Don Leopold appointed to replace the late John Alley

Newest Dukes County commissioner talks about his priorities.

Chilmark resident Don Leopold was appointed a Dukes County commissioner on Wednesday, June 3. - Rich Saltzberg

Dukes County commissioners voted 5-0-0 to appoint Chilmark finance committee member Don Leopold to replace the late John Alley. Discussion was short ahead of the vote. Commissioner Leon Brathwaite noted Leopold has filed papers to be on the ballot in the fall so he can continue the commitment beyond the remainder of Alley’s term.

On Thursday, Leopold, a former management consultant, sat with The Times for a short interview. Further exploration of the efficacy of the county as a vehicle for coordination among the six towns came through as his burgeoning platform. 

“I think a couple of things made me interested,” Leopold said of seeking the seat. “One is the pandemic, and seeing what happens when we have kind of heroic efforts to coordinate across towns, but they’re kind of emergency efforts as opposed to — certain kinds of things from an Island-wide perspective” — he added, things that “might be more effective.”

Leopold referenced diplomatic work he engaged in between the Chilmark Fire Department and the town’s selectmen as putting his mind to work on how local government might be more coordinated. “And while it didn’t, by any means, have me conclude that there should necessarily be one fire department or one police department,” he said, it did foster questions such as, “How do we coordinate what services would be better coordinated, if not single [services]?”

Leopold said he sees the county as the best foundation for such ideas. “From what I can tell, it looks like the commission may have the body with the most potential to do this kind of cross-Island thinking — Where do we gain the greatest effectiveness?” he said. “And from what I can tell based on the press over the years, and from watching and talking to people, it has not been terribly effective at being able to do that.”

Leopold said he had an internal debate: “I think there’s a lot of potential here; do I really want to step into it? And obviously, yeah, guess I will.”

Leopold said he was previously impressed to learn through Chilmark’s climate working group that a large amount of study and planning was afoot in each town on the Vineyard relative to climate change. 

“But what was also kind of starling was [except for] people like the MVC, they were all disjointed, and literally we could have been in a position where we had six towns applying to the state for the same funds.” 

He said he also found that one threat explored in the working group, from his perspective, seemed to overshadow most others. “When you looked at what impacts might be and how they would affect the different towns, what kept emerging was fire,” he said. He went on to specify wildfire was what kept rearing its head, and presenting problems most people don’t think about, like how much cleared or fuel-free space they might have around their home. That led him to point out that wildfire doesn’t confine itself to the boundaries of a given town. 

“Boy, if a fire started in West Tisbury, or a fire started here [Chilmark], the fire is not going to say, Sorry, can’t go to West Tisbury or Chilmark. And so this idea of looking at climate by town as opposed to Island-wide, I think that was really a large part of what at least had me start to think about what does make more sense …”

As to where the six towns appear to coordinate well, Leopold pointed to the boards of health: “It looks to me as if the boards of health do a great job of coordinating, but it’s kind of up to individual heroics to do that.” Leopold wondered if it would be better to inquire whether one board of health would work more effectively, or encourage even more coordination between boards of health. 

“I don’t know enough about the boards of health to have a particular point of view,” he said, “but those are the kinds of things that seem to be worth looking at.”

Leopold went on to say he’s been a seasonal resident for decades, and moved to the Vineyard about five years ago. When he did settle here permanently, he was struck by the redundancy of government. “Your first instinct is to say, My God, why do we have six town halls, and all the costs and all of that? I’ve actually moved on from that. I actually am fine with that. I don’t think the issue is efficiency.”

Leopold noted each town has its own character, and they employ people: “For me it’s not about efficiency, it’s about effectiveness.”

He went on to specify it’s about the most effective use of tax dollars, and how that can be explored. 

“I’m coming into this with very little knowledge of the commission,” he said, noting he read the charter study that was done in 2008, has attended a few meetings, and dug into newspaper articles. “I come in with a pretty blank slate,” he said. 

Climate, health and the homlessness are on his shortlist, he said: “Places where I have passions.” 


  1. Another one that doesn’t understand his role as a county Commisioner. You talk regionalization as a county commissioner and you’ll be shut down real quick. Fix your airport mess first.

  2. Well then why doesn’t New England become one state? That would be “effective”. Three of the island towns are in the top ten lowest taxes in the state and have good facilities and relatively new schools, seems pretty effective to me. Regionalization is a M&A, corporate raider type mindset, that thinks we should save money on toilet paper but loose our individual town culture and independence that has created the island we all love.

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