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When Winchester searched for a town manager in 2022, Christopher Senior, then Cohasset’s town manager, and Anthony M. Ansaldi Jr. were both finalists. The Select Board chose Beth Rudolph.
Nearly four years later, Senior runs Winchester’s Town Hall, and Ansaldi is his new deputy.
On Oct. 19, the Select Board voted 4-0 to waive the 15-day period it has to reject a town manager’s appointments, making Senior’s choice of Ansaldi as deputy town manager effective immediately.
Ansaldi came to Winchester after a contested departure from Concord, where he was chief financial officer until the town placed him on paid leave in June 2025 and terminated his employment that September, The Concord Bridge reported.
He has since sued Concord and its town manager, Kerry Lafleur, alleging he was punished for raising concerns about the town’s finances. Concord disputes his account, and the case remains open in Middlesex Superior Court.
Work since May
Under Section 4-2b of the Winchester Home Rule Charter, the town manager makes appointments and the Select Board may reject one within 15 days. Senior described Ansaldi as serving on an interim basis and becoming the full-time deputy.
Senior’s Oct. 16 memo to the board said Ansaldi has worked on an interim basis since May, taking central roles in the capital plan, project management and procurement while helping lead day-to-day operations.
“His appointment will fill a critical role in the Town Manager Office,” Senior wrote.
On Sept. 28, Ansaldi and Building Commissioner Thomas Kennedy presented a proposal to buy OpenGov and ClearGov software, now Article 33 on the fall warrant, the minutes show.
In July, Senior told the board Ansaldi had worked with the Winchester Youth Baseball and Softball Association on a revised field study proposal; it is now a $50,000 Nutile Field master plan on the warrant.
Later, Vice Chair Bill McGonigle praised the briefing sheets Ansaldi prepares for meetings.
“The additional information that you’re putting in here is answering all the questions I would have had, so it’s making these meetings go faster,” he told Ansaldi.
Ansaldi succeeds Mark Twogood, the longtime assistant town manager, who retired July 31 after 44 years with the town.
Concord departure and lawsuit
Concord hired Ansaldi as chief financial officer in October 2023. Lafleur said he “stood out for his breadth of experience and versatility,” The Concord Bridge reported.
In spring 2025, the two spoke on opposite sides of a Town Meeting debate over Concord’s “rainy day” reserves, according to the Bridge.
Concord placed Ansaldi on paid leave June 26, 2025. After an Aug. 20 hearing, the town issued a notice of termination Sept. 8. Lafleur called it a personnel matter, the Bridge reported.
According to Ansaldi, an August 2025 letter from Lafleur cited unauthorized contract execution, budget errors, management failures and a delayed payroll conversion. In later-released internal emails, Lafleur called the dismissal a “management and organizational fit issue,” the Bridge reported.
Ansaldi disputed the town’s concerns in a letter presented at the hearing.
“This was not a performance issue,” he wrote. “It is a political issue.”
He said he inherited a dysfunctional Finance Department, found what he called unwarranted Social Security payments for employees not eligible for pensions and objected to transferring funds without proper legal authority.
Concord’s labor counsel said none of his claims involved illegal conduct.
His lawsuit, filed Dec. 17, 2025 in Woburn, accuses the town of whistleblower retaliation and Lafleur of violating the Massachusetts Civil Rights Act, intentionally inflicting emotional distress and intentionally interfering with advantageous business relations, according to court records and the Bridge’s reporting. He seeks more than $1.3 million, including $750,000 in anticipated future wages.
Concord’s lawyers have called the complaint “outlandish and conspiratorial,” and Lafleur has said the town acted “in good faith,” the Bridge reported.
On Sept. 1, Judge Julie Green dismissed the civil rights and emotional distress counts against Lafleur and allowed the interference claim against her to proceed, according to the Bridge.
The whistleblower claim against the town, which Concord did not ask the court to dismiss, also remains. Ansaldi’s lawyer, Timothy Burke, has said a trial might not come before 2028, the Bridge reported.
No State Ethics Commission or Inspector General matter naming Ansaldi was found.
Earlier posts
Before Concord, Ansaldi worked in several other Massachusetts towns. Brookline hired him in 2004 as public safety business manager, after about five years at the Middlesex Sheriff’s Office, according to Brookline’s annual report.
He became Littleton’s assistant town administrator in 2017. As Wenham’s town administrator from 2019 to November 2020, he led the town’s early COVID-19 response and helped create its Human Rights Committee, according to town announcements.
He returned to Littleton as town administrator in December 2020. The Littleton Select Board decided not to renew his contract in 2023, according to its minutes. Board members described the separation as jointly negotiated, the New Hampshire Union Leader reported, and the Lowell Sun reported severance of $232,371.
Littleton’s April 10, 2023, minutes record that employees afterward raised concerns about the Town Hall working environment and asked for “guardrails” between staff and the board. Those concerns were aimed at the board; the minutes do not say employees defended Ansaldi.
Ahead at Town Meeting
Ansaldi’s salary and contract terms are not public; the fiscal 2027 budget document still lists Twogood.
Fall Town Meeting opens Nov. 5. A preliminary motion in the draft motion book would seat Ansaldi with Senior, Comptroller Stacie Ward and town counsel at the front of the auditorium alongside the Select Board, as members take up Article 33, the software purchase he helped present.
Neil Zolot has been a freelance journalist more than 40 years. He has worked for newspapers on the North Shore and in the Boston area.
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.
