On February 16, 1959, Fidel Castro became prime minister of Cuba. Until 1959, Cuba was a US-backed military thug-dictatorship under the rule of Fulgencio Batista, and Havana was a hedonistic playground for the world's elite. At the end of the 1950s, Havana alone had some 270 brothels, and drugs, from marijuana to cocaine, were so plentiful that any narcotic one desired was, as a 1950 article proclaimed, "hardly more difficult to obtain than a shot of rum and only slightly more expensive."
Batista encouraged large-scale gambling in Havana and established a relationship with US organized crime, notably Meyer Lansky and Lucky Luciano, who had control of Havana's racetracks and casinos. Batista was incredibly corrupt and profited immensely from this and other illicit activities, as did various US interests.
Unfortunately, the Cuban people did not participate in the largesse, and death came swiftly to those who opposed the wanton despotism. Batista killed over 20,000 of his citizens in seven years. The US Government became a co-conspirator with this brutal, murdering despot.
This then was a fertile field for Castro's Communist Revolution. Castro ousted Batista and assumed the reins of power, kicking out the US interests along with the Mobsters and nationalizing their abandoned infrastructure. So naturally, powerful US interests, including the US Government, were severely pissed off.
Batista had been a US ally, admittedly a terrible one. He was a brutal dictator but loved the US. Castro proved to be something much worse — an avowed communist supported by the Soviet Union, who viscerally hated the US for propping up Batista. So, the Cuban people went from one despotic, corrupt, evil dictator to another.
The second lacked the questionable benefit of US dollars lavished on the local economy, questionable owing to so remarkably few trickling down to the people.
Giving the new devil his due, however, under Castro's rule, the new government significantly reduced prostitution and executed the corrupt police and politicians — those who did not practice Castro's brand of corruption, that is. Those who won a revolution—for democracy, justice, and honest government—themselves picked up the arrogant tools of dictatorship. Many of Batista's people were smart enough to adapt and remain in power.
Crackheads became rare, and the quality of life for the masses improved a bit — but only somewhat, as the people remained impoverished and lacked opportunities. Literacy improved, but reading material was highly censored and propagandistic. Medical care improved, albeit rationed and restricted — under the Marxist economy, there simply wasn't enough of the "other people's money" to fund the dream. There never is. Castro postponed the promised free and fair elections indefinitely.
Democide accelerated under Castro, with estimates ranging from 73,000 to as high as 141,000 killed by the new regime, making Batista seem like a piker. Moreover, lacking any sort of capitalistic incentives, his economy disintegrated, especially after the failed 1961 Bay of Pigs invasion and the 1962 Trade Embargo. Castro was desperate to ignite conflict between the Soviets and the US, believing that would bring a massive influx of Soviet support. Castro slammed his fist through a wall when Khrushchev told him about his agreement with Kennedy to remove the missiles.
Cuba was a powerful chess piece, and its loss was devastating. Both the Mafia and the US Government badly wanted it back. Thus formed an unholy alliance between organized crime and the US Government, united to oust Castro and regain control of Cuba.
Interestingly, while the Intelligence communities were courting the mobsters, the Justice Department was busily trying to put them in jail. But the most intriguing aspect of the Cuba conundrum was the attempt to connect Castro to the JFK assassination. Fidel Castro hated Kennedy for the Bay of Pigs invasion and the Trade Embargo. He hated the US in general but held JFK primarily responsible for these acts. The CIA tried to cast suspicion on Castro, but there is no credible evidence.
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