My dissertation examines the vitally important and heretofore-overlooked role of oil in shaping the domestic and international dimensions of the Cuban Revolution from the 1950s through the 1980s. Cuban efforts from the early 1950s onward to overcome the island’s dependence on imported oil and U.S. efforts to exploit that dependence provide a new lens through which to investigate the development of the Cuban Revolution, continuities and changes between pre- and post-Revolutionary Cuba, relations between Cuba and the United States, and between them and such key third countries as Venezuela, Mexico, and the Soviet Union. The project examines the material base and highlights the underlying ecological and economic constraints that shaped the contours of the Batista and Castro eras, and demonstrates the marked continuities between the two regimes’ domestic and foreign policies despite their very different languages of development and relationships with the United States. The dissertation blends international, political, economic, and environmental history, based on research in governmental and non-governmental archives and publications in the United States, Cuba, Venezuela, and Mexico.