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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The years following the Cuba Project were not kind to the major players. Giancana, hounded to tell Congress about the CIA-Mafia connection, fled to Mexico. Maheu's relationship with Hughes fell apart in a flurry of bitter accusations on both sides. Roselli landed in the Los Angeles County Jail for a gambling scam at the Friars Club in Los Angeles, where he had helped card cheats fleece Hollywood celebrity players. He was also nailed for having failed to register as an alien. (When Roselli's lawyer asked Maheu to confirm for the court Roselli's involvement with the CIA plot, Maheu told him, "I don't know what you're talking about." Roselli "wasn't very pleased with that, as you might imagine," Maheu says.)

Eventually, though, word of the CIA's ties to the Mafia was leaked to the press. In a front-page story on August 16, 1963, the Chicago Sun-Times' Sandy Smith reported that the CIA had been dealing with Giancana for years. (The paper did not make the connection between Giancana and the Castro assassination attempts.) In early 1971, Jack Anderson wrote a column for The Washington Post detailing the operation, naming Maheu, Roselli, Jim O'Connell, and William Harvey. Maheu thinks Roselli leaked the information to Anderson to help with his own legal troubles.

Four years later, Roselli testified before the Church Committee about his CIA work. Shortly after, his decomposing body was found in Miami in a 55-gallon steel fuel drum. He had been strangled and stabbed and his legs were sawed off. Many attribute the death to a hit put out by Trafficante, payback for Roselli's having broken the mob's omertà (code of silence).

Giancana never had the chance to testify. By 1975, the godfather had moved back to Chicago—actually, to Oak Park. Already, he'd spent a year in jail for having refused to talk to Congress. Now, he was facing another congressional subpoena. Just before he was to appear, a gunman shot the 67-year-old mobster seven times in his basement while he was frying Italian sausage and spinach, his favorite snack. The weapon, a .22 Duramatic automatic pistol, was found in brush along the Des Plaines River. The crime was never solved.

Maheu assumes the mob was behind the hit. "They didn't want to take the chance that rather than to go to jail again he might talk," Maheu says. Antoinette Giancana suspects the CIA killed her father. "The government didn't like my father and my father didn't like the government," she says.

Whoever killed the Chicago Mafia don, his daughter insists that her father had the last laugh. "Sam, in his heart of hearts, had absolutely no intention to kill Castro," she told me. "None at all. He used to chuckle, periodically, and say . . . he was never going to take Castro out. It was all a game to Sam. He was milking the government for all he could get and chuckling on the side."

"That's not true," Maheu fires back. "Why the hell would he spend all that time and have these meetings and so forth? All he had to say is 'I'm not interested.' He may have said that to her, but it just doesn't fly."

Maheu also got hauled before the Church Committee in 1975. "I was pissed," he says—furious at both the Bay of Pigs debacle and the congressional summons to reveal the plots. Maheu also feared Castro would have him killed. "He might have had a lot of friends that would want to avenge this plot," he says.

Maheu believes the congressional probe was a grandstanding effort by Senator Frank Church to gain publicity for a contemplated presidential run. Still, Maheu told the committee what he knew about the mob plot, repeating his comments afterwards to the more than 100 international press representatives who had gathered for a press conference. "I still feel we should have never disclosed the mission," he says today. "I'm very bitter. When your country pledges you into secrecy . . . and 16 years later they decide to throw you in front of a bus. I had held up my part of the bargain. That was hard to swallow."

The final irony for Maheu is that the plots revealed by him and other CIA agents helped create overwhelming pressure for President Gerald Ford to do something to ban future schemes like the one Maheu fought so hard to keep secret. The year after Maheu's testimony, Ford issued Executive Order 11905: "No employee of the United States Government shall engage in, or conspire to engage in, political assassination."

Every U.S. president since then has reissued the ban on assassinations. Peter Kornbluh, of the National Security Archive, argues, however, that the zealous adherence to the law has faded in recent decades. The Reagan Administration "ignored it in its work with the [Nicaraguan] Contras and in efforts to assassinate [Libyan strongman Muammar] Qaddafi in Libya," he says. "Clinton decided to let the CIA go after bin Laden," and Kornbluh maintains that George W. Bush has tacitly endorsed the targeting of suspected terrorists.

* * *

The Fixer is stirred up. Having cleared away the muffin plates, he pours us both a last cup of coffee. It's morning in Las Vegas, nearly 50 years removed from his role in the twisted tale of the Cosa Nostra and The Company. His wife died many years ago. His four children are all grown. The jets and limos and mansions he once enjoyed as alter ego to Howard Hughes are all gone, having vanished from his life like desert mirages. He lives now in a comfortable ranch-style house, with sliding glass doors that look out onto the Las Vegas National Golf Course. Next door sits the home used in Martin Scorsese's mob flick Casino. Losing the fast-lane lifestyle doesn't bother him. "I'm right back where I should be," he says. "Living a modest life." He pauses. "It's been a helluva ride."

In his book, he wrote that if given the chance for a do-over he would never have become involved in the Cuba Project. But sometimes, late at night, The Fixer still turns the thing over in his mind. Right, wrong. Good, bad. "I guess the best way to say it," he concludes, "is if I were called upon tomorrow again, and I thought it would save one American life, I think I'd be tempted." The thought intrigues. Old spies, after all, don't die; they just fade back into shadow. But the thoughts don't keep him up at night. These days, in the twilight of his extraordinary life, The Fixer can sleep.

This article appears in the November 2007 issue of Chicago magazine.

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