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June 21, 2025

Chestertown Spy

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3 Top Story Archives

Spy vs Spy: A Chat with Carol “Rollie” Flynn

July 9, 2024 by James Dissette 1 Comment

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You don’t have to go far to discover one facet that makes life in Chestertown unique—the individuals who make up the community and the work lives they’ve led.

A casual encounter at the Saturday Market, an event at Charles Sumner Hall, or celebrations like Sultana Downrigging and exhibits at Kent Cultural Alliance offer opportunities to connect with someone whose life story adds a distinctive layer to our diverse community fabric.

One significant aspect of our community’s warp and weave is its proximity to the nation’s capital and the promise the Shore holds for a more relaxed pace for weekends or residency. This connection has drawn many professionals, including federal employees who seek respite for a weekend only to discover Kent County as the place they would eventually call home.

Like many others, especially during the years of the pandemic, Carol “Rollie” Flynn found the Eastern Shore a perfect break from her professional life. Flynn began her weekend jaunts to visit friends, but the tradition eventually lured her into becoming a full-time resident.

The respite was from 30 years in the CIA and as President of the Foreign Policy Research Institute (now President Emerita), along with a stint as an adjunct Professor at Georgetown University’s School of Foreign Service/Security Studies Program. To top it off, Flynn is also a member of the Advisory Board of the International Spy Museum in Washington D.C.

Here, Flynn talks about how her experience in the Central Intelligence Agency and Foreign Policy Research Institute has given her a unique lens to observe how media shapes our perceptions, the dangers inherent in “bias,” and some of the risks we face in a high-tech world.

This interview was conducted in May and is one of two long-form discussions the Spy will offer this summer as we seek to meet and explore the lives of our neighbors, new and those whose families are rooted in centuries of Eastern Shore life.

This is a long-form video and is approximately sixteen minutes 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: 3 Top Story, Archives

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Letters to Editor

  1. David A Turner says

    July 9, 2024 at 12:51 AM

    What a lovely discussion by Ms. Flynn. Her perspectives on media, foreign affairs, governance, intelligence and the education of the public are useful to Spy readers and beyond. More please.

    Reply

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