On November 25, 2016, Fidel Castro, Cuba’s longtime “Maximum Leader,” died at the age of 90.

Old age and disease had finally achieved what years of CIA plotting and Mafia assassins could not.

To his supporters he was a tireless champion of the poor and a foe of American imperialism. To his enemies he was a ruthless dictator who drove his country to economic ruin in the name of a failed ideology—communism.

His reign began on January 1, 1959, when he swept triumphantly into Havana after a two-year guerrilla campaign against Cuban dictator Fulgencio Batista.

Fidel Castro

Almost immediately, hundreds of thousands of Cubans began fleeing to America. The first émigrés were more than 215,000 Batista followers. The exodus increased, peaking at approximately 78,000 in 1962.

In October, 1962, Castro stopped regularly scheduled travel between the two countries, and asylum seekers began sailing from Cuba to Florida.

Between 1962 and 1979, hundreds of thousands of Cubans entered the United States under the Attorney General’s parole authority.

By 2017, more than 1.53 million Cubans were living in Florida, where the population of Miami was about one-third Cuban. Their sheer numbers transformed the state’s political, economic and cultural life.  And not entirely for the better.

Many of these Cubans viewed themselves as political exiles, rather than immigrants, hoping to eventually return to Cuba after its Communist regime fell from power.

With so many discontented immigrants concentrated in Florida, they became a potential force for politicians to court. 

And the issue guaranteed to sway their votes was unrelenting hostility to Castro. Unsurprisingly, most of their votes went to Right-wing Republicans.

John F. Kennedy was the first President to face this dilemma.

During the closing months of the administration of President Dwight D. Eisenhower, the CIA had begun training Cuban exiles for an invasion of their former homeland.

The exiles’ goal: To do what Castro had done–seek refuge in the mountains and launch a successful anti-Castro revolution.

But word of the coming invasion quickly leaked: The exiles were terrible secret-keepers. (A joke at the CIA went: “A Cuban thinks a secret is something you tell to only 300 people.”)

Kennedy insisted the invasion must appear to be an entirely Cuban enterprise. He refused to commit U.S. Marines and Air Force bombers.

More than 1,400 invaders landed on April 17, 1961 at the Bay of Pigs—and were quickly overwhelmed, with hundreds of the men taken prisoner.

Kennedy publicly took the blame for its failure: “Victory has a hundred fathers but defeat is an orphan.” But privately he seethed, and ordered the CIA to redouble its efforts to remove Castro at all costs.

To make certain his order was carried out, he appointed his brother, Robert—then Attorney General—to oversee the CIA’s “Castro removal” program.

Robert F. Kennedy and John F. Kennedy

It’s here that America’s obsession with Cuba entered its darkest and most disgraceful period.

The CIA and the Mafia entered into an unholy alliance to assassinate Castro—each for its own benefit: 

• The CIA wanted to please Kennedy; 
• The mobsters wanted to regain their casino and brothel holdings that had made Cuba their private playground in pre-Castro times; and
• They also hoped to use their pose as patriots to win immunity from future prosecution.

The CIA supplied poisons and explosives to various members of the Mafia. It was then up to the mobsters to assassinate Castro.

The CIA asked Johnny Roselli, a mobster linked to the Chicago syndicate, to go to Florida in 1961 and 1962 to organize assassination teams of Cuban exiles. They were to infiltrate their homeland and assassinate Castro.

Johnny Roselli

Roselli called upon two other crime figures: Chicago Mafia boss Sam Giancana and Santos Trafficante, the Cosa Nostra chieftain for Tampa, for assistance.

Sam Giancana

Giancana, using the name “Sam Gold” in his dealings with the CIA, was meanwhile being hounded by the FBI on direct orders of Attorney General Robert Kennedy.

The mobsters were authorized to offer $150,000 to anyone who would kill Castro and were promised any support the Agency could yield.

Giancana was to locate someone who was close enough to Castro to be able to drop pills into his food. Trafficante would serve as courier to Cuba, helping to make arrangements for the murder on the island.

Roselli was to be the main link between all of the participants in the plot.

The available sources disagree on what actually happened. Some believe that the Mob made a genuine effort to “whack” Fidel.

Others are convinced the mobsters simply ran a scam on the government. They pretended to carry out their “patriotic duty” while in fact making no effort at all to penetrate Castro’s security.

The CIA’s war against Castro was known as Operation Mongoose—the mongoose being a traditional enemy of the cobra. And those entrusted with this assignment were known as the Special Group.

“We were hysterical about Castro at about the time of the Bay of Pigs and thereafter,” Secretary of Defense Robert S. McNamara later testified before Congress about these efforts. “And there was pressure from JFK and RFK to do something about Castro.”