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.

Robert Maheu looks back on an extraordinary life from the comfort of his Las Vegas home. The 90-year-old former spymaster may be the last living major player in the CIA’s efforts to assassinate Castro. Photograph: Josh Sanseri

The old man who putters around the corner with a cup of coffee and a plate of fresh-baked blueberry muffins hardly seems the cloak-and-dagger operative at the nexus of what may have been the strangest covert undertaking in U.S. history. More like a kindly grandfather delighted by the chance to chat with a visitor. The trim form Robert A. Maheu once enjoyed as an FBI agent has yielded to the comfortable stoutness of old age. A palm-treed Hawaiian shirt and black slacks with the waist pulled high have replaced the standard issue white shirt and tie.

He is 90 now, with eyes that show a pleasant, kind twinkle, but you’d be mistaken to underrate Robert A. Maheu’s toughness. He seizes your hand with a clamplike grip and rattles off an impressive list of ventures with which he’s still involved. Among them is the intelligence firm he helped build with his son, a group with 160 investigators in Nevada and operatives in more than 80 countries.

As for his mental acuity, ask him about his involvement in the Cuba Project: His memories come as fast and fresh as his morning muffins.

That project—the CIA’s targeting of Fidel Castro, and its willingness to rely on the Mafia to achieve that end—has resonated with intrigue, drama, and mystery ever since details of it began to surface in newspaper columns during the early 1970s. The five-year program of propaganda, sabotage, and murderous intent has been linked to everything from Richard Nixon’s Watergate downfall (some of the Watergate burglars, including E. Howard Hunt, were major players in the Castro plots) to the hit on the Chicago godfather Sam “Mooney” Giancana. Many think the answer to who killed JFK lies buried beneath the layers of plots and subplots in the efforts to assassinate Castro—specifically, that the project may have resulted in a counterplot by Castro to kill Kennedy.

Today, the tale has taken on fresh relevancy, thrust back into the nation’s consciousness by questions over intelligence activities—the Bush administration’s domestic spying program, for example, and the CIA’s “rendering” of terrorist suspects to countries where torture is believed to occur.

Still, until June of this year, the CIA had failed to acknowledge publicly that its plots to murder Castro even existed. Books had been written, congressional testimony given, and newspaper columnists had uncovered detailed evidence. But an official admission to citizens of the United States and the world, no.

That changed with the release of what The Company called its Family Jewels—693 pages of declassified top-secret memos confirming some of the CIA’s most infamous and illegal past activities. The Jewels grew out of the anger of CIA director James Schlesinger, who had learned through the press that his agency had provided support to two ex-CIA agents arrested in the Watergate break-in (E. Howard Hunt and James McCord). In May 1973, Schlesinger ordered “all senior operating officials of this agency to report to me immediately on any activities now going on, or that have gone on in the past, which might be construed to be outside the legislative charter of this agency.”

That charter barred the CIA from spying inside the United States, but did not expressly forbid assassination plots against foreign leaders. Instead, the vaguely worded National Security Act of 1947 permitted the CIA to collect and analyze intelligence and perform “other functions and duties related to intelligence affecting the national security.”

“It is through the loophole of those [last] vague 11 words that hundreds of major covert actions were undertaken, including efforts to assassinate foreign leaders like Fidel Castro,” says Peter Kornbluh, a senior analyst at the National Security Archive, a private research group in Washington, D.C. (The group was instrumental in getting the Jewels declassified, having filed Freedom of Information Act requests some 15 years ago.)

The violations revealed in the Jewels are “unflattering,” admitted the current CIA director, Michael Hayden, in a public statement after release of the documents. Not to mention embarrassing. The documents, in fact, confirm plots against Castro that are so absurd, so harebrained, they seem more like fantasies dreamed up by drunken frat boys than the product of the best and brightest minds in the intelligence community. Exploding cigars, poisoned wetsuits, chemicals to make Castro’s beard fall out—even a phony Second Coming—all were brainstorms of The Company’s masterminds. The plots do indeed “go beyond James Bond,” says Don Bohning, author of The Castro Obsession: U.S. Covert Operations Against Cuba. “They are really screwy.”

Which raises the question: How did such schemes come to dominate the plotting? “You have to realize the enormous pressure the intelligence community was under to do something about Castro,” says Bohning. “The people above them were willing to consider about anything.”

As it happens, almost all of the masterminds have died, as have the people tapped to carry out their plots. Old age has claimed some; causes suspicious and violent, others. Robert Maheu may be the last living major player, the sole survivor who can bear witness to this bizarre intelligence undertaking.

Which is how I find myself at a dining-room table in Las Vegas with a plate of homemade blueberry muffins in front of me, listening to the voice of Patsy Cline drift down from ceiling speakers, while the grandfatherly spymaster across the table from me—The Fixer, Bob Maheu—unravels the tale of how he presided over the star-crossed marriage of the Chicago mob to the feds.

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.”

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.”

By September 1960, the project was proceeding apace. Roselli would report directly to Maheu. The first step was a meeting in New York. There, at the Plaza Hotel, Maheu introduced Roselli to O’Connell. The agent wanted to cover up the participation of the CIA, so he pretended to be a man named Jim Olds who represented a group of wealthy industrialists eager to get rid of Castro so they could get back in business.

“We may know some people,” Roselli said. Several weeks later, they all met at the Fontainebleau Hotel in Miami. For years, the luxurious facility had served as the unofficial headquarters for Mafioso leaders seeking a base close to their gambling interests in Cuba. Now, it would be the staging area for the assassination plots.

At a meeting in one of the suites, Roselli introduced Maheu to two men: Sam Gold and a man Roselli referred to as Joe, who could serve as a courier to Cuba. By this time, Roselli was on to O’Connell. “I’m not kidding,” Roselli told the agent one day. “I know who you work for. But I’m not going to ask you to confirm it."

Roselli may have figured out that he was dealing with the CIA, but neither Maheu nor O’Connell realized the rank of mobsters with whom they were dealing. That changed when Maheu picked up a copy of the Sunday newspaper supplement Parade, which carried an article laying out the FBI’s ten most wanted criminals. Leading the list was Sam Giancana, a.k.a. “Mooney,” a.k.a. “Momo,” a.k.a. “Sam the Cigar,” a Chicago godfather who was one of the most feared dons in the country—and the man who called himself Sam Gold. “Joe” was also on the list. His real name, however, was Santos Trafficante—the outfit’s Florida and Cuba chieftain.

Maheu alerted O’Connell. “My God, look what we’re involved with,” Maheu said. O’Connell told his superiors. Questioned later before the 1975 U.S. Senate Select Committee on Intelligence (later nicknamed the Church Committee after its chairman, Frank Church, the Democratic senator from Idaho), O’Connell was asked whether there had ever been any discussion about asking two men on the FBI’s most wanted list to carry out a hit on a foreign leader.

“Not with me there wasn’t,” O’Connell answered.

“And obviously no one said stop—and you went ahead.”

“Yes.”

“Did it bother you at all?”

“No,” O’Connell answered, “it didn’t.”

For his part, Maheu was impressed with Giancana. “He didn’t come off as thuggish,” Maheu recalls. “You could tell, he wanted attention and he got it. When he walked down the hallway, you could just sense his power. He didn’t have to say a word. It was just how he carried himself. But I never heard him use foul language. He was always very well dressed and in very good shape.”

The mobster could be sentimental. In his autobiography, Maheu recalls Giancana getting “tears in his eyes whenever he heard the song ‘You’re Nobody Till Somebody Loves You.’ . . . He said, ‘Someday I’ll explain it to you.’ But he never did.” He could also be menacing. In the book, Maheu recalls a young man going up to Giancana at the pool and talking tough. “Without even looking at the punk, Giancana grabbed his necktie and yanked him close,” Maheu writes. “Sam stared right into the kid’s eyes and said, ‘I eat little boys like you for breakfast. Get your ass out of here before I get hungry.’”

Born to Sicilian immigrants in a section of Chicago’s Little Italy called “The Patch,” Sam Giancana had forged a reputation as a crack getaway driver, a high earner, and a vicious killer. Lean and banty, he could be charming or monstrous. In his CIA-Mafia book, The Fish Is Red, the author Warren Hinckle describes Giancana as “a trampy little man with hairless legs who wore baggy white socks and generally walked around looking as glum as an unpaid undertaker.” Giancana’s daughter, Antoinette, who lives in Elmwood Park, paints a more flattering portrait: “Sam worked at looking young,” she writes in Mafia Princess: Growing Up in Sam Giancana’s Family. “And except for his balding head and graying hairline, he usually succeeded. . . . I can’t think of anyone who looked less like the public’s conception of a Mafia boss than my father in May of 1961.”

Maheu forged a friendship with Giancana, meeting him every day, sounding the gangster out on his views toward Castro. Maheu quickly realized that Giancana needed little persuading to go after the Cuban leader. Not only had Castro robbed him of his casino income; Giancana had lost out on a shrimp boat operation he was trying to build, as well as on a plan to offer gambling on tourist boats traveling from Miami to Cuba. “He had all these wonderful things going for him,” Antoinette Giancana told me. “As an heir to [Giancana’s] estate, I can say that we lost everything to Fidel Castro. He took everything away from us.” The mere mention of Castro’s name in the Giancana house, the daughter recalls, “would make him flip his lid.”

Accordingly, the conversations between O’Connell, Maheu, Roselli, and Giancana focused on how, not whether, to kill the Cuban leader. The CIA initially suggested a gangland-style hit, with Castro going down in a hail of bullets. Giancana balked. Too risky. It would be a suicide mission. After considering and discarding different tactics, the two sides settled on deploying what they called a Mickey Finn—a poison pill that would be slipped into Castro’s food or drink.

To create the lethal capsule, the CIA turned to its “Office of Medical Services” and Dr. Edward Gunn, the CIA’s equivalent of the fictional “Q,” who provided James Bond with his shooting cigarettes and exploding alarm clocks. Gunn devised a pill containing botulinum, a powerful nerve toxin, but capsules didn’t dissolve in water. A second batch did dissolve, but when tested on guinea pigs, they weren’t lethal. It turned out that guinea pigs had a high resistance to botulinum. They tried the pills on monkeys. Success.

The pills were delivered to Giancana and Trafficante in March 1961 at the Fontainebleau. The timing was auspicious—and provided the perfect cover. The city brimmed with gangsters in town for the third heavyweight championship fight between Floyd Patterson and Ingemar Johansson. Thus, while crowds packed the hotel’s Boom Boom Room to see the two fighters knock each other around, Trafficante knocked on the door of Giancana’s suite without raising the least suspicion.

Waiting inside were Giancana, Roselli, Maheu, and Juan Orta, a disaffected Cuban official. Orta was angry at Castro for shuttering the gambling casinos and thereby ending his lucrative kickbacks. As payback, Orta had offered to help kill Castro, relying on the services of a chef at a restaurant frequented by Castro. The chef could put the botulinum pills in Castro’s food, Orta claimed.

Testifying before the Church Committee 14 years later, Roselli recounted what happened next. Maheu “opened the briefcase and dumped a whole lot of money on [Orta’s] lap,” Roselli recalled. Maheu “also came up with the [poison] capsules and he explained how they were going to be used. As far as I remember, they couldn’t be used in boiling soups and things like that, but they could be used in water or otherwise. . . .” (Maheu disputes the money-dumping story and says he simply passed the pills to Roselli, who gave them to Orta.)

But then something went awry. The mobsters later claimed that Orta got cold feet, a view shared today by Maheu. “It’s not like delivering a case of booze,” he says. The more likely explanation is that Orta, who had lost his position in Castro’s government, no longer had the means to pass the pills to his contact. Either way, Orta returned the poison. And Giancana and Trafficante had to find another killer.

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.

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.”

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. Subscribe to Chicago magazine.

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