Killing Kennedy

were charismatic, idealistic young men beloved by their fanatical followers. Both enjoyed a good cigar and had had long political winning streaks that resulted in each man ruling his nation. But each had a setback during his rise to power—Castro was imprisoned in the early years of his revolution; Kennedy’s painful back condition and a potentially deadly adrenal gland condition known as Addison’s disease each nearly killed him. Perhaps the most striking similarity between the two men is that Kennedy and Castro were the sort of highly competitive alpha males who never accept losing, no matter what the circumstances, no matter how high the cost.
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    In Cuba the costs of revolution are very high. With blood running in the streets of Havana, it was only a matter of time before America comprehended the truth. In February 1960, thirteen months after Castro seized power, a CIA briefing to the National Security Council warned of the Soviet Union’s “active support” for Castro, while also lamenting the disorganization of anti-Castro forces. The Eisenhower administration quietly began making plans to overthrow Castro’s regime, authorizing the CIA to begin paramilitary training of Cuban exiles at a secret base in Guatemala.
    Castro became a hot-button issue of the 1960 presidential campaign. Kennedy vigorously attacked the Eisenhower administration, using the situation in Cuba to illustrate its weakness against communism. “In 1952 the Republicans ran on a program of rolling back the Iron Curtain in Eastern Europe,” Kennedy warned the nation. “Today the Iron Curtain is 90 miles off the coast of the United States.”
    The question of a Cuban invasion became not a matter of if, but when. In a speech on December 31, 1960, Castro warned America that any landing force would suffer far greater losses than on D-Day. “If they want to invade us and destroy the resistance they will not succeed … because as long as a single man or woman with honor remains[,] there will be resistance,” he railed. A few days later, on January 3, 1961, Castro inflamed the cold war fears of every American by announcing that “Cuba has the right to encourage revolution in Latin America.”
    As John Kennedy prepared to take office, roughly one in every nineteen Cubans was a political prisoner. America had severed diplomatic relations with Havana. On January 10, the New York Times ran a front-page story entitled “U.S. Helps Train Anti-Castro Forces at Guatemalan Air-Ground Base,” revealing that commandos were being trained in guerrilla warfare for a planned attack against Cuba. The Times article got the attention of Castro, who responded by ordering the placement of land mines at potential invasion zones.
    Inside the Washington Beltway, the CIA and its longtime director, Allen Dulles, have become obsessed with killing Fidel Castro. It will one day be estimated that they concocted more than six hundred plans to assassinate him, including such unorthodox methods as a Mafia-style hit and exploding cigars. On March 11, a year after Dwight Eisenhower authorized the training of rebel forces, President Kennedy was formally presented with CIA plans for a landing. The invasion would take place in daylight, and the location would be a beach code-named Trinidad.
    The operation presented Kennedy with a major dilemma. On the one hand, he had run for president on a platform of change, promising the nation a new start after the cold war policies of Dwight Eisenhower. On the other hand, he had fanatically ridiculed Eisenhower about Castro and knew he would look soft on communism if he did nothing to deter the brutal dictator. On April 7 the New York Times ran another front-page story, this one saying that the Cuban rebels were breaking camp and preparing to launch their invasion, prompting Kennedy to remark privately that Castro didn’t need spies in the United States—all he had to do was read the paper.
    On April 12 the Communist Party in Guatemala reported to Moscow that the anti-Castro American-sponsored guerrillas would launch their invasion within a matter of days. The Soviets, however, were unsure of the intelligence and didn’t pass along the news to Castro. That very same day, President Kennedy attempted to disavow any American involvement in an invasion, explaining, “There will not be, under any conditions, any intervention in Cuba by United States forces.” Kennedy carefully left out any mention of U.S. financing,