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Michelle Prior did not run for office until her oldest daughter left for college.
For six years she sat on Winchester’s Finance Committee, one as its chair, watching town budgets and learning the machinery of local government from the inside.
People told her she should run for the Select Board, for the School Committee, for something. She declined every time — not, she said, until her daughter was out of high school and clear of whatever political grief a parent on the ballot might bring home.
“I was never going to do that to my kids,” she said. “Be out there and have her get grief at school.”
When her daughter graduated in 2022, Prior pulled papers. She won a three-year seat in 2023, became chair and has held the gavel since. Now, with the March 21 election approaching, she is asking Winchester voters to keep her there.
Standing between her and a second term is Shamus Brady, a former School Committee and Finance Committee member, running as a progressive challenger. Brady’s wife, Anthea Brady, already serves on the Select Board. If he wins, two members of the same household would hold two of the board’s five seats.
Who is running and why
Prior, a public-sector consultant with 35 years of professional experience, has worked across 17 states, the U.S. Virgin Islands and the District of Columbia. She came to the Finance Committee in 2010 between consulting jobs, looking to volunteer and get to know her neighbors after years of being too busy to meet them.
Six years and six budgets later, she understood Winchester’s finances well enough that a path to the Select Board began to seem natural. She spent one year as chair of the Finance Committee, another as what she called chair emeritus and then stepped back to private life — until she didn’t.
“I just wanted to have my voice at the table,” she said. “That was really it.”
Brady arrived in Winchester in 2014 with his wife, two years before their first child. His first memory of the town was older: As a high schooler from Arlington, he traveled to Winchester Town Hall for a battle of the bands hosted by the teen center, which he noted no longer exists.
He served on Winchester's School Committee from 2021 to 2024 and did not seek re-election. He entered the race, he said, only after searching for a progressive candidate willing to challenge Prior and finding no one willing to step forward.
“I can think of 20 to 50 people who I would rather have on the ballot than me,” he said. “But none were willing to do it.”
By day, Brady is director of special education for Everett Public Schools, overseeing a program serving more than 1,200 students with a budget exceeding $10 million. He sees that professional role as directly relevant to the work of governing a town.
“I’m already managing millions of public dollars,” he said. “I have thousands of constituents that I am accountable to every day at work.”
Two philosophies, one seat
The race unfolds as Winchester confronts fiscal pressure. A Proposition 2½ override is before voters, the town is working to grow its commercial tax base and housing production has drawn criticism for moving too slowly.
Both candidates support the override and agree the town must generate new revenue. But their governing instincts — how they think about time, risk, dissent and the mechanics of decision-making — point in different directions.
Brady is drawn to disruption as a signal of democratic health. He looks back on his School Committee tenure as defined by motions that died without a second, by 3-2 votes he considers preferable to unanimity and by a willingness to be the one dissenting voice in a room.
“I think it’s better to have three to two votes than five to zero votes,” he said.
He made motions knowing they would fail because he believed the act of making them had value.
His theory of governance is built on urgency. Decision-making, in his telling, is a moral act as much as a procedural one.
“Every day that passes that you don’t make a decision, the problem is impacting people,” he said. “And some people are being seriously harmed.”
He is openly critical of what he sees as Winchester’s reliance on studies and consultants to create political cover for decisions that, he argued, leaders already know must be made — citing, as one example, a lengthy school literacy review that he said delayed action on a problem already well understood.
He is also blunt about the town’s civic insularity. Winchester draws repeatedly from the same small pool of volunteers, he argued, and discourages newcomers from getting involved.
“It’s very insular. It’s almost clicky,” he said. “We’re not inclusive. We’re more often to be exclusive.”
He traced his own path onto the Finance Committee to a personal recruitment by its chair after he lost a School Committee race in 2020 — a level of outreach he believes the town rarely extends to those it turns away.
Prior sees process as the mechanism through which communities reach decisions they can sustain. As chair, she makes a deliberate practice of speaking last on votes — a habit rooted, she said, in 35 years of consulting work that trained her to move rooms toward conclusions without losing people along the way.
“If a consultant can’t derive a decision and be able to move forward, they’re not coming back,” she said. “Consultants aren’t just there to make friends.
“I don’t want to have my thumb on the scale,” she said of her approach to chairing. Steering debate toward a predetermined outcome, she added, “is not what we’re elected to do.”
That same discipline shapes how Prior thinks about challenging her own assumptions. She said she regularly consults former Select Board members, staff in Town Hall and fellow board and committee chairs who she trusts to tell her when an idea is not ready.
She measures success through concrete outcomes. In a second term, she said, voters should ask whether the town succeeded in finding new revenue beginning in fiscal year 2027 and whether engaging with town hall had become simpler.
“Is it easier to know what to do and how to get your needs met?” she asked.
On the Select Board’s relationship with the town manager, she was precise: “mutual respect, an assumption of trust and an expectation of accountability. Bad news doesn’t get better with age and time.”
Brady offered a broader standard. Voters should measure him, he said, by “what I am able to get done that helps them have a better daily life in Winchester.”
If he loses, he said, voters may be signaling two things: that they preferred a more conservative approach to governance and that his personal situation worked against him.
On Prior specifically, Brady criticized her record. He called her, on the record, “the most conservative person on the board” and recalled a Town Meeting motion she made years ago to cut the school budget — a moment he said stuck with him and that he believes her supporters have underexamined.
Prior declined to categorize herself ideologically, noting her support includes residents across the political spectrum. Her campaign signs are purple, she said, by design.
The question voters are weighing
“I don’t think it’s a great look,” Brady said, of the prospect of serving alongside his wife. “I’m frankly, a little embarrassed by it. I know my wife is. I feel badly about that fact.”
He did not, however, apologize for running. “It’s not a rational thing that we should be here, but here we are.” And if voters reject him partly on those grounds, he said: “Frankly, I mean, I don’t blame them.”
Prior, asked directly about the scenario, did not dismiss the concern. She named two governance issues she sees as credible.
The first involves the state’s Open Meeting Law. Massachusetts law does not appear to forbid a husband and wife from both serving on the same select board, but it does impose real recusal, disclosure and anti-favoritism obligations that would become unusually salient in that arrangement.
“I think that sub quorum OML concern is a concern,” she said. “To have a sub quorum existing in the same household, then you have to assume that they never talk to another member of the board about anything.”
On a five-member board, a quorum is three. Two members under the same roof fall below that threshold — but, as Prior noted, questions could arise if communications with a third member follow.
The second concern involves votes that could directly benefit the household.
“To vote on things like a residential exemption, if it were to benefit my house because my house is below a certain value, or if 40% of the board can benefit from a decision,” she said, “I think that’s a concern.”
She framed the broader issue carefully, though she was clear the concern was less about voting power — two members cannot carry a decision on a five-member board without a third vote — and more about the quieter dynamics that precede one.
“It’s uncomfortable,” she said. “The sub quorum piece — two fifths of the board in a household — is a balance of power thing, and there could be votes that benefit individual households, or individual budgets, or individual neighborhoods, where the locus of power seems to shift to that address.”
She paused.
“I don’t think that’s malice,” she said. “I think that’s fact.”
Winchester voters will render their judgment March 21. Early in-person voting began March 14.
Will Dowd is a Massachusetts journalist who covers municipal government and community life for Winchester News. He runs The Marblehead Independent, a reader-funded digital newsroom.
