This article examines the transnational activism of the Directorio Revolucionario Estudiantil (Revolutionary Student Directorate, DRE), a group of exiled Cuban anti-Castro students. In the wake of the Bay of Pigs invasion, with CIA funding, the DRE attempted to challenge student support for the Cuban Revolution in Latin America and elsewhere in the global South. This article uses the DRE's trajectory to rethink the 1960s as a period of anti-communist, as well as leftist, youth ascendancy. It challenges the idea that Cuba garnered universal youth support, stressing instead that the Cuban Revolution helped turn student politics into a key battleground of the Cold War.