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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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.

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.

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Photograph: Josh Sanseri


6 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

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,

4 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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