Twilight of the Assassins

It was the first act of airline terrorism in the Americas: thirty years ago, seventy-three people died in the bombing of a Cuban passenger plane. Now, one alleged mastermind lives freely in Miami, while another awaits trial on other charges in Texas. With Fidel Castro and Hugo Chávez insisting the CIA was behind the bombing, why won’t the Bush administration at last resolve enduring suspicions? A tale of thwarted dreams, frustrated justice, and murder in the sky
Operations in Miami

In the 1940s Posada and Bosch were schoolmates of Castro’s at the University of Havana. “I knew him very well,” Bosch recalled, sitting in a rocking chair, next to a photograph from his university years. “We lived across the street from each other. He was intelligent, it’s true. He studied law, and I studied medicine. I was the president of the medical school, and Fidel was a delegate for the law school. He could never win an election. I was also secretary-general of FEU [the student union], and he wanted to be president of that as well, but he could never win.”

Bosch strongly opposed the dictatorship of Fulgencio Batista, and after university he commanded rebel forces in the province of Las Villas. When Castro declared victory in early 1959, he rewarded Bosch with the governorship of the province. But it wasn’t long before Bosch accused Castro of betraying the revolution, abandoned his post, and led a deadly and effective guerrilla insurgency against Castro’s new government. In July 1960, he fled to Miami.

Posada says he too remembers the intense law student from Birán, whom he describes as handsome but with a weak chin, adding that the beard improved his looks. Unlike Bosch, Posada was not politically engaged during his student years. His family ran a small publishing house in Cienfuegos, on Cuba’s southern coast. In the mid-1950s, he secured a job with the Firestone Tire and Rubber Company and commuted between its headquarters in Akron, Ohio, and Havana. Posada says it was in the first months of Castro’s reign, when revenge and retribution ran riot, that he became politicized.

At some point, Posada made the acquaintance of David Atlee Phillips, the CIA’s man in Havana, who was busy recruiting operatives to overthrow Castro. He would also undoubtedly have rubbed shoulders with Phillips’s colleague E. Howard Hunt, if not in Havana, then in Miami, where the CIA set up a secret substation to run covert operations in Cuba called JMWave.

Headquartered in a nondescript office building on a secluded, woodsy 1,500-acre tract on the University of Miami’s southern campus (once a Navy blimp base), JMWave would become one of the biggest employers in South Florida. Some 400 full-time CIA staffers, with a $50 million annual budget, would over time employ an estimated 15,000 Cuban exiles. According to Ted Shackley, the spymaster who oversaw the station, 300 to 400 “front” corporations hired thousands more. JMWave boasted its own armory of cutting-edge weaponry, a fleet of airplanes, and hundreds of boats. (One distinguished alumnus of Miami operations was Porter Goss, who was appointed CIA chief in 2004.)

By 1959, Posada was carrying out operations in Cuba, for which, he told me, the CIA provided him with “time-bomb pencils, fuses, detonator cords, and everything necessary for acts of sabotage.” He would slip into Miami and return to Cuba with “war materials.” In January 1961, his luck in Havana finally ran out, when a sabotage operation went awry. He arrived in Miami in time to sign up for the disastrous Bay of Pigs operation. Its failure, after President Kennedy refused to authorize air cover, deeply embittered Cuban exiles. Kennedy’s subsequent deal with the Russians to end the Cuban missile crisis—with a promise not to invade Cuba—further angered anti-Castro exiles and many veterans of JMWave.

Posada was one of 212 exiles chosen by the CIA to attend officer-training school at Fort Benning, Georgia, after the Bay of Pigs. He graduated as a second lieutenant in the U.S. Army in August 1963. At Fort Benning, he formed two crucial relationships: with Jorge Mas Canosa, who would become the exiles’ most powerful lobbyist as chairman of the Cuban American National Foundation; and with Félix Rodríguez, later notorious for his roles in the death of Che Guevara and the Iran-Contra affair.

Posada was a charmer, fluent in English, a dashing ladies’ man who could knock back half a bottle of Johnnie Walker Black Label and not make a fool of himself. He was a world-class marksman, an expert at demolition, and a master of black propaganda. He delighted in confecting noms de guerre for himself: Comisario Basilio, Bambi, and Solo (after the spy in the TV series The Man From U.N.C.L.E.). In time, he would have dozens of bogus passports from a host of countries, including the United States. Unlike Bosch, Posada was not garrulous; his only ideology was anticommunism. “There are no good communists,” he told me. “All are bad.” In short, he was the perfect Cold War spook.

In 1968, JMWave was decommissioned. “It made sense to have a base in Miami,” CIA counterintelligence chief James Angleton would later confide to the author Dick Russell. “It was a novel idea. But it got out of hand; it became a power unto itself.” The CIA had spawned a monster, a semi-rogue agency with some staffers openly contemptuous of the White House and Congress. The agency would have its first experience with a phenomenon called blowback. It had trained an army of saboteurs and assassins, then changed its mind. But for the Cuban exiles, and some of the station’s officers, the war against Castro would continue.

The Casablanca of the Caribbean

Posada writes in his memoir that in the late 1960s, while having his usual pre-lunch daiquiri at Centro Vasco, a popular Miami restaurant, he was approached by “an elegantly dressed man” and offered a lucrative position in Venezuelan intelligence. With a recommendation from the CIA, he was made Venezuela’s chief of security and, in 1971, chief of operations at DISIP, Venezuela’s counterintelligence agency. Caracas had become a front line in the war against communism, with Venezuelan intelligence functioning almost as a satellite station of Langley. In an earlier variant of “rendition,” some of the CIA’s dirtier chores were farmed out to DISIP. Roiling with guerrilla groups, wildcatters, spies, and drug lords, Caracas was the Casablanca of the Caribbean—and, as such, the perfect home for Luis Posada.

Posada’s move from Miami to Caracas suited the CIA. In 1972, four Bay of Pigs veterans were indicted along with Howard Hunt for trying to burglarize the Democratic Party’s headquarters at the Watergate. The CIA awkwardly sought to distance itself from the burglars, and from other former employees. Caracas was a hospitable refuge: the CIA station chief from July 1972 to May 1973 was none other than David Atlee Phillips, who would later tell congressional investigators that Posada had worked with him on Track II, an operation to “thwart by whatever means” the inauguration of President Salvador Allende in Chile.

Throughout the 1960s, much of the ’70s, and again in the mid-’80s during Iran-Contra, Posada was a paid asset of the CIA, a detail his defense attorneys hammer home at every opportunity. But his relationship with the agency was not entirely smooth. CIA memos published by the National Security Archive questioned his coziness with drug dealers and mobsters and a “tendency’’ to become involved with “gangster elements’’ and in “clandestine sabotage activities.’’ A 1973 memo reported that “Posada may be involved in smuggling cocaine from Colombia through Venezuela to Miami, also in counterfeit US money in Venezuela.” Another noted that Posada was “seen with known big time drug trafficker,” and a third referred to him as a “seriou[s] potential liability.” The CIA severed formal relations with Posada in February 1976, but even after that he continued as a paid informer, according to former agency officers.

With or without the CIA, Posada would always have a paycheck, even when pursuing his personal passion of eliminating Castro. (“I’m the only one who didn’t make money,” Bosch told me with dismay.) In his closest miss, Posada partnered with Antonio Veciana, a former banker who founded the paramilitary group Alpha 66 with the backing of the CIA. The plan, conceived by Veciana’s CIA handler, was to take out Castro at a summit in Santiago, Chile, in November 1971. Veciana hired two hit men, both cohorts of Orlando Bosch, to pose as news reporters, equipped with a 16 mm camera that doubled as a machine gun.

According to Veciana, the assassins fixed the lethal camera on Castro but got cold feet after spotting Cuban security agents guarding the exits. Posada was furious. The men regrouped to plot another attempt, in Ecuador. This time, Posada was taking no chances: he would fire the weapon himself, using a state-of-the-art sniper rifle with a silencer. Knowing Castro would fly into Quito’s airport, Posada positioned himself in an elevated alcove several hundred feet away. But at the last moment, the wily Castro changed his arrival to a military base. Posada dispatched another set of assassins with the killer camera to Caracas, but when Castro appeared, Posada’s men were nowhere to be found.

From his perch in Venezuelan intelligence, Posada ran a campaign to hunt Castro-backed leftist guerrillas. “I persecuted them very hard,” he told me. “Many, many people got killed.” He saw to it that all Cuban offices and businesses in Venezuela were under continuous surveillance and also poked into the private business of some of Venezuela’s politicians—including Carlos Andrés Pérez, who didn’t appreciate having Posada listen to secret wiretaps of his conversations with his mistress. When Pérez was elected president in 1974, he promptly fired his operations chief. Posada quickly rebounded, recycling his high-powered contacts into an even more profitable venture: a security and detective agency.

Presented by

Ann Louise Bardach is the author of Cuba Confidential: Love and Vengeance in Miami and Havana and the editor of Cuba: A Traveler’s Literary Companion.

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