Soon after settling in Paris, Hemingway met Henry Strater, a painter who shared his enthusiasm for boxing and tennis. A Princeton graduate, Strater could already claim a significant connection to modern literature, for he had been the model for a secondary character in This Side of Paradise, the best-selling novel by his Princeton contemporary F. Scott Fitzgerald. Soon he would also be working on illustrations for a publication containing a portion of Ezra Pound's major work, The Cantos.
The Hemingway-Strater friendship grew quickly, and soon Hemingway was posing for this portrait, the first of two likenesses of him by Strater done in fairly quick succession. This portrait is dated 1922, but Strater always claimed it was done early the following year in Rapallo, Italy, where both were visiting with Pound. In any case, Hemingway apparently did not like this first Strater effort, which he claimed made him look "too literary." So Strater obligingly created a second likeness.