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Town manager finalist Eric Duffy has withdrawn from Winchester’s search for a permanent town manager, Select Board member Mike Bettencourt said Wednesday, as residents raised questions about two finalists’ backgrounds and the town’s vetting process ahead of scheduled public interviews and community events.
Select Board Chair Michelle Prior declined to comment on specific questions about candidates’ backgrounds before Wednesday night’s proceedings, but said related issues would be addressed.
“I will not comment beyond saying some of these items will be discussed this evening such as due diligence and outreach,” Prior said in an email message.
Select Board member Paras Bhayani deferred comment to fellow board member Anthea Brady, who is leading the search committee but had not yet returned comment Wednesday.
The developments came as the Select Board was scheduled to interview candidates Wednesday evening at Winchester Town Hall, 71 Mt. Vernon St. The interviews are expected to be recorded, but will not be broadcast live, meaning residents who wish to observe the proceedings must attend in person.
Two additional opportunities for residents to see and interact with finalists are scheduled for Thursday, including a community meet-and-greet hosted by the Winchester Chamber of Commerce from 3:30 to 6:30 p.m. and a capital-project presentation and discussion session at Town Hall from 6 to 9 p.m.
Under the published schedule, the first Wednesday interview slot had been listed for 6:15 p.m., followed by Joseph Domelowicz Jr., town manager in Hamilton, at 7:15 p.m., and Christopher Senior, former town manager in Cohasset, at 8:15 p.m.
The search for a permanent town manager is unfolding amid an already rough transition in Winchester’s corner office, following the unexpected July resignation of longtime Town Manager Beth Rudolph after more than two decades of service.
Interim Town Manager Stephen Delaney, appointed in September to provide stability during this critical period, is now set to depart prematurely and unexpectedly by the end of the year — adding further uncertainty as the town grapples with pressing fiscal challenges, including projected operating deficits of $3 million to $5 million in coming years and the need for major infrastructure investments.
This impending vacancy heightens the urgency of the ongoing selection process, as Winchester seeks a leader capable of navigating constrained revenues under Proposition 2½, advancing a comprehensive fiscal plan potentially involving a March 2026 operating override, and engaging with the community’s highly informed and active citizenry.
Domelowicz, Duffy and Senior were identified as finalists following a screening process supported by the Collins Center for Public Management out of the University of Massachusetts, Boston.
Search process becomes focus of public scrutiny
In Winchester, the timing and structure of the search have themselves become part of the public discussion. Residents have been scrutinizing how the search has been conducted, including how finalists were vetted, which Select Board members participated in early screening and how information about candidates has been shared as the process moves into its public phase.
Some residents have pointed to publicly available reporting and court records involving finalists and pushed for an explanation on what was reviewed during the screening process and how unresolved issues are being weighed before a final decision is made.
While the search committee interviewed six candidates and narrowed the field to three finalists, most current Select Board members have not yet had direct contact with the candidates.
Brady, who serves on the search committee alongside former Select Board chairs Lance Grenzeback and Jennifer Wilson, Town Comptroller Stacie Ward and Bettencourt, has been the primary current board member involved in the initial candidate evaluations.
The other Select Board members were scheduled to meet the finalists for the first time during this week’s public interviews. According to meeting discussions, the board has been planning the interview format, including how to assign questions among members and structure the sessions with the remaining candidates: Senior and Domelowicz, following Duffy’s withdrawal.
The search committee’s work focused on identifying qualified candidates and conducting preliminary interviews, while the full Select Board is expected to evaluate the finalists during the public phase of the process before making a final hiring decision.
The Collins Center job posting for the position emphasizes financial acumen, strategic budgeting experience, capital project management skills, labor relations expertise and the ability to engage with a “highly informed and active citizenry.” The starting salary range is anticipated to be $225,000 or more, depending on qualifications, according to Winchester News.
Vermont litigation and reporting involving Duffy
Duffy, the municipal manager in Woodstock, Vt., has been the subject of Vermont reporting tied to a dispute involving Woodstock Police Chief Joseph Brian Swanson and related litigation.
A civil complaint filed April 29, 2025, in Vermont Superior Court names Duffy and other defendants and alleges “extraordinary unlawful efforts” by the Town and Village of Woodstock, through officials, employees, contractors and agents, to remove Swanson as police chief and demote him to patrol officer.
The complaint alleges the actions damaged Swanson’s professional reputation and caused emotional distress and economic damages. Those are allegations in a lawsuit and have not been adjudicated in the materials provided.
The Bridge, in a story republished by VTDigger, described the case as a $5 million lawsuit and reported the dispute included Swanson being placed on leave, a private investigator being hired and Swanson being demoted after a hearing.
The Bridge reported Duffy placed Swanson on paid leave in October 2024 following a traffic incident involving Swanson’s husband and another driver and that a Vermont State Police investigation later determined no charges could be filed against either driver.
The Bridge also reported that a court later reversed Swanson’s demotion and remanded the matter for further proceedings.
In the same reporting, Duffy defended his actions.
“I am always going to do what I think is right and in the best interest of my staff, my community and the municipality, and if needed, hold people accountable for their actions or lack thereof,” Duffy said, according to the article.
The Bridge also quoted from the court decision reversing the demotion, reporting that the judge concluded the village issued a written decision giving reasons for the demotion but did not evaluate whether “cause” existed, and that demoting a police chief effectively removes the chief from office and requires a different legal standard.
Cohasset reporting involving Senior
Senior has drawn scrutiny based on coverage in Cohasset.
The Cohasset Anchor reported that Senior told the Cohasset Select Board on Oct. 29, 2025, that he would not seek renewal of his contract after the board voted 3-2 in February to express its “intent to renew” the agreement.
“I want to thank the board for 12 amazing years of service to Cohasset,” Senior said, according to the Cohasset Anchor. “I’ll be working with them to do whatever is necessary to help with the transition [to a new town manager].”
The Anchor reported Senior made the announcement at the beginning of a well-attended meeting before public comment and that during public comment “a number of citizens expressed various concerns about unsatisfactory experiences they have had with the town manager and some board members.”
Some speakers indicated they had planned to call for Senior’s resignation before his announcement and said they felt their concerns had not been taken seriously, according to the story.
Bridging the corner office gap
With Delaney’s impending departure, the Select Board has initiated discussions on bridging the interim period until a permanent successor assumes the role. Prior indicated the transition interval could range from two to eight weeks, contingent upon the selected candidate’s availability and required notice period.
“It is essential that an individual remains authorized to execute contracts,” Prior stated, noting the board might need to deliberate on the structure of any interim arrangement, including the possibility of dividing responsibilities among multiple internal staff members to ensure continuity.
Prior further emphasized the necessity of addressing compensation within this framework.
“We will need to consider stipends and compensation, though responsibilities could potentially be shared,” she remarked. “I do not believe it is practical to conduct an external search, given the limited time frame of approximately two weeks.”
In the course of the conversation, board members identified several internal candidates, including Ward, Town Clerk Mary Ellen Marshall and Assistant Town Manager Mark Twogood.
Prior proposed the board formally authorize Delaney to engage in preliminary discussions with these individuals.
This is a developing story. Winchester News has previously reported the interview schedule, public events and identities of the finalists.
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.
