Mr. H. Patrick Hackett, Jr. has been the Chairman of Wintrust since 2017. Prior to this, he served as a Principal of HHS Co. Previously, Mr. Hackett served as the President and Chief Executive Officer of RREEF Capital, Inc and as Principal of The RREEF Funds. Earlier, he served as a Director at First Industrial Realty Trust, Inc. and Wintrust Bank.

Mr. Timothy S. Crane has been the Chief Executive Officer, President and Director of the company since February 2023. Prior to this, he served as an Executive Vice President, Senior Market Head and the Treasurer from 2017 to 2020. Mr. Crane joined the company in 2008. Before joining Wintrust, he served as President of Harris Bank in Chicago, where he was employed for 24 years.

Mr. Richard B. Murphy has been the Vice Chairman and the Chief Lending Officer of the company since February 2020. Prior to this, he served as the Chief Credit Officer and Executive Vice President of Wintrust from 2002 to 2020. Mr. Murphy served as the President at Hinsdale Bank from 1996 to 2005 and served as its Executive Vice President and Senior Lender from 1993 until his promotion as the President. He served as the President at the First State Bank of Calumet City. Mr. Murphy serves as a Director at Hinsdale Bank and Town Bank.

Mr. David Alan Dykstra has been the Chief Operating Officer and Vice Chairman of the company since February 2020. Prior to this, he was a Senior Executive Vice President at Wintrust. Mr. Dykstra joined the company in 1995 and served as its Chief Financial Officer prior to 2002. He has been a Regional Market Head overseeing Crystal Lake Bank, State Bank of the Lakes and Tricom. Mr. Dykstra was employed at River Forest Bancorp from 1990 to 1995 and has also held the positions of Senior Vice President and Chief Financial Officer. He spent around seven years at KPMG LLP, most recently as the Audit Manager in the banking practice. Mr. Dykstra serves as a Director at First Insurance Funding, First Insurance Funding of Canada, State Bank of the Lakes and Tricom.

Mr. David L. Stoehr is the Chief Financial Officer and Executive Vice President at Wintrust. Mr. Stoehr joined the company in 2002. He was the Senior Vice President of Reporting and Analysis at Firstar/US Bancorp and a Director of Finance and Controller at Associated Banc-Corp with primary responsibility for financial accounting and reporting, business unit financial management, and data warehouse design and implementation. Prior to his association at Associated Banc-Corp, Mr. Stoehr was an Assistant Vice President of Balance Sheet Management at Huntington Bancshares from 1993 to 1995 and a Financial Reporting Officer at Valley Bancorporation from 1983 to 1993.