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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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.

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7 years ago
Posted by Anonymous

Bryan Smith did a terrific job with this story about the plot to kill Castro. We will be featuring it on the Society of Professional Journalists' "News Gems," which highlights the best in American journalism at www.spj.org/gems.

Jon Marshall and Brian Summers

6 years ago
Posted by brains missing use your head

The bullet taken from Connelly leg well that supposed fell out and landed on another stretcher if added to the fragments removed from his leg would give substantially more weight than CEc99 had in its origin meaning quite simply in more instances than I can site here there were more than four bullets including the missed James Tague "over shot" from the County records of Dal-Tex building and it s nice to seen how Gary s Mack has been trucked to the "Bull oh with glee I don't see " Vince's view that Lee Henry Oswald another operative name for the Alek Hidell patsy used in the CIA's MK Ultra double identity drug hypnosis program that led Sirhan Sirhan in the Kitchen at the sight of the operative in the polka dot dress in Los Angeles almost five years after to fire and be the only one seen firing from atop a table while Senator Kennedy was killed point blank mt a missile inserted behind his right ear.To keep Bobby not only from Vietnam extraction but also to determine "the true murders of my brother John"But hes writing a book , strangely enough to bring down the other MK Ultra searching for a brain to wash Bush who would have preferred the excitement of Sirhan's job rather than to run the free world into one world order demise, and his father Herbert walker who was in charge o Operation 40 assassination group in Miami delivering a letter to DQ Hoover declaring innocence that he typed, (or someone for him) on the eighteenth????????????of November in Houston??????????? His father Prescott some sixteen years prior introduced Nixon to Jack Ruby who he would work for on H.U.A.C., As Jack had given a speech at the Waldorf Astoria seeking in 1961 April for dismiss the world of all secret organizations , ie: the Masons , Mossad, Skull and Bones ect, ect, ect,

5 years ago
Posted by MrHell

Oh, If someone was willing to pay me $1.5 Million, and just $500.000.00 up front in cash, I would Kill Castor. All they have to do is give me what I ask to do the Job. and there won't be a Castro any more. He would be a faded memory. And Justice would be served for our country. So I challenge anyone to accept my offer. As long as you're sincere.

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