If the Berlin Tunnel operation was a career highlight in Allen Dulles’ retirement rear-view mirror, an ill-fated landing on the shores of a nearer communist stronghold must be judged as his nadir, and it cost the long-serving DCI his job. Communist Cuba, floating menacingly in ‘America’s’ own hemisphere’, was perceived both at CIA and in Washington more generally as the alligator nearest the boat, requiring constant attention. In fact, the CIA spent enormous amounts of time, money and effort to dislodge Cuba from its Soviet sponsor, but to no avail. Outrages from the Fidel Castro regime were not limited to leftist rhetoric; Castro expropriated and then nationalised several American assets, including oil refineries. American officials felt that left unchallenged, the communist contagion could spread from Cuba and infect other Latin American countries. Aside from various farcical assassination attempts, the most notorious effort to ‘liberate’ the island from Fidel Castro, encrypted JMATE, was a failed small-scale invasion by CIA-trained and backed Cuban exiles at the Bay of Pigs on 17 April 1961.

Although it was most closely associated with the John F. Kennedy administration, planning for the Bay of Pigs invasion actually began in 1960, during the waning days of the Dwight D. Eisenhower administration. Seen in global historical perspective, the Eisenhower administration did enjoy a relatively successful track record in the realm of covert action, having orchestrated the overthrow of several odious leaders such as Iranian Premier Mohammad Mossadeq in Iran in 1953 and Jacobo Arbenz nearer to home in Guatemala the following year. It seemed like things were going Eisenhower's way in political subversion, but by his second term things were coming off the rails. Perhaps a harbinger of stormy subversion seas ahead, CIA's effort to topple Indonesian president Achmed Sukarno foundered, as would the Bay of Pigs invasion, between the Scylla of operational insecurity and the Charybdis of wishful thinking.

The failed coup in Indonesia would not be the last time that American policymakers confused nationalism with communism in Southeast Asia, but planning for the invasion of Cuba, under the direction of Deputy Director for Plans Richard M. Bissell Jr, was well under way by the time Eisenhower left office in January 1961.