Fidel Castro’s curious and clandestine relationship with Bobby Kennedy reminds us just how close Cuba and America came to war — and to peace.
In the wake of the failed Bay of Pigs invasion in 1961, Kennedy spearheaded a secret campaign against Castro code-named Operation Mongoose. It officially lasted just a year, until shortly after the Cuban Missile Crisis in October 1962, although it didn’t truly cease operations until the end of John F. Kennedy’s administration. On paper, it was overseen by a brigadier general who had earned his anticommunist stripes in the jungles of the Philippines and Vietnam. In practice, Mongoose was Bobby’s operation. He left no doubt what he had in mind at a January 1962 meeting of his team: The “Cuban problem” is “the top priority in the United States Government — all else is secondary — no time, money, effort or manpower is to be spared.”
Kennedy got what he asked for. Two weeks after that meeting, the Defense Department started proposing increasingly outlandish schemes for undermining the Caribbean nation. Operation Free Ride would airdrop into Cuba one-way plane tickets on Pan American or KLM to Mexico City, Caracas and other “free-world” destinations. Another U.S. military official offered up an even quirkier scheme. Knowing Cuba’s shortage of toilet paper, he wanted to airdrop cases of the white rolls. “To make it an effective psychological impact, my recommendation was to print a picture of Fidel Castro and Nikita Khrushchev on alternate sheets,” he recounted. “The idea was accepted, and plans were made to carry it out, until President Kennedy put the squash on it.”
While most of the bizarre blueprints met that same fate, some were embraced by the CIA. It assembled its largest peacetime spy operation ever, with 600 agents and nearly 5,000 contract workers devoted to Mongoose. Some of what this army of spies did was merely annoying, like pouring untraceable chemicals into lubricating fluids bound for Cuba to make equipment wear out faster. But there were paramilitary missions, too, targeting resources critical to the Cuban economy, such as sugar mills and petroleum refineries. And believing that the only way to bring down the Communist regime was to eliminate Castro, Mongoose planners hatched eight separate plots to do just that. Knowing how much Castro treasured cigars, the agency laced a box of his favorites with a strain of botulism so toxic he would have died hours after he smoked one. It was the kind of stuff Ian Fleming, so admired by the Kennedy brothers, invented for his agent 007, James Bond.
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Bobby Kennedy’s fixation with keeping Communists out of Latin America was understandable in the context of the early 1960s, when America really was engaged in an ongoing undeclared war with the Soviet Union and the stakes seemed to be the very future of both capitalism and democracy. Castro represented not just a Russian toehold in our hemisphere but a launching pad for leftist revolutions as far away as the African Congo. But Operation Mongoose was based on logic as flawed as the Bay of Pigs incursion — that the Cuban population would rally to the anti-Castro cause, and that America’s secret army of CIA-trained Cuban exiles could vanquish anybody. And rather than discouraging Moscow from backing Cuba, Mongoose — coming on the heels of the Bay of Pigs — helped convince Khrushchev he was doing the right thing by installing nuclear missiles to defend the island against U.S. aggression.
The world made it out of the Missile Crisis intact, but less known is that in the wake of that near-Armageddon, Bobby Kennedy was exploring creative and politically risky ways to defuse hostilities with Fidel Castro. Those subterranean initiatives started in the spring of 1963 and continued until the day JFK was assassinated. A New York superlawyer who had helped negotiate the release of the Bay of Pigs prisoners probed the Cuban leader’s willingness to reconcile with America. The Kennedys also used journalists to test Castro’s openness to negotiate. This “sweet approach” recognized that Castro was furious at Khrushchev for taking away his nuclear missiles without consulting him, and what a coup it would be to push Cuba out of the Soviet orbit. The president and his brother knew that anything but a hard-line approach to Castro would cost them votes in Florida and elsewhere, but they seemed willing to take the gamble in an anticipated second term. What would happen, they asked themselves for the first time, if they simply left Cuba alone? Better still, what if Castro could be remolded into another Tito, leader of not just Yugoslavia but of the 25-nation Non-Aligned Movement?
Whether those explorations would have led to real détente is impossible to know, although Castro later said that, “Kennedy would not have received a rebuff from us.” What we do know is that after his brother’s death, Bobby pushed Secretary of State Dean Rusk to lift the ban on U.S. citizens traveling to Cuba.
As for a more history-bending initiative, Bobby said he and Jack had been “trying to work it out,” which is more than any subsequent American administration did until President Obama’s normalization agreement with President Raúl Castro in December 2014. Bobby’s widow, Ethel, is convinced that Jack and Bobby could have achieved a comparable breakthrough with Fidel Castro, based on five or six private meetings she has had with him in recent decades. Fidel, she says, saw her husband as a practical man with whom he could have struck a deal.
Larry Tye is the author of the biography “Bobby Kennedy: The Making of a Liberal Icon.”