During World War II, Bissell served in the Office of Strategic Services (OSS), beginning his career in intelligence. After the war, he worked in the Department of War Mobilization and Reconversion from 1945 to 1946 and then joined the Economic Cooperation Administration in 1948, later becoming its head. Bissell joined the CIA in 1954 and was named head of the Directorate of Plans (or covert operations) in 1958.
The operations of the Directorate of Plans were soon dubbed "Black Operations" for their clandestine mandate to eradicate world leaders unfriendly to the United States. Bissell and his deputy, Richard Helms, engineered the ouster of Guatemala's Jacobo Arbenz in 1954 and later became nearly obsessed with overthrowing Cuban leader Fidel Castro after his 1959 revolution. During Bissell's tenure with the CIA, he was also instrumental in the development of the U-2 spy plane and the Corona spy satellite. It was, however, the unsuccessful 1961 Bay of Pigs operation for which Bissell gained the most notoriety.
In March 1960 CIA Director Allen W. Dulles was tasked with devising a strategy to remove Castro from power, a mission that he turned over to Bissell and Helms. Code-named Operation mongoose, the plan called for a paramilitary invasion of Cuba that involved nearly 400 CIA officers as well as some 1,400 Cuban exiles, who were to carry out the attack itself. Bissell and Helms devised and organized the strategy, which ultimately ended in disaster. The invasion force, trained and armed by the CIA, landed at Cuba's Bay of Pigs on 17 April 1961. Before long, they had been routed by Castro's forces, blowing the cover on the operation and greatly embarrassing the Kennedy administration. The Bay of Pigs fiasco effectively ended Bissell's CIA career, as he was forced to leave the agency in February 1962. He subsequently worked for a think tank and then held positions in a number of private corporations. Bissell died in Farmington, Connecticut, on 7 February 1994.
Jeffreys-Jones, Rhodri. The CIA and American Democracy. 2nd ed. New Haven, CT: Yale University Press, 1998.; Thomas, Evan. The Very Best Men: Four Who Dared; The Early Years of the CIA. New York: Simon and Schuster, 1995.