South Kent School has released its 2026 State of the School Address, delivered by its 10th Head of School, Brian Sullivan, marking a defining moment in the School’s history and formally launching The South Kent Initiative, the most ambitious financial endeavor in the School’s 103-year history.
Recorded in St. Michael’s Chapel, the address reflects on the School’s momentum and outlines a clear and definitive path forward. “As South Kent enters its second century, our mission to form young men of character, resilience, and purpose remains as vital today as it was in 1923,” Sullivan shared. “At the midpoint of my third year as Head of School, I am deeply encouraged by the momentum across the Hillside.”
That momentum includes record growth in The South Kent Fund, the highest boarding enrollment in the School’s history, expanded academic and co-curricular offerings, and a revitalized North Campus now serving as a living classroom. Sullivan emphasized that these gains are not accidental, but the result of a dedicated community working quietly and steadily to ensure the School is prepared not only to endure, but to lead.
The address also introduces The South Kent Initiative, a multi-year effort designed to position the School for long-term, sustainable growth by investing in its people, programs, and place. As of February 2026, South Kent has already raised $28 million in gifts and future commitments toward the Initiative, with $17 million remaining to reach its goal.
“This is a moment of shared responsibility,” Sullivan noted in his remarks. “One that calls for thoughtful investment in our people, programs, and place.” To that end, the School announced that all funds raised between now and June 30, 2028 will count toward The South Kent Initiative, including gifts made during Spring for South Kent, the School’s Annual Day of Giving, taking place on Tuesday, February 24.
With this announcement, South Kent invites alumni, parents, grandparents, friends, and community partners to participate in shaping the School’s next chapter. “With your partnership,” Sullivan said, “we can continue building on our proud legacy and help write the next chapter of South Kent’s storied Hillside.”
WATCH the 2026 State of the School Address.