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 Fixer couldn't sleep. But in that shadow hour when his wife still slumbered and the 101 Strings murmured over his rec room speakers and his swimming pool lights threw green wavy diamonds into the muggy Virginia night, he knew that sleep was not what he needed. What he needed was to think. To weigh. Good or bad. Right or wrong. Could he do it? Should he? The questions had gnawed at him ever since the proposition had been made earlier that evening.

The setting had been his recreation room, the comfortable redoubt where he often took visitors to discuss potential assignments from his most reliable client: the Central Intelligence Agency. On this occasion, the visit was from James O'Connell—"Big Jim" to his friends—and Sheffield Edwards, two operatives in the highest reaches of The Company, as the CIA was known. They had an assignment for him, they said, one so top secret that even the president, Dwight D. Eisenhower, had been kept in the dark.

The Fixer was no stranger to intrigue. As a former FBI agent turned private eye, he had built his career on operating in the shadows. His fledgling detective agency had a standing arrangement with the CIA: For $500 a month, he would perform various "cut-out" operations—missions ordered by the CIA, but with which the agency could deny official involvement. One such assignment, for example, required him to procure "feminine companionship" for Indonesia's President Sukarno during a state visit to New York, with the understanding that the woman would use her wiles to gather information from the leader. In another, he helped queer a deal that would have given Aristotle Onassis, already one of the richest men in the world, control over nearly all of the oil exports coming out of Saudi Arabia.

The Fixer served other clients, too, including one almost as secretive as the CIA. Howard Hughes—the "phantom billionaire"—may have been the most paranoid, reclusive public figure in the country at the time, but he trusted The Fixer with his most sacred secrets.

Still, for all his covert, high-level adventuring, even The Fixer found the operation the two CIA agents were now describing hard to believe. The subject was Cuba. The target was Fidel Castro. The mission was assassination. And The Fixer's role was to recruit the killer.

This was August 1960, about a year and a half after Fidel Castro had led the revolution that overthrew Cuba's longtime strongman, Fulgencio Batista. At first, much of the West celebrated the young revolutionary's success. But quickly, Castro's leanings toward Communism became evident. He began cozying up to the Soviet Union. Among the disturbing implications of this partnership was the potential for a missile base 90 miles from U.S. shores—a base from which Moscow could launch nuclear weapons at virtually any part of America.

That must not happen, Edwards and O'Connell said. Castro and his regime needed to be dealt with—"neutralized." Which was where The Fixer came in. After taking power, Castro had kicked out all the CIA agents. As a result, the best contacts left in Cuba belonged to the Mafia, which, with the blessing of Batista, had largely run the island's hugely profitable casinos. Castro had effectively robbed the Mafia of those profits by closing the casinos—first temporarily, then permanently.

If he agreed to help, The Fixer would use his contacts in the underworld to recruit someone who could get close enough to Castro to carry out the assassination. The hit would be timed to coincide with the Bay of Pigs invasion, loosely planned for some eight months from then. Killing the leaders, the reasoning went, would improve the odds for the military operation. The assignment obviously was considered "super eyes-only"—perhaps only half a dozen CIA agents knew of it. Would The Fixer do it?

He was speechless. The CIA. In bed with the mob. With him as the matchmaker? It was . . . crazy. How could an arm of the federal government team with Murder, Inc.?

The two men acknowledged his discomfort, shared it, even. In a perfect world, they would never have asked this of him or any citizen. But in this case, the interests of national security justified it. Think of Hitler, the lives that could have been saved had he been taken out before the launch of World War II, they said.

The analogy pricked The Fixer's conscience. Still, he said, "I have to think about it, think very deeply. I'll give you my answer tomorrow." That night, he recalls, "I told my wife I wouldn't be coming to bed. I went down to the recreation room and locked myself in. I realized that if anything went wrong, I was the fall guy. My family could be hurt. My friends could be hurt. I could be hurt. Furthermore, I considered myself a reasonably good Catholic, and I did not like the idea of getting involved with murdering anybody. I put on some music and began to do some soul searching."

He reached his decision at dawn. As morally questionable as the plan was, he agreed with the agents. Killing Castro would serve a greater good. That day, The Fixer called with his answer: He was in.

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

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