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Interim Town Manager Stephen Delaney will leave his post earlier than expected for personal reasons, the Select Board announced at its Dec. 15 meeting, departing as Winchester prepares for a potential override vote in the tens of millions and searches for a permanent hire.
Delaney, who began serving as interim town manager in September following Beth Rudolph’s July resignation, was originally expected to remain until a permanent town manager began work. When asked during the meeting why Delaney is leaving early, Select Board members Anthea Brady and Michelle Prior replied, “personal reasons.”
After the Winchester News sought clarification on a departure date, Brady replied, “End of this year, I don’t know exact date.”
The timing of Delaney’s departure intersects with critical planning milestones. The 25-member State of the Town Committee is developing a comprehensive fiscal plan that will likely include an operating override on the March 2026 ballot to help stabilize the fiscal 2027 budget.
Finance Committee Chair Derek Ross has warned of projected operating deficits of roughly $3 million to $5 million in coming years as expenses outpace revenue growth under Proposition 2½.
Winchester also faces identified capital needs from fiscal 2027 to 2031 totaling $85.6 million against available resources of $31.7 million, leaving $53.9 million unfunded, according to an October Capital Planning Committee report. The five-year capital plan includes about $43 million in building projects and $51 million in other capital needs.
With Delaney’s departure approaching, the Select Board began discussing how to cover the gap before the permanent manager starts. Prior said the transition window “could be a matter of two weeks to eight weeks,” depending on a candidate’s availability and notice period.
“I think it’s important that someone’s signing contracts,” Prior said, adding the board may need to consider how to structure the interim arrangement.
Prior said the board may need to address compensation as part of the plan.
“We’ll need to think about stipend and compensation, but we could share a responsibility,” she said. “I don’t think it makes sense to go out to the market. We have, like two weeks.”
During the discussion, board members referenced internal options, including Comptroller Stacie Ward, Town Clerk Mary Ellen Marshall and Mark Twogood, who is Winchester’s assistant town manager.
Prior suggested the board could formally direct Delaney to begin discussions with potential interim candidates.
“Could we take a vote to direct Steve … [to] explore those conversations with Stacy, with Mary Ellen, with if there’s a third, if it’s Mark,” she said.
Town Meeting recently approved $4.4 million in appropriations, including $2.15 million to replace Lincoln Elementary School’s failed chiller and rooftop HVAC unit. Town Hall alone faces an estimated $8.5 million in HVAC work that the Capital Planning Committee was unable to fund this year. The committee has recommended bundling Town Hall’s high-cost, near-term needs into a comprehensive renovation package.
About 95% of Winchester’s $165.7 million budget comes from residential property taxes, with the commercial tax base generating about $8 million to $9 million annually. This creates limited room to maneuver within the 2.5% levy limit, with modest new-growth projections of $800,000 for fiscal 2026.
Delaney brought more than 40 years of municipal management experience to the interim role. He previously served as town administrator in Georgetown from 2003 to 2009 and Wenham from 1995 to 2002, with interim town manager roles in Coventry, R.I., and Winchendon, Mass.
The Select Board appointed Delaney in August following Rudolph’s unexpected July resignation after two decades of service to Winchester. Rudolph joined Winchester in 2004 as assistant town engineer, became town engineer in 2010 and served as acting town manager beginning in 2021 before being named permanent town manager in December 2022.
During her tenure, Rudolph oversaw substantial completion of Winchester’s multi-decade flood mitigation and stormwater work, numerous transportation projects and delivery of multiple new school buildings. In March 2025, she received strong marks in her first formal performance review as permanent town manager.
Rudolph submitted her resignation July 7, with her last day Sept. 3. Select Board member Bill McGonigle said her brief letter offered no explanation beyond her intention to leave.
The Select Board has been conducting a search for a permanent town manager with assistance from the Collins Center for Public Management. The board interviewed three finalists during the week of Dec. 15: Joseph Domelowicz Jr., town manager in Hamilton; Eric Duffy, municipal manager in Woodstock, Vermont; and Christopher Senior, former town manager in Cohasset.
Brady, who heads up the search committee, said the board expects to make a final decision later in December, with the new manager’s start date dependent on the candidate’s availability. The position’s starting salary range is anticipated to be $225,000 or more, depending on qualifications.
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.
