Message from the Headmaster

Dear Gilman Alumni, Parents, and Friends,

Throughout my life and career, I have had the good fortune of being a part of some very special schools, places that are distinguished at least in part by beautiful, iconic buildings. Gilman has certainly been no exception. In fact, during my seven years here, I have often remarked that I would hold Carey Hall up against any building, on any campus, anywhere. Surrounding Carey Hall, of course, is a beautiful campus that provides a state-of-the art space in which our students can learn and grow. Indeed, we are truly blessed at Gilman to enjoy such impressive buildings and grounds.

While I never want us to take our outstanding facilities for granted, I also fully understand that they are little without the people who bring them to life. As past headmasters, Mr. Henry H. Callard and Mr. Redmond C. S. Finney, have rightly observed, “The true measure of any school is the quality of the character of its members.” Gilman is a place of people. What’s more, it is a place of people of high character. Since its founding in 1897, our School has been built on a foundation of human interaction and the inherent value of bringing together boys of great promise and educators of immeasurable dedication. It is a proven formula that sets our students up for success at Gilman and beyond. That success is marked by college and career choices that match our high aspirations for them and, most importantly, for lives of meaningful engagement and purpose.

First Things First: Endowing Gilman’s Promise and People is a bold commitment to that bedrock foundation. By raising funds to strengthen our endowment, we are investing in what makes Gilman such a special community of learning and growth. Bringing together promising students and dedicated faculty and providing them with the resources and programs that cultivate the growth of the whole boy in mind, body, and spirit challenge us to meet two important demands. On one hand, we must support our excellent teachers by paying them well and investing in their professional growth. On the other, we must maximize our ability to make Gilman accessible to all families whose boys are great fits. By more fully endowing funds for faculty support and financial aid, we will strengthen our ability to offer assistance to families who need it while keeping in check the tuition growth that all families face.

We live in a rapidly changing world in which a Gilman education is, perhaps, more needed than ever. We strive to prepare young men to be their best, fullest selves so that, in turn, they will make the world the best version of itself. As we look to the future and embrace that charge, let us build on the foundation that has always made Gilman a leader in education. Please join me in investing in our promise and people.


Henry P. A. Smyth P'24, '26


Henry Smyth
Gilman is a place of people. What's more, it is a place of people of high character.