Tampa crime boss Santo Trafficante Jr. plays a central role in thriller 'Mafia Spies'

Tampa organized crime boss Santo Trafficante Jr. is pictured at the Sans Souci nightsclub in Havana, Cuba. [Skyhorse Publishing/Library of Congress]
Tampa organized crime boss Santo Trafficante Jr. is pictured at the Sans Souci nightsclub in Havana, Cuba. [Skyhorse Publishing/Library of Congress]
Published Aug. 16, 2019

We're awash in conspiracy theories these days, and most of them are laughable. But one reason we might tend to believe them is that every once in a while a conspiracy theory turns out to be true.

The conspiracy recounted in Thomas Maier's new nonfiction book, Mafia Spies: The Inside Story of the CIA, Gangsters, JFK, and Castro, is a humdinger.

Its cast of characters includes Allen Dulles and J. Edgar Hoover, Dwight Eisenhower and Robert Kennedy, Frank Sinatra and Howard Hughes, Marilyn Monroe and the Maguire Sisters, and a real-life Murderers' Row of gangsters, headlined by Sam Giancana, Johnny Roselli and, in a central role, Tampa crime boss Santo Trafficante Jr. All of them crossed paths at some point in a secret, multiyear effort in the 1960s to assassinate Cuban leader Fidel Castro. And yes, those tales about exploding cigars are true.

Maier notes that for many years the plot remained a secret. Rumors about it seemed so outlandish they were dismissed. But two sources, the 2007 CIA internal report known as the "Family Jewels" and the 2017 release from the National Archives of thousands of files about the 1963 assassination of President John F. Kennedy, allowed Maier to bring the dark, complex story together.

At the center of the book is the relationship between two powerful criminals. In the '60s, Sam Giancana was the Mafia boss of Chicago, a position he won with a combination of careful strategy and ruthless violence. His longtime friend and colleague Johnny Roselli ran many of the mob's operations in Las Vegas and Los Angeles. Of the handsome, charming Roselli, Maier writes, "Murder never looked so good."

The two, Maier notes, "at the height of their careers, controlled a multi-million-dollar Mafia empire unprecedented in the annals of American crime — arguably bigger than the five families of New York's La Cosa Nostra combined."

So how did they get involved in a harebrained scheme to assassinate the charismatic Cuban dictator?

It's complicated. The pair turned down an offer of $150,000 from the CIA, declaring they would kill Castro for free because they were "patriots." But they might also have expected the occasional favor from the government going forward — and they had their own beef with Castro, who had kicked them out of their wildly profitable Havana casinos and other crime operations when he took control of Cuba in 1959.

Giancana and Roselli were chosen by CIA director Allen Dulles and his men, who viewed Castro's Communist politics as a dire threat to the United States. But they didn't want to take him out themselves.

"Instead," Maier writes, "these Ivy League-educated spies and West Point-trained colonels wanted Mafia figures to be recruited to kill Castro in a 'gangster-type action' — a bloody, bullet-riddled mess that would be untraceable to the CIA and especially the White House."

That last part is notable. The scheme was originally given the green light by an outgoing President Dwight Eisenhower; when Kennedy found out about it, he was all on board. Maier ascribes Kennedy's enthusiasm in part to his admiration for Ian Fleming's James Bond novels, an admiration soon shared by Dulles. That led in turn to the CIA's labs being tasked with developing Bond-style spy gadgets — including exploding cigars designed to kill the stogie-loving Castro.

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To recruit Giancana and Roselli, the CIA used a "cutout," private investigator and fixer Robert Maheu, whose other main client was the odd (to put it mildly) billionaire Howard Hughes.

In addition to the web of gangsters, intelligence agencies and politicians, Maier explains the roles of anti-Castro Cuban refugees and of celebrities, especially Frank Sinatra, who was such a fanboy of Giancana he gave the mob boss a ring that matched his own.

Throughout the book, Maier ties in the bizarre three-way relationship among Giancana, Kennedy and a beautiful young woman named Judith Campbell. A regular on the party scene in Las Vegas with Sinatra and his Rat Pack, she was romantically involved with the mob boss and the president at the same time.

But the book is not all dishy details. To get to Castro, Giancana and Roselli worked with Trafficante. They had all been associates in Havana, and the Spanish-speaking Trafficante could be a big help with contacts there, they reasoned. But, as Maier tells it, there is evidence that suggests that Trafficante's allegiance was not to his Mafia associates but to Castro — that he was a double agent.

Maier pulls no smoking gun, but he raises the inevitable questions about whether this whole hot mess was tied to the assassination of John Kennedy. Did Castro, angered by the multiple attempts on his life, seek revenge? Were the mobsters, who expected kid-glove treatment from the administration, infuriated by Attorney General Robert Kennedy's aggressive legal pursuit of organized crime?

An investigative reporter at Newsday for more than 30 years, Maier has published several other books, notably Masters of Sex: The Life and Times of William Masters and Virginia Johnson, the Couple Who Taught America How to Love, the basis for the Emmy-winning Showtime series Masters of Sex. He has also written books about Winston Churchill, Benjamin Spock and the Kennedy family.

Much of Mafia Spies reads like a fictional thriller. Maier writes with a brisk, colorful style and a headlong pace. The story itself is often confusing, but it was meant to be: All of the factions involved lied and misled about what they were doing, to each other, to various investigators and sometimes to themselves. Maier wisely structures the book in short, focused chapters to help the reader follow each thread.

Those threads don't all end up tied in a neat bow. The Warren Commission that investigated JFK's assassination never heard about the attempts to kill Castro and what they might have provoked, because Dulles sat on the commission and never revealed what he knew.

As they aged, Giancana and Roselli saw their power in the mob diminish, but their role in the Castro plot still made them targets of investigations.

In 1975, just before Giancana was scheduled to testify before a Senate committee about his CIA involvement, he was executed in his home. Roselli did testify, but not truthfully. In Miami in 1976, he had dinner at a restaurant with Trafficante. A few days later Roselli went to play golf and never came back. His body was found, carved into pieces, in a barrel bobbing in the waters off North Miami.

Neither murder was solved.

Sinatra was never called to testify about his relationships with any of them. Trafficante did come before a congressional committee but was skillfully evasive. Maier writes that, after the deaths of Giancana and Roselli, when Sinatra performed in Florida, Trafficante was often in the audience, as Giancana had been in the old days.

Trafficante died of heart failure at his home in Tampa in 1987, at age 72. His true allegiances remain an enigma.

And Castro, of course, outlived them all, retaining his hold on power for over five decades and dying, by all reports peacefully, at age 90 in 2016, not an exploding cigar in sight.

Contact Colette Bancroft at or (727) 893-8435. Follow @colettemb.

Mafia Spies: The Inside Story of the CIA, Gangsters, JFK, and Castro

By Thomas Maier

Skyhorse Publishing, 388 pages, $25.99

Meet the author

Thomas Maier will be a featured author at the Tampa Bay Times Festival of Reading on Nov. 9 at the University of South Florida St. Petersburg.