Fort Street was established in 1850 as an academically selective public high school reserved for intellectually gifted students. He got to know James McAuley at Fort Street and the budding poets shared a common interest in literature which provided the foundation for the exchange of ideas and the opportunity to develop a friendship. McAuley won the school Poetry Prize in 1933, while Stewart achieved the same honour in the two years that followed. In a letter to Michael Heyward, he writes: "Jim and I were not good friends at Fort Street, but rather rivals".