His Greatest Gamble is a 1934 American drama film directed by John Robertson from a screenplay by Sidney Buchman and Harry Hervey, based on a story by Salisbury Field. The film stars Richard Dix, Dorothy Wilson, Bruce Cabot, and Erin O'Brien-Moore. Edith Fellows also has a role, playing the character of Alice Stebbins as a child.

A print is held by the Library of Congress.