For new Wilton High School Principal James D’Amico, his teachers had a big impact on his chosen career path, particularly a high school social studies teacher he had at New Fairfield High School.
Bob Poodiack, now in his 80s, was teaching his students about seminal Supreme Court cases, allowing students to argue both sides of different issues, including whether citizens should get Miranda rights, which require police to inform people in their custody about their constitutional rights before questioning.
“I just remember in that class, the freedom. He let us think, right? Like he very easily could have had us write an essay about Miranda rights or talking about different scenarios, but he let us argue. And he let our classmates serve as justices,” D’Amico recalled. “You know, he really involved us in what we were learning and let us kind of make meaning out of it.”
This assignment taught D’Amico — who would himself become a social studies teacher before moving into administration — that letting students chew on meaty issues showed them how to think outside the box.
D’Amico just started his position as Wilton High School’s principal, beginning on July 13 after he completed seven years as, appropriately enough, New Fairfield High School’s principal.
“That’s where I graduated from high school actually,” D’Amico said. “My parents still live there.”
His first year as New Fairfield High School’s principal was interrupted by the start of COVID, and not only did he lead the district through the pandemic but he also helped oversee the development of New Fairfield’s new $85 million high school, which opened in September 2023.
D’Amico said he’s particularly proud of that effort.
“Schools are really about the people. That’s first and foremost,” D’Amico said. “I think we left something that generations of students will really enjoy and benefit from.”
He made sure New Fairfield students had a voice in how things came together.
“As we really got to different parts of the design, we worked with the architects [and] the interior designer, and actually brought in different classroom setups and types of furniture and had students come in and try it and give us feedback about it and tell us, ‘Why did you like this?’” D’Amico recalled. “‘What would you like to see in classrooms in the building?’”
D’Amico added that staff wanted to capitalize on bringing in a sense of community and collaboration into the space, especially at a time where technology and phones are so prevalent.
“New Fairfield is a small town and the high school really is the center of town. Everybody wants to be in the high school for their event,” D’Amico said. “So, we wanted to create spaces that would do that educationally, but also really be inspirational and exciting for the community.”
D’Amico said he wasn’t necessarily looking to leave New Fairfield, but he had known Bob O’Donnell, Wilton High School’s most recent principal who just retired, for 10 years. He had heard that O’Donnell was retiring, but at first, didn’t really see himself moving over to the Wilton job.
“I was like, ‘I don’t know, I’m happy [in New Fairfield],’” he said.
D’Amico said Wilton is an exciting place, with exceptional programs for students, beyond academic achievement. In talking to people in Wilton, D’Amico said he would hear that they want to continue with someone who puts students first and who has knowledge of how an excellent school runs.
And they said, “‘Hey, maybe if you’re lucky, our building might need some tender loving care in the next few years,’ which was personally very exciting to me,” D’Amico said.
Wilton School Superintendent Kevin Smith said he’s known D’Amico for years.
“He is a tremendous educator and profoundly good human being. His commitment to children and especially those who feel marginalized really came through during our extensive interview process,” Smith said. “We’re fortunate to have him in Wilton and I’m very excited to work with him.”
Prior to New Fairfield in 2019, D’Amico worked in the Westport school system beginning in 2001, where he started as a social studies teacher at Staples High School, then became the social studies department chair for grades 6-12, then director of secondary education, and finally as principal of Staples High School in 2016.
Even though he has heard that some people believe moving into an administrative role means “going to the dark side,” D’Amico said that, while he loved teaching, being a high school principal is one of the best jobs in education.
“I’m not teaching social studies anymore, but you do get to design students’ experiences. You do get to listen to the students, you know, and figure out what students need,” D’Amico said. “Obviously being a classroom teacher is hugely important, and that’s where kids spend most of their day. And what motivates me is to really look at systems, to look at how a school works so that you can create the environment where teachers can do their best work and students can grow the most.”
D’Amico was also looking forward to meeting with the staff as they return for the fall so he can get to know everyone.
“I think coming into a highly successful school, my job isn’t to come in and start changing things,” D’Amico said, adding he prefers to do a lot of listening first, and has spent part of his time since starting with the district already meeting with students, teachers and administrative team members.
“The things that so far I’ve learned is that everybody from top to bottom really loves the school, and loves working in Wilton,” he said. “And what I have found, everybody has been so friendly and welcoming and has a lot of pride in the school and the community.”
D’Amico and his wife Jennifer, residents of Bethel, have four sons — their oldest just graduated college and their youngest is about to enter his junior year at Bethel High School. What’s more, not only is Jennifer his wife, but she is in the same field as the principal at Weston Intermediate School.
