Kerry Brennan has spent all of his professional life teaching in and leading schools. The 11^th Headmaster of Roxbury Latin, Kerry is in his 19^th year in that role. Headmaster of New York City’s venerable K-12 Collegiate School prior to that, Kerry spent 14 years as a principal at Cleveland’s University School, first as Head of the Shaker Campus (K-8), and then as Head of the Hunting Valley Campus (9-12). His first secondary school position was as Director of Music, English teacher, basketball coach, class dean, Chair of the Arts Department, and member of the Admission Committee at Roxbury Latin. In anticipation of that appointment, he served at Amherst College as Associate in Music, founder and director of the Amherst College Chorus (the school’s first co-ed chorus for underclassmen), director of the Amherst Freshman Glee Club, and director of the Amherst College Glee Club. He also worked at Harvard University as assistant dean of the Summer School.

A native of Schenectady, New York, and a graduate of its public schools, Kerry went on to Amherst College from which he graduated magna cum laude with a degree in music and political science. At Amherst, he was deeply involved in music and theatre, including directing the Amherst Zumbyes and several musical productions; he was also an elected college-wide representative. Named a Klingenstein Fellow in 1982, he earned his master’s in philosophy and education from Teachers College, Columbia University.

Kerry’s contributions to education and the arts beyond the schools in which he has worked are significant. He has served as a trustee of the Civic Symphony of Boston, Lyric Opera Cleveland (president), the Cleveland Institute of Music, the Intercollegiate Men’s Choruses, Nightingale Bamford School, George Jackson Academy (founding trustee), Winsor School, and as a founding member of the day school executive committee for the University of Pennsylvania Graduate Program in Independent School Teaching. He has also participated in and led school evaluation teams in the Central States, New York, and New England. A longtime member of the Board of Trustees of the International Boys’ Schools Coalition (200 schools, 250,000 students), Kerry was named its president in 2015. A member of the Heads Collegiate Forum (formerly Country Day School Headmasters Association), Kerry currently serves as President of the Heads and Principals Association (formerly the Headmasters Association).

A lifelong musician, Kerry is musical director of Mastersingers USA, a 25-year-old, 80 member men’s chorus that has traveled abroad extensively. He is also the founder and director of The Sly Voxes, a Boston-based, men’s a cappella group.

During his time as Headmaster of Roxbury Latin, the school has expanded its programs in international education, social sciences, STEM, the arts, public speaking, student leadership, community and culture, and service. In addition to modernizing existing buildings, in 2016 the school opened its Indoor Athletic Facility, a state-of-the-art hockey rink, turf surface, and training and wellness space, as well as synthetic surface playing fields and 12-tennis courts. Kerry led efforts to join with other independent schools in support of a two-year teachers’ education program offered in collaboration with the University of Pennsylvania. Four fellows are on campus each year thanks to that program. Kerry has emphasized access and affordability and broad representation in the student body from all Greater Boston demographics. Impressive fundraising has largely been in service to realizing those goals, as well as attracting, developing, and retaining a world-class faculty. Currently, Kerry also teaches a civics course for eighth graders (an effort he spawned), assists with the direction of the 100-voice Glee Club, and advises ten students.