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May 8, 2025

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Spy Highlights

A “Come-back” Looks at Dorchester County Education: A Long-From Chat with Chris Wheedleton

June 22, 2024 by Dave Wheelan Leave a Comment

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While most on the Mid-Shore are quite familiar with the terms “From Heres” and “Come-Heres” to describe one’s longevity and cultural tribe, there is also a somewhat rare but growing number of folks who can be labeled as “Come Backers” in almost every town as well. Those are a certain breed who grew up in places like Chestertown or Cambridge and reaped the benefits of a first-class public school education, which opened the doors to some of the most selective colleges in the country.  They then were placed on a professional track that led to great financial success in some of the big cities of the Northeast. But rather than have the story end there, quite a few of those “Come Backers” have recently and consciously decided to return to their roots and a quality of life not available in metro areas. Most of them also came back intentionally to find a way to help their native community.

One of those “Come Backers” is Chris Weedleton. The proud product of farmers and preachers from the very rural Eastern part of Dorchester County, Weedleton was one of those who graduated from high school and found himself studying education at Penn State as an undergraduate and later a lucrative career in sales and marketing for Nabisco for more than a decade. But increasingly eager to return to his first love, education, Chris serendipitously met and eventually joined the Edison Project, a well-financed initiative to redesign American schools from the ground up and open by creating charter private schools throughout the country. With the financial support of billionaire Chris Whittle and board leadership with the likes of Benno Schmidt, former president of Yale, Edison had risen to be one of the most interesting education experiments in the world.

But with the unexpected news that his sister had been diagnosed with a serious form of cancer, Chris made a decision to return to Dorchester and began a private consulting firm to help struggling public school systems throughout the country. The move also motivated him to use the skills he had learned over his unique career to give back locally. The first experience was Weedleton’s leadership role in the creation of Moving Dorchester Forward, described as a neutral convener to bridge gaps to ensure all in Dorchester thrive, including education.

The second call to duty was Chris’s recent appointment to fill the District 5 board seat on the Dorchester County Board of Education.

In our Spy long-form format interview with Chris, he talks about the scope of his experiences and observations about Maryland public education in the 21st Century. He also addresses his recent disagreement with fellow board members on how the budget was approved and his decision to go public with those concerns. Finally, Chris outlines the need for the community to move forward and remains optimistic that Dorchester’s public schools can rise again to some of the best in the state.

This video is approximately 26 minutes in length.

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

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