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Town Manager Christopher Senior cleared the performance bar his contract sets for a second year, but the Select Board did not renew him Aug. 10 after a motion to do so failed to draw a second.
Senior’s first formal evaluation returned overall category ratings above the “satisfactory” mark required under his employment agreement, and board members’ completed forms indicated support for extending him through Dec. 31, 2027.
The agreement, signed Jan. 9, runs through Dec. 31 with a one-year renewal option that hinges on an evaluation completed no later than Sept. 30.
Vice Chair William McGonigle moved to exercise that option, citing the scores. No one seconded.
Michelle Prior said she wanted the board’s February goals for Senior, his self-assessment of progress against them and a proposed set of new goals in one packet before voting.
“One thing I specifically asked is to see Chris’s goals and his own self-assessment in the next packet,” Prior said.
She said her position on the renewal itself had not changed.
McGonigle objected that the contract conditions renewal on the evaluation alone.
“We had a contractual obligation based upon past performance, and now you’re saying that you want to base a vote upon future expectations,” he said. “That’s a shift, and it’s outside the contract.”
He pressed the point further as the exchange sharpened.
“Why are we creating additional hurdles?” McGonigle said. “We should be adhering to the contracts that we sign. That’s the whole point of contracts — to have expectation and finality.”
Michael Bettencourt sided with waiting, saying the delay was short.
“We’re not asking for months, just two weeks until our next meeting, so we can, you know, have everybody on the same page,” Bettencourt said.
Chair Anthea Brady read aloud the motion as it appeared in the meeting packet, which board members received Aug. 7, and said the anticipated vote should not have surprised anyone. She said the contract ties the renewal option to the evaluation, not to future goals, and that changing the process might require consulting town counsel.
Senior interjected to cool the exchange.
“Can I take the temperature down a few degrees, please?” he said.
He offered to resend the self-assessment he had given board members in July and said he was comfortable settling the matter in two weeks.
Brady said the board would take up Senior’s goals at its Aug. 24 meeting and could discuss in executive session whether to extend Senior’s term beyond what she described as the next 18 months.
Senior earns $230,000 in his first year. Renewal would raise his salary 2.5% to $235,750. Under the agreement, if the board fails to complete a good-faith evaluation by Sept. 30, Senior may exercise the renewal option himself with written notice by Oct. 15.
Senior became Winchester’s first permanent town manager since Beth Rudolph’s Sept. 3, 2025 departure, taking the oath Jan. 14 after a search in which two of three finalists withdrew and the Select Board weighed restarting the process. He previously spent 12 years as town manager in Cohasset.
Brady said Senior came into a hard situation and did good work getting the town through its override vote and its budgeting in the spring, after a period in which Winchester cycled through several town managers in a matter of months.
“It’s been a very active ride,” Senior told the board. “I appreciate the feedback I’ve gotten so far. I know there’s always things to improve upon.”
The Select Board meets again Aug. 24, and Brady said members will be back in person.
Will Dowd is a Massachusetts journalist who covers municipal government and community life for Winchester News. He is also the founder and editor of The Marblehead Independent, a reader-funded digital newsroom.
