Donald Ogden Stewart was born in Columbus, Ohio. The son of Gilbert Holland Stewart, a judge, and Clara Ogden Stewart, he attended Phillips Exeter Academy and Yale University. While at Yale, he served as assignment editor on the News and was elected to the Skull and Bones secret society. Stewart graduated from Yale in 1916, assuming that he would be a banker or businessman like most of his classmates. After graduation, he served in the U.S. Navy and then began a short career with AT&T.

Stewart's work with AT&T, in the capacity of clerk, moved him to Minneapolis in 1919. Living in Saint Paul, Stewart became friends with an as-yet-unpublished writer, F. Scott Fitzgerald. Disillusioned with his "safe" job, Stewart quit AT&T in 1920 and moved to New York City, where Fitzgerald was able to recommend him to Edmund Wilson, who worked for Vanity Fair. Seeking a...