This article explores the literary and historical connections between William Faulkner, Jean Toomer, and the influential 1920s literary magazine The Double Dealer. It argues that examining Faulkner’s published work and interactions with The Double Dealer — a journal known for promoting Southern and modernist writers — reveals important insights into Faulkner’s literary development and his relationship with the Harlem Renaissance and other contemporary movements. The article situates Faulkner and Toomer within broader cultural conversations of the early twentieth century, showing how The Double Dealer provided a forum for writers of diverse backgrounds and helped shape Southern modernism.