By Robert Riggs
A Deadly Pact Born in Panic
I’ve reported on some dark corners of American history during my time on the True Crime Reporter® podcast, but few stories have left me as stunned as the CIA’s covert partnership with the Mafia during the Cold War.
This tale documented in released JFK assassination files begins in Havana’s once glitzy Mafia-controlled casinos and ends in blood-soaked betrayals, all in the name of national security.
In my interview with investigative journalist Thomas Maier—author of Mafia Spies—he peels back layers of secrecy on this astonishing alliance. “It’s kind of like Butch Cassidy and the Sundance Kid,” Maier told me. “These two gangsters recruited by U.S. intelligence to do a dastardly deed and kill a foreign leader, Fidel Castro, at the height of the Cold War.”
The Mob’s Golden Havana Crumbles
Before Castro’s revolution, the mob had turned Havana into a gambling mecca. Mob bosses like Sam Giancana and Johnny Roselli ran casinos and brothels with impunity—until Castro’s Communist revolution in 1959 slammed the door shut on their multimillion-dollar empire.
“The outfit, as the Mob was known in Chicago, was headed by Giancana then. It was on the scale of a Fortune 500 company,” Maier said. When Castro kicked out the American underworld, he torched their cash pipeline. The mob was livid—and hungry for revenge.
The Sputnik Effect and the Fear of Cuba
Simultaneously, Cold War paranoia had reached a fever pitch. The Soviets had just launched Sputnik. “The idea that a rocket could have an atomic bomb attached to it really sent shudders through official Washington,” Maier explained. The second gut punch? Castro’s Cuba was becoming a Soviet satellite just 90 miles from Florida’s shores.
Fueling the fear, Castro invited Soviet Cosomonaut Yuri Gagarin to Havana and rubbed shoulders with Soviet Premier Nikita Khrushchev.
The relationship sent chills through The White House.
It wasn’t long before President Eisenhower greenlit covert action. “We couldn’t shoot Sputnik out of the sky, but we sure could try to get rid of Castro,” Maier noted. That torch passed to the Kennedy administration.
Enter Frank Sinatra, the CIA, and a Poison Cigar
The CIA wanted to keep its fingerprints off the operation. That’s where mobster Johnny Roselli entered the picture. According to Maier, Roselli had ties to Bill Harvey—a real-life CIA spy nicknamed “America’s James Bond.” Through a middleman named Robert Maheu, a former FBI agent working for Howard Hughes, the CIA used Roselli to connect with Sam Giancana.
Together, they devised plots straight out of a Bond movie. “There was a lab at the CIA actually exploring ideas like exploding cigars, gadgets that could be killing devices,” Maier said. Ironically, JFK himself was a James Bond superfan—so much so that Jackie Kennedy even sent Bond novels to CIA Director Allen Dulles.
And the Fontainebleau Hotel in Miami, the very site of early assassination meetings, later became the backdrop of a Bond film. “Frank Sinatra, a pal of Giancana and Roselli, was performing there. You can still find footage of him and Elvis from that time,” Maier added.
Betrayal and Payback
The mob thought backing JFK through Sinatra’s campaign support would earn them a get-out-of-jail-free card. They were wrong.
“Once Bobby Kennedy became Attorney General, he turned the heat up on the Mafia like never before,” Maier explained. Giancana and Roselli felt betrayed—and watched as the FBI began to close in.
Still, they pressed forward with CIA-sanctioned attempts on Castro’s life. Poison pills, toxic cigars, and assassination squads—it all sounded slick, but nothing worked. “It became like the gang that couldn’t shoot straight,” I said during our talk. Maier agreed, adding that both his book and the Paramount+ series based on it capture the “level of craziness” and “hubris” of the whole scheme.
Vegas, Sinatra, and Big Ambitions
With Havana lost, the mob shifted its focus to Las Vegas. Roselli became a Hollywood fixer, mingling with studio heads and entertainers. Giancana, meanwhile, eyed even greater ambitions. “They wanted to expand the mob into international business. Getting in with the CIA was their way to do it,” Maier said.
Their friendship—rooted in Chicago, hardened in Cuba, and entangled with the CIA—was the heart of this story. “It fascinated me,” Maier told me. “On a personal level, the way they operated with Sinatra, the Rat Pack—it was something else.”
When the Plot Unravels
The Castro assassination plot unraveled in the mid-1970s when Senator Frank Church’s committee investigated abuses in the wake of the Watergate scandal.
Some of the operatives involved in the Mafia Spies plot were part of the bungled burglary of the Democratic National Committee at the Watergate office complex on June 17, 1972.
President Richard Nixon, facing likely impeachment for his role in covering up the scandal, resigned two years later.
Sam Giancana and Johnny Roselli were both subpoenaed by the Church committee to testify about the CIA plot to use the Mafia to kill Castro..
But neither would live to tell their tale.
Giancana was found in the basement of his home in Tampa, Florida, with six bullets to the head. “The killer used the telltale mark—shots around the mouth. It was a message: talk, and this happens to you,” Maier said.
Roselli’s fate was even grimmer. Fearing deportation due to his secret identity—his real name was Filippo Sacco—he hinted to the Senate he knew something about the JFK assassination. Before he could testify, his body was found stuffed in a 55-gallon oil drum floating in Miami’s waters.
“As they say,” I remarked, “sleeping with the fishes.”
“Exactly,” Maier replied.
Final Secrets and the Last Man Standing
The murders of Giancana and Roselli remain unsolved. But Maier’s Mafia Spies offers clues to a possible master of the hit: Santo Traficante, the enigmatic Florida mob boss who outlived them all.
As Maier put it, “Castro was the last man standing on one level. But I think Traficante had a hand in both murders.”
From Castro to Watergate
When the scandal exploded into the news, I was a young Congressional aide to House Banking Chairman Wright Patman.
I later conducted Watergate-related investigations on his behalf.
It was my first exposure to how deep these covert rabbit holes ran.
Up Next: Part 2 of Mafia Spies
Think the story ends with a failed plot and two dead mobsters? Think again.
In Part Two, we dive deeper into a chilling revelation: how the CIA may have steered the JFK assassination investigation away from its dirty secrets.
What did the Warren Commission overlook—or ignore—on purpose?
Why were the same men plotting Castro’s death linked to Watergate years later?
And could the silencing of Giancana and Roselli have been a warning to others who knew too much?
Cast of Characters
THE TWO GANGSTERS AND THEIR TARGET
Sam Giancana—Boss of Chicago’s Mafia organization called “the Outfit,” with lucrative casinos and other illicit businesses around the world. He and long-time mob pal Johnny Roselli agreed to help the CIA assassinate Cuban Communist leader Fidel Castro as a way of gaining favor with US officials.
Johnny Roselli—The mob’s charismatic fixer in Hollywood and Las Vegas, who befriended many entertainment figures and countless women. He acted as the main “patriotic” go-between with the Mafia, the CIA, and Cuban exiles wanting to kill Castro.
Fidel Castro—The Cuban revolutionary leader who seized power in 1959. During the Cold War, Castro ousted American Mafia figures from their Havana casinos and turned his Communist nation into a Soviet ally. In return, Castro became the target of a CIA assassination plot that recruited Giancana and Roselli as his avenging killers.
THE OTHER GANGSTER
Santo Trafficante Jr.—Florida don who joined Giancana and Roselli in the CIA plot but may have been a “double agent” for Castro.
THE CIA
Allen Dulles—The CIA’s first director secretly approved the Castro murder plot in the final days of the Eisenhower administration and curried favor with the Kennedys until the 1961 Bay of Pigs invasion fiasco forced his departure.
William King Harvey—Touted as the American “James Bond,” this tough-talking CIA agent oversaw the Castro assassination plan and became Johnny Roselli’s faithful friend.
Robert Maheu—The private eye who acted as a “cutout” middleman between the CIA and the two mobsters, while also serving as a frontman for multi-millionaire Howard Hughes in Las Vegas. Howard Hughes was a movie tycoon and wealthy aviator. He employed private eye Robert Maheu and wound up learning of the CIA’s secret Castro assassination plot. With the help of Roselli and Maheu, Hughes later bought several Las Vegas casinos
THE WASHINGTON POWER BROKERS
Dwight D. Eisenhower—Two-term president in the 1950s who oversaw the Cold War against the Soviet Union and approved the overthrow plan of the Cuban leader in 1960.
John F. Kennedy—As Ike’s successor, he inherited the CIA’s disastrous “Bay of Pigs” invasion plan and took blame when it failed yet favored aggressive covert action against Castro. JFK’s 1963 assassination prompted widespread rumors of a conspiracy and whether the Warren Commission should have known about the Mafia-CIA plot against Castro.
Robert F. Kennedy—Former Senate rackets investigator and US Attorney General during his brother’s term, RFK personally oversaw the government’s anti-Castro efforts after the failed Bay of Pigs invasion.
THE WOMAN IN THEIR LIVES
Judy Campbell— aka Judith Exner Voluptuous California divorcée whose succession of controversial affairs with Roselli, Frank Sinatra, JFK, and Giancana were chronicled in numerous FBI investigative reports and eventually caused a national scandal.
THE INVESTIGATORS
J. Edgar Hoover—The longtime FBI director didn’t know initially about the CIA’s recruitment of mobsters against Castro—or the infidelities of JFK with Giancana’s girlfriend—but once he did, he wielded the information like an anvil.
Frank Church —US Senator whose mid-1970s hearings revealed many of the deepest secrets of the CIA’s plot against Castro during the Eisenhower-Kennedy years. His demands for Giancana and Roselli’s testimony had fateful consequences.
Earl Warren—US Supreme Court Justice who presided over the official 1964 probe by the Warren Commission into the JFK assassination, though commission member Allen Dulles, the ex-CIA director, never revealed what he knew about the Castro murder conspiracy.
THE ENTERTAINER
Frank Sinatra—One of America’s best-known stars, he campaigned for JFK in 1960, introduced him to girlfriend Judy Campbell and befriended Giancana, Roselli, and other Mafia figures. He invested with Giancana in Cal-Neva casino resort until Nevada authorities learned of the mobster’s secret interest.
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