BREAKING NEWS: RTC Recommends Departing Finance Chair Raimondi for Open Bd. of Selectmen Seat

Sunday evening, Nov. 23, the Wilton Republican Town Committee announced it has put forward outgoing Board of Finance Chair Matt Raimondi to fill the current vacancy on the Board of Selectmen. The seat became open when former Second Selectman Josh Cole informed the BOS he was resigning effective Nov. 19.

An email from RTC Chair Peter Wrampe to First Selectman Toni Boucher and the other members of the Board of Selectmen named Raimondi as the RTC’s unanimously-approved choice to fill the vacancy for the two years remaining on Cole’s term (through November 2027).

Wrampe wrote that the RTC voted unanimously to recommend Raimondi to the BOS at its Wednesday, Nov. 5 meeting.

“Matthew Raimondi … in our unanimous view, is exceptionally well qualified to serve on the Board of Selectmen,” Wrampe wrote.

Raimondi told GOOD Morning Wilton he is “grateful” for the RTC’s support.

“Public service has always been a serious responsibility to me, and Wilton’s long tradition of steady, thoughtful leadership sets a standard I’ve worked hard to uphold. If the Board of Selectmen chooses to move forward with my candidacy, I would bring the same principles that have guided my work for the town: fiscal discipline, a collaborative bipartisan approach, and a commitment to long-term stewardship,” Raimondi said.

“My focus will remain what it has always been: serving Wilton in the way that best strengthens and supports our community,” he added.

Under Connecticut’s state statutes, minority-representation rules dictate that Wilton’s five-member Board of Selectmen may have no more than three members from the same political party. That means when the BOS convenes its new term on Monday, Dec. 1, with one Republican — Boucher — and three Democrats — Ross Tartell, Rich McCarty and David Tatkow — no more Democrats can be appointed.

State law (CGS §9-167a(d)) also requires that any vacant seat previously occupied by a minority party member must be filled by someone of the same political party. As a result, the seat that had belonged to Cole, a registered Republican, must be filled by another Republican.

Although he is not a member of the RTC, Raimondi is a registered Republican.

Elected to the Board of Finance since 2021, Raimondi has been its chair since 2023, but was not reelected in the November 2025 municipal elections.

Wrampe’s letter cited a “broad respect” Raimondi earned for his leadership, fiscal expertise and collaborative approach.

“He strengthened communication and cooperation among Wilton’s elected boards, expanded transparency through initiatives such as the community budget survey and regular public updates, and consistently helped residents better understand the town’s financial priorities,” Wrampe wrote, adding that Raimondi’s efforts increased public engagement and trust. [Editor’s note: the full text of Wrampe’s letter is at the end of this story.]

After releasing the letter, Wrampe told GOOD Morning Wilton that Raimondi was the top choice for the RTC. “While other candidates may come forward before the BOS makes its appointment, I hope nonetheless the selectmen’s choice will be Matt, and I would certainly hope that people across the spectrum will be supportive and let the BOS know Matt is the best choice to be appointed.”

Boucher’s response to Wrampe’s email said that the board would be taking up the vacancy appointment in December, adding, “We appreciate your help in recruiting an excellent candidate who can help move the important work of the board and the town forward.”

Support for Raimondi from Republicans — and Democrats

Sunday evening, there was a strong showing of bipartisan support for Raimondi, and several town officials told GMW that Raimondi not only would be a successful addition to the Board of Selectmen but the Town would benefit from his experience and skills.

Most notably, Wilton Democratic Town Committee Chair Tom Dubin gave his support for Raimondi’s nomination.

“I am pleased to learn about the RTC’s endorsement. During his time on the Board of Finance, Matt has proven himself deeply knowledgeable, detail oriented and tireless. Importantly, he listens, communicates well and builds consensus. I expect that the DTC will endorse him at a special meeting early this week,” Dubin said.

Outgoing BOS member Kim Healy, a Republican who will be starting her first term as a member on the Board of Finance in December, was pleased with the idea of Raimondi joining her former board.

“Great news that Matt has been endorsed to fill Josh’s vacancy. His demonstrated leadership and financial expertise will serve as a strong asset to the Board of Selectmen. I wish him and the other board members the best of luck as they commence the new term,” Healy said. 

Cole, whose seat Raimondi would fill, was in strong support. “Over the last four years as a member of the BOF and more recently as its Chair, Matt has exemplified all of the qualities of a great leader and a tireless commitment and dedication to the betterment of our town. I support him wholeheartedly and strongly encourage the remaining members of the BOS to make his appointment to the BOS. I know he will do an excellent job for our town.”

Board of Education Chair Ruth DeLuca, a Democrat who said she’s “had the pleasure to work with Matt” over the last several years, also called the news “great.”

“Matt is a trusted colleague and valuable town leader. His collaborative, thoughtful, and comprehensive approach to policy and problem solving will be an asset to the Board of Selectmen and Wilton. I welcome the RTC’s endorsement and am thankful for his willingness to serve. I look forward to his appointment and continuing to work together,” DeLuca said in a statement to GMW.

Raimondi’s fellow Board of Finance members added their voices to the chorus of supporters for his appointment, starting with Democratic member Tim Burch, who said he worked closely with Raimondi on the BOF for the last two years but was writing with support “not as a member of the BOF but as a private Wilton resident for the last 33 years.”

“It is my pleasure to provide an unqualified endorsement of Matt Raimondi as a member of the BOS,” Birch wrote. “First, let me state the obvious that Matt knows and understands the Town’s finances better than any board member. He has advocated greater transparency and data driven decision making. Second, Matt has tried to work in a collaborative fashion. He has always been willing to discuss alternative views and try to find a middle ground for a consensus.”

“For this town, the biggest mistake we could make is not to use Matt’s talents,” Birch added.

“I am very excited about Matt’s nomination to the BOS board,” BOF member Rudy Escalante, a Republican, wrote in a statement to GMW. “He was a great asset to the Board of Finance which he chaired for the last two years. I found him to be very professional, and he always worked hard to get a consensus from the group. He will be an a positive addition to the BOS.”

Former first selectman Lynne Vanderslice, who worked with Raimondi during the last two years of her term (2021-2023) also had compliments for him. “We all know the meaningful and positive impact Matt had as a member of the Board of Finance. I’m confident he’ll do the same as a member of the Board of Selectmen. I wish him and newly constituted board good luck.”

Full text of RTC Letter of Recommendation to the BOS for Matt Raimondi

Dear Members of the Board of Selectmen,

On behalf of the Wilton Republican Town Committee, I like to let you know that, following the recent resignation of Selectman Joshua Cole, the RTC unanimously voted at our November 5^th meeting to recommend Matthew Raimondi to fill the vacant position for remainder of the term.

As you are aware, the Wilton Town Charter requires that the individual appointed to this vacancy be a registered Republican. Mathew Raimondi meets this requirement and, in our unanimous view, is exceptionally well qualified to serve on the Board of Selectmen.

During his highly effective tenure as Chair of the Board of Finance, Matthew Raimondi earned broad respect for his steady leadership, fiscal expertise, and collaborative approach. He strengthened communication and cooperation among Wilton’s elected boards, expanded transparency through initiatives such as the community budget survey and regular public updates, and consistently helped residents better understand the town’s financial priorities. His clear, solutions-focused communication style elevated public trust and engagement.

Equally important, Matt Raimondi brought discipline and long-term thinking to Wilton’s financial planning. He reinforced the town’s budget guidance process, advanced long-range forecasting tools, and supported sustainable capital planning that maintained Wilton’s AAA credit rating. Under his leadership, the BOF managed complex financial challenges with clarity and rigor while positioning the town for future capital needs without undue burden on taxpayers.

This combination of proven financial oversight, strategic judgment, and constructive, respectful collaboration makes Matthew Raimondi exceptionally well suited for service on the Board of Selectmen. For these reasons, the Republican Town Committee strongly and enthusiastically recommends him for appointment, confident that he will continue to serve with integrity, diligence, and a steadfast commitment to what is best for Wilton.

Thank you for your consideration. We stand ready to assist in any way as you move forward with this process.

Respectfully,
Peter Wrampe
Chair, Wilton Republican Town Committee