By any measure, the past 30 years have been transformational for Millbrook School, driven in large part by the extraordinary leadership of Drew Casertano. So, it is with deep gratitude for Drew’s dedicated service that we announce that he has decided that the 2020-2021 school year will be his last as headmaster.
Soon after his appointment, Drew encouraged the board to embark on the school’s first-ever strategic plan, which would articulate the goal for Millbrook to become the “finest, coeducational, ideal-sized boarding school in the country.” What seemed like a dream in 1990 has become a reality, resulting in growing public recognition of Millbrook’s excellence. Enrollment has grown from 170 to 320, our endowment has increased from $6 million to $50 million, and we have raised annual and capital funds of over $160 million to support more than 223,000 square feet of new and renovated spaces. We have designed an academic program that encourages our students’ curiosity and demands rigorous analysis and critical thinking, developed an arts curriculum that is second to none and rivals many college programs, and elevated our athletic program to compete with any school in New England. All of this has been accomplished while preserving what makes Millbrook, Millbrook, namely a community where every student is known and needed and where we prepare our students for college and lives of meaning and consequence. Drew and his wife, Linda, have given so much to our school, and on behalf of my colleagues on the board, I thank them for all they have done to shape Millbrook into the exceptional school it is today.
There is no greater responsibility for the Board of Trustees than selecting the school’s headmaster, which is why succession planning has been a critical component of Millbrook’s last two strategic plans. Our intention was to ensure a smooth transition when Drew and Linda ultimately decided it was time to retire. Our process led us to form a Transition Committee, comprised of trustees and faculty who worked with a consultant, to conduct a thorough review of the best path forward for our school. Guided by Millbrook’s mission at each step, and after considering the landscape of leaders working in peer schools, the best candidate clearly emerged—an alumnus and current administrator whose demonstrated leadership, talent, and vision will continue advancing our school. I am pleased to announce that the board unanimously and enthusiastically voted to appoint Jon Downs ’98 as Millbrook’s seventh headmaster beginning July 1, 2021.
We have the utmost confidence that Jon is the right leader at the right time to build on the momentum of the past 30 years and usher our school into a new era. Jon and his wife, Erin, who served as chair of Millbrook’s English department and now as associate director of college counseling, have three fantastic children, Atticus (7), Aurora (6), and Finley (2). For those of you who have not had the pleasure of meeting Jon, I am sure that once you do, you, too, will be confident that Millbrook’s future is in great hands under Jon’s leadership.
Between now and July 1, 2021, Drew and Jon will continue to work together closely to sustain and enhance Millbrook’s momentum, just as they have since Jon returned to his alma mater as director of admission in the summer of 2010 and in his current role as assistant headmaster. We will honor Drew and Linda’s three decades of exceptional service at the appropriate time. Until then, please join me in congratulating Jon on his appointment as Millbrook’s seventh headmaster.
