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Charley Stillwell understands boarding schools. He has seen how they operate from the inside as the child of a boarding school faculty member, as a student, and as a boarding school faculty member himself. He is familiar with the unique and empowering relationships that are fostered between and among students and their teachers. His experiences over the last three decades in both boarding and day schools, including 18 years of experience as a head of school, prepared him to take the helm of Episcopal High School.

Charley received his bachelor's degree in American History with honors from Princeton University, where he was a four-year member of the lacrosse team. Upon graduation, he joined the faculty of St. George’s School in Newport, R.I., where he taught history, and coached JV girls' basketball, varsity football, and boys' lacrosse. He also served as a dorm parent for 9th-grade girls and 9th and 10th-grade boys, all while earning his master's degree in American History from Brown University. After six years at St. George's, Charley went on to teach and coach at Collegiate School in Richmond, Va., and later moved to the Gilman School in Baltimore, Md., where for five years he served as head of the upper school. Charley served as the headmaster of St. Christopher’s School in Richmond beginning in 1998 until his arrival on the Hill in the summer of 2016.

A passionate educator, Charley is determined in his pursuit of excellence in academic and student life programming, global outreach, strategic growth, and student-faculty relationships. He has traveled extensively and served as the vice president for North America of the International Boys Schools Coalition Board.