In April, 1961, the CIA tried to overthrow the Communist regime of Cuba’s “Maximum Leader,” Fidel Castro, at the Bay of Pigs.

When that failed, President John F. Kennedy ordered Castro’s removal through a campaign of sabotage and assassination.

These covert operatives became known within the CIA as the Special Group, and were ultimately supervised by Robert F. Kennedy, the President’s brother and Attorney General.

The war against Castro became known within the CIA as Operation Mongoose.

But not everyone in the CIA was enthusiastic about the “get Castro” effort.

“Everyone at CIA was surprised at Kennedy’s obsession with Fidel,” recalled Sam Halpern, who was assigned to the Cuba Project. “They thought it was a waste of time. We all knew [Fidel] couldn’t hurt us. Most of us at CIA initially liked Kennedy, but why go after this little guy?

“One thing is for sure: Kennedy wasn’t doing it out of national security concerns. It was a personal thing. The Kennedy family felt personally burnt by the Bay of Pigs and sought revenge.”

It was all-out war. Among the tactics used:

• Hiring Cuban gangsters to murder Cuban police officials and Soviet technicians.
• Sabotaging mines.
• Paying up to $100,000 per “hit” for the murder or kidnapping of Cuban officials.
• Using biological and chemical warfare against the Cuban sugar industry.

“Bobby (Kennedy) wanted boom and bang all over the island,” recalled Halpern. “It was stupid. The pressure from the White House was very great.”

Among that “boom and bang” were a series of assassination plots against Castro, in which the Mafia was to be a key player.

Chicago Mobster Johnny Roselli proposed a simple plan: through its underworld connections in Cuba, the Mafia would recruit a Cuban in Castro’s entourage, such as a waiter or bodyguard, who would poison him.

The CIA’s Technical Services division produced a botulinus toxin which was then injected into Castro’s favorite brand of cigars. The CIA also produced simpler botulinus toxin pills that could be dissolved in his food or drink.

But the deputized Mafia contacts failed to deliver any of the poisons to Castro. 

Roselli told the CIA that the first poisoner had been discharged from Castro’s employ before he could kill him, and the back-up agent got “cold feet.” 

Other proposals or attempts included:

• Planting colorful seashells rigged to explode at a site where Castro liked to go skindiving.
• Trying to arrange for his being presented with a wetsuit impregnated with noxious bacteria and mold spores, or with lethal chemical agents.
• Attempting to infect Castro’s scuba regulator with tuberculous bacilli.
• Trying to douse his handkerchiefs, tea and coffee with other lethal bacteria.

Former members of the Kennedy Administration later insisted that neither John nor Robert Kennedy knew or approved of these assassination plots. But the sheer weight of available evidence indicates otherwise.

Bobby, in particular, was constantly pressing the CIA to “do something” about Castro. In the world of covert action, words like “Kill Castro” aren’t committed to paper. Or even spoken.

Castro, rightly seeing his life and regime threatened, appealed to Nikita Khrushchev, leader of the Soviet Union, for assistance.

1960s poster of Fidel Castro and Nikita Khrushchev

Keizers [CC BY-SA 3.0 (https://creativecommons.org/licenses/by-sa/3.0)%5D

Khrushchev quickly complied: “We must not allow the communist infant to be strangled in its crib,” he told members of his inner circle.

By October, 1962, the Soviet Union had sent more than

• 40,000 soldiers,
• 1,300 field pieces,
• 700 anti-aircraft guns,
• 350 tanks and
• 150 jets

to Cuba to deter another invasion.

Most importantly, Khrushchev began supplying Castro with nuclear-tipped ballistic missiles.

Their discovery, on October 15, 1962, ignited the single most dangerous confrontation of the 50-year Cold War.

Suddenly, the United States and the Soviet Union—bristling with nuclear weapons—found themselves on the brink of nuclear war.

At the time, Kennedy officials claimed they couldn’t understand why Khrushchev had placed nuclear missiles in Cuba. “Maybe Khrushchev’s gone mad” was a typical public musing.  

This remained the official American view for years afterward—as depicted in Robert Kennedy’s memoir, Thirteen Days: A Memoir of the Cuban Missile Crisis, published in 1969, the year after his death. 

No admission was made that JFK had been waging a no-holds-barred campaign to overthrow the Cuban government and assassinate its leader.

The same proved true for the 1974 doc-u-drama, The Missiles of October, starring William Devane as John F. Kennedy and Martin Sheen as Robert Kennedy. 

On October 16, President Kennedy was informed of the missile installations. He immediately convened a group of his 12 most important advisers, which became known as Ex-Comm, for Executive Committee.

Then followed seven days of guarded and intense debate by Kennedy and his advisers. Some of the participants—such as Air Force General Curtis LeMay—urged an all-out air strike against the missile sites.

Others—such as Adlai Stevenson, the United States delegate to the United Nations—urged a reliance on quiet diplomacy.

It was Secretary of Defense Robert S. McNamara who suggested a middle course: A naval blockade—a “quarantine” in Kennedy’s softened term—around Cuba. This would hopefully prevent the arrival of more Soviet offensive weapons on the island.

Finally, the President decided to to impose a naval blockade.

On October 22, Kennedy went on nationwide TV to announce the discovery of the missiles and his blockade of Cuba.

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.”