Within just a month of becoming president, the issue of Communist Cuba became central to John F. Kennedy and his administration. On February 3, 1961, President Kennedy called for a plan to support Cuban refugees in the US. A month later, he created the Peace Corps, a program that trained young American volunteers to help with economic and community development in poor countries. Both programs were integral pieces of the Cold War. They were attempts to align disadvantaged groups abroad with the United State and the West against the Soviet Union and its communist satellites. Meanwhile, covert operations were laying the groundwork for overthrowing Cuban leader Fidel Castro, and he knew it. Castro railed against CIA involvement among Cubans who were trying to overthrow him and his still-young revolution.

Matters came to a head that April, when the Kennedy Administration moved beyond soft measures to direct action. From April 17-20, 1,400 CIA-trained Cuban exiles landed on the beaches of Western Cuba in an attempt to overthrow Castro. This plan, known as the "Bay of Pigs", had originally been drafted by the Eisenhower Administration. The exiles landed in Cuba and were expected to be greeted by anti-Castro forces within the country, after which the US would provide air reinforcement to the rebels, and the Castro regime would slowly be overthrown.

Soviet leader Nikita Khrushchev's belief that he could push the inexperienced American leader around grew in the wake of the Bay of Pigs fiasco and the inconclusive Vienna summit in June 1961, which left Kennedy complaining to his brother Bobby that Khrushchev was, "[L]ike dealing with Dad. All give and no take."