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Fidel Castro led his guerilla force to Havana on January 1, 1959, where they deposed Fulgencio Batista, the country's American-backed leader. Despite being a corrupt and authoritarian dictator, Batista was seen as pro-American and an ally of American businesses, controlling half of Cuba's sugar plantations and mines, utilities, and cattle ranches. He consistently opposed communism, but Castro disagreed with how the US handled its commercial and interests in Cuba.

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Castro started making moves to lessen American influence on the island almost as soon as he gained office, promoting land reform initiatives, nationalizing American-dominated industries, and urging other Latin American nations to exercise greater autonomy. President Dwight D. Eisenhower gave the CIA permission to enlist 1,400 Cuban exiles living in Miami to topple Castro in 1960. Cuban sugar imports were outlawed by the United States when Castro established diplomatic ties with the Soviet Union in May 1960, but the U.S.S.R. agreed to purchase the sugar to keep the Cuban economy from imploding.

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The United States administration broke off diplomatic ties with Cuba in January 1961 and intensified invasion preparations. Eisenhower's CIA campaign to arm and train a guerrilla force of Cuban exiles was carried over to John F. Kennedy, but he had his misgivings about the strategy. If everything went as planned, the campaign would lead to an anti-Castro insurrection on the island, according to CIA personnel who spoke with him. This would demonstrate to doubting Americans, China, and the Soviets that he was committed to ending the Cold War.

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The plan's initial step was to take out Castro's air force. A squadron of American B-26 bombers painted to look like stolen Cuban aircraft took off from Nicaragua on April 15, 1961, carrying a number of exiled Cubans. The Bay of Pigs, a remote area on the island's southern shore, was where the Cuban exile brigade launched their invasion on April 17. However, the invasion was a failure. As the exiles' ships approached the coast, unanticipated coral reefs sank part of them, and replacement paratroopers landed in the incorrect spot. After less than a day of fighting, the invaders submitted to Castro's men after being cornered down on the shore. 114 people were slain and more than 1,100 were captured.

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The CIA and the Cuban exile brigade, according to many historians, thought President Kennedy would eventually permit the American military to act in Cuba on their behalf. Although he did not want to "abandon Cuba to the communists," the president was adamant that he would not initiate a conflict that could lead to World War III. Although Kennedy authorized Operation Mongoose, an intelligence and sabotage campaign, in November 1961, his efforts to topple Castro never wavered, but they never went as far as to start a war. The Cuban Missile Crisis in 1962 heightened tensions between the United States, Cuba, and the Soviet Union.