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The Select Board voted Dec. 22 to offer the position of town manager to Christopher Senior, following a prolonged debate over contract length and performance evaluation timelines that exposed divisions among members about the collapsed search process.
The board ultimately approved a two-year contract for the former Cohasset town manager that includes a performance review between nine and 12 months into his tenure, with renewal of the second year contingent on a successful evaluation by a majority vote.
The decision came after two of three finalists withdrew from consideration in recent days, leaving Senior as the sole remaining candidate.

Select Board member Bill McGonigle initially voted no on moving Senior forward as a candidate, but later supported the final contract terms.
The board voted unanimously 5-0 on the two-year contract framework after McGonigle indicated the performance review structure addressed his concerns about the process.
Collapsed search leaves single finalist
The board’s discussion reflected tension between those who wanted to move decisively to fill a leadership void that has persisted since July and those uncomfortable with evaluating only one candidate.
Winchester has been without a permanent town manager since Beth Rudolph’s unexpected resignation in July, relying on interim town manager Stephen Delaney, who is departing at year’s end.
Senior has faced scrutiny based on reporting in the Cohasset Anchor, which reported he 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.
According to the Anchor, Senior made the announcement at a well-attended meeting before public comment, during which a number of citizens expressed concerns about unsatisfactory experiences 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.
“I don’t know that anyone can say that this is not a qualified candidate who can do the work,” said Select Board Chair Michelle Prior of Senior on Monday night. “I don’t see the downside risk.”
Prior outlined the mounting costs of the vacancy, including stalled goal-setting, delayed department head performance reviews tied to potential bonuses, union contract negotiations on hold and concerns about operational stability ahead of a Moody’s bond rating call in early 2025.
“We’ve been without a permanent town manager since Sept. 3,” Prior said. “Some duties have defaulted to the chair.”

Contract length debate
McGonigle expressed discomfort with the process that left the board with a single finalist.
“I’m still not comfortable with the way this has played out,” McGonigle said, though he added he could support a one-year contract with a discussion in June about extending it based on performance during the critical period of budget development, a potential override vote and Spring Town Meeting.
Select Board member Michael Bettencourt defended Senior’s qualifications and pushed back against characterizing a short-term contract as appropriate for an experienced town manager.
“I can understand how that would be convenient for us because we’re kind of keeping one foot out the door, but I don’t think long term it really benefits the community,” Bettencourt said. “This sounds like an interim position that we’re creating.”
He added that offering only a one-year contract could damage Winchester’s reputation in future searches.
“I don’t know if we move on from Chris that we will be in a better position in a year than we are now with recruiting other town managers if we are the community that only offers one year probationary periods,” he said.
The board heard from consultant Mary Aicardi, of the Collins Center for Public Management, who advised that contracts shorter than one year typically signal an interim position and that performance reviews in town manager contracts are common.
Aicardi suggested any review would more realistically occur in September rather than June, given the need to close and open a fiscal year.
“It’s very common to have a review built in,” Aicardi said. “We frequently see any renewal beyond a year to be pending a successful performance evaluation.”
Board member Paras reported that his reference praised Senior’s relationship management skills across five superintendents and his work achieving a AAA bond rating for Cohasset.
Select Board member Anthea Brady said her references were positive but declined to share details publicly, saying she had not asked permission to disclose specifics.

The contract length debate consumed much of the meeting. Paras Bhayani initially proposed a one-year contract renewable to three years based on a midyear performance discussion, while others pushed for two or three years. The board ultimately settled on two years with the nine-to-12-month review window.
Brady proposed the final motion: a two-year contract renewable after one year pending a successful performance review conducted between months nine and 12. The motion passed unanimously after McGonigle said the terms were acceptable.
The board also voted to authorize Prior to work with town counsel, the human resources director and other staff as needed to negotiate contract terms with Senior and report back to the full board for final approval.
Senior responds to criticism from Cohasset
In a hallway interview last week with Winchester News, 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 regarding how major decisions were handled and whether public input was accurately reflected.
“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.”

Delaney’s departure looms
Separately, the board directed Delaney or Prior to continue discussions with Town Comptroller Stacie Ward and Town Clerk MaryEllen Marshall about covering interim town manager duties starting Jan. 2, with the understanding that if the interim period extends beyond four weeks, the board will reconsider the arrangement.
The board also voted to authorize outreach to Assistant Town Manager Mark Twogood, whose last day is Jan. 2, to request he stay through the transition during January. Brady moved the request be made “with gratitude for his many years” of service.
Senior’s start date was not announced and will depend on contract negotiations and his availability. The board plans to finalize terms in coming weeks.
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.