In the search for a Cuban road to socialism, those advocating a gradualist and pragmatic approach clashed with Che Guevara and his supporters, who called for a radical and voluntarist development strategy. While criticized by Cuba’s Soviet and Eastern Bloc allies, Che’s radical economic ideas, which dominated Cuban policy by 1968, were shaped by North Korea’s example as well as its material support. North Korea appeared to show a tested path through which a small country emerging from colonialism and underdevelopment could transform rapidly into a modern, industrialized, socialist republic. The Cuban–North Korean ideological encounter reflected a broader discourse taking place within the international Left at the time reflecting disillusionment with the Soviet Union and the appeal of alternative models of socialism from the global South. As an ideological consensus between Cuba and North Korea solidified in the 1960s, the two governments became principal defenders of voluntarist economics within the socialist world, in resistance to the dominant trend towards “market socialism.” This partnership was given its most vibrant expression in the 1970 sugar harvest, Cuba’s pivotal experiment in voluntarist economics, in which North Korea participated directly.

By early 1965, new dynamics were taking shape within the international communist movement. Cuba and North Korea were at the forefront of this challenge. Relations between the two countries date back to the Korean War, when many Cubans, like young people across Latin America, mobilized to prevent their countries from joining the US-led war effort. When the Cuban Revolution of 1959 brought the island into the socialist camp, a bond began to grow between the Cuban and North Korean leaderships reflective of their shared history of anti-colonial struggle, and their common interests as small countries within a community of socialist states dominated by the Soviet Union and China. Political, cultural, and economic cooperation between Havana and Pyongyang grew steadily, including Che’s historic visit to North Korea in December 1960. By 1965, a nascent Third Worldist tendency affirming its independence from the two major socialist powers was coalescing around North Korea, Cuba, and North Vietnam. At its core was the conviction that it was those on the frontlines of the anti-imperialist struggle which most clearly recognized the true historic task at hand: the defeat of US imperialism.

Following the Cuban Revolution, the Cold War heated up in Latin America. To some, the Revolution was a sign of the spread of Soviet-directed Communist movements and the pressing need to stop this by any means possible. To others, Castro’s success was a symbol of hope: the United States was not all-powerful, and so radical reform was within the realm of possibility. The United States sought to undermine the Cuban Revolution and to prevent similar developments from happening elsewhere. It supported a number of initiatives to prevent the spread of Communism in the hemisphere, including the Alliance for Progress, strengthening ties with the region’s militaries, and overt and covert programs to support “friendly” governments and destabilize “unfriendly” ones. The resulting clashes led to one of the darkest periods of U.S.–Latin American relations.

The chapter traces the development of Guevara’s revolutionary consciousness and the concurrent creation of a militant program of armed struggle on three continents (Asia, Africa, and Latin America). It places Guevara’s intellectual and revolutionary project in the context of the emerging and evolving alliance between the Cuban revolution and the Soviet Union, the simultaneous confrontation with the realities and legacies of US imperialism, and the quixotic quest for Third World solidarity. An exploration of Che’s beliefs, ideas, and actions relating to revolutionary warfare reveals a man ahead of his time. Guevara synthesized and built upon the foundation of guerrilla strategies and tactics promulgated most famously by Mao Zedong but also exhibited by Augusto Sandino, hero of the struggle to liberate Nicaragua from the US occupation. In doing so, he championed an agenda of political and militant solidarity that would continue to attract adherents long after his death at the hands of Bolivian security forces in 1967.

Mercenaries are controversial components of contemporary warfare but became common as decolonization and the Cold War intersected to cause conflict in the Global South. Under Fidel Castro, Cuba understood mercenaries as the products of capitalism, neocolonialism, and imperialism, using the term to describe a range of intermediates that acted on behalf of the United States and other Western nations. This global projection of counterrevolutionary force legitimized Cuba’s own deployments and revolutionary fights to combat these threats. Both of these opposing forces consisted of foreign militants fighting alongside rebels or for governments, but they had different motivations and relationships to allied movements or states. The chapter examines Cuban theorizing about mercenarism and the revolutionary fighter, ranging from the events at Playa Girón to the deployment of Cuban troops to Angola in the 1970s. At the same time, Cuba championed an expansive legal definition of mercenarism that sought – ultimately unsuccessfully – to incorporate its Tricontinental critique of Western intervention into international law.

While anarchists across the Caribbean – especially in Cuba – were being deported, jailed, and killed in the 1920s and early 1930s, Cuban anarchist authors Marcelo Salinas and Adrián del Valle found the height of their literary success. Both won national literary prizes during the dictatorship while keeping the spirit of anarchism alive in their fiction. The epilogue concludes by looking at the long dry spell of anarchism from the 1930s to the 1990s when global anarchism reemerged. In the Caribbean, anarchist groups began rediscovering their roots and new organizations began to emerge to challenge capitalist globalization in the twnety-first century.