The Plots to Kill Castro
in the June 2000 issue of GEORGE

by Edward Jay Epstein

November 22, 1963: Even as the open limousine carrying President John F. Kennedy was moving into the cross-hairs of an assassin aiming a rifle with telescopic sights in Dallas, a high-ranking CIA official in Paris, representing himself as the emissary of Attorney General Robert Kennedy, was delivering to a Cuban assassin the weapons to kill Castro.

The assassin was Major Rolando Cubela, a close associate of Castro's who worked without portfolio in the Havana government. He had contacted the CIA and volunteered to eliminate Castro, asking specifically for "a high-powered rifle with telescopic sights that could be used to kill Castro from a distance." The CIA official was Desmond FitzGerald, chief of the Special Affairs Section (SAS), the covert unit responsible for orchestrating the overthrow of Castro. He was accompanied at the meeting by Cubela's CIA case officer. They gave Cubela a fountain pen with a hidden needle, capable of injecting lethal Blackleaf 40 toxin into a victim without his knowledge. FitzGerald explained that the rifle with telescopic sights would be delivered to Cubela inside Cuba.

But the CIA's counterintelligence staff, under the legendary James Jesus Angleton, had had concerns about Cubela's provenance prior to November 22nd, the counterintelligence officer working under FitzGerald, had warned that the operation was "insecure." And in September, only hours after Cubela had first broached, in Brazil, the idea of assassinating the Cuban leader, Castro had given an extraordinary interview to an American reporter in Havana, saying he knew the American government was behind plots to kill him and ominously warning he would "answer in kind" any attempts. So in the parallax universe of deception, it was a distinct possibility that Cubela was an agent provocateur, testing the CIA on behalf of Castro. If so, in working with Cubela, FitzGerald had inadvertently given Castro evidence of the involvement of the highest echelon of American government in the assassination plots.

As we now know, Castro's fear of American assassination plots was well founded. Subsequent investigations by the CIA's Inspector General (1967) and the Church Committee (1975) uncovered at least eight separate murder plots against Castro, beginning in the summer of 1960, the halcyon days of the Eisenhower Administration. Initially, when 32-year old Fidel Castro had won power in Cuba in 1959 and toured America in triumph, there was hope in Washington that he was a democratic reformer. But by mid-1960, after he had nationalized foreign property in Cuba, U.S. intelligence concluded that he was a Communist, allied with Moscow in the Cold War. At the CIA, planning for an American-led invasion of Cuba was already underway.

As part of its contingency planning, the CIA assigned Colonel Sheffield Edwards, thedirector of its office of security, to arrange less expensive ways of getting rid of Castro by assassination. Edwards approached an ex-FBI agent, Robert Maheu, who had worked with him in the past on CIA counterespionage investigations, including black bag break-ins, unauthorized wiretaps, and other covert operations. He told Maheu there was $150,000 available for Castro's assassination. Maheu suggested John Roselli, a Mafioso who recruited his two mob bosses, Sam Giancana from Chicago and Santo Traficante from New Orleans. The advantage to employing the Mafia for this sensitive mission, aside from the mob's contacts in the Cuban underworld, was providing the CIA with credible cover. If the assassins were killed or captured, it would seem plausible to the public that the Mafia had ordered the "hit" because Castro had taken away its brothels, casinos, and other enterprises in Havana. In return, by cooperating with the CIA, the three Mafiosi got protection against FBI investigations into their domestic criminal enterprises.

Rosselli proposed a simple plan: through its underworld connections in Cuba, the Mafia would recruit a Cuban in Castro's entourage, such as a waiter or bodyguard, who would poison Castro. The CIA's Technical Services Division, informally known as its "workshop," was given the job of producing and testing on monkeys an untraceable poison. It came up with a botulinus toxin that the CIA's Office of Medical Services then injected into Castro's favorite brand cigars. It also produced simpler botulinus toxin pills that could be dissolved in his food or drink. But the deputized Mafia contacts failed to deliver any of the poisons to Castro. As Rosselli explained to the CIA, the first poisoner had been discharged from Castro's employ before he could kill him, while a back-up agent got "cold feet."

While the Mafia continued its unsuccessful machinations, John F. Kennedy became President and, in April 1961, launched the Bay of Pigs invasion, an attack on a swamp in Cuba by CIA-trained Cuban exiles that ended in disaster. Furious at this humiliating failure, Kennedy summoned Richard Bissell, the head of the CIA's covert operations, to the Cabinet Room and chided him for "sitting on his ass and not doing anything about getting rid of Castro and the Castro regime" (as Bissell recalled). Richard Helms, who succeeded Bissell, also felt "white heat," as he put it, from the Kennedys to get rid of Castro.

By then, the Kennedys had set up their own covert structure for dealing with the Castro problem the Special Group Augmented, which Attorney General Robert Kennedy and General Maxwell Taylor effectively ran and which, in November 1961, launched a secret war against the Castro regime, codenamed Operation Mongoose. Secretary of Defense Robert Strange McNamara, who was not a formal member of this group but attended meetings, later testified: "We were hysterical about Castro at about the time of the Bay of Pigs and thereafter. And there was pressure from JFK and RFK to do something about Castro." It was a "no holds barred" enterprise, as Helms termed it, for which the Special Group Augmented assigned such "planning tasks" as using biological and chemical warfare against Cuban sugar workers; employing Cuban gangsters to kill Cuban police officials, Soviet bloc technicians, and other targeted people; using agents to sabotage mines; and, in what was called Operation Bounty, paying cash bonuses of up to $100,000 for the murder or abduction of government officials.

It was in this heightened atmosphere that the Richard Bissell turned to a super-secret, codenamed ZR/RIFLE, which was meant to give the CIA to on-demand "executive action" capacity that could be used against defectors and, as a "last resort," could be used to assassinate foreign leaders. The head of this program was William "Two Gun" Harvey, who had proved himself a dedicated hands-on cold warrior as the CIA station chief in Berlin in 1960. For the Castro assignment, he was instructed by Bissell to work through Rosselli, who was still believed to have underworld agents inside Cuba, and finally put ZR/RIFLE to the test by killing Castro.

Harvey had a serious security problem, however, with Rosselli's two associates, Maheu and Giancana. They had invited the unwanted attention of the FBI by citing their CIA connection to block an unrelated criminal investigation into a wiretap Giancana had planted in a girlfriend's hotel room in Las Vegas. Through this intervention, J. Edgar Hoover learned about their "dirty business" in Havana. Compromising this sensitive operation even further, Hoover also found out that another girlfriend of Giancana's named Judith Campbell Exner was also a girlfriend of President Kennedy's during this period. Hoover then briefed Attorney General Kennedy on the Mafia-CIA liaison as well as the more personal liaison between Exner and the President. And on April 10, 1962, Hoover wrote a memo for the files that Kennedy told him that the CIA had briefed him that it had retained Maheu to offer Giancana "$150,000 to hire some gunmen to go into Cuba and to kill Castro." Although this maneuver by Hoover greatly vitiated the possibility of total deniability for the Attorney General, it mentioned only Maheu and Giancana, not Rosselli. So the plan could proceed.

As a first step, later that April, Harvey ordered Rosselli to break off all contacts with Maheu and Giancana. Then he gave Rosselli four new lethal pills which "would work anywhere and at any time with anything." Rosselli, who was to use his putative Cuban agents to slip a pill into Fidel Castro's beverage, volunteered that he would use the others pill on Raul Castro, Fidel's brother, and Che Guevara, his revolutionary colleague. He also asked Harvey for a cache of rifles, pistols, radios, and explosives for a three-man Cuban team that he claimed was now preparing to penetrate Castro's bodyguards. Harvey personally drove the cache in a U-Haul truck to a parking lot in Miami, where it was picked up by Rosselli's men. Despite this bravado, the ZR/RIFLE phase of the assassination plans did not fare any better than the earlier plots. The pills again failed to reach their target, and the weaponry disappeared.

That November, as part of the deal by Kennedy and Soviet leader Nikita Khrushchev to remove the Soviet missiles that ended the confrontation, which almost ignited a nuclear war with the Soviet Union, Kennedy pledged not to invade or infiltrate Cuba, and Operation Mongoose was nominally ended. There was also a change in nomenclature and personnel. The name of the CIA unit responsible for covert actions against Cuba was changed from JM WAVE to the Special Affairs Section, and Harvey was replaced in early 1963 by Desmond Fitzsgerald. The mafia connection was also dispensed with Harvey telling Rosseli the operation was over.

Desmond FitzGerald, a socially adept veteran of the clandestine cold war, whose rugged good looks and name led many people in Washington to mistakenly believe he was a distant relative of John Fitzgerald Kennedy, ran things very differently from Harvey . He preferred the technological ingenuity of CIA's workshop to underworld hitmen. After it was established from Castro's psychological profile that he was avid diver and sea shell collector, hehad the division build a booby-trapped seashell that would explode if someone tried to remove it from the ocean floor. The idea was to place it where Castro frequently swam underwater in the hope that he would see it and attempt to bring it to the surface. If so, he would be blown up, and it would appear he had been killed by a derelict mine. It would leave no witnesses, and unlike hitmen, no assassin that could be captured. And if he ignored it, nothing would be lost. The workshop, however, decided that the construction of a lethal sea-shell that would not explode accidentally or be lost was technically too difficult. The CIA went back to the drawing board.

The next idea out of the workshop was a killer gift for Castro a wet suit whose breathing apparatus was impregnated with tubercle bacilli and other deadly germs. The concept was that the bacilli and other evidence would be destroyed by the seawater, and the Cubans would not be able to determine how Castro contracted tuberculosis. Again, this device would leave no witnesses. The problem was to find a means of delivering it. At the time, James Donovan, an American lawyer, was negotiating the release of the Cuban exiles captured in the Bay of Pigs disaster. Castro had apparently let Donovan know that he would like a wet suit. The CIA's idea was that somehow Donovan, who was not privy to its machinations, would give the contaminated suit to Castro. But before it could be delivered, Donovan, acting on his own, coincidentally gave Castro a pristine wet suit. The plan then had to be aborted.

All along, the Kennedy administration had been struggling to find a means to get rid of Castro by one means or another, and even though Kennedy had pledged to cease its attacks on Cuba to end the missile crises, Robert Kennedy continued to press the CIA for tangible results. Richard Helms testified that Robert Kennedy frequently bypassed the chain of command and directly called FitzGerald (as he had previously called Harbey). The pressure described by Helms was relentless. So when Major Roland Cubela came to Brazil with a Cuban delegation and, on September 7, 1963, made contact with a CIA officer and volunteered to kill Fidel Castro, it was an offer Fitzgerald was in no position to refuse.

Cubela was already known to the CIA. In late March 1961, when the planning for the Bay of Pigs invasion was moving into high gear, he had approached the CIA and offered to defect, but little came of that initial contact. The CIA knew he had the access for the mission. He was a personal friend of Castro's and saw him in the privacy of his office as well as at government functions. He also had experience as an assassin. Before Castro came to power in 1959, Cubela had killed Batista's chief of military intelligence, Blanco Rico, on behalf of Castro. To be sure, the SAS' counterintelligence chief had concluded that Cubela was "insecure." Nevertheless, Fitzsgerald decided the rewards outweighed the risks.

Cubela had made an extraordinary request that the CIA case officer in Brazil reported to FitzGerald. Cubela, now code-named AM/LASH, wanted to meet personally with Attorney General Robert Kennedy and be assured that the Kennedy Administration was behind the operation. Such a meeting was out of the question, but FitzGerald, ever resourceful, sought an alternative way of satisfying Cubela's demand. With the approval of his superiors in the CIA chain of command, he arranged to meet personally with Cubela and claim to be acting as a special emissary for Robert Kennedy.

The contact plan for the meeting stated: "FitzGerald will represent himself as personal representative of Robert F. Kennedy who traveled to [Paris] for specific purpose of meeting AM/LASH and giving him assurances of full support with the change of the present government." Although FitzGerald would not use his real name, he was physically recognizable from press photographs and identifiable as a social friend of the Kennedys. Top-ranking executives of the CIA usually did not meet operatives themselves that was the function of case officers but in this situation, FitzGerald made an exception. Their first meeting took place on October 29th 1963. FitzGerald explained he had been sent by Robert Kennedy. To further convince the assassin of his bona fides, FitzGerald wrote a "signal" into a Presidential speech, a phrase that described the Castro regime as a "small band of conspirators" that needed to be "removed" which would serve as an unambiguous alert to Cubela when President Kennedy himself delivered those very words, which he did in Miami on November 18th. The next meeting, where FitzGerald would deliver a weapon, was scheduled in Paris.

That meeting took place in a hotel room in Paris in the late afternoon of November 22nd. FitzGerald arrived with Cubela's case officer. He handed over the ingeniously crafted poison pen to Cubela and explained that the longer-range weapon, the rifle with telescopic sights, was en route to Cuba. It was only at the end of that star-crossed rendezvous that FitzGerald learned that his commander-in-chief, and friend, had been gunned down in Dallas by another assassin using a rifle with telescopic sights. So ended the thousand days of the Kennedy Administration, and, with Lyndon Johnson's succession, so ended the CIA's assassination attempts against Castro, all of which turned out to be ineffectual.

How much did Castro know about these plots at the time? The interview in which Castro stated that he knew the American government was attempting to murder Cuban leaders and suggested that, unless they ceased, he would retaliate in kind, took place on September 7, 1963 only hours after his long-time associate Cubela had received, in Brazil, confirmation of the plots from the CIA's willingness to recruit him. Unless the timing was a remarkable coincidence, Castro appears to have known about Cubela supposedly secret liaison with the CIA. And if that was the case, he could also have learned that the CIA was constructing sophisticated weapons to poison him and shipping sniper's rifles to Cuba to shoot him. He could also have known that the Kennedys were sufficiently involved to send a personal representative to reassure the assassin a representative close enough to President Kennedy to write a signal into his speech. Castro would then himself have been delivering a message to the Kennedys with the timing of his extraordinary interview on September 7th.

Cubela's motives entangling the CIA in yet another assassination plot, and attempting to provoke Robert Kennedy to give his personal seal of approval, remain murky. After the plans were called off, Cubela returned to Havana rather than defecting to the U.S. The fact that he was never prosecuted by the Cubans for attempting the assassination he was proposing to the CIA, even though it became public knowledge, suggests he may have been acting on behalf of Castro to determine the involvement of the upper echelons of the American government or even to gain evidence in the form of traceable weapons made in the CIA's work shop. In 1966, Cubela was convicted for post-1964 subversion in Cuba, but unlike more than 500 other Cuban officials who were executed for similar crimes, he was granted clemency when Castro personally intervened on his behalf. After a prison sentence, he was allowed to resettle in Spain in 1977, where he has lived ever since.