Cuba is a paradise of white sand beaches and tropical sea breezes. It is a perfect vacation retreat, and being 90 miles from the mainland U.S. makes it a perfect place for business beyond the laws and regulations of the United States government.
It was therefore a perfect place for the financial, agricultural and commercial interests of the United States to seek to develop as a destination for their business. Cuba was easy to get to and free from democratic controls. In fact, it was perfect for commercial domination, as was done in neighboring Haiti and the Dominican Republic, except that Cuba was the largest of all Caribbean islands, making it even more attractive.
The one problem, of course, was the pesky Cuban dictator, Fidel Castro. He would not comply with American dictates when it came to capitalism and American dominance. Therefore it was preferable that Castro go away, either voluntarily or by coercion. Many attempts to overthrow Castro failed, and assassinating him became the obsession of the Central Intelligence Agency.
The CIA had actually helped Castro to come to power in the 1950’s but soon soured on the young revolutionary. Castro threw out American military advisers that had trained the Batista government, and began justice tribunals against the former government officials that had convicted and imprisoned so many innocent Cubans. The United States argued against this move, but became incensed after Castro began agrarian reforms that redistributed U.S. owned land from corporate control to ownership of small Cuban farmers.
This violation of American ownership rights, along with the support Castro was receiving from the Soviet Union in the form of petroleum imports, made Castro seem incompatible with American interests on the island. The interests of the United States were aligned with maintaining control of the islands economic resources for American benefit, and continuing the denial of local control for the benefit of Cuban farmers and the Cuban people as a while.
Thus is was not that Castro was a Communist, but that he wasn’t sufficiently Pro-American enough.
Castro even traveled to Washington D.C. to meet with American leaders. He was denied a meeting with Eisenhower, even though the President was in town at the time. Instead he met with Richard Nixon, who lectured Fidel on the merits of American capitalism, only to be rebuffed by the Cuban dictator.
The idea to remove Castro then moved into action. As Johnathan C. Brown writes in his article, “How Washington Help Fidel Castro Rise To Power”,
At that point that President Eisenhower ordered Director Allen Dulles of the CIA to devise the means to get rid of Castro’s regime in which Washington’s “hand would not show.”
Agents attached to the US embassy in Havana contacted Catholic and other youth groups who objected to Fidel’s communist friends. They received airline tickets to leave the country and salaries to train as soldiers in Guatemala.
Fidel had spies in Miami and Central America sending him progress reports on the émigré brigade in training. Now he had Eisenhower’s diplomats on the defensive. They had to deny Castro’s accusations about an upcoming CIA invasion.”
The invasion, of course, was the infamous debacle called The Bay Of Pigs Invasion, which failed in spectacular fashion. The impact of this failure ultimately led the Soviet Union to place nuclear weapons in Cuba, ;leading to the Cuban Missile Crisis. All of doomsday game of chicken started with a disagreement about American control over Cuba, and was never really about the threat of Communism. It was made to appear so, however, because American hegemony in the Caribbean is not a defensible foreign policy position. Defense against a Communist threat, however, plays well with the American voter, and so the rationale was determined, but nevertheless, inaccurate.
After JFK realized the misdirection and obfuscation of the CIA in Cuba, he began an internal campaign to minimize and eliminate the CIA. He placed all responsibility for decisions about military action against Cuba on the Joint Chiefs of Staff, making them accountable for any assassinations or coup attempts in the future. This was an ingenious way of countering the CIA, as the military would reign in any subversion in order to limit their own accountability.
James Douglas wrote of this reversal by JFK in his amazing book, JFK and The Unspeakable. He described the perspective of Kennedy toward Castro using this quotation from the American President:
…October 24, 1963 Kennedy said, “I approved the proclamation Fidel Castro made in the Sierra Maestra, when he justifiably called for justice and especially yearned to rid Cuba of corruption. I will go even further: to some extent it is as though Batista was the incarnation of a number of sins on the part of the United States. Now we will have to pay for those sins. In the matter of the Batista regime, I am in agreement with the first Cuban revolutionaries. That is perfectly clear.” Such sentiments were anathema, shall we say treasonous, to the CIA and top generals.”
Here is Douglass describing his narrative of JFK and his conversion to peace maker with Cuba:
Ultimately this effort was as short lived as the Kennedy Administration, and soon after LBJ ascended to the White House, the attempts to assassinate Castro continued unabated.
The over six hundred attempts to kill Castro began in earnest, with one of the plots to take advantage of Castro’s love of shelling on the beaches of Cuba.
The idea was to take an unusually spectacular sea shell, load it with explosives and place it on a beach where Castro would see it during one of his strolls.
The plan was abandoned because no shell large enough and native to the Caribbean could be found, and the ability to put the shell on the beach unnoticed was found to be impractical.
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 Johnathan C. Brown, “How Washington Helped Fidel Castro Rise To Power” Notevenpast.com