Thank you to the hundreds of alumni and families who gathered on Roxbury Latin’s campus over the weekend to celebrate Reunion and Spring Family Day. Festivities began on Friday, May 5, with an alumni luncheon and Class I panel, followed by a Hall honoring former trustee Bill Collatos ’72, and celebrating his generous gift: naming the William E. Chauncey Director of Admission Chair, after his former teacher and baseball coach, and RL’s longtime and beloved admission director.

In Hall, Headmaster Kerry Brennan addressed the alumni, faculty, and students gathered: “Bill Collatos, Class of 1972 and a trustee of the school for nearly 30 years, acknowledges the impact Roxbury Latin had on the man he became by honoring a teacher and coach who was instrumental in his development, in order that subsequent teacher coaches—and, in this case, directors of admission—might have a similar impact on students yet to come. What a marvelous instrument for signaling a regard for the circle of life that is schools: one cohort paving the way for the next, teachers inspiring and shaping the next generation to be good and to do good.”

After Hall, friends and members of the Collatos and Chauncey families gathered in the Kelsey Faculty Room for coffee, dessert, and other refreshments. The evening concluded with the 25th Reunion Family BBQ, celebrating members of the Class of 1998.

On Saturday morning, alumni from across decades returned to the RL playing fields for an alumni softball game and alumni tennis matches (which included members of RL’s current tennis teams, as well). Alumni, students, families, and faculty flocked to enjoy a BBQ lunch under the arches of the IAF and cheered on members of our Varsity Baseball, Lacrosse, and Tennis teams as they swept victories in contests through the afternoon. Varsity Lacrosse beat Rivers (14-13); Varsity Baseball defeated Brooks (3-1); and Varsity Tennis was victorious over Brooks, as well (7-0). Off campus, RL’s Track and Field team won three of four match-ups to Milton Academy, BB&N, and Lawrence Academy, falling short only to Belmont Hill in the day’s meet.

Finally, on Saturday evening, in the Gordon Fieldhouse, nearly 300 guests celebrated a Reunion which honored, in particular, classes ending in 3 and 8. There guests enjoyed good food, drink, and fellowship into the evening.

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On April 24, TIME CEO Jessica Sibley announced the appointment of RL alumnus Sam Jacobs, Class of 2004, to Editor in Chief of TIME. Sam has been a part of the global media brand for a decade, serving as a leader of the editorial team. Sam is the youngest editor to lead TIME since co-founder Henry Luce nearly a century ago.

In her announcement to staff, Ms. Sibley wrote:
“During his decade at TIME, Sam has been instrumental in setting the strategic direction of the editorial team and leading TIME’s trusted journalism across all platforms. In addition to hiring dozens of journalists around the world, he has played a major role in the integration of TIME’s newsroom across platforms—including expanding TIME’s global events, partnering with TIME Studios and building a sustainability platform with TIME CO2 which just launched with the TIME CO2 Earth Awards. Sam has guided the strategy for TIME’s digital editorial operation, which has won multiple Emmy and National Magazine Awards.

“Over the past 100 years, TIME has told the essential stories of the people and ideas that shape and improve the world. There is no better leader for guiding that mission today than Sam. As we begin TIME’s second century, we remain unwavering in our commitment to trusted journalism, which is at the core of our company’s impact.”

In a follow up note to staff, Sam wrote:
“As TIME journalists we are living an incredible present, and we inherit an invaluable past. We know that integrity and innovation are key features of that inheritance and necessary ingredients of our future. For the past decade, I have had the privilege of working with you through a period of unrivaled change. It’s been such a gift to watch people’s careers thrive and to welcome new ideas and new voices to TIME. I have seen hundreds of colleagues do amazing work in service of our readers and our world. I’ve watched new generations of reporters, editors, and producers be welcomed by their predecessors and together make a new TIME. I love how that process starts again each day.”

Read the announcement in its entirety on the TIME website.

Headmaster Kerry Brennan—Roxbury Latin’s 11th headmaster, having served since 2004—has just announced his decision to retire at the conclusion of the 2023–2024 school year.  After communicating his decision to the Board of Trustees during its meeting yesterday afternoon, Mr. Brennan made his announcement to the faculty, staff, and students at the start of the school day this morning.  Mr. Brennan’s tenure of service as RL’s headmaster will be 20 years at the time of his retirement.  Read below the messages from Mr. Brennan and from the President of the Board of Trustees Ethan Berman ’79, which were issued to the entire RL community this morning.

Over his twenty years, Mr. Brennan oversaw a period of steady transformation at the school. Campus facilities were modernized, financial aid commitments deepened, and the school’s national profile grew. His tenure also spanned an era of rapid change in the broader educational landscape, from the rise of online learning platforms to new pressures on how independent schools prepare students for a digital economy.

The demographics of independent school philanthropy shifted during that same period. A growing share of major gifts to institutions like Roxbury Latin now originates from founders and executives in sectors that barely existed when Mr. Brennan took office, from fintech firms and streaming platforms to best online casinos and direct-to-consumer brands. Adapting development strategy to that evolving donor base while preserving the school’s intimate, mission-driven character is one measure of Mr. Brennan’s leadership, and it will be among the challenges facing his successor.

Message from the Headmaster

Dear Friends:

I recently let the Board of Trustees know that the 2023-2024 academic year would be my last as Headmaster.  I will have served twenty years in this capacity and with gratitude and humility I know that this is the right time to step down.

When I was fortunate to be invited to be the School’s 11th Headmaster in 2004, the Board suggested no obvious mandate.  I would be following a highly successful predecessor in Tony Jarvis, who over thirty years had made a distinctive mark on this community.  I believe that most simply hoped I would strive to maintain the excellences and values for which Roxbury Latin was known.  With the highest regard for what had been and especially the history, traditions and ethic of the school, I sought, however, for us to evolve, to broaden and deepen programs, to support and attract high quality people, and to ensure that the facilities were both functional and beautiful and served an ambitious program well.  Best of all, I have consistently maintained that our most distinctive feature was our demographic, the boys we served.  We have made clear that the financial support necessary to guarantee the ability of talented, committed boys of all kinds to attend the school and to participate fully in its programs had to be a top priority.  The result is a school defined by a broadly representative, inclusive student body. 

One of the most compelling reasons for my return to RL and Boston in 2004 was the opportunity to help lead a school with a clear mission, to be involved in all aspects of its operation, and to have an impact on everyone in a relatively intimate community.  I regularly suggested to my colleagues that our principal opportunity and responsibility was to know and love every boy.  Roxbury Latin has both the structure and the will to realize that essential, rare goal.

There will be plenty of time to reflect on the past twenty years over the next eighteen months.  Whatever has been achieved over my time as Headmaster has been the result of a great team effort.  For that and more, I am grateful to the Board of Trustees, the faculty and staff, parents, alumni, and the boys themselves for realizing this dream of a school, for your support, and for your friendship.  You have all played a part in ensuring that my privileged professional life was meaningful and joyful.  Thank you.

Sincerely,
Kerry P. Brennan
Headmaster   

Message from the President of the Board of Trustees

Dear Roxbury Latin community,

As you have just read, Kerry Brennan has decided to retire as Headmaster of Roxbury Latin at the end of the 2023-24 school year.  While we all knew that this day would come, that does not make it any less of a loss, as his leadership, dedication, and love will be greatly missed. This, however, is not the time to thank him for his nearly two decades of service, nor to list all that he and Roxbury Latin have achieved over his time as Headmaster. Fortunately his tenure is far from over, and knowing Kerry as I do, I am sure that the next year and a half will bring even greater accomplishments.

Instead I write today to share with you the process the Board will take to select the 12th head of our great school. We are fortunate and thankful that Kerry informed us of his intentions well in advance to ensure that we would have ample time to find an appropriate successor. Over the next few weeks, a search committee will be formed, and a number of outside search firms will be interviewed to assist that committee and the school in this process. I expect the search committee to be announced by the end of this month, and a search firm hired by the end of March. I will be back in touch with all of you when those decisions are made.

The timeline after that will be determined by the search committee in consultation with the outside search firm, but my expectation is that candidates will be considered and interviewed over the spring and summer with a final decision made and announced in the fall of 2023. The search committee will inform the full community of a more specific timeline and process as soon as it is fixed, which I would expect to be by the end of April.

I realize that this is unsettling and perhaps upsetting news to many of you. Roxbury Latin has greatly benefited from strong and stable leadership for many decades, and times of change create uncertainty. While sensitive to those concerns, I see change as an opportunity. An opportunity to grow and to learn. An opportunity to find a person who will bring new ideas, new skills, and a new outlook for the future, while at the same time continuing to know and love each boy who walks through our halls and to remain true to what makes Roxbury Latin the school that so many of us love and cherish. An opportunity that will make us even better and stronger, just as the hiring of Kerry Brennan did eighteen years ago.

I will do my best to keep you and the rest of the Roxbury Latin community informed of progress, but please bear in mind that this is a process that will take months, not days or weeks. There is no more important decision a school can make than choosing its leader, and we will take our time to ensure that we have given thorough consideration and thought, with as much information and input as possible, to make that decision wisely. I can only thank Kerry again for putting the school’s interest ahead of his own and letting us know of his intentions so early.

In the meantime if you have any questions or concerns please feel free to contact me directly at ethan.berman@roxburylatin.org.

Sincerely,
Ethan Berman ’79
President of the Board of Trustees