New Castle Town Administrator Shapiro to Retire at End of March

New Castle Town Administrator Jill Shapiro will be retiring from her post in late March after filling that role for more than a decade and 35 years of continuous service to the town.

Shapiro, who made the announcement just after the start of the Town Board’s annual organizational meeting last Tuesday, said she and her husband are new grandparents and would like more time to visit their children who live in the Boston area. Shapiro also had a health issue last summer that helped to convince her to call it a career.

“I love my job. All things being equal, with everybody here and if I had all the time in the world, I’d stay forever,” Shapiro, 66, told The Examiner.

Current comptroller Robert Deary will take over as town administrator after Shapiro’s last day on Mar. 28, Supervisor Victoria Tipp announced. Deary, who has been comptroller for 17 years, has also served as Shapiro’s deputy administrator.

Tipp said the board will disclose their plans for the comptroller’s position in the near future.

“You’ve survived (five) town supervisors who are all very different, and you’ve done it with such equanimity and grace and professionalism, and there aren’t enough laudatory words to describe your work here in our town,” Tipp said.

Shapiro, an attorney, began as a part-time town prosecutor in New Castle in 1990, then became town clerk and receiver of taxes in 2006. At the start of 2014, when Robert Greenstein began as supervisor, she was appointed by that board as its town administrator. In addition to Greenstein, she served under Ivy Pool and Lisa Katz before serving under Tipp for the past year. For several months in 2021, Councilman Jeremy Saland served as acting supervisor following Pool’s resignation.

A nearly 40-year town resident, Shapiro praised the town’s staff for their dedication and professionalism, which has made her time working for the town enjoyable and rewarding.

“Our staff remains outstanding in its service and dedication to our residents,” she said. “Our residents are lucky to have such committed professionals work on their behalf. Our elected officials are exceptional in their work, in their integrity and commitment to public service. It’s been an honor and privilege to work with you.”

Saland said when he became town prosecutor in 2010, Shapiro was one of the first people he consulted.

“You really are a friend to so many people,” Saland said. “You have a hard job every day, with residents, with jobs that get done, with us on the Town Board, but you do it and you do it well.”

Councilwoman Jennifer Klein said Shapiro will be missed once she retires.

“You’re quiet but strong and a very certain leadership style is fabulous, and I really benefitted from it, so I’m going to miss you,” Klein said.

To ensure continuity when Shapiro retires, the board will be appointing Deary as the next administrator, Tipp said.

“Rob has served very admirably in his position as town comptroller and deputy administrator,” she said. “He’s been with Jill every step of the way. Rob has historical knowledge, the work ethic, the intelligence and the skill to pick up where Jill left off and we have every confidence that he will do a terrific job.”

Deary said he appreciates the board’s confidence in him, and with its backing as well as the support of the staff, the transition should go smoothly.

“They are big shoes to fill but I am confident with the staff that we have, that it’ll be a seamless transition,” Deary said.

In the 2025 town budget, the town administrator’s salary is $220,000 while the town is paying the comptroller $187,000.

Martin Wilbur

Martin has more than 30 years experience covering local news in Westchester and Putnam counties, including a frequent focus on zoning and planning issues. He has been editor-in-chief of The Examiner since its inception in 2007. Read more from Martin’s editor-author bio here. Read Martin’s archived work here: https://www.theexaminernews.com/author/martin-wilbur2007/