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The Select Board continued its deliberations on a Proposition 2 ½ vote on Jan. 26, but it left unresolved how large it should be and how long it should last — with members split between a cautious three-year plan and a more ambitious four-year approach.
The discussion came with barely two weeks before a Feb. 9 special Town Meeting where the Select Board will present its case to Town Meeting members, followed by a public hearing at 8 p.m. that evening.
Using the newly accepted State of the Town financial model, board members debated operating needs, capital repairs, homeowner tax impacts and whether projected new revenue can realistically stretch an override beyond three years.
Positions range from $9 to $19 million
Board member Bill McGonigle made the case for a longer timeline.
“I still would like to see a four-year override, or plan — a four-year plan is what I should say, and an override that covers our goals for that four years,” McGonigle said. “I think that is a period of time that actually allows us to get enough work done and doesn’t force us to go back out to the electorate with another override vote sooner than they might want to have to deal with it.”
But board member Mike Bettencourt expressed concern about projecting too far ahead given uncertainties around health insurance costs and union contracts.
“I think finding the right number is more important than the length of time, because what we’ve seen is it’s a little bit out of our control,” Bettencourt said. “Health insurance costs have been the game changer. When I first came on the board, we were seeing 1% and 2% year-over-year increases. Now we’re averaging north of 10%.”
The Select Board reviewed scenarios ranging from roughly $9 million to $19 million in total override amounts, according to tax impact models presented by Select Board member Paras Bhayani. The figures combine operating budget increases with capital project funding, though no final proposal emerged from Monday’s discussion.
Select Board Chair Michelle Prior positioned herself at the lower end, supporting $8 million for operating costs plus $1 million for capital, totaling $9 million.
McGonigle suggested a range of $13 million to $19 million. Bhayani proposed $14 million to $15 million total. Vice Chair Anthea Brady suggested $12 million to $16 million, and Bettencourt indicated support for $10 million.
“I think the range is going to give the voters, candidly, very little information, and that’s what I think we owe people now,” Bhayani said, urging the Select Board to narrow its options before upcoming public sessions.
Schools, capital drive needs, affordability concerns surface
The override would address what the State of the Town report describes as a structural deficit exceeding $4 million in fiscal year 2027, driven by costs growing faster than the 2.5% annual revenue increase allowed under state law.
Health insurance premiums are projected to rise 15% annually, measured against the prior year’s premium expenses and significantly outpacing the inflation rate that drives other cost increases.
Winchester Public Schools requested $4.5 million in new programming over four years for literacy curriculum, math specialists, expanded course offerings and academic supports, according to the State of the Town report.
The School Committee proposed phasing in $2.3 million of those additions in fiscal year 2027.
Brady emphasized the importance of meeting school needs.
“I think we really need to meet the requests of the schools to commit to the literacy program and to reach similar objectives with the math program,” Brady said. “What they provided was very clear about what the upcoming needs were.”
Municipal departments requested $1.6 million in strategic additions, of which the Select Board accepted roughly $800,000, according to meeting materials.
Capital needs also figured prominently. The Capital Planning Committee has identified $85.6 million in projects over five years against $31.7 million in available funding, leaving a $53.9 million gap, according to the State of the Town report.
Projects include a $19.4 million Town Hall restoration and $17.2 million in critical systems repairs at McCall, Ambrose and Lincoln schools.
A central tension involved assumptions about new revenue and cost savings. The State of the Town model assumes the town will generate an additional $1.2 million annually through measures including increased interest income, solar power revenue, higher fees and fines, and departmental budget turnbacks, according to materials presented Monday.
“I would feel comfortable baking $1.2 million in,” Bhayani said. “I think we can make a number, and then the rest of it, the Select Board has to commit to finding that additional six months or whatever it may be.”
But Prior emphasized affordability concerns alongside the commitment to find new revenue.
“I looked at food stamp caseloads in Winchester,” Prior said. “In 2021, Winchester had 105 active food stamp cases. In 2025, we had 400 cases. Our cases have more than tripled, almost quadrupled in four years. I don’t take lightly a decision to place a ballot question to permanently raise my neighbors’ taxes, and I don’t think any of us should.”
Tax impact projections presented Monday showed that a $14 million override would increase the annual tax bill for a home valued at the town median of approximately $1.5 million by roughly $1,835 in fiscal year 2027, with smaller increases in subsequent years as the override is phased in, according to models presented by Bhayani.
Tight timeline before Town Meeting
The Select Board has scheduled a budget summit with the School Committee, Capital Planning Committee and Finance Committee on Wednesday, Jan. 28, from 4:30-6:30 p.m., to continue deliberations.
The Select Board must finalize a ballot question by Feb. 13 to submit to the town clerk.
The special Town Meeting on Feb. 9 at 7 p.m. at McCall Middle School will allow Town Meeting members to hear reports on the State of the Town and budget outlook, according to the warrant issued Jan. 21. A public hearing open to all residents will follow at 8 p.m.
Public information sessions are scheduled for Feb. 2 and Feb. 4. The actual vote on any override would occur at a later election, likely in March.
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.
