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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

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Roselli and Maheu’s relationship was detailed in the CIA’s recently declassified “Family Jewels” documents. Click to enlarge the document.

Though much of the thinking surrounding the Cuba Project seems bafflingly, almost comically flawed, the decision to tap Maheu as the intermediary between the CIA and the Mafia made sense. Born in Waterville, Maine, a small mill town best known as home of the Hathaway shirt, Bob Maheu stumbled into intelligence work. In search of a little extra money while in college, he applied to be a translator for the FBI. Desperate to get men into the field, the FBI hired him as an agent.

After working under cover during World War II, he quit the bureau at the end of the war to open his own intelligence gathering firm. His first clients were old FBI friends who had gone to work for the CIA. Howard Hughes heard about his success and put him to work handling minor blackmail cases from starlets Hughes had bedded. Eventually, Maheu became Hughes’s most trusted adviser. Among the perks of the $500,000-a-year job were mansions to call home, access to Hughes’s fleet of limos and private jets, and an introduction to a glittering Hollywood life in which he gained a first-name acquaintance with stars such as Bing Crosby and Dinah Shore.

One assignment required Maheu to serve a subpoena on the elusive owner of a prominent Las Vegas hotel. Maheu asked his friend the lawyer Edward Bennett Williams, who had represented mobsters, to pull some strings. The man who ended up obliging Maheu was a fast-talking, sharply dressed, silver-haired Mafioso named Johnny Roselli.  

Many months later, with the CIA’s Castro assignment in hand, Maheu turned to Roselli again. Tall and hawk-nosed, Roselli had been born Filippo Sacco in Esperia, Italy, on July 4, 1905, and had immigrated with his mother to America in 1911. After settling for a time in a Boston suburb, Roselli fled to Chicago in 1922 in the wake of a murder. He changed his name to Roselli in honor of an Italian Renaissance sculptor, Domenico Rosselli, and promptly began to work his way up the ranks of the Chicago Outfit under Al Capone. By the time he met Maheu, he was the Chicago mob’s representative in Los Angeles, where he was married for a time to a movie actress, June Lang. Eventually, he took over the ice concessions for the Mafia in Las Vegas.

Maheu and Roselli became fast friends. In fact, Roselli even spent a Thanksgiving at Maheu’s house, where he was referred to by Maheu’s children as “Uncle Johnny.”

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On an afternoon in late August 1960, Maheu watched Roselli swagger toward his booth at The Brown Derby in Beverly Hills. The gangster’s shoes, as always, gleamed with polish. His cuticles suggested a fresh manicure. This wasn’t the Uncle Johnny that visited on Thanksgiving, but “Handsome Johnny,” the mob capo.

Maheu waited until coffee was served to drop the bombshell. The mobster, Maheu recalls, laughed. “Me? You want me to get involved with Uncle Sam?” Roselli said, according to Maheu’s 1992 autobiography, Next to Hughes. “The feds are tailing me wherever I go. They go to my shirt maker to see if I’m buying things with cash. . . . They’re always trying to get something on me. Bob, are you sure you’re talking to the right guy?”

Yes, Maheu said. He was serious. The fee would be $150,000. Roselli could pick whomever he wanted to execute the hit. The only condition, Maheu said, was that “Uncle Sam isn’t involved. If anyone connects you with the U.S. government I will deny it. If you say Bob Maheu brought you into this, that I was your contact man, I’ll say you’re off your rocker, you’re lying, you’re trying to save your hide. I’ll swear by everything holy that I don’t know what in the hell you’re talking about.”

Roselli gazed steadily at him. He tapped his fingers on the table. “I would have to be satisfied that this is a government project,” he said. Maheu assured him, “It comes from high level sources.” After a long pause, Roselli nodded. He would do it. But he, too, had a condition: The CIA could keep its money. Assassinating Castro, he claimed, would be his patriotic duty. Whether Roselli was simply trying to curry favor with the feds in case he needed it later, Maheu didn’t care. The plot was in motion.

* * *

Unknown to either man, the CIA already had spent months brainstorming and discarding ways to get Castro, schemes ranging “from the cockamamie to sinister,” says Kornbluh, with the National Security Archive.

The initial plots were aimed at merely discrediting the Cuban leader. One scheme called for treating a box of cigars with a chemical, possibly LSD. “The thought was to somehow contrive to have Castro smoke one before making a speech and then to make a public spectacle of himself,” according to a declassified 1967 CIA inspector general’s report. Exploding cigars and cigars laced with poison were also considered. Another scheme called for agents to flood the radio studio where Castro broadcast his speeches with LSD gas so that he would ramble incoherently on the air.

One plot (the account of which some officials have claimed is apocryphal) was dubbed “Elimination by illumination.” This scheme turned on spreading the word that the Second Coming of Christ was imminent. Because Castro opposed Christianity, the reasoning went, his people would turn against him. To add a bit of Hollywood flair, a U.S. submarine stationed just over the horizon would hurl star shells into the night. The glow “would be the manifestation of the Second Coming and Castro would be overthrown,” explained a 1975 Senate Intelligence Committee probe of assassination attempts against foreign leaders, soon after the assassination of Chile’s President Salvador Allende.

On another front, agents thought they could diminish Castro’s charisma—not to mention subvert his nickname, “The Beard"—by dusting his boots with thallium salts, a powerful depilatory. Without his whiskers, the agents argued, Castro would lose the manly authority that had helped him overthrow the Batista government.

Kornbluh points out that the far-fetched schemes underscore the intense, almost hysterical paranoia that marked the cold war in those days. “The bottom line is that the agency, feeling pressure from the White House for . . . a ‘creative solution’ to the Castro problem, wanted to ‘neutralize’ the Cuban leader any way it could. Poison pens and pills, exploding conch shells, sniper rifles—whatever would possibly work.”

The difference between the “screwy” plots and those involving the Mafia, says author Don Bohning, “was that the others were just crazy schemes that were come up with under pressure. The Mafia plots were much more serious. They were meant to do something.”

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