This chapter explores the Venceremos Brigade (VB) as both a public solidarity movement with Cuba and a covert instrument of Cuban intelligence and paramilitary objectives. While most brigadistas joined out of ideological support, solidarity, or curiosity, declassified documents reveal that the Cuban government used the program to collect intelligence, train ideological and paramilitary cadres, and disseminate propaganda. The chapter traces the Brigade’s origins, showing a blend of New Left initiative and Cuban oversight, with Fidel Castro and Cuban officials guiding recruitment, organization, and political activities. Economically, brigadistas contributed little beyond symbolic labor, but politically and strategically, they were leveraged for intelligence collection, guerrilla training, and preparation of potential operatives abroad. Some members received instruction in espionage, military tactics, and explosives, sometimes in collaboration with other socialist countries. Though the VB did not present an immediate large-scale threat, its activities illustrate the complex interplay of ideological commitment, propaganda, and clandestine operations in Cold War transnational activism.