Jack was very popular and had many friends at Choate, a boarding school for adolescent boys in Connecticut. He played tennis, basketball, football, and golf and also enjoyed reading. His friend Lem Billings remembers how unusual it was that Jack had a daily subscription to the New York Times . Jack had a "clever, individualist mind," his Head Master once noted, though he was not the best student. He did not always work as hard as he could, except in history and English, which were his favorite subjects.