On October 22, 1962, President John F. Kennedy went on nationwide TV to announce the discovery of nuclear missiles in Cuba—and his blockade of that island.

He warned that any nuclear missile launched from Cuba against any nation would be regarded as an attack on the United States by the Soviet Union—and would trigger “a full retaliatory response” upon the U.S.S.R.

President John F. Kennedy addresses the nation

And he demanded that the Soviets remove all of their offensive weapons from Cuba:

“The path we have chosen for the present is full of hazards, as all paths are, but it is the one most consistent with our character and courage as a nation and our commitments around the world.

“The cost of freedom is always high, but Americans have always paid it. And one path we shall never choose, and that is the path of surrender or submission.”

On October 26,  the United States raised the readiness level of Strategic Air Command forces to DEFCON 2—the step just short of war. For the only time in U.S. history, B-52 bombers were dispersed to various locations and made ready to take off, fully equipped, on 15 minutes’ notice.

Other measures taken included:

• One-eighth of America’s 1,436 bombers were on airborne alert.
• About 145 intercontinental ballistic missiles stood on ready alert.
• Air Defense Command redeployed 161 nuclear-armed interceptors to 16 dispersal fields within nine hours with one-third maintaining 15-minute alert status.
• Twenty-three nuclear-armed B-52 were sent to orbit points within striking distance of the Soviet Union.

An invasion date was set for October 29. But the Kennedy Administration—and the American military–didn’t know that the Russian soldiers guarding the missiles had been armed with tactical nuclear weapons.

Had the Marines gone in, those mini-nukes would have been used. And a fullscale nuclear exchange between the United States and the Soviet Union would have almost certainly followed.

At the height of the crisis, Attorney General Robert F. Kennedy offered a solution.

Khrushchev had sent two teletypes to Kennedy. The first had agreed to remove the missiles, but the second had demanded that the United States remove its own missiles from Turkey, which bordered the Soviet Union.

Robert Kennedy’s solution: The administration should ignore the second message—and announce that it had accepted Khrushchev’s offer to remove the missiles.

After this announcement was made, President Kennedy said to his advisers: “It can go either way now.”

John F. Kennedy in the Oval Office

The crisis ended on October 28. Under enormous pressure, Khrushchev agreed to remove the missiles from Cuba.

Behind his decision lay a secret promise by the Kennedy administration to remove its obsolete nuclear missiles from Turkey, which bordered the Soviet Union. And a public pledge to not invade Cuba.

On the night the crisis ended, there occurred a prophetic exchange between the two Kennedy brothers.

JFK: “Maybe this is the night I should go to the theater”—a reference to Abraham Lincoln’s fatal attendance of Ford’s Theater at the end of the Civil War.

RFK: “If you go, I want to go with you.”

John F. and Robert F. Kennedy

But President Kennedy was not finished with Castro. While continuing the campaign of sabotage throughout Cuba, the Kennedys were preparing something far bigger: A fullscale American invasion of the island.

On October 4, 1963, the Joint Chiefs of Staff submitted its latest version of the invasion plan, known as OPLAN 380-63.  Its timetable went:

• January, 1964:  Infiltration into Cuba by Cuban exiles.
• July 15, 1964:  U.S. conventional forces join the fray.
• August 3, 1964:  All-out U.S. air strikes on Cuba.
• October 1, 1964:  Full-scale invasion to install “a government friendly to the U.S.”

During the Cuban Missile Crisis, Robert Kennedy—referring to the 1941 Japanese attack on Pearl Harbor—had resisted demands for a “sneak attack” on Cuba by saying: “I don’t want my brother to be the Tojo of the 1960s.”

Now the Kennedys planned such an attack on Cuba just one month before the November, 1964 Presidential election.

Then fate—in the unlikely figure of Lee Harvey Oswald—intervened.

On November 22, 1963, while the President rode through Dallas in an open-air automobile, a rifle-wielding assassin opened fire. He scored two hits on Kennedy—in the back of the neck and head. The second wound proved instantly fatal.

The nation and the world were shocked—and plunged into deep mourning.

But for some of those who had waged a secret, lethal war against Fidel Castro for the previous two years, Kennedy’s death—at least in retrospect—didn’t come as a surprise.

Robert Kennedy, in particular, spent the remaining years of his life agonizing over the possibility that his highly personal war against Castro had backfired.

That Castro, fed up with the CIA’s assassination plots against him, had retaliated with one of his own.

Robert Kennedy’s fears and guilt were compounded by the fact that, while waging war on Castro, he had waged an equally ruthless crusade against organized crime.

He knew that some of the mobsters he had tried to send to prison had played a major role in the CIA’s efforts to “hit” Castro. Had the Mafia—believing itself the victim of a double-cross—put out a “contract” on JFK instead?  

It was a question that haunted him until the day he died.

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 assassination. 

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 finally achieved what years of plotting by CIA 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 2008, more than 1.24 million Cubans were living in the United States, mostly in South 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.

The large number of Cubans in South Florida, particularly in Miami’s “Little Havana,” allowed them to preserve their culture and customs to a degree rare for immigrant groups.

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. 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

Rosselli called upon two other crime figures: Chicago Mafia boss Sam Giancana and Santos Trafficante, the Costra 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.

Rosselli 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 deadly 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.”