Headmaster Casertano Awarded the 2019 Ruzicka Compass Premier Leadership Award

The Association of Boarding Schools (TABS) presented Millbrook School Headmaster Drew J. Casertano with their most prestigious award, the Ruzicka Compass Premier Leadership Award, at the 2019 TABS Annual Conference in Boston, MA, on December 6, 2019. Named in honor of the late Steven D. Ruzicka, TABS Executive Director from 1995-2007, the award recognizes extraordinary contributions to the excellence, advancement, and success of boarding schools.

“Presenting the Ruzicka Compass is a yearly tradition and an honor for TABS. The award recognizes outstanding leaders – individuals who have made extraordinary contributions to the wider boarding school community through their integrity, commitment and inspiring service,” said TABS Executive Director Peter Upham.
Mr. Casertano was appointed as Millbrook School’s sixth headmaster in 1990. Under his leadership the school’s applications have tripled, the enrollment has grown from 170 to 315, the endowment has increased from $6.7 million to more than $45 million, and annual and capital funds of nearly $150,000,000 million have been raised to support more than 223,000 square feet of new and renovated spaces. He remains ever thoughtful in his governancecollaborating with trustees, faculty, parents, and alumni to build talented teams with a shared vision for Millbrook students.
1990 will remain a pivotal year in Drew’s life and in Millbrook’s, for that is when the relationship between Drew and his school began. Myriad capital campaigns, enrollment initiatives, building projects, and accreditations later finds Millbrook at its most robust, energetic, and mission-centric…But the greatest architecture is not visible from a balance sheet or an aerial view. Thirty years Drew has led the school. That in and of itself is remarkable. Drew’s career is characterized by innovation, advancement, and results. Steve Ruzicka was guided by the belief that anything is possible, and I think we can safely say this belief guides Drew. TABS Board is pleased to recognize his continuing achievements with the Ruzicka Compass,” said Ben Williams, TABS board chair. To read Mr. Williams' entire introduction, click here.
Prior to Millbrook, Mr. Casertano served as director of admission and financial aid at The Gunnery and at The Loomis Chaffee School, where he began his career – teaching, coaching, living and working in a dormitory, directing student activities, and working in admissions. He is a graduate of The Choate School and Amherst College, and earned his Master of Education degree at Harvard University.
Mr. Casertano has also held principal roles within numerous other educational organizations, serving as a trustee at Dutchess Day School, Parents League of New York, Washington Montessori School, the Secondary School Admission Test Board (now the Enrollment Management Association), and at TABS, where he chaired the executive committee that developed the North American Boarding Initiative. He was president of the Headmasters Association and the board of trustees of the New York State Association of Independent School (NYSAIS). Currently, he is a board member at Indian Mountain School and New Canaan Country School and served as a long-time board member of Safe Passage.

Millbrook School is thankful to Mr. Casertano for his 30 years of outstanding leadership and to TABS for recognizing all that he has done for Millbrook and for boarding schools in the U.S.
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