfied During Fiscal Year ($)(f) | (Minus) Fair Value as of Prior Fiscal Year- End of Stock Awards Granted in Prior Fiscal Years that Failed to Meet Applicable Vesting Conditions During Fiscal Year ($)(g) | Equals Compensation Actually Paid ($) | | Mr. Crane (PEO) | | | | | | | | | | 2025 | 7,037,919 | (3,850,000) | 4,279,571 | 1,600,272 | — | 11,653 | — | 9,079,415 | | 2024 | 6,082,951 | (3,575,000) | 4,862,945 | 1,618,863 | — | 49,552 | — | 9,039,311 | | 2023 | 4,893,480 | (2,750,000) | 2,585,759 | 227,640 | — | 23,604 | — | 4,980,483 | | Mr. Wehmer (PEO) | | | | | | | | | | 2023 | 3,600,802 | — | — | 1,078,267 | — | 143,545 | — | 4,822,614 | | 2022 | 7,542,089 | (2,878,750) | 2,848,340 | 847,537 | — | — | — | 8,359,216 | | 2021 | 7,140,312 | (2,530,000) | 4,319,490 | 985,783 | — | — | — | 9,915,585 | | Other NEOs(h) | | | | | | | | | | 2025 | 2,883,470 | (655,953) | 729,053 | 342,131 | — | 21,414 | — | 3,320,115 | | 2024 | 2,733,850 | (624,000) | 848,728 | 1,039,504 | — | 108,842 | — | 4,106,924 | | 2023 | 2,058,687 | (955,663) | 898,474 | 229,985 | — | 26,516 | — | 2,257,999 | | 2022 | 2,350,417 | (771,875) | 763,616 | 165,512 | — | — | — | 2,507,670 | | 2021 | 2,066,281 | (511,438) | 873,110 | 193,123 | — | — | — | 2,621,076 |

  63. PAY VERSUS PERFORMANCE

    (a) Represents Total Compensation as reported in the Summary Compensation Table for the indicated fiscal year. With respect to the other NEOs, amounts shown represent averages. (b) Represents the grant date fair value of the stock awards granted during the indicated fiscal year, computed in accordance with the methodology used for financial reporting purposes. (c) Represents the fair value as of the indicated fiscal year-end of the outstanding and unvested stock awards granted during such fiscal year, computed in accordance with the methodology used for financial reporting purposes and, for awards subject to performance-based vesting conditions, based on the probable outcome of such performance-based vesting conditions as of the last day of the fiscal year. (d) Represents the change in fair value during the indicated fiscal year of each stock award that was granted in a prior fiscal year and that remained outstanding and unvested as of the last day of the indicated fiscal year, computed in accordance with the methodology used for financial reporting purposes and, for awards subject to performance-based vesting conditions, based on the probable outcome of such performance-based vesting conditions as of the last day of the fiscal year. (e) Represents the fair value at vesting of the stock awards that were granted and vested during the indicated fiscal year, computed in accordance with the methodology used for financial reporting purposes. (f) Represents the change in fair value, measured from the prior fiscal year-end to the vesting date, of each stock award that was granted in a prior fiscal year and which vested during the indicated fiscal year, computed in accordance with the methodology used for financial reporting purposes. (g) Represents the fair value as of the last day of the prior fiscal year of the stock awards that were granted in a prior fiscal year and which failed to meet the applicable vesting conditions in the indicated fiscal year, computed in accordance with the methodology used for financial reporting purposes. (h) See (1) above for the NEOs included in the average for the indicated fiscal year. (4) Pursuant to rules of the SEC, the comparison assumes $100 was invested on December 31, 2020. Historic stock price performance is not necessarily indicative of future stock price performance. (5) The Peer Group TSR utilizes the Nasdaq Global Select Market bank stock as the peer group index, which is the same industry index used in the Company’s Annual Report on Form 10-K. (6) As noted in the “Compensation Discussion & Analysis,” for 2025, the Committee views Adjusted EPS as an important metric of Company performance. Fifty percent (50%) of the performance-based restricted stock units vest based on the Company’s three-year cumulative earnings per share as adjusted to exclude income taxes, acquisition-related charges, and the provision for credit losses with such amount being further reduced by actual net charge-offs of loans. Relationship Between Pay and Performance We believe the “Compensation Actually Paid” in each of the years reported above and over the five- year cumulative period are reflective of the Committee’s emphasis on “pay-for-performance” as the “Compensation Actually Paid” fluctuated year-over-year, primarily due to the result of our stock performance and our varying levels of achievement against pre-established performance goals under our short-term incentive awards and the LTIP. The following charts display the “Compensation Actually Paid” to the PEO and the average of the “Compensation Actually Paid” to the other NEOs as compared to the Company’s Adjusted EPS, Net Income and TSR over the five most recently completed years as well as the relationship between the Company’s TSR and the Peer Group TSR over such five-year period. Performance Measures Used to Link Company Performance and Compensation Actually Paid to the NEOs The following is a list of financial performance measures, which in our assessment represent the most important financial performance measures used by the Company to link compensation actually paid to the NEOs for 2025: • Adjusted EPS • Net Income • TSR relative ranking within KRX Index Policies and Practices Related to the Timing of Grants of Certain Equity Awards The Compensation Committee and senior management monitor the Company’s equity grant practices to evaluate whether such policies comply with governing regulations and are consistent with good corporate practices. When making regular annual equity grants, the Compensation Committee’s practice is to approve them at its meeting in January of each year as part of the annual compensation review and after results for the preceding fiscal year become available. Because the Compensation Committee’s regular meeting schedule is determined in the prior fiscal year, the proximity of any awards to other significant corporate events is coincidental. In addition, the Compensation Committee may make grants at any time during the year it deems appropriate, including with respect to new hires or transitions. The Company does not schedule its equity grants in anticipation of the release of material non-public information (“MNPI”) nor does the Company time the release of MNPI based on equity grant dates. During 2025, no stock option grants were made to any of our NEOs.