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 Rosselli 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. 

Rosselli 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 was quick to comply: “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.