The plot by Llaca and Andreu—who both boycotted the Orange Bowl ceremony in protest against JFK—was sinister enough on its own terms. But what made the scheme even more unsettling was the two exiles’ source of support. Llaca and Andreu were “backed by the same Bircher-type Republicans who figure in the Goldwater movement,” according to the State Department memo. These were the same well-heeled “movers and shakers,” the memo further illuminated, who were also underwriting the Citizens Committee for a Free Cuba. This anti-Castro propaganda group was founded in 1962 by Paul Bethel, a former head of the U.S. Information Agency in Cuba who was close friends with David Atlee Phillips, the agency’s disinformation chief for the Guatemala coup and the Bay of Pigs. Other prominent members of the group included the Kennedys’ old bête noire, retired admiral Arleigh Burke; William Pawley, a right-wing Miami businessman deeply embedded in the intelligence world; CIA-linked Miami newspaper reporter Hal Hendrix; and the formidable Clare Boothe Luce—wife of Time-Life media baron Henry, journalist, playwright, former ambassador to Italy, and a woman who was also closely affiliated with the intelligence agency.
In other words, the Llaca-Andreu plot represented a perfect political storm for the Kennedys, a dangerous convergence of the brothers’ most avid enemies—coming together from the worlds of anti-Castro extremism, right-wing wealth, and U.S. intelligence to shake the White House. There is no record of how Robert Kennedy responded to this threat. Apparently the two exiles never succeeded in taking control of a Cuban town. But this was not the only brazen enterprise that summer aimed at humiliating the Kennedys. Nor was it the only plot involving Pawley and the Luces.
ON A BRIGHT JUNE morning in 1963, the Flying Tiger II, a sixty-five-foot yacht owned by William Pawley, slipped away from its dock on fashionable Sunset Island in Miami’s Biscayne Bay and headed for the Florida Straits. It was the beginning of a high-stakes expedition that its planners hoped would damage the Kennedy presidency so badly that voters would decide to terminate it in 1964. On board the boat was a collection of venomously anti-Kennedy characters who would later attract the attention of the Warren Commission and other assassination investigators. Among them were John Martino, a former security expert in the Havana casinos run by Santo Trafficante who later hooked up with Johnny Rosselli to assemble anti-Castro hit teams; William “Rip” Robertson, a veteran of the CIA’s Guatemala and Bay of Pigs operations who had shifted his allegiance to the Somoza dictatorship in Nicaragua; and Eduardo Pérez, better known as Eddie Bayo, a heroic Castro guerrilla who had turned against the revolution, joining the violent exile band, Alpha 66, one of the more defiantly anti-Kennedy groups.
It was Bayo and Martino who had kicked off the expedition when they began circulating a letter that had supposedly been smuggled out of the anti-Castro underground in Cuba. The letter claimed that two Soviet colonels stationed in Cuba knew where Russian nuclear weapons were hidden on the island in violation of the Kennedy-Khrushchev missile crisis settlement. The two Russians wanted to defect and win asylum in America. Right-wing circles in the United States had been buzzing with rumors of Soviet treachery ever since the superpower leaders negotiated an end to the nuclear crisis. Kennedy was certain to run for reelection the next year on his act of diplomatic glory that pulled the world back from the precipice. If JFK’s political enemies could produce shocking proof that he had been tricked by the Soviets, they were certain the American people would turn against his presidency.
As soon as Bayo and Martino began waving around the letter, the right-wing anti-Kennedy machinery churned into gear. After hearing the story, a conservative journalist named Nathaniel Weyl, who had testified against Alger Hiss in the early 1950s, phoned Jay Sourwine, chief counsel for the Senate Internal Security Committee. This was the notorious witch-hunting panel chaired by Senator James O. Eastland, the powerful Mississippi racist who had clashed swords with the Kennedys over Ole Miss. If the two Soviet defectors testified before Eastland’s committee, the administration would be forced to defend itself in a decidedly hostile forum. But Weyl’s friend, fellow conservative journalist Ralph de Toledano, had a better idea. After Toledano conferred with Barry Goldwater, it was decided that “the Russians would be immediately invited to Goldwater’s ranch in Arizona,” Weyl later recalled, “that [the senator] would call a press conference, enabling them to tell their story to the world, and that he would also give them enough money so they could start a new life in America.”
The publicity stunt would be a stunning one-two punch against the Kennedy presidency. The media spectacle would not only humiliate Kennedy before the eyes of America and the world, it would rocket-propel the campaign of the man who was determined to replace him.
To mount the expedition, the plotters turned to a wealthy businessman with a mysterious background, Bill Pawley. The sixty-seven-year-old Pawley had led the kind of colorful life that was the stuff of “old-time dime novels,”as his New York Times obituary later remarked, combining overseas financial exploits with cloak and dagger intrigue. After making a fortune in the Florida real-estate boom of the 1920s, Pawley developed airlines in Cuba and China and sold them to Pan American Airways. In China he helped organize the Flying Tigers, the legendary team of American pilots who fought against Japan before Pearl Harbor. After the war, he turned his attention to Latin America, buying Havana’s bus system and serving as ambassador to Peru and Brazil. This was his official resume, but unofficially Pawley was part of the CIA’s old boy network. A close friend of Allen Dulles, he used his diplomatic and business covers to carry out clandestine tasks on behalf of the agency, playing a key role in the Guatemala coup and talking President Eisenhower into approving the Bay of Pigs plan.
Pawley was an enthusiastic proponent of assassination as a foreign policy tool, especially when it came to Castro. He would pay any price if someone could just get close enough to eliminate the Cuban leader, Pawley mused aloud. When Eisenhower appointed him in 1954 to a CIA review panel known as the Doolittle Committee, Pawley made sure that its final report gave Dulles the full license the CIA director desired to fight the Cold War his way. In the face of “an implacable enemy,” the report concluded, the United States had to learn how to fight even more viciously than its opponents. “There are no rules in such a game,” the panel lectured, in language that reflected Pawley’s black-and-white world view. The American people might not like it, but they would have to grow accustomed to “this fundamentally repugnant philosophy.”
Vociferously anticommunist, Pawley railed against alleged Castro sympathizers in the State Department, whom he blamed for losing Cuba. He chaired the Nixon presidential campaign in Florida, after working closely with the vice president on the secret Cuba invasion plan. Following the Bay of Pigs, he blamed the disaster on President Kennedy’s “betrayal.”
Afterwards, Eisenhower arranged a meeting between JFK and Pawley to see if his old advisor’s hawkish views might sway the young president. The encounter—which took place in the Oval Office on May 9, 1962—was a disaster. Kennedy began by asking Pawley what he should do about Cuba in the wake of the Bay of Pigs. “I think we have to drop ten thousand Marines in the environs of Havana,” the brash tycoon replied. Pawley knew a sugar plantation on the outskirts of the city “that would be an excellent assembly area.” Afterward, another thoughtful suggestion occurred to the old Cuba hand, which he sent off in a letter to the CIA: The president might want to consider invading the sovereign country on a day when the United Nations was conveniently not in session. Kennedy, Pawley later complained, gave him the brush-off, never again asking him for advice despite Eisenhower’s repeated recommendations that he do so.
But Pawley continued to operate his own private war on the Castro regime. After the DRE’s abortive attempt to blow up the Cuban leader at the seaside Hotel Icar, the millionaire soldier of fortune adopted the daring young militants. He even convinced some of his wealthy acquaintances to sponsor DRE speedboats, “much the way Catholic schoolchildren used to sponsor foreign o
rphans whom they called ‘pagan babies,’” according to one mordant observation. One of these adoptive mothers was Clare Boothe Luce, who referred to the three-man crew she sponsored as “my young Cubans,” bringing them to New York on several occasions to shower them with maternal affection. Luce later claimed that the earliest revelations about Russian missile sites in Cuba—which politically embarrassed the Kennedy administration when they were fed to Senator Kenneth Keating of New York—came from her young speedboat rebels. “The information they came out with was remarkably accurate,” she later gushed proudly.
The swashbuckling Pawley brought the same entrepreneurial gusto to his covert operations that he did to his far-flung business ventures. He was willing to carry out the high-risk jobs that the CIA, with whom he maintained close ties, thought unwise to officially undertake. He was a wildcat operator with friends high up in “the Company” and he gave them a convenient cloak of deniability. At the CIA’s request, he had tried to talk his old friend Fulgencio Batista into leaving his palace as Castro’s guerrillas closed in on Havana, in a last-ditch effort to head off the revolution by replacing the despised despot with a military junta. He had also tried and failed to persuade the Dominican Republic’s bloodthirsty Rafael Trujillo to do the same in a midnight meeting, shortly before CIA-armed assassins took the matter into their own hands. When Pawley got a phone call from Senator Eastland, asking him to organize the secret Cuban mission that JFK’s enemies hoped would bring down his presidency, the millionaire told him he would have to check with the CIA, only agreeing to undertake the high-risk mission after getting agency approval and assistance.
Ever the hands-on operator, the dapper, bespectacled, gray-haired tycoon was on board the Flying Tiger II as it sailed into Cuban waters. He had frisked every man who boarded his yacht, to make sure there were no Castro double agents who might hijack the boat. Just to make sure, he had the three CIA men on board keep their machine guns trained on Bayo and his Cuban commandos during the trip.
Like the Llaca-Andréu affair, the Bayo-Pawley mission was a perfect convergence of Kennedy haters. In addition to the men from the anti-Kennedy trinity—the CIA, Mafia, and anti-Castro exile underworld—there were two representatives from the Luce press, a Life reporter named Richard Billings and a freelance photographer hired by the magazine (neither of whom were known for any anti-Kennedy fervor). Pawley was uncomfortable with the idea of having the media along for the ride, but his government superiors approved it. The expedition’s sponsors thought a spread in the popular picture magazine would ensure maximum political impact. And according to Weyl, they were concerned that Kennedy might frustrate their plans by having the yacht intercepted and the Russian defectors whisked away “to an undisclosed location…on the grounds of national security.” To make sure Kennedy did not spoil their plans, Weyl recalled, “The Russians would be photographed on board by a Life magazine camera man. Henry Luce would see that their revelations reached the world.”
Sitting atop his Time-Life empire, Luce was one of the country’s most powerful media moguls as well as one of the most influential proponents of American global power. The son of a Presbyterian missionary, Luce believed that the United States had a messianic duty to save the world through the spread of capitalism and American values. “The American mission is to make men free,” he declared, a philosophy he avidly promoted in his publications during the Cold War, which he believed should be fought not just to contain communism but to eradicate it.
Despite their sharp differences over war and intervention, Luce and Joseph P. Kennedy shared a long-term friendship, “a good, tough one that both men enjoyed,” in the words of Time-Life political correspondent Hugh Sidey. It was the comfortable, cigar-puffing accommodation of two powerful, self-made men and apparently it was undisturbed even when Kennedy slept with Clare during a visit the Luces made to the U.S. embassy in London before the war. Joe Kennedy went to Luce’s Waldorf-Astoria apartment to watch JFK accept the Democratic nomination. “It was a memorable moment in my life,” Luce later recalled. “It’s quite a thing to sit with an old friend and watch his son accept the nomination for president of the United States.”
Joe Kennedy failed to persuade Luce to support his son for president, but the Luces were both in attendance on the biting cold January afternoon when JFK was sworn in. The press lord was heartened to hear echoes of his own exuberant American theology in the new president’s vow that we shall “oppose any foe to assure the survival and the success of liberty.” His wife predicted that Kennedy would prove to be Eisenhower’s equal as a leader, and, as a bonus, he was decidedly more pleasing to look at. “The Kennedy clan is fun to watch and very easy on the eyes,” she noted.
But the Luces grew dismayed with Kennedy after the Bay of Pigs, using their magazine pulpit to routinely scold the administration for its perceived weaknesses. Turning her pen against the young president she had once favored, Clare lectured him that Cuba was an issue “not only of American prestige but of American survival.” By spring 1963, relations between the Time-Life juggernaut and the Kennedy administration were so frayed that JFK tried to mend fences by inviting the Luces to lunch at the White House. The afternoon quickly went sour. Luce browbeat Kennedy at length about the urgency of going to war with Cuba until the president finally lost his patience. When JFK suggested that Luce was a “warmonger,” the lunch came to an abrupt end. The Luces got to their feet before dessert was served and marched out of the White House.
Luce went directly back to the Time-Life headquarters in midtown Manhattan, where he convened a remarkable meeting of his top editorial command. He told his editors that if the Kennedy administration could not be counted on to confront the communist bastion in the Caribbean, Time-Life Inc. would. The corporation began channeling funds to anti-Castro raiders, paying them for exclusive stories on their escapades and even providing life insurance for the commandos and the correspondents who accompanied them. “With this directive,” wryly remarked Warren Hinckle and William Turner, authors of Deadly Secrets, revealing 1981 book on the secret war against Castro, “Luce, the great editorial innovator, invented a new form of journalism for which he is yet to be credited…paramilitary journalism.” But the Bayo-Pawley raid, to which Henry Luce contributed $15,000 (with Pawley himself kicking in another $22,000), had an even more disturbing mission. It was designed not only to wound the Castro regime, but to bring down an American presidency. If his son ever “shows any signs of weakness in general toward the anti-Communist cause, or to put it more positively, any weakness in defending and advancing the cause of the free world,” Luce had once warned his friend Joe Kennedy, “why then we’ll certainly be against him.” The press baron was now making good on his threat.
The fact that Luce, an old family friend, was willing to underwrite such an extraordinary assault on the Kennedy presidency shows how fractured the country’s elite circles had become over JFK’s policies. The young president’s fitful attempts to break away from the country’s Cold War regimen ignited a backlash from the old guard, who felt Kennedy was putting the country at risk.
Like the Llaca-Andreu enterprise, the Soviet defector caper also proved to be a bust. On the night of June 8, 1963, the Flying Tiger II dropped anchor ten miles off Cuba’s Oriente province. The city of Baracoa was “lit up like a church” in the murky distance, Pawley later recalled. Bayo and a dozen or so commandos piled into a speedboat loaded with CIA-supplied weapons that was to zip them ashore. The raiding party was never heard from again. Pawley, who had pleaded with Bayo not to crowd the speedboat with so many men, concluded that the craft sank before it could reach land. Others thought the raiders were captured or killed by Castro’s forces. In any case, no Russian defectors were ever spirited out of Cuba. Later, some researchers concluded that the defector story was a hoax created by Bayo and Martino to cover the smuggling of high-powered weapons into Cuba to assassinate Castro. But Weyl insisted to the end of his life this was not the case. When he was approached by the plotte
rs “to find a yacht and meet the defectors at sea,” the journalist noted in his 2003 memoir, they knew he did not “have any access to assault weapons.” They came to Weyl for one simple reason: because he was part of the anti-Kennedy propaganda network. There was no doubt about the purpose of the failed mission, Weyl wrote: it was “to defeat Kennedy.”
There is a curious end note to the William Pawley story. Years later, the elderly international adventurer came under the suspicion of Kennedy assassination investigators. Some conjectured that Pawley would have been precisely the type of independent operator to whom the CIA would have subcontracted the extremely delicate “executive action” assignment in Dallas. Gaeton Fonzi—a Florida-based investigator for the House Select Committee on Assassinations, which reopened the JFK case in the late 1970s—put Pawley high on his list of people he planned to interview for the congressional investigation. But on January 7, 1977, one week after Fonzi sent his target list to the committee, Pawley was found by police at his Sunset Island mansion, slumped in bed and dying of a bullet wound to the chest. Investigators, who said the eighty-year-old Pawley had been suffering from “nervous disorders,” concluded the gunshot was self-inflicted. He left a brief handwritten note for his wife, Edna: “The pain is more than I can bear.”
WHEN IT CAME TO Cuba, the Kennedys were masters of artifice. Their sleight of hand was designed to keep the Caribbean hot spot off the front pages and ensure that it would not burst into flames as an issue in the 1964 presidential race. Did they intend to invade Cuba again before the election to finally finish off Castro? The president vehemently denied it in public, but then quietly ordered the Pentagon and CIA to prepare for such an invasion. The Kennedys told one thing to certain Cuban exile leaders, and the opposite to others. Even decades later, conflicting testimony from administration insiders and a tortuous government documents trail led JFK researchers into confusing thickets and contrary conclusions.
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