Headmaster Kerry Brennan Announces Retirement at End of 2023-2024 School Year

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.

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.

Kerry P. Brennan

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.

Ethan Berman ’79
President of the Board of Trustees