During the height of the Cold War, Latin America became a strategic pillar of the hemispheric defense doctrine, serving a key to the power struggle between East and West. Following the Cuban Revolution and the overthrow of the US-friendly government of Fulgencio Batista, the United States became concerned with the spread of the Soviet Union's influence in Latin America, becoming heavily invested in retaining as much influence as possible. With the nuclear arms race at its peak, a Soviet transfer of nuclear warheads to its Latin American ally in Cuba nearly concluded in the onset of World War III in October 1962. Afterward, the United States hardened its influence throughout Latin America, involving itself in what became known as the "Dirty War", a process that involved questionable actions including supporting or overthrowing governments depending on political leaning, supporting subversive groups such as the Contras with weaponry and funding, or participating in controversial operations such as Operation Charly and Operation Condor. The fallout from these actions affect Latin America–United States relations to this day.
Having been annexed from Spain in 1898, the unincorporated territory of Puerto Rico represented a paradox during the Cold War, politically belonging to the United States but culturally to Latin America. Its location in the Caribbean converted it in the American response to Cuba, directly affecting the development of its political status. Puerto Rico was allowed to enact a heavily revised local Constitution, but its attempts to employ its sovereignty and use it to remove the application of the Territorial Clause of the United States Constitution ended in failure. The United States military played a key role in perpetuating the status quo, not wanting to risk the possibility that a change in status could affect their presence in the Caribbean. A situation further complicated by the emergence of Marxist guerrillas, including the notorious Fuerzas Armadas de Liberación Nacional Puertorriqueña and Boricua Popular Army, within the pre-existing independence movement in Puerto Rico. Ultimately, the status issue stagnated throughout the remainder of the Cold War, but the pro-sovereignty efforts undertaken during this time frame eventually led to the current incarnation of the free association movement in Puerto Rico.