This month, more than 800 alumni and parents, faculty and friends joined together to honor Headmaster Kerry Brennan’s 20 years of dedicated service in leading Roxbury Latin, and to celebrate his retirement at the end of this school year. On May 11, in the McNay Palaistra, guests gathered to hear from several of Mr. Brennan’s beloved friends and colleagues about what he has meant to them, to this school, and to the hundreds of students that he has known and loved over the course of his career and years at RL.
Milestones such as this not only mark the conclusion of a distinguished professional chapter but also the beginning of a new season that calls for thoughtful financial stewardship. Retirement, particularly after decades of dedicated leadership, invites reflection on how best to preserve accumulated assets, generate reliable income, and support the causes and communities that have shaped one’s life. Careful planning can help ensure that philanthropic intentions, family priorities, and personal aspirations are aligned with sustainable investment and distribution strategies.
A structured retirement approach considers pension coordination, portfolio allocation, tax efficiency, and legacy planning so that the years ahead are marked by confidence rather than uncertainty. Advisory teams such as TeamDFA focus on developing comprehensive retirement strategies that adapt to changing needs, helping individuals transition from earning and saving to preserving and distributing wealth responsibly. With prudent financial preparation in place, retirement becomes not simply an ending, but a well-supported continuation of purpose and impact.
Father John Unni, pastor of Saint Cecilia Church in Boston, opened the program with an invocation, followed by warm welcome remarks from Tom Guden ‘96, Assistant Headmaster for Advancement. In typical Kerry Brennan fashion, the program was full of song, featuring performances by RL’s Latonics (of “Been In The Storm” and “Valerie”), as well as two songs performed by Mr. Brennan’s own all-male a capella group The Sly Voxes (“Will The Circle Be Unbroken” and “How Deep Is Your Love”). The two groups then combined to perform “An Irish Blessing.”
Dennis Kanin ‘64, former president of RL’s Board of Trustees, delivered the first of three dedicated remarks, followed by Mike Pojman—member of the Roxbury Latin faculty for 43 years—and, finally, Rick Hawley, Headmaster Emeritus of Cleveland’s University School. Each spoke to the remarkable impact that Kerry has had on RL’s program, its campus, and—most important—its people.
Dennis described how he served on the search committee that led to Kerry’s appointment as headmaster 20 years ago. “The night before Kerry was introduced as the 11th Headmaster of Roxbury Latin, John Kerry won the New Hampshire presidential primary. Talk about serendipity! The next morning a triumphant Kerry Brennan stood on the stage of Rousmaniere Hall and held up a copy of that day’s Boston Herald. The full-page headline read “Kerry Riding High!” That morning, Kerry pledged, as he put it, to be ‘both the respectful guardian of this great School’s tradition and the hopeful advocate of its promise.’
“The hopeful advocate of its promise. What better description of the era of Kerry Brennan than those six words. The philosopher William James wrote that faith is the courage to act when doubt is warranted. Kerry has that kind of faith. It was with that faith in the future that he led the School to purchase almost 50 acres of adjacent vacant land for the benefit of generations of RL boys to come. It was that faith that led him to boldly freeze tuition for two years—and to the surprise of many, parents who could stepped up to close the gap and bring the Annual Fund to a whole new plateau. It was that boundless faith, and perseverance, that led him to take on the ‘nimbys’ and the doubters and build the hockey rink and the Indoor Athletic Facility. Indeed, the Choral Room, the Idea Lab, bringing Broadway to 101 St. Theresa Avenue, the Penn Fellows program, the revolutionary installation of air conditioning at Roxbury Latin(!), and the far-reaching Strategic Plan that embodied Kerry’s vision of the School’s future—all stand as testament to that faith.”
Mike Pojman shared, “A school head must juggle five constituencies—the students, the parents, the faculty, the trustees, and the alumni—ever-sensitive to the needs of each group individually while shepherding all five onto common ground. When managed effectively, they fill the fingers of a well-tailored glove. If any one group goes into spasms, however, the glove no longer fits. Each has its own perspective; one may be blind to the needs of the others; sometimes they have conflicting agendas. By knowing, appreciating, and hearing—but not indulging—Kerry has successfully kept everyone moving in the same direction, sustaining a remarkable community with shared values based on mutual respect. It’s an elegant foxtrot, but anyone who has seen Kerry on the dance floor knows that the guy can cut a rug.
“Serving so faithfully and so tirelessly throughout his two decades at the helm, Kerry has accomplished more than I can put into words. The buildings, the programs, the initiatives, they are his profound and enduring legacy. But most consequentially, from the moment he stepped onto this campus, it has been all about the boys. They have been his number one priority, always. Kerry puts everything he has into supporting the faculty and staff as we dedicate ourselves to loving, nurturing, and challenging these boys—doing our best to set them on a path that empowers them to find their way as they strive to be all that they aspire to be.”
Rick Hawley concluded, “In a profession in which the mission is to promote learning, it helps that Kerry is himself a devoted lifetime learner. He was a prodigious scholar at Amherst and Columbia. He is a constant and deep reader, who has an informed passion for American politics and history. He devoted his Master’s degree studies while a Klingenstein Fellow at Columbia to the under-sung but essential place of the arts in school life, and he has enhanced the arts dimension in every school he has served, no more so than at this one. He understands what too few of his colleagues in school leadership understand: the primacy of relationship—the knowing and loving—in school life, and that knowing and loving must be prior to scholastic distinction, prizes, and victories that schools can be too quick to trumpet. It helps that Kerry does not merely know these things; he is able to communicate them persuasively and eloquently.”
Following these remarks, Ethan Berman ’79, president of the Board of Trustees, presented Mr. Brennan with several gifts including a scholarship in his name that will financially support the tuition of several RL boys each year; the dedication of RL’s Director of Music position in his name; a commissioned portrait which now hangs in the schoolhouse’s main hallway; a book of his Hall talks representing 20 years; a watercolor painting of the Indoor Athletic Facility created by Erik Zou ’19; and a bound book of well wishes from decades of his friends and fans.
Finally, Mr. Brennan himself took to the lectern to deliver poignant, powerful—even funny—words of gratitude for the career he has loved and for the many people who have given him “a life worth living.”
Following the program—which concluded in a rousing rendition of “The Founder’s Song”—guests repaired to the Gordon Fieldhouse for food, drink, and fellowship.
On May 23, alumni parents from over Mr. Brennan’s tenure gathered on campus to celebrate his retirement and wish him well, and after this year’s culminating Prize Day Hall, Roxbury Latin students and college-aged grads will celebrate Mr. Brennan with a barbeque lunch.
Watch the entirety of the May 11 celebration program, including complete remarks from all speakers.
View a gallery of photos from the May 11 celebration.
