The CIA is known to have attempted an invasion of Cuba after the dictator Fidel Castro’s revolution and of various attempts to assassinate him. Before the revolution put Castro in power the CIA helped finance his movement.
Tad Szulc, author of “Fidel: A Critical Portrait,” said the CIA’s apparent goal in providing the movement with “no less than $50,000” was to purchase good will for the United States among the rebels in the event that they triumphed LA Times
It is the opinion of Szulc the money was to play both sides of the upcoming struggle. The US would be in good standing with the victor either way it played out. Castro’s purges killed nearly11,00 people by this count (AEI.org). Estimates range from 30,000 to 140,000. This and the Castro regime’s Orwellian style of governance caused the US to backtrack and relations with Castro soured.
Did you know? Castro’s chief executioner was Milwaukee born Herman Marks (Milwaukee Public Library)
The Bay of Pigs Invasion was planned by the CIA during the Eisenhower administration. It was designed to fail. The CIA determined the plan, using Cuban expats would not work. Military analysts close to Kennedy kept their mouth shut about their doubts.
The planes used were unmarked US bombers with the political spin they had been flown out of Cuba by pilots fleeing Castro’s regime. It is believed the CIA expected that president Kennedy would throw in naval and air support, and possibly US troops, once the plan started to go south. Kennedy did not.
After the debacle Kennedy limited the CIA to only small operations in National Security Action Memorandum 57 (Office of the Historian).
He confided to Arthur Schlesinger Jr. that “I have learned one thing from this business—that is, that we have to deal with CIA… no one has dealt with CIA”. Schlesinger writes that the failure of the invasion “stimulated a wide variety of proposals for the reorganization of the CIA” within the Kennedy administration. Wikipedia
The Church Committee claimed eight proven CIA assassination attempts between 1960 and 1965. In 2006 former chief of Cuban intelligence, Fabián Escalante, stated that there had been 634 assassination schemes or attempts (Wikipedia). They tried to dose him with LSD, give him botulism, hired mafia hitmen to attempt to poison him. They provided poison to a restaurant employee opposed to Castro. None of these acts succeeded, Castro always seemed to know ahead of time and avoided the attempts.
Note that everything the CIA did has an assumed intent applied to it by outside sources. We assume the CIA helped Castro to play both sides. The rest of the US government supported Batista during the revolution. We assume the CIA launched the Bay of Pigs invasion thinking Kennedy would go all in once it started to falter. Perhaps they knew he wouldn’t bite. We assume the failed CIA assassination attempts were to kill Castro and not to make it look like they never supported his rise to power.