Mr. Stewart won an Open Scholarship in History to Wadham College, Oxford, where he studied law as an undergraduate. He stayed at Oxford to do a graduate degree in law (B.C.L.), and then won a Harmsworth award to the Middle Temple. He was a barrister in London, both as prosecuting and defending counsel at the Old Bailey, for three years. In 1964, Mr. Stewart met Jayme, his wife, while they were counselors at Tripp Lake Camp in Maine. In 1968 they were married.
Mr. and Mrs. Stewart came to New York in 1969 and started York Prep School in a former music school on East 85th Street. Until 1981, they also were co-directors of Tripp Lake Camp. In 1997, the Stewarts’ moved York Prep School to its present building on West 68th Street.
Mr. Stewart currently is celebrating his 49th year of being headmaster of York Prep. He teaches Ethics to all members of the Senior Class as well as Philosophy to students in the York Prep Scholars Program. He strongly believes that a head of school should teach on a regular basis.
Mr. Stewart currently serves on the Executive Committee of the Dean’s Council of Weill Cornell Hospital, the Education Update Advisory Council, the Board of Directors for the Alexander Robertson School, the Board of the Macaulay Honors College of CUNY, and has served on a variety of educational boards. He has served as Chairperson on six Middle States Evaluation Committees (and served numerous times as a committee member); and was a regular speaker at the Klingenstein Program of Teachers College, Columbia University. Most recently, Education Update named Mr. Stewart one of the Distinguished Leaders in Education (2015).
The Stewarts have three children and five grand-daughters.