Chestertown Futures Case Study #23: Margo Bailey


It doesn’t take long for Margo Bailey to come out swinging on the subject of Chestertown’s future. As mayor for eighteen years, nothing has been more on her mind as she actively took a leadership role with some of the town’s most significant projects and controversies. From the early days of fighting Wal-mart to the more current issues like the town armory and marina, Margo has never blinked, rightly or wrongly, on the big stuff.

The mayor continues this tradition when asked about her thoughts on the town’s future. While her determination is strong, one can also hear a sobering tone as she takes stock of a flat local economy and a very slow crawl back from the Great Recession in 2008. As she candidly admits, the task of restoration goes well beyond the capacity and resources of one town council and one mayor.

Letters to Editor

  1. I had to break the silence. After almost three months since publication, it is frightening that no one has commented on this piece (at least one that passed editorial muster).

    A few choice snip-its: “Things are coming together.” “We just need to get in line and wait our turn.” “I have wanted a fishing pier for 19 years.” “45 percent of this town can’t be taxed.”

    Why can’t she have a fishing pier, she’s the mayor? Actually, she could have had one, but nixed the expansion of the Chestertown Marina when it is was in private hands. Why? She got in bed with yet one more non-taxpaying non-profit that opposed an expanded pier system. The little guy (the code for local non-profits that are for the most part funded by the rich and often anti-growth) prevailed, the marina lacked the capacity to grow, the economic tanked, and one more property falls in to town hands. She appears completely oblivious to the economic death swirl she has helped to foster over the past 20 years. To blame the College is absurd. This is the old argument she has used time and again.

    I can’t imagine that she can expect to run on her record and win. But who are the next generation of leaders?

    After 23 of these Chestertown’s Future posts, I thought we would see more leadership material surface.

    Keep at it.

  2. Instead of all the elderly people on Chestertown futures, why not do one on Doug Rae–one of the few young people staying around–and an entrepreneur who employs a surprising and whopping 20 people?

  3. Aleks Smolens says

    So is the Chestertown Spy making a subtle political statement here – Chestertown’s Future ends with Margo?

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