A Farewell Message from Headmaster Kerry Brennan

Dear Friends:

And so it comes to an end. I sit finally at my desk in the Headmaster’s Office, one that has been occupied with distinction by my predecessors—beginning with Daniel Varney Thompson, during whose administration the school moved from Kearsarge Avenue in Roxbury to its spatial digs here in West Roxbury. This perch has seen its fair share of travails and joys over the years, but no pleasure is more significant than the perspective it affords on the life of the school, the joyful churn of our boys about their business, and the opportunity between classes each and every day to be reminded of our central focus: to know and love every boy.

Since in February 2023 I announced my retirement, people have been extraordinarily thoughtful in their accounting of what my twenty years as Headmaster have meant to the school, and how we would together look forward to my remaining time in this role. But the past few, fleeting months have offered joyful affirmations of our time spent together—too many and too much to recount appropriately in this missive. Suffice it to say that I have felt affirmed and appreciated through these flattering valedictions. I am so grateful for the many kindnesses shown me over these past few months. I hope people will forgive me if I do not respond personally—as I should—but offer here my profound, humble thanks to all of you for your remarkably generous remembrances and good wishes.

As I have said repeatedly, it is I who should be offering thanks. First, for hearing the call to this vocation—so meaningful and so enriching. Next, that in 1978, and again in a new capacity in 2004, that I should be matched with a peerless school whose distinctive mission changes positively the lives of a democratically gathered group of boys who themselves will change their various communities and our world for the better; and, finally, that I should be drawn together with a peerless set of colleagues, blessedly supportive trustees, trusting parents, loyal alumni, and, best of all, talented, committed, caring, quirky, funny, loving boys who want to do their best and want to be their best. In this calling, I could not have had a more challenging, satisfying, meaningful life. For that, I shall always be grateful.

Tomorrow, my friend, Sam Schaffer, takes up the baton as our leader. As you have read, Sam has distinguished himself as an educator, especially as a brilliant teacher. He has cut his teeth at a wonderful boys’ school, St. Albans, and has served in a number of significant capacities there. His own intellectual fervor and his sense of excellence will serve him well at RL. Best of all, though, Sam loves kids. He is engaged by and delighted by the boys in his care. He has already found RL boys irresistible. You can imagine that I am especially reassured that we share that priority: always boys first. As you have done for me, I ask you to do for Sam: to be supportive, encouraging, and patient as he comes to know Roxbury Latin, its programs, its principles, and its people. He deserves the earnest hopes and prayers of all of us.

Finally, as I continue to live in Boston, I hope that our paths will cross regularly. I have pledged my support for Sam, and I will be delighted to help as needed. I am especially eager to extend and deepen the relationships you and I share, and I hope I will see you often. Thank you for all you have said about me, all that you have done for me, and all that you have meant to me. I have felt known and loved. Ave atque vale.

Kerry P. Brennan