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Rusk’s reluctance to advise him in an open and honest fashion is the least of the president’s troubles at this point. Nobody, it seems, will level with Kennedy. As JFK awaits word from the battlefront, he craves the company of someone who will tell him the unvarnished truth.

Sensing a crisis, the president picks up a phone and dials.

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Cuba.

Americans of means once made this steamy, rum-soaked paradise their favorite tropical playground. The country’s sandy white beaches are sensual and the casinos legendary. Ernest Hemingway wrote of Cuba’s many charms, then unwound with his favorite rum libation, the daiquiri. Behind the scenes, America’s organized crime bosses such as Meyer Lansky and Lucky Luciano were as comfortable in the Cuban capital, Havana, as they were in New York City. And for decades, U.S. corporations took advantage of Cuba’s climate and thoroughly corrupt government to set up vast sugarcane plantations, oil fields, and cattle ranches.

In fact, ever since that epic moment in 1898 when Teddy Roosevelt and his Rough Riders charged up San Juan Hill to liberate Cuba from Spain, the Cuban-U.S. relationship was mostly peaceful, free of tension, and, in a word, easy.

Until 1959.

Corruption reached an all-time high under the American-friendly regime of General Fulgencio Batista, sparking rebellion among Cubans. After four years of fighting, Fidel Castro, the thirty-two-year-old bastard child of a wealthy Cuban farmer, led his guerrilla army into Havana and toppled Batista. (The general died of a heart attack in exile in Portugal, just two days before Castro’s team of assassins could complete its mission.) The United States responded to Batista’s overthrow by officially recognizing the new government.

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Castro is a man of many secrets. In perhaps his most egregious episode, eleven days after overthrowing Batista’s government in 1959, seventy-five political prisoners were marched in the dead of night toward an open field outside the city of Santiago, hands tied behind their backs. There was no path, and those who slowed down or stumbled felt the sharp jab of a soldier’s bayonet in their ribs. Suddenly, a row of army trucks turned on their headlights, revealing a trench six feet deep and fifty yards long. Bulldozers were parked alongside the trench, blades lowered and ready to plow the fresh mounds of dirt back into the massive hole.

The executions were supposed to be a secret, but the prisoners’ wives and girlfriends found out and kept vigil, following the procession from a distance and gasping with horror as those headlights illuminated what would soon be a mass grave. As the women’s sobs and wails punctured the still night air, Castro’s soldiers lined their husbands and sons and boyfriends shoulder to shoulder along the edge of the ditch, all the while taunting the women with jeers and catcalls. The women wept and prayed right up until that inevitable moment when the machine guns opened fire and their loved ones toppled into the abyss.

Thus marked the beginning of Fidel Castro’s reign of terror. Soon after, a Cuban judge was shot through the head for pardoning military pilots who had flown against Castro’s forces during his guerrilla campaign. Castro then ordered the pilots convicted of genocide. When the new judge sentenced them to hard labor instead of death, he, too, was shot dead. The Cuban leader, in his own words, is “violent, given to tantrums, devious, manipulative, and defiant of all authority.”

The Cuban people soon realized that they were paying a high price for supporting the rise of Castro. But overseas, Castro’s popular facade as a revolutionary hero took hold. One British newspaper wrote that “Mr. Castro’s bearded, youthful figure has become a symbol of Latin America’s rejection of brutality and lying. Every sign is that he will reject personal rule and violence.” In April 1959, Castro spoke at the Harvard University Law School in Cambridge, Massachusetts. Even though he had used his knowledge of the law to suspend Cuba’s writ of habeas corpus, and even though the January 12 massacre was reported in the New York Times, Castro’s Harvard speech was interrupted time after time by enthusiastic cheering and applause.

On that same trip to America, the Cuban leader met with Vice President Richard Nixon, who was immediately impressed by Castro. In fact, Nixon wrote in a four-page secret memo to Eisenhower that “the one fact we can be sure of, is that he has those indefinable qualities which makes him a leader of men.”

John F. Kennedy, then a U.S. senator still months away from beginning his campaign for the presidency, knew that Batista was a ruthless despot who had murdered more than twenty thousand of his own people. Kennedy saw nothing wrong with Castro’s rise to power. And, like Hemingway, he was also fond of a daiquiri from time to time.

In 1959, Kennedy and Castro were on the verge of becoming two of the twentieth century’s greatest rivals. Both 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.