Ernest Hemingway and Cuban author Guillermo Cabrera Infante met at least twice: on a fishing trip in Cuba on the American writer’s famous boat, El Pilar; and briefly in passing at a restaurant in Madrid. Many scholars have documented Hemingway’s clear influence on Cabrera Infante’s style, as well as how often he surfaced in the Cuban writer’s many works of fiction and non-fiction. However, scholarship has never comprehensively examined the extent of Hemingway’s influence and the relationship between the writers’ identities, vocation, and body of work. My dissertation transcends current scholarship, analyzing the interstices of Hemingway and Cabrera Infante’s lives, in addition to how and why their work intersects at critical points. It also considers the factors that influenced Cabrera Infante’s imagination of Hemingway, which I argue is inherently tied to U.S.-Cuban relations before and after the Cuban Revolution. While my scholarship accounts for the impact of U.S. hegemony on this perspective, it also foregrounds refreshing camaraderie regarding how Hemingway and Cabrera imagined Cuba in their respective works. In all, this dissertation represents a fruitful juxtaposition of U.S.-Cuban authors–a treasure trove for the aspirational fields of Inter-American, transatlantic, and comparative studies.