The Light Keeper

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.

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.”

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.

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.”

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.

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.