Many of the conspiracy theories center on the island nation of Cuba. Located just ninety miles off the coast of Florida, Cuba was a paradise for gamblers and gangsters in the years prior to the Cuban Revolution in 1959. The Mafia was partners with the Batista government, a cruel dictatorship that was very friendly to United States business, both legitimate and illegitimate. Meyer Lansky was the hood who personally dealt with Batista in a mutually beneficial business arrangement. Santo Trafficante Jr. took over his father's interests in a number of casinos, including the lavish Sans Souci. The Mafia flourished under Batista's regime, but the peaceful existence was in jeopardy with the rise of Fidel Castro.

In 1959 Fidel Castro won a hard-fought revolution and ousted the Batista regime. While he was fighting the Batista government, Castro was also receiving guns and money from the mob. The gangster casino bosses reasoned that if they supported both sides in the conflict, whichever side won would be eager to do business with them. They made a huge mistake. A former major-league baseball player and one-time seeming friend of the United States, Castro became allied with the Soviet Union after his victory, and the island became a communist enclave, which caused alarm in the U.S. intelligence community. But Castro also kicked out the mobsters and jailed a few of them, including Santo Trafficante Jr.

Bay of Pigs

Before Kennedy became president, there were plans to invade Cuba and oust Castro. It would not be an attack by American armed forces, however; instead the assault would come from exiled Cubans who had planned and trained in the United States with the help of the CIA and the Mafia, who helped staff the operation with Cuban gangsters. Kennedy did not veto the plan when he took office, but when it was launched, he refused, at the last minute, to aid the assault with air cover from the United States Air Force. It was a total disaster, and thousands of exiled Cubans were killed or captured. Those taken alive probably came to wish that they had died on the beach.

Kennedy made many enemies in many circles by his refusal to provide air support in the Bay of Pigs invasion. He earned the hatred of the Cubans who wanted their nation back, those in the CIA who felt betrayed and humiliated, American big business, which had enjoyed great profits in Cuba, and, of course, the Mafia, for whom Cuba was once a cash cow and pleasure palace. Many of the Cubans who felt betrayed by the Kennedy administration drifted into covert operations run by the CIA out of Miami.