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.

Americans would rightly label such methods as ”terrorist” if another power used them against the United States today. And that was how the Cuban government saw the situation.

So Castro appealed to Nikita Khrushchev, leader of the Soviet Union, for assistance.

Fidel Castro 

Nikita Khrushchev

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.

None of these officials admitted that JFK had been waging a no-holds-barred campaign to overthrow the Cuban government and assassinate its leader.

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

Then followed seven days of guarded and intense debate by Kennedy and his advisors.  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.

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. 

John F. Kennedy address 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.”

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

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.

John F. Kennedy address the nation

And he demanded that the Soviets remove all of their offensive weapons from Cuba: “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 SAC 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 advisors: “It can go either way now.”

John F. Kennedy

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. 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.

And some of the mobsters he had done his best to put into 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?

“John and Robert Kennedy knew what they were doing. They waged a vicious war against Fidel Castro—a war someone had to lose.”

And the loser turned out to be John F. Kennedy.

So writes investigative reporter Gus Russo in Live By the Sword: The Secret War Against Castro and the Death of JFK, published in 1998.