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He founded the Choate School (later Choate Rosemary Hall) in 1896, and from 1902 to 1903 he served as president of the New York City Bar Association.
In January, 1970, Prescott published A World of Our Own: Notes on Life and Learning in a Boys' Preparatory School, which described his alma mater, The Choate School, (now Choate Rosemary Hall).