The Peddie Chronicle received a Bronze Award in the Independent School Magazine category of the Council for Advancement and Support of Education (CASE) Circle of Excellence Awards.
Peddie’s new head of school, Jim Hamilton, has built a career on steady guidance, “humbitious” leadership and a belief in meeting every student where they are.
On a winter night in 1991, The Roxbury Latin School’s basketball team clinched the New England Championship in a storm of three-pointers, eight of them from a guard named Jim Hamilton. While teammates celebrated, Hamilton was already thinking ahead. Catching his breath, he turned to his parents: “We’ve got to go.”
Hours later, still buzzing with adrenaline, he was on the Roxbury Latin School stage, performing in the school musical.
For Hamilton, toggling between roles — athlete, performer, student — was natural. Excellence, he realized, doesn’t belong to a single arena. Real growth happens when you inhabit all of them.
That belief has guided Hamilton ever since, from his early days at a prep school in Boston to his leadership roles in independent schools across New England. And now, it shapes the kind of leader he intends to be for Peddie. If there’s a theme in Hamilton’s career, it’s the conviction that presence and balance matter as much as ambition.
Follow our new head of school for 13 hours and you’ll quickly see how much energy, heart and humor he brings to campus life. From early morning walks with his dog, Coco, to nighttime duty, this full, varied and student-centered schedule is a day in the life of Jim Hamilton.
6:30 AM — Morning walk with Coco
7:10 AM — Hoist the Peddie flag in front of his home (Left)
7:15 AM — Cross campus to the office (Right)
7:40 AM — Breakfast in the dining hall with students
10:25 AM — Greet those arriving for chapel, take the podium
11:00 AM — Meet with Trustee Sean Woodroffe P’19 (Left)
12:30 PM — Lunch in the dining hall with colleagues (Right)
1:25 PM — Observe Field Ecology class (Left)
3:45 PM — Visit after-school activities (Right)
7:30 PM — Close the day with evening administrator on call duty
Anchored Leadership
In his office, Hamilton keeps a photograph of a lighthouse, waves crashing at its base. For him, it’s more than decoration. When asked about meaningful mementos, he gestured toward it.
“I want to be a lighthouse for people,” he said. “I want them to know that when things are churned up, I’m going to be here. That I’m willing to take that on.”
Lighthouses provide clarity, steadiness, light. Hamilton sees his role in the same way: offering presence and consistency so that others — students, professional community members and families — can navigate forward.
Colleagues at Berwick Academy, where Hamilton served as head of school before coming to Peddie, witnessed those qualities firsthand. Michael Buensuceso, MSW, assistant head of school for community and equity at Berwick, recalled: “I always looked forward to my meetings with Jim. Whenever I brought him an idea for an initiative or a challenging issue, he met me with genuine curiosity and thoughtful questions.”
His leadership style, Hamilton explained, is anchored in humility and ambition, what he called “humbition,” a term from Amer Kaissi’s book “Humbitious.” It’s a spirit he finds prevalent at Peddie. “We need to walk that line of being really confident about what we’re doing and sharing with the world, without being arrogant. That’s something I’m excited to champion.”
Photo courtesy of The Roxbury Latin School
The roadmap of Jim Hamilton’s journey took him from Massachusetts (first as a student at The Roxbury Latin School, then beginning his independent school career at Brooks School) to Rhode Island (St. George’s) to Maine (Berwick Academy) and finally to his new home in New Jersey with The Peddie School.
Boston Beginnings
Hamilton’s journey began in Boston, where his mother pushed for him to be admitted to public school a year early. She brought him to dance class with his sisters, where he learned to tap dance. “It was very important for her that I had great academic opportunities,” he said. He entered the city’s Advanced Work Program, a pipeline for high-achieving students, and, in sixth grade, thanks to the persistence of a football coach who literally drove him to a visit, landed a place at The Roxbury Latin School (RL).
At RL, he thrived as a “master generalist.” A three-sport captain in football, basketball and baseball, he also sang in the glee club and performed in school plays (The tap dancing made him a valuable member of the cast.). His days shifted from the locker room to rehearsals, from game-winning shots to curtain calls. Belonging to many worlds at once was exhilarating. “That is the spirit of the school,” he recalled.
I want them to know that when things are churned up, I’m going to be here. That I’m willing to take that on.
Seasons of Leadership
After graduating from Amherst College, and following one year in the finance world, Hamilton began his independent school career at Brooks School in Massachusetts, where he worked in admissions and financial aid. From there, he moved to St. George’s in Rhode Island as director of admission. Teaching soon called, and with the help of a mentor who encouraged him to sit in on his classroom daily, Hamilton eventually taught English while still working in admissions and earning his master’s at Wesleyan.
He returned to Brooks as associate head of school, where he oversaw the school’s largest fundraising campaign and expanded financial aid by a third. In 2018, he became head of school at Berwick Academy in Maine, where his leadership left a lasting mark.
Mary Jo Carabatsos, Ph.D., director of the Upper School at Berwick, worked closely with Hamilton during his time there. “Jim’s goal to create a ‘One Berwick’ culture was not lost on me when we were gathering as a community,” she said. “He provided space for thoughtful dialogue when problems and challenges presented themselves.”
Her perspective reflects the balance Hamilton strives for, leading with vision while creating space for others to grow.
“I don’t mind being in the front,” Hamilton said. “My style has been one that has given people room to grow into leaders themselves.”
Education as a Journey
These experiences helped shape Hamilton’s philosophy. He sees a student’s education, at schools like Peddie, as a journey from a personal Point A to a personal Point B. Each student has a unique starting point, he believes, and it’s a school’s responsibility to help them move forward, whatever that looks like.
“It’s about making sure that opportunities are available for kids and that the people working most closely with them have the resources and expertise to provide transformational experiences,” he said.
Success, he emphasized, should be measured less by how polished an 18-year-old appears at graduation and more by how a 30-year-old alumnus is impacting the world around them.
“My hope is that our alumni look back and say, ‘I am where I am because of what I learned at Peddie.’ And that includes not only what they learned in the classroom, but the lessons from peers, from challenges, from developing a work ethic and a moral and ethical compass.”
I am proud to be the head of school and proud of Peddie for choosing me for who and what I am. It’s a meaningful step for the school.
First Impressions
When Hamilton arrived at Peddie this summer, two things struck him immediately: longevity and pride.
Employees spoke with affection about decades spent at the school. Alumni returned not just for reunions but to mentor and support. “I’m excited to foster and further that,” he said.
He is especially taken with Peddie’s motto: “We finish our labors to begin them anew.” For Hamilton, it captures the rhythm of school life. “That growth mindset of what’s next versus what’s finished is an incredible gift. It grounds us.”
Hamilton is Peddie’s first head of school of color, a milestone he acknowledged with both humility and nuance.
“I appreciate that it means a lot to a number of people in our community. That’s important and exciting. I am proud to be the head of school and proud of Peddie for choosing me for who and what I am. It’s a meaningful step for the school.”
Raised in a biracial household and now father to a multiracial family, Hamilton spoke less about identity as a label than as a perspective. Authentic leadership, he said, comes from being grounded in who you are, and then making space for others to do the same.
In Jim Hamilton’s office, not only will you find a lighthouse photograph, symbolizing clarity and steadiness, but also his 1985 acceptance letter from Roxbury Latin School. It’s sort of my “why,” Hamilton explains.
Number-One Cheerleader
Hamilton described himself as Peddie’s “number-one cheerleader.” Students are already used to seeing him in the bleachers, the theater, and at meets and tournaments.
“I want the kids to know me,” he said. “To see that I have a sense of humor, that I don’t take myself too seriously. I’m here to support them.”
The same goes for parents. “I want them to feel like, ‘That’s Jim,’ not ‘That’s the head of school.’” He added, “I’ll be in regular communication with parents in a way that assures them I’m in the trenches with their kids.”
And for alumni: “One of my main jobs is to make sure that Peddie remains a place that they’re super proud of and that they are eager to support.”
Morning Light
Most mornings, Hamilton walks Coco, his English Springer Spaniel, around campus at dawn. “I’ll think, ‘How lucky am I to be here, in a place this beautiful, with tradition and hopes.’ I love those moments before the campus comes awake.”
During these quiet walks, Hamilton takes in the weight and privilege of his role. It occurs to him: “Wow, this is pretty amazing.” In the stillness of morning, he sees the promise of a brand new day. And the responsibility to help Peddie navigate toward its next horizon.
In honor of Jim Hamilton stepping into his role as the 17th Head of School, we asked him 17 Questions.
What’s the first thing you do when you arrive on campus in the morning?
Play Wordle and send the result to my daughter.
Coffee or tea? How do you take it?
Coffee. Black.
What’s the last book you read or listened to that wasn’t work-related?
A Jack Reacher novel.
Which head of school, living or deceased, would you most want to have lunch with?
Tom DeGray. I’d like to learn more about the run-up to the Annenberg gift in 1993 and the subsequent strategic planning that shaped the school’s future.
If your life had a soundtrack, what would the opening song be?
“Lovely Day” by Bill Withers.
What’s been your favorite meal in the dining hall so far?
A sandwich from the deli bar.
You’re stranded on an island with one person. Who do you choose and why?
My wife — because I love her.
Who was your favorite teacher?
Jack Brennan, my former Latin teacher, basketball and baseball coach at Roxbury Latin School, and one of my early mentors.
What did high school Jim think he would grow up to be?
In my yearbook superlatives, I was named “Most Likely to Come Back and Teach and Coach.” Even if I didn’t see that in myself at the time, my classmates did.
You have 30 minutes with no meetings. What do you do?
Mostly plan, try to deal with the mass that is email. And, if possible, take a walk.
What was your first job?
I worked in a cemetery, mostly cutting grass and weed-whacking. That’s where I learned to drive. I also sold soda and popcorn at Fenway Park.
Favorite movie to rewatch on a rainy day?
“The Shawshank Redemption.”
Describe your leadership style in three words.
Aspirational. Empathetic. Strategic.
What’s a phrase you find yourself saying all the time?
It’s becoming, “We finish our labors to begin them anew.”
What’s a hidden talent that no one would expect?
I was a tap dancer as a kid. I even performed on “Community Auditions” with Dave Maynard, a Boston TV talent show that aired Sunday mornings.
What’s in your office that has a story behind it?
My acceptance letter from Roxbury Latin. I keep it on the wall to remind me where I come from and the opportunity I was given in 1985. It’s sort of my “why.”
Fill in the blank: “At Peddie, I’ve found _____.”
A home. An enduring community, full of possibility. A place I want to be for a long time.
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