Interview: Samantha Nestor, Tony Pesco

First Selectwoman Samantha Nestor has held the town’s top job since 2021 and is unopposed for reelection. She previously served on the Board of Selectmen and the Board of Education.

Dr. Tony Pesco seeks (and will get) his second term on the Board of Selectmen. He previously served on and chaired the Board of Education.

As recent accomplishments in office, Ms. Nestor cited a number of infrastructure improvements, including an array of ARPA-funded projects, construction of the dog park, and completion of a long awaited upgrade to the emergency response radio system.

Her list also includes replacement of three bridges and installation of the first phase of sidewalks. She said the Town will soon solicit bids for the second phase and is progressing on design for the third. She also cited remediation of the Town and Ravenwood water supply systems and highlighted completion of the two-year paving project that rehabilitated 47 Weston roads.

“We’ve gotten a lot done, and I’m proud of that,” she said. “We laid out a plan for ourselves and implemented it.”

Dr. Pesco added that the hiring of a new town administrator brought “leadership, experience, and know-how” to Town Hall, and that several new department heads bring outstanding “proficiency and professionalism” to the municipal government.

Ms. Nestor said work still remains to address improvements to Town facilities and create “an appropriate working environment” that serves the public effectively.

And decisions about the schools loom. Dr. Pesco said he hopes to see “a comprehensive plan for Weston Middle School and all schools in the next term,” but that he and the first selectwoman “can’t spearhead it on our own.”

“I look forward to a partnership with the Board of Education and school district,” said Ms. Nestor. “We have to address issues at the schools, but Tony and I need to look out for the whole town, including those without kids. When it comes to going to a referendum, I want to have one that will be approved.”

“We know this will take a whole team approach,” said Dr. Pesco. “So does the new superintendent. I think we are all eager to work together.”

Challenges

“One disappointment,” said Ms. Nestor, “is the politicalization of certain projects. At times there seems to be a breaking into camps and an assumption of ill intent.” She said she is not the only first selectperson experiencing it.

“Maybe it’s a sign of the times,” said Dr. Pesco. “But this is a job where you have to look out for the whole town and not get caught up in politics.”

Both expressed a desire to get more people involved in town affairs and, in particular, to engage younger residents. To do that, said Dr. Pesco, “people need to be able to respect and have confidence in leaders. If they have reason to question motives, they won’t engage.”

“As a leader, you have to accept that this is public service,” said Ms. Nestor. “You have to recognize that your role is rooted in empathy and compassion, doing the work for all the people.”

Leadership

Asked to describe the qualities and skills that go into the making of an effective member of the Board of Selectmen, Ms. Nestor said, “the job is to keep people safe and help make their lives better. That has to be your north star.”

“An effective member needs to come in understanding how the town works,” she said. “You have an oversight role, but need to respect expertise. Oversight does not mean undermining. You have to realize that it’s not about me, it’s about we. It’s serious work, not performance.”

“And it helps to be a little thick-skinned,” said Ms. Nestor, “because there will be times when you have to make serious decisions and stand up to your own team. You can’t only listen to the loudest voices. You can’t pander. You represent 10,000 people, not just your own bubble.”

“You have to have an open mind,” said Dr. Pesco. “You have to be apolitical. You have to do the work, and above all you have to collaborate.”

“If you come in thinking ‘I’m going to get these things done,’ you’ve got it wrong,” he said. “Your power comes from a board, not from you. If you can’t collaborate, you can’t get anywhere.”

“Patience is important too,” said Ms. Nestor. “‘Municipal time’ is a real thing. There are many steps, many approvals, and a lot of oversight in everything we do. People who come in from the private sector without any civic involvement are shocked by that.”

Editor’s Note: Weston Today also invited Lauren Traum, the Republican candidate for the Board of Selectmen, to join us for an interview. Ms. Traum declined.