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Bay of Pigs Invasion and Missile Crisis

On 17 April 1961, 1,400 US-trained Cuban exiles invaded Cuba during the Bay of Pigs Invasion. Guevara did not play a key role in the fighting, as one day before the invasion a warship carrying Marines faked an invasion off the West Coast of Pinar del Río and drew forces commanded by Guevara to that region. However, historians give him a share of credit for the victory as he was director of instruction for Cuba's armed forces at the time. Author Tad Szulc in his explanation of the Cuban victory, assigns Guevara partial credit, stating: "The revolutionaries won because Che Guevara, as the head of the Instruction Department of the Revolutionary Armed Forces in charge of the militia training program, had done so well in preparing 200,000 men and women for war." It was also during this deployment that he suffered a bullet grazing to the cheek when his pistol fell out of its holster and accidentally discharged.

In August 1961, during an economic conference of the Organization of American States in Punta del Este, Uruguay, Che Guevara sent a note of "gratitude" to United States President John F. Kennedy through Richard N. Goodwin, Deputy Assistant Secretary of State for Inter-American Affairs. It read "Thanks for Playa Girón (Bay of Pigs). Before the invasion, the revolution was shaky. Now it's stronger than ever." In response to United States Treasury Secretary Douglas Dillon presenting the Alliance for Progress for ratification by the meeting, Guevara antagonistically attacked the United States' claim of being a "democracy", stating that such a system was not compatible with "financial oligarchy, discrimination against blacks, and outrages by the Ku Klux Klan ". Guevara continued, speaking out against the "persecution" that in his view "drove scientists like Oppenheimer from their posts, deprived the world for years of the marvelous voice of Paul Robeson, and sent the Rosenbergs to their deaths against the protests of a shocked world." Guevara ended his remarks by insinuating that the United States was not interested in real reforms, sardonically quipping that "U.S. experts never talk about agrarian reform; they prefer a safe subject, like a better water supply. In short, they seem to prepare the revolution of the toilets." Nevertheless, Goodwin stated in his memo to President Kennedy following the meeting that Guevara viewed him as someone of the "newer generation" and that Guevara, whom Goodwin alleged sent a message to him the day after the meeting through one of the meeting's Argentine participants whom he described as "Darretta," also viewed the conversation which the two had as "quite profitable."

Guevara, who was practically the architect of the Cuban–Soviet relationship, played a key role in bringing to Cuba the Soviet nuclear-armed ballistic missiles that precipitated the Cuban Missile Crisis in October 1962 and brought the world to the brink of nuclear war. After the Soviets proposed planting nuclear missiles in Cuba it was Che Guevara himself who traveled to the Soviet Union on 30 August 1962, to sign off on the final agreement. Guevara argued with Khruschev that the missile deal should be made public but Khruschev insisted on secrecy, and swore the Soviet Union's support if the Americans discovered the missiles. By the time Guevara arrived in Cuba the United States had already discovered the Soviet troops in Cuba via U-2 spy planes.

A few weeks after the crisis, during an interview with the British communist newspaper the Daily Worker, Guevara was still fuming over the perceived Soviet betrayal and told correspondent Sam Russell that, if the missiles had been under Cuban control, they would have fired them off. While expounding on the incident later, Guevara reiterated that the cause of socialist liberation against global "imperialist aggression" would ultimately have been worth the possibility of "millions of atomic war victims". The missile crisis further convinced Guevara that the world's two superpowers (the United States and the Soviet Union) used Cuba as a pawn in their own global strategies. Afterward, he denounced the Soviets almost as frequently as he denounced the Americans.