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How the CIA Enlisted the Chicago Mob to Put a Hit on Castro

Ever wonder about the sanity of America’s leaders? Take a close look at perhaps the most bizarre plot in U.S. intelligence history

(page 5 of 6)

Meanwhile, another crisis had surfaced. Giancana had fallen for Phyllis McGuire, the beautiful lead singer of the McGuire Sisters. The two had been seeing each other for several months before Giancana was approached about the Castro operation. As the plotting unfolded, Giancana, who was living at the Fontainebleau, began hearing rumors that McGuire was having an affair with the comedian Dan Rowan while the two were performing in Las Vegas.

Unhinged by jealousy, Giancana threatened to leave Miami to confront the pair. “Well, we didn’t want him to leave,” recalls Maheu. “We were right in the thick of things.” To ease Giancana’s mind, Maheu arranged for Rowan to be followed. Maheu called upon a Miami private eye he knew, Ed DuBois, to carry out the surveillance. DuBois, in turn, farmed the job out to another private investigator, Arthur J. Balletti.

What followed was a series of blunders O’Connell would later liken to the Keystone Kops. Balletti tapped the phone in Rowan’s hotel room. “That was the first mistake,” Maheu says. “Guys don’t make phone calls when they’re making love.” The more serious—and ridiculous—mistake came after Rowan left his room to play golf. Balletti, apparently wanting to see McGuire’s act, left his bugging equipment out—in plain view and running—in his own room, where a maid discovered it.

Had evidence of an affair been uncovered, Maheu believes Giancana would have dropped everything and gone to Las Vegas to confront McGuire. “We could not have kept him in Miami,” Maheu says. “You have to remember, these two people were really in love.”

As it happened, the sheriff’s office was called, then the FBI. A chagrined Maheu called O’Connell. “Well, the damned fools got themselves caught,” he said. Suddenly, Maheu found himself hauled before federal agents. Charges were eventually dropped against him and the detectives he hired, but not before the FBI had discovered the Castro assassination plots and Sheffield Edwards had been summoned before attorney general Robert F. Kennedy to explain why the CIA—without his knowledge—was using two men on the ten most wanted list to kill Castro. Kennedy was furious, though not enough to nix the plan. He allowed the operation to continue with the stipulation that he must be kept informed.

The assassination plot resumed its footing with word that Trafficante had turned to another contact in Cuba to carry out the hit. Tony Varona had been prime minister of Cuba in the late 1940s and early 1950s under President Carlos Prío and now wanted to finance the overthrow of Castro. Already, according to FBI reports, Trafficante had given money to Varona for the effort, hoping to secure gambling and dope monopolies in the event Varona was successful. Now, Varona identified a contact who could poison Castro’s food. Jim O’Connell took a new set of pills from a safe and delivered them—along with between $20,000 and $25,000 in cash for expenses—to Roselli, who passed the poison and the cash to Varona.

This was it. All that was needed, Maheu believed, was the “go” signal from the CIA, so that the assassination would coincide with the invasion. He waited. As did Varona. But, as Maheu would later testify, “the go signal never came.”

Hinckle, author of The Fish Is Red, offers an explanation. According to his theory, at the very moment Varona was supposed to give the signal, he was being sequestered by another group of CIA agents unaware of Varona’s crucial role in the hit. That group had planned to install Varona, along with several other Cuban exiles, as the provisional government to take over Cuba once the counterrevolution dispatched Castro. But fearing Varona might gab and spill the Bay of Pigs plan, the agents kept Varona locked up until the invasion was over. As a result, Varona could not get word to his contact at the restaurant.

On April 15, 1961, the drone of U.S. bombers disguised as Cuban revolutionary planes sounded over the three major airfields in Cuba, signaling the launch of the Bay of Pigs. Ill conceived, tragically executed, the invasion sent a ragtag invasion force of American-trained and -funded Cuban exiles into a Custer-style ambush. Dozens of exiles were killed and more than 1,000 taken prisoner.

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For a time, that squashed the assasination project. But the CIA had not given up on killing Castro. By late 1961, the agency had turned the operation over to William K. Harvey. Squat, bald, profane, with a headlong stride that gave him the appearance of a charging bull, Harvey was considered something of a legend within The Company. And indeed, he seized control of the Castro assassination mission with the kind of slash-and-burn aggressiveness that had gilded his reputation.

Among the casualties of the new leadership were Giancana and Maheu. Harvey “told me he wanted me to have nothing to do with [them],” Roselli told the Church Committee. Roselli still had the contacts, so he stayed with it. Giancana and Maheu were dumped. Maheu says it was just as well. “To tell you the truth, I’d had it up to my bald head with the whole operation after the way the whole invasion thing was handled,” Maheu told me. “I was so pissed that we allowed these kids to land there and not furnish them with the proper air cover. We put ’em in the ring; we led them there to die.” Over the months of plotting, Maheu and Giancana had become friends. After the final failed attempt, however, The Fixer never saw Giancana again.

When the operation resumed under Harvey, the schemes were as absurd as ever. One idea, for instance, based on Castro’s avid interest in scuba diving, involved booby-trapping a conch shell with explosives so that it would detonate when Castro picked it up off the ocean floor. (An operative “bought two books on Caribbean Mollusca,” according to the inspector general’s report. But “none of the shells that might conceivably be found in the Caribbean area was both spectacular enough to be sure of attracting attention and large enough to hold the needed volume of explosive.") The agency also considered arranging a gift for Castro, a scuba diving suit coated inside with a fungus that would produce Madura foot, a disabling and chronic skin disease. As it happened, someone had just given Castro a diving suit and the plan was abandoned.

One of the most curious occurrences, at least in terms of timing, came with the final unsuccessful plot. The CIA had been cultivating a dissident named Rolando Cubela since the early days of the assassination discussions. In November 1963, the same Dr. Gunn who had created the poison pills came up with a new device: a Paper Mate ballpoint pen rigged as a hypodermic syringe. Filled with Black Leaf 40, a lethal mixture of nicotine and insecticide, the pen’s “needle was so fine that the victim would hardly feel it when it was inserted,” according to the 1967 inspector general’s report.

On the afternoon of November 22, 1963, a CIA operative met with Cubela in Paris to give him the pen. As the men were coming out of the meeting, they were given terrible news: President Kennedy had been assassinated. Conspiracy theorists have noted the timing, but nothing substantial has ever linked the CIA’s plotting against Castro to the Kennedy assassination. “How could it be anything other than a coincidence?” says Kornbluh. “For it to be otherwise would mean that a whole crew of people somehow knew [Lee Harvey] Oswald would shoot Kennedy on that day.”

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