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July 6, 2025

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1 Homepage Slider Spy Chats Spy Highlights

Exit Interview: Glenn Wilson on Banking and Giving Back

November 24, 2020 by Dave Wheelan

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The Spy “Exit Interview” series is part journalism and part oral history. Over the last eleven years, the Spy has interviewed dozen local leaders at the moment of their retirement to reflect on their work and some of the challenges they have faced in their professional careers and the nonprofit organizations they have helped as trustees.

In this installment, the Spy talks to Glenn Wilson, president of Chesapeake Bank and Trust in Chestertown. After almost forty years in banking, which included leadership positions at Maryland National Bank, AmeriServ Financial Inc. in Pennsylvania, and the past five years with Chesapeake, Wilson and his wife, Diana, will be heading down to Florida to be closer to their two sons.

Wilson is the first to note that he leaves Chesapeake amid significant challenges. While he is pleased that his bank has come out of the COVID-19 induced 2020 recession in good shape and on the course of a full recovery, he still feels the pain of the coronavirus crisis as Chestertown’s merchants and restaurateurs continue to pick up the pieces of a damaged local economy.

Glenn also talks candidly about the challenges of nonprofit organizations that he served in leadership roles. Starting with the United Way of Kent County and the needs assessment, he helped determine the area’s most pressing issues and the Sultana Education Foundation, which remains severely impacted by the pandemic shutdown. And on a brighter note, his conviction that UM Shore Regional Health, where he also served on their board, and the State of Maryland will find a way to keep Chestertown’s hospital open and thriving for many years to come.

This video is approximately minutes eleven in length. 

 

 

The Spy Newspapers may periodically employ the assistance of artificial intelligence (AI) to enhance the clarity and accuracy of our content.

Filed Under: 1 Homepage Slider, Spy Chats, Spy Highlights

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Letters to Editor

  1. kurt landgraf says

    November 24, 2020 at 10:13 AM

    Glenn is one of the most outstanding people I have ever known His caring for the community is extraordinary The United Way of Kent Country, the Maryland Health System and Chestertown are all so much better off because he has been here….. He was one of the first people I met after moving to Chestertown to become President of Washington College.

    I consider it a honor and true privilege to have known him. We should all wish him the very best!!!!!!

  2. Andy Scott says

    November 24, 2020 at 5:05 PM

    Glenn and Diana Wilson have left an indelible mark on Chestertown. We will miss them both. Our very best wishes go with them.

  3. Jamie Williams says

    November 24, 2020 at 6:43 PM

    Thank you Glenn for your professional insights over the years and your service to the Kent County community.

  4. Deirdre LaMotte says

    November 25, 2020 at 12:02 PM

    Glenn was a superb Board President for our United Way. Thank you for all you have done; Coral Gables is
    lucky to have you.

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