The article discusses the participation of the Communist International (Comintern, 1919–1943) in the Caribbean region throughout most of the 1930s, mapping an international dimension for local and regional developments and counting the Soviet Union as an imperialist contender along with the customary colonial powers. The essay also enumerates examples of the sort of international, cultural networks fostered by the Comintern’s agenda and its political agents throughout the area, pointing out the connection between this sort of communication and the region’s leap into modernity that defined the decolonization process in the late 1940s. In these developments, New York as the center of a Caribbean diaspora becomes instrumental as the point of departure and confluence for the agents of international communism and Caribbean nationals during the decade of the 1930s. The evidence, in turn, implies a call to reformulate the historical evolution of the Caribbean diaspora in New York between the 1920s and the 1940s, taking into consideration the Comintern’s contribution to the transnational aspect of Caribbean radicalism, politics and culture in the post-war era. Finally, it also suggests a possible revision of the chronological framework for the Soviet Union’s presence in the Caribbean region long before the Cuban revolution of 1959, in view of declassified documentation from the Comintern archives.