Nothing epitomizes the disastrous Cuba policy of the United States better than the abortive, three-day, failed Bay of Pigs invasion conducted by anti-Castro Cuban exiles in April 1962. In the annals of half-assed CIA operations, this debacle ranks close to the top of the list of Agency disasters. Although he had no personal involvement in the snafu, Che Guevara eventually thanked an American government official at a South American diplomatic affair for providing such a colossally unifying blunder.
Because of the hostility generated within the CIA and the paranoia it engendered in the Castro regime, the Bay of Pigs invasion propagated numerous JFK assassination conspiracy theories. It also emboldened the USSR and Cuba to bring the entire world to the brink of nuclear catastrophe with the subsequent Cuban missile crisis. Small wonder Castro and Khrushchev had little regard for a government that involved itself in the following insane Bay of Pigs stories and blunders. Behold one of the most notorious CIA disasters of all time.
The first casualty of the Bay of Pigs catastrophe was Carlos Rodriguez, an exiled Cuban living in the United States who fell off a 6,000 foot cliff while training on an anti-communist farmer's land in Guatemala. Which, hey, it happens. The squad of Cuban exiles to which Rodriguez belonged assumed the portentous name Brigada Asalto 2506, in honor of its fallen member, whose dog tag number was 2506.
The CIA training exiles to invade Cuba is so flagrantly insane it sounds like a Marx Brothers movie. What was the conversation at Langley like when that decision was made?
John: So, ah, Cuban exiles invading?
Steve: Invading what?
Dan: Sounds good. When's lunch?
Steve: Don't we have to train them?
John: Sure, yeah. There's an anti-communist farm in Guatemala, it's perfect.
Dan: Did you have those bagels this morning? The cream cheese did something awful to my gut.
Steve: And then just, what, given them weapons and drop them off in Cuba?
John: Yeah, basically. I don't know. Or launch them from Nicaragua.
Dan: Speaking of launching, I need a toilet, stat.
This same group of Cubans appear in Oliver Stone's film JFK, and a number books and documentaries, as one of the many potential parties peripherally involved in the Kennedy assassination.
Luis Somoza, president and de facto dictator of Nicaragua from 1956 until 1963, was concerned when approached by the American CIA and asked to allow the invasion force for the Bay of Pigs to embark from Nicaraguan territory. He was afraid he would be punished by the Organization of American States and UN for allowing an invasion of another sovereign nation from Nicaragua. To assuage Somoza's trepidation, the CIA arranged for a $10 million payment. He agreed to help.
CIA intervention in Guatemala was even more pronounced. When an attempted coup against the pro-US military junta that ruled the country occurred in 1960, covert CIA air support and anti-communist Cubans already in training for the invasion were used to put down the rebellion. Ultimately, the US government utilized the hospitality of two of the most repressive regimes in the Western Hemisphere to advance the cause of "democracy." It was also believed involving these two countries would give the CIA and the United States deniability when the invasion occurred.
Perhaps no story better shows the complete chaos of the actual invasion better than that of CIA operative Grayston Lynch, who, abandoned by the Cuban exiles posted aboard a transport ship with him, gathered whatever machine guns and rifles he could find and fired willy-nilly into the sky as airplanes streaked overheard. Because the American planes involved in the invasion were disguised as Cuban planes, Grayson had no idea who he was firing at. As it turns out, he was shooting at the Americans.
As described in CIA historian Jack Pfeiffer's formerly top secret history of the Bay of the Pigs, the debacle was a bit like an episode of Arrested Development: everyone in the CIA tried to out scheme everyone else, with little attention paid to the original goal of the mission. In the midst of this absurd pageant, a CIA operative appropriated funds to “pay the mafia types” to assassinate Castro. This operation-within-an-operation was kept secret from Jacob Esterline, who was the chief officer of the invasion.