Thomas Maier is author of five books, including When Lions Roar: The Churchills and the Kennedys and Masters of Sex, which became a Showtime series. This article is adapted from his upcoming book The Killing Games, which is being developed by Warner Bros. Television Group.

Spies, sex, Mafia hit men and James Bond-like killing devices. They sound like the stuff of an Ian Fleming novel or a movie thriller. But these are true-life details from America’s first foray into the assassination business—a rather messy affair, as 007 might say.

They can be found, many for the first time, in recently declassified files about the 1963 assassination of President John F. Kennedy. The JFK files, released by the National Archives in batches since last year, have already been picked over for signs of any new information about Kennedy’s death in Dallas. (To the chagrin of conspiracy theorists, the documents contain little evidence that anyone besides gunman Lee Harvey Oswald was responsible for the tragedy.) But far less noticed were the files’ fascinating new insights about another much-debated Cold War conspiracy: a top-secret killing plan centered on the CIA’s recruitment of gangsters Sam Giancana and Johnny Roselli to murder Cuba’s young communist leader, Fidel Castro.


The conspiracy, including the mobsters’ involvement in it and the CIA’s oversight of it, has been known about for years. But the documents—from the CIA, FBI and other agencies, which had kept the files secret in full or in part for decades—provide several new details about the gangsters, their plot and their friendship. Together, these sources paint the most comprehensive picture yet of America’s first confirmed attempt at state-sponsored assassination of a foreign leader.

The files reveal, for instance, the range of Giancana’s and Roselli’s world of co-conspirators, including CIA spies and handlers, a fellow Mafioso (and former cop) in Chicago, Castro’s double agents in Miami, beautiful Hollywood women, “Rat Pack” entertainers like Frank Sinatra, a snooping J. Edgar Hoover and zealously anti-communist White House officials. The documents also provide new details about the mobsters’ violent schemes to kill Castro, which included everything from explosions and gunfire during midnight boat raids to hidden poisons prepared by the agency’s lab. During the early 1960s, the CIA’s quest to kill Castro turned southern Florida into a secret war zone and became a wild whack-a-mole hunt inside Cuba—all without luck. The ever-elusive despot died of old age in 2016.

Although more JFK files are expected to be released through April, important questions about Giancana and Roselli will likely remain unanswered, given the shadowy nature of this long-ago spy tale. Still, as further details emerge from the files, we can better trace the outlaw friendship of Giancana and Roselli, the CIA’s homicidal conspiracies against Castro and how the Cuban leader reacted by setting up his own spy network around Miami. Like strands in a ball of yarn, these individual memos and documents unwind to reveal a complicated tale far greater than Americans ever realized at the time.

In the scope of history, the Mafia spy scheme against Castro shows how easily U.S. espionage and law-enforcement agencies were corrupted more than a generation ago, with government-sanctioned murder justified on claims of national security. But it also holds important lessons at a time when some Americans fear their trusted institutions could go astray.



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The unholy marriage of the CIA and the Mafia in the Castro plot first became public knowledge in the mid-1970s, amid congressional hearings into the agency’s misdeeds and a growing national paranoia about the JFK assassination. Not until 2007 did the agency finally admit that Allen Dulles, its legendary director a half-century earlier, had agreed to a sizable bounty for the two gangsters in exchange for Castro’s head. But for more than a decade, the plot was known to only a few.

John F. Kennedy and CIA Director Allen Dulles discuss foreign affairs on July 23, 1960. | Getty Images

The story begins in the late 1950s, when America’s postwar confidence was suddenly rattled by the Soviet Union, which adopted Castro’s revolutionary government as a political satellite. By August 1960, the CIA’s top leaders had launched their plan to get rid of the pesky young Castro, according to a 1967 inspector general’s report stamped “Secret Eyes Only.” The policy to get rid of Castro had been initiated under President Dwight D. Eisenhower and was embraced by Kennedy when he took office in 1961. (Historians debate how much both presidents knew of the CIA’s precise plans). Reluctant to get blood on their own hands, CIA officials called for “a sensitive mission requiring gangster-type action.”

Giancana and Roselli, then 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. Giancana, the gruff, violent mob boss based in Chicago, dreamed of exporting his Midwest criminal enterprise to Latin America. And Roselli, known as “Handsome Johnny” for his movie star looks, served as the mob’s smooth-talking man in Hollywood before overseeing its casinos in Las Vegas. The two began as young Turks for Al Capone’s gang and, well before their CIA mission, had a history of working together, running gambling palaces in Cuba and Nevada and exerting the mob’s will in other ways. (One amusing JFK file recalls how Roselli, a pal of movie studio tycoons, once collected a gambling debt from a delinquent actor as a favor to his Marx Brothers friends, Harpo and Chico. Another file details how Roselli took phone calls about his CIA scheme while relaxing at the Friars Club in Beverly Hills, where Sinatra sponsored his membership.)

With a drink in hand or a woman on their lap, the two roustabouts could be found at the Boom-Boom Room at Miami’s Fontainebleau Hotel, where the CIA scheme to kill Castro was hatched in September 1960. Initially, Roselli and Giancana were approached by Robert Maheu, a glib middleman for the CIA. The agency referred to him as a “cutout,” a buffer who shielded the CIA and the White House from any messy consequences of their actions. Maheu also simultaneously worked for a handsome salary as a private fixer for multi-millionaire Howard Hughes. When Maheu offered the CIA’s $150,000 kill fee for Castro, the two gangsters declined—they said they would do it for free, the files show.

Although they cited “patriotic” reasons for accepting the assignment, Giancana and Roselli had their own motivations for eliminating the bearded dictator. When he came to power, Castro closed down the Mafia’s very lucrative casinos in Havana, costing the two gangsters dearly. They still hoped to revive the swank San Souci resort that they had run in Cuba with Spanish-speaking Mafia boss Santos Trafficante. The JFK files suggest that Giancana and Roselli also believed that cooperating with the government in such a high-risk venture as Castro’s assassination would earn them a kind of “get out of jail free” card that would keep the feds off their backs as they pursued their criminal activity at home. And for a time, their arrangement seemed to work.

As the CIA’s deadly deal with the two mobsters got underway in 1961, the arrangement was nearly derailed because of a comical “love triangle” incident. Late that year, the FBI discovered that CIA operatives, as a favor to Giancana and Roselli, had illegally bugged a Las Vegas hotel room belonging to comedian Dan Rowan, a suspected rival for the affections of Giancana’s girlfriend, Phyllis McGuire, a well-known entertainer at the time. FBI Director J. Edgar Hoover’s G-men wanted to pursue charges against the CIA operatives and the two mobsters. But the CIA wanted to save Giancana and Roselli for a more pressing concern—killing Castro. Documents in the JFK files show that when CIA officials explained the situation to Attorney General Robert Kennedy in May 1962, he agreed to drop the criminal probe against the gangsters because of the ongoing Cuban effort. Visibly annoyed, RFK asked the spy agency to let him know in advance “if you ever try to do business with organized crime again”—but let the CIA operation proceed, according to one memo.

Santos Trafficante at the helm of his gaming room concession in the Sans Souci night club, 1958. | Getty Images

Despite their deadly reputation, the Mafia duo failed repeatedly to rub out Castro, as the JFK documents show. One would-be assassin, given CIA poison pills by Giancana, Roselli and Trafficante, supposedly got cold feet before he could spike Castro’s food in Havana. Other failed commando attempts launched from Florida were chalked up to ill luck or bad timing. CIA-trained fighters caught attacking along Cuba’s shores during nighttime raids were often jailed and sometimes executed by firing squad. The JFK files also reveal that Castro’s own spy network of double agents and sympathizers within Florida undermined the CIA’s efforts and helped keep the communist leader from harm. Some conspirators involved with the two gangsters double-crossed them for their own purposes.

When the poison pills failed, Trafficante suggested to Roselli and Giancana that a Cuban exile leader in Miami known as Tony Varona be given CIA money for weapons to kill Castro. Varona was liked by the Kennedy administration and hailed as a freedom fighter by the American press. But early on, Hoover warned the attorney general about Varona’s ties to “gambling elements.” And Trafficante, a major Mafia boss in Florida whom the two mobsters described to the CIA as their “translator” with the exiled Cubans, was linked by the FBI to “hopes of securing the gambling, prostitution and dope monopolies in the event Castro was overthrown,” according to a December 1960 bureau memo to the CIA. Nevertheless, with CIA support, Varona built up his anti-Castro forces in Miami, hoping to return someday to Cuba as its new leader. And in the shadows, Trafficante kept his illicit empire humming along uninterrupted.



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After the disastrous U.S.-backed Bay of Pigs invasion of Cuba in 1961, the CIA began phase two of its unsuccessful Castro assassination mission, which continued throughout 1962 and into early 1963.

The agency stepped up covert activity under one of its most trusted agents, William Harvey, a pistol-packing, martini-swilling savant of the dark arts. Harvey slowly warmed to wiseguy Roselli, though he suspected the CIA’s effort had been penetrated by an informant and told Roselli to stop dealing with Giancana and Trafficante. As a Mafia “made man”, Roselli didn’t follow this instruction. But he proved himself a flag-waving champion against Castro, saying in late 1961 that he felt “sorry for the poor bastards left on the beach” at the Bay of Pigs. “Roselli felt indirectly responsible for their deaths since he had encouraged many of them to participate in the invasion,” reads one lengthy report in the recently released JFK files.

In June 1975, Johnny Roselli arrives to testify before the Senate Select Committee on Intelligence about his connection with the CIA and the alleged 1961 plot to assassinate Fidel Castro. | Getty Images

In Washington, the Kennedy brothers demanded results from their hidden CIA outpost in the Florida swamplands. “Why can’t you gentleman get things cooking the way 007 does?” RFK asked Harvey sometime in 1962, according to Harvey’s secret testimony in one of the files.

While dealing with the two mobsters, who sometimes used aliases, the CIA itself operated in Florida under a phony business name—Zenith Enterprises—and did a lot to mask the fact that it was running a quasi-military encampment that appeared to violate its own rules against domestic spying. In Key Largo, Roselli was known as “Colonel,” training Cubans as fighters and earning Harvey’s admiration. On midnight missions, these exile soldiers reportedly traveled in twin powerboats to secret landing spots along the Cuban coastline to provide armaments to other anti-Castro conspirators. One JFK file includes a heroic account of Roselli going along on some of these trips, once saving himself from a sinking boat riddled with bullets after being attacked by a Cuban patrol waiting in the shadows. According to another JFK file, Roselli was gone for so long on one mission that Giancana worried that he had been killed.

Sometime in 1962, the CIA created a file called “Project Johnny” about Roselli’s heroics and kept it locked in a safe. Documents show this file was given a number—667 270—though years later it could not be found by congressional investigators, who mentioned looking for it to trace the actions of this mobster spy.

The JFK files also suggest Giancana launched his own anti-Castro operation with another Chicago mobster under his command, Richard Cain. A defrocked Chicago cop who spoke Spanish, Cain claimed to have smuggled himself into Cuba in another failed bid to murder Castro. Like a good double agent, Cain also volunteered with the CIA to spy on Cuban exiles living in Chicago.

JFK’s November 1963 assassination changed everything for the two gangsters. By then, Harvey had been reassigned by CIA superiors who were tired of his antics. The anti-Castro plans went into hibernation under President Lyndon B. Johnson, who told the CIA to “get out of the cloak and dagger business,” according to a secret memo written by CIA Director John McCone, Dulles’ successor.

Meanwhile, as documents make clear, Giancana and Roselli found themselves more than ever under the FBI’s investigative glare. Over the next decade, Giancana evaded the law by fleeing with Cain to Mexico, where they tried to create floating gambling casinos for the mob in the Caribbean and the Middle East. Back in Las Vegas, Roselli helped Maheu, his old CIA “cutout” pal, buy out several mob-controlled casinos for Howard Hughes.

FBI agents stake out the home of Sam Giancana in July 1963. | Getty Images

But Roselli got into trouble when the FBI discovered a card-playing scheme he ran at the Friars Club. He had cheated fellow members by planting a spy peeking through a hole in the ceiling. Worst of all for Roselli, Hoover’s G-men discovered his real name as an illegal Italian immigrant and urged the feds to deport him. (Tastefully, he had chosen “Roselli,” inspired by a 15th-century painter of religious scenes inside Rome’s Sistine Chapel, according to a 1977 New York Times account.)

Hoping to cash his CIA “get out of jail” dispensation, Roselli threatened to fully expose the CIA/Mafia murder scheme against Castro—then still a secret kept from Congress and the American public. As word leaked out from Maheu and the press, the two gangsters were called to testify before a Senate committee examining CIA wrongdoing. Their loyal friendship had frayed but remained intact. Giancana even offered Roselli money if his legal bills became overwhelming.

Before he could take the stand in 1975, however, Giancana was shot to death in his Chicagoland home, murdered in the same “gangster-type action” the CIA had once wished him to inflict upon Castro. Upset by the loss of his friend, Roselli offered testimony so dissembling about their Cuba mission that authorities considered perjury charges and moved ahead with deportation plans. In a desperate ploy, Roselli’s attorneys claimed to congressional investigators that he had inside information about a possible conspiracy behind Kennedy’s assassination. A House panel sought Roselli’s testimony. Around that same time in 1976, Roselli went to dinner in Florida with Trafficante, his old Mafia co-conspirator. Two weeks later, before he could testify again, Roselli was found dead in a metal barrel, dumped in a waterway not far from the Fountainbleau Hotel. The JFK files show that police detectives suspected Trafficante of murdering Roselli, if not both gangsters. By the mid-1970s, House investigators had concluded that Trafficante was “playing both sides” in dealing with Castro’s communist regime and his fellow U.S.-backed Mafiosi.

Frustrated Senate investigators quizzed the CIA about why “pertinent files do not contain more documents dated during the 1960 through 1963 period relating to the Castro assassination attempt.” But the CIA offered a rationale for its top-secret mission (one that provides some insights into why the United States remains so obsessed with Cuba’s fate today). “There were a lot of Cubans who worked with the Americans to free Cuba,” the CIA wrote in a 1977 memo. “They carried their plans to desperate extremes, risking their lives at the Bay of Pigs and in hundreds of smaller incursions. Some were associated with scheming to assassinate Castro himself; some did this on their own as patriots; and some, also as patriots, did it with the support of representatives of the United States government. Right or wrong, the identity of those people constitute [sic] a trust of the American Government. If betrayed it would be a breach of honor and a demonstration to our allies today, and to those individuals around the world who work with us, that they must review the risk they take in our association.”

Somewhere in this eloquent retort—an apologia for America’s first attempts at state-sponsored assassination using Mafia killers—there seemed a lasting lesson for all presidents. In addition to the Castro plot, 1970s congressional hearings showed evidence of CIA involvement in plots against Congolese leader Patrice Lumumba and Rafael Trujillo in the Dominican Republic in the early 1960s. President Gerald Ford’s 1976 ban on killing foreign leaders during peacetime loosened amid talk of targeted enemy drone killings and regime change in the post-9/11 era. And President Donald Trump, the man who approved the release of these JFK files, appeared unfazed last year when asked about political assassinations tied to Russian president Vladimir Putin. Instead, his answer almost seemed to refer to America’s own history with men like Giancana and Roselli.

“There are a lot of killers,” Trump told Fox News. “You think our country’s so innocent?”