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Senior pitches reset-weary Winchester residents, board on fiscal crisis, open process

Christopher Senior speaks during a public forum with residents as Winchester’s Select Board weighs whether to continue with a single candidate or reset its town manager search at Town Hall in Winchester on Dec. 18. WINCHESTER NEWS STAFF PHOTO / WILL DOWD

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Winchester’s search for a permanent town manager will face a pivotal decision Dec. 22 after two of three finalists withdrew from consideration, leaving Christopher Senior, former town manager in Cohasset, as the sole remaining candidate and prompting the Select Board to weigh whether to reset the process entirely.

Senior, who led Cohasset for 12 years before announcing in late October he would not seek contract renewal, delivered a public pitch to residents Dec. 18 in the Waterfield Room at Town Hall and sat for a Select Board interview broadcast live — both events proceeding despite the rapid collapse of the finalist pool in the final days before a planned hiring decision.

The town confronts projected operating deficits of $3 million to $5 million in coming years, more than $100 million in capital needs over the next five years and the unexpected early departure of Interim Town Manager Stephen Delaney by year’s end.

Joseph Domelowicz Jr., town manager in Hamilton, withdrew late Dec. 16, Select Board member Anthea Brady confirmed Dec. 18. Eric Duffy, municipal manager in Woodstock, Vt., withdrew Dec. 17, leaving Senior as the only candidate for a position with a starting salary range anticipated to be $225,000 or more.

The withdrawals came as residents raised questions about the vetting process and publicly available information regarding the finalists.

Senior has faced scrutiny based on reporting in the Cohasset Anchor, which reported Senior announced Oct. 29 that he would not seek renewal of his contract after the Cohasset Select Board voted 3-2 in February to express its “intent to renew” his agreement.

Christopher Senior speaks during a public forum with residents as Winchester’s Select Board weighs whether to continue with a single candidate or reset its town manager search at Town Hall in Winchester on Dec. 18. WINCHESTER NEWS STAFF PHOTO / WILL DOWD

According to the Anchor, Senior made the announcement at a well-attended meeting before public comment, during which “a number of citizens expressed various concerns about unsatisfactory experiences they have had with the town manager and some board members.” The newspaper reported that some speakers indicated they had planned to call for Senior’s resignation before his announcement.

In a hallway interview with the Winchester News on Dec. 18, Senior said he felt it would not have been appropriate to sign a new contract in Cohasset and then actively apply for another job.

“I’m like, ‘That’s just not appropriate,’” he said. “It’s not reasonable. And I’ve been there 12 years, too — and it was hard to leave, right?”

Senior also addressed questions about governance and process concerns raised by some Cohasset residents. When asked about how major decisions were handled and whether public input was accurately reflected, Senior pointed to Cohasset’s Town Meeting structure.

“The structure is a full committee structure of residents, right?” he said. “It’s all about being as transparent as you can get, because residents are making all the decisions.”

He acknowledged that disagreements are inherent in democratic governance.

“People don’t get their way. Doesn’t mean they aren’t heard,” Senior said. “And it’s important that people understand that the fact that we’re heard doesn’t mean that they get to decide.”

The community forum

At the community forum, Senior framed his candidacy around his experience navigating complex municipal governance and fiscal constraints.

“I am a big believer in local government,” he told residents, describing his background covering local government as a reporter and his subsequent career in municipal administration.

He described working in North Hempstead, N.Y., a town of 220,000 people with 31 villages, before moving to Cohasset, a full-service community with water and sewer plants, a school system and career firefighters and paramedics.

Senior said he interviewed for the Winchester position three years ago as a finalist, but did not get the job.

“I was very excited. I think I thought it was a great, tremendous fit, and I didn’t get the job, that’s OK,” he said. “I figured the job would never open again.”

He emphasized the importance of community partnerships, describing his volunteer work with a local road race in Cohasset where he helped direct traffic and move equipment.

“I would literally get in and do that,” he said. “I had a lot of fun doing that right. It was great.”

Senior’s Select Board presentation

In his Select Board interview, Senior presented a detailed framework for navigating Winchester’s fiscal challenges, emphasizing the need for multi-year planning, operational efficiency and state-level advocacy.

“One of the things that was pointed out in their report is it understood the local aid, unrestricted local aid is down on an inflation adjustment basis, 25% so a lot less money coming to communities, all communities that can be used for anything,” he told the board, referring to declining state support.

When asked how he would approach the operating budget if an override passed or failed in March, Senior said the key was learning immediately what the policy priorities were.

“If the override failed by five votes, it’s different than the fact by 3,000 votes,” he said. “So it’s like was there just two things — what changes should made? Or people saying, ‘I’m done’ (with tax increases).”

Christopher Senior, the sole remaining finalist in Winchester’s town manager search, gestures as he answers questions during a Select Board interview at Town Hall in Winchester on Dec. 18. WINCHESTER NEWS STAFF PHOTO / WILL DOWD

Senior stressed the importance of using data to guide decision-making and resource allocation, citing his experience implementing a 311 system in North Hempstead that became the first suburban community to adopt the technology.

“It made everybody’s life better,” he said.

He described how tracking metrics helped his team in Cohasset identify inefficiencies and demonstrate value.

“We have a 48-hour pothole,” he said, referring to a performance standard his team met consistently.

Brady asked Senior how he would envision his relationship with Winchester’s superintendent of schools.

“We’re partners,” Senior said. “We’re serving the same people, the same families that are coming from the same pot of money. So we get to work together and collaborate.”

Senior closed his interview by emphasizing his fit for the role and his commitment to the community.

“I really feel, if I can say this even more strongly that this is a place that I think I can really, really help you get to the next level,” he said. “I think it’s a place that my skill set matches really well.”

What’s next

Brady, who leads the search committee, said the board will deliberate Dec. 22 about whether to continue with Senior or restart the search. She acknowledged the difficulty of assessing a single candidate in isolation.

“As a member of the screening committee, I found it to be very helpful to be able to assess candidates compared to each other and how they respond,” Brady said. “I think it just makes it really difficult to have a fair assessment when your assessment is somebody or nobody, versus looking at a slate of candidates who may have different strengths and skills.”

The search began in August following the unexpected July resignation of Beth Rudolph. A screening committee comprising Brady, Bettencourt, former Select Board chairs Lance Grenzeback and Jennifer Wilson and Town Comptroller Stacie Ward reviewed applications and conducted initial interviews in executive session with support from the Collins Center for Public Management at the University of Massachusetts, Boston. The committee interviewed six candidates and advanced three as finalists.

Bettencourt said candidate withdrawals have become commonplace in municipal searches.

“Candidates withdrawing is expected as part of this process and has, unfortunately become the norm in the Commonwealth,” he said.

Will Dowd is a Massachusetts journalist who covers municipal government and community life for Winchester News. He previously co-founded the Marblehead Current and now runs The Marblehead Independent, a reader-funded digital newsroom.

Winchester News is a non-profit organization supported by our community. If you appreciate having local Winchester news, please donate to support our work, and subscribe to our free weekly newsletter. Copyright 2025 Winchester News Group, Inc. Copying and sharing with written permission only.

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