In March 1961, a CIA operative placed an envelope on a table at the Fontainebleau Hotel in Miami Beach. Inside were poison pills and $10,000 in cash. Across the table sat three of the most dangerous men in America: Sam Giancana, boss of the Chicago Outfit; Santo Trafficante Jr., Florida's most powerful mobster; and Johnny Roselli, a Hollywood fixer with ties to Las Vegas, the film industry, and multiple murders.
The United States government was hiring the mafia to commit murder.
At the exact same moment, Robert F. Kennedy, the president's brother and U.S. attorney general, was launching the most aggressive campaign against organized crime in American history. Prosecutions for racketeering by his organized crime section rose by 300 percent above 1961 levels, and convictions of organized criminals grew by 350 percent.
One part of the Kennedy administration was prosecuting the mafia. Another part was paying them to kill a foreign leader.
The story begins not with the Kennedys but with Dwight Eisenhower. In 1959, Fidel Castro seized power in Cuba. He nationalized American businesses, shut down the casinos, and turned Cuba into a Soviet ally just 90 miles from Florida.
For the CIA, Castro was a communist threat. For the mafia, he was something worse. Before Castro, Havana was the jewel of organized crime's empire. The mob had lucrative investments in Cuban casinos. Giancana ran operations there. Trafficante controlled much of Havana's underworld. Roselli had connections throughout the Caribbean gambling scene.
When Castro shut it all down, the mobsters lost fortunes. Giancana had also lost out on a shrimp boat operation and a plan to offer gambling on tourist boats traveling from Miami to Cuba. As an heir to Giancana's estate, his daughter later said the family lost everything to Fidel Castro. The mere mention of Castro's name in the Giancana house would make him furious.
The CIA recognized an opportunity. The mafia wanted Castro dead. The CIA wanted Castro dead. Why not work together?
In September 1960, Giancana and Trafficante, both on the FBI's Ten Most Wanted list at the time, were indirectly contacted by the CIA about the possibility of assassinating Castro. The CIA could not approach the mobsters directly, so it used an intermediary: Robert Maheu, a former FBI agent who worked for Howard Hughes.
On September 14, 1960, Maheu met with Roselli in a New York City hotel and offered him $150,000 for the removal of Castro. Roselli was the perfect go-between. Known as Handsome Johnny, he dated actresses including Lana Turner and Donna Reed. He had Hollywood connections, Vegas connections, and mafia connections.
He had something else too: a twisted sense of patriotism. Roselli was an Italian immigrant who had made his fortune in America. When the CIA came calling, claiming to represent international businesses hurt by Castro's expropriation, Roselli believed he was serving his adopted country.
The mobsters refused to take any money. Despite efforts to keep CIA involvement secret, they quickly figured out the agency was behind the offer. They had another motive. They thought helping kill Castro would earn them a get-out-of-jail-free card. Giancana was convinced by Frank Sinatra that JFK would go easy on them. That assumption would prove catastrophically wrong.
On March 12, 1961, the plan moved forward. William Harvey arranged for CIA operative Jim O'Connell to meet Giancana, Trafficante, Roselli, and Maheu at the Fontainebleau Hotel. O'Connell brought poison pills manufactured by the CIA's Technical Services Division. Small, tasteless when dissolved, deadly.
The plan was simple. Get the pills to someone in Castro's inner circle with access to his food or drinks. Poison him. Make it look natural. It was Giancana who suggested poison pills as the means. The pills were given to his nominee, Juan Orta, a Cuban government official with access to Castro.
But there was a problem. Roselli's purpose was not just to assassinate Castro but to set up the mafia's partner in crime, the United States government. He laid a long, bright trail of evidence that unmistakably implicated the CIA in the Castro plot. This evidence, whose purpose was blackmail, would prove critical in the CIA's cover-up of the Kennedy assassination.
The mobsters were not stupid. They were creating leverage and insurance. If the government ever came after them, they could threaten to expose the CIA's role in plotting murder. They would need that insurance, because while the CIA was recruiting mobsters in Miami, Robert Kennedy was planning to destroy them in Washington.
On January 20, 1961, John F. Kennedy was inaugurated as president. His first major appointment was his 35-year-old brother Robert as attorney general. The appointment was controversial. Bobby Kennedy had never argued a case in court or tried a criminal trial. Critics called it nepotism.
But Robert Kennedy had something more important than courtroom experience: obsession. Previously, individual gang members had been investigated for crimes. This was the first time the government attempted to take on a whole criminal organization.
When Bobby became attorney general, the crime and racket section of the Justice Department employed only 17 people. By 1963, it had swelled to 60. Kennedy opened federal investigative bureaus in cities outside Washington charged with gathering information on racketeers.
Kennedy's strategy was unprecedented. He was the first attorney general to encourage the government's investigative agencies, including the DOJ, FBI, and IRS, to work together to investigate large-scale crimes and national crime syndicates.
He faced immediate resistance. FBI Director J. Edgar Hoover had spent decades claiming the mafia did not exist. Hoover was more interested in catching communists, bank robbers, and car thieves, cases where the media made him look good when he went to Congress for money.
Kennedy forced Hoover's hand. He coordinated all 26 federal law enforcement agencies. He opened files on top racketeers. He created task forces. He got wiretaps. He seized financial records. He went after specific targets: Jimmy Hoffa, Teamsters Union president; Sam Giancana, Chicago boss; Santo Trafficante, Florida don; and Carlos Marcello, New Orleans kingpin. The very men the CIA was working with.
In May 1961, Bobby announced his first drive to root out racketeers in Chicago with a special prosecutions unit assigned to bust an automobile theft ring. Think about the timing. Two months after O'Connell gave Giancana poison pills to kill Castro, the CIA was paying Giancana while the Justice Department was investigating him.
In 1961 and 1962, Congress approved seven anti-crime laws authorized by the attorney general. In the first six months of 1963, 171 racketeers were indicted, compared with 24 in 1960. During his term, convictions against members of organized crime rose by 800 percent.
Bobby Kennedy was not playing. This was total war, and the mafia knew it. Despite foot-dragging by Hoover, the Justice Department indicted 116 members of the mob.
But here is where it gets complicated. The FBI did not know about the CIA-mafia plot. Neither did Bobby Kennedy, at least not at first.
A level of cooperation between the mafia and the CIA was first exposed early in the planning process. A technician illegally wiretapping a Las Vegas entertainer's telephone for Giancana was arrested and sought help from the CIA. The CIA became involved and succeeded in having charges dropped, but the FBI investigated the matter.
As the FBI reported to Attorney General Robert Kennedy about the incident, the bureau warned that any CIA-mafia arrangement and the need to keep it secret could subject the U.S. federal government to underworld blackmail. Robert Kennedy was furious, but he was trapped.
The FBI recorded Kennedy's concern that the CIA action adversely affected the Department of Justice. Because of this matter, it would be difficult to prosecute Giancana or Maheu then or in the future. The CIA's secret alliance was sabotaging Bobby's war on organized crime.
The mobsters knew it and exploited it several times with varying degrees of success. Giancana and Roselli sought to use the CIA relationship to their personal advantage. In 1963, when Giancana sued the FBI to halt its surveillance, he was required to take the witness stand and was legally subject to cross-examination. Perhaps because of his role in the Castro matter, the Department of Justice reportedly ordered the prosecutor not to question Giancana.
The mobster who worked for the CIA could not be questioned under oath because he might expose the plot.
Meanwhile, the plot itself was failing spectacularly. After several unsuccessful attempts to introduce the poison into Castro's food, Orta abruptly demanded to be let out of the mission, handing the job to another unnamed participant. The first poison plot failed.
They tried again. In April 1962, William Harvey, a real-life CIA spy nicknamed America's James Bond, took control of the anti-Castro operations. Harvey told Roselli that Trafficante and Giancana had to cease involvement in the project. But Harvey needed Roselli.
In April 1962, Roselli was contacted by Harvey, who wanted to revive the idea of poisoning Castro. Roselli suggested giving poison pills to Tony Varona, who would forward them to a chef in a restaurant frequented by Castro. The suggestion was adopted, although the chef placed the pills in a freezer, making them unusable. The second poison plot failed.
The CIA developed James Bond-like killing devices at the behest of the Kennedys, who loved the Bond novels. A CIA lab explored ideas like exploding cigars, poison diving suits, toxic pens, and chemical sprays to make Castro's beard fall out, hoping humiliation would destroy his image.
One attempt involved a chemical with effects comparable to LSD, sprayed in the air of the room where Castro would broadcast from his radio station, with the goal of making him lose composure and speak erratically on air. All of it failed. It became like the gang that could not shoot straight.
According to CIA director Richard Helms, Kennedy administration officials exerted heavy pressure on the CIA to get rid of Castro. The Church Committee stated that it substantiated eight attempts by the CIA to assassinate Fidel Castro between 1960 and 1965.
But Cuban intelligence chief Fabian Escalante had a different count. Escalante estimated the number of assassination schemes or actual attempts by the CIA to be 638, split among U.S. administrations as follows: Dwight D. Eisenhower, 38; John F. Kennedy, 42.
That is 638 attempts, none successful. Why? Because Castro's intelligence service was better than anyone expected. Because the Cubans had infiltrated the Cuban exile groups the CIA was using. And possibly because Santo Trafficante was playing both sides.
Trafficante was the Florida don who joined Giancana and Roselli in the CIA plot, but he may have been a double agent for Castro. One of the mafia bosses the CIA hired to kill Castro might have been working for Castro all along.
In February 1963, William Harvey was removed from the operation and sent to Italy. Harvey was convinced that Robert Kennedy had been responsible for his demotion. A friend of Harvey's said he hated Bobby Kennedy's guts with a purple passion. The CIA operatives hated Bobby Kennedy. The mobsters hated Bobby Kennedy. Everyone involved in the secret war against Castro had reason to despise the attorney general.
And then came November 22, 1963, in Dallas, Texas, at 12:30 p.m. John F. Kennedy was shot. As men were coming out of a meeting about the CIA-Castro plot, they were given terrible news. President Kennedy had been assassinated.
Minutes before hearing of the shooting, RFK had just ended a meeting on organized crime with Justice Department officials at his estate at Hickory Hill. When Ed Guthman, spokesman for the Justice Department, rushed to Hickory Hill to speak with his boss that day, RFK said, "There's so much bitterness."
Bobby Kennedy's first thought was whether his war on organized crime had gotten his brother killed.
On November 22, 1963, rumors began to circulate that Giancana and other gang bosses such as Trafficante, Marcello, and Roselli were involved in the crime. The Warren Commission investigated. It interviewed thousands of witnesses, examined ballistics, and analyzed Oswald's background.
But there was one thing the commission did not know. The CIA did not tell them. The Church Committee in 1975 finally revealed this to the public, noting the CIA had deliberately kept such plots from the Warren Commission.
Why? Because revealing the CIA-mafia connection would have opened Pandora's box. It would have exposed illegal assassination plots. It would have revealed that the U.S. government hired criminals. It would have shown that the mobsters had blackmail material on the CIA. And it would have made the mafia suspects.
Think about the logic. If the CIA hired the mafia to kill Castro, and if Bobby Kennedy was simultaneously prosecuting those same mobsters, and if JFK was killed shortly after, the connection was too dangerous to explore. So the CIA hid it from the Warren Commission, from Congress, and from the American people.
The secret festered. CIA director Allen Dulles and three different CIA directors lied about this secret murder plot so it would never be learned by the public.
Then in June 1975, the Senate created the Church Committee to investigate intelligence abuses. Johnny Roselli was called to testify. On June 24 and September 22, 1975, Roselli testified before the U.S. Senate Select Committee about the CIA plan to kill Castro.
Shortly before Roselli testified, an unknown person shot and killed Sam Giancana in the basement of his Illinois home. This happened just days before Giancana was to testify before the committee. Giancana was murdered on June 19, 1975. He was shot seven times in the head and neck, with one bullet in the mouth.
In a traditional mafia hit, a bullet in the throat signifies that the victim had been talking, and a bullet in the mouth means he will never rat again. Giancana was silenced before he could tell Congress what he knew.
Roselli testified anyway. He told the Church Committee about the poison pills, the CIA meetings, and the failed attempts. Then in July 1976, Roselli disappeared. On August 7, 1976, fishermen discovered his body stuffed in a 55-gallon oil drum floating in Biscayne Bay near Miami. He had been strangled, shot, and dismembered, his legs sawed off and stuffed into the drum with his torso.
The manner of Roselli's death fit a mafia pattern. He was lured to his death by someone he trusted. The dumping of his body in the bay was another message. The killers either wanted to give the impression that he had deliberately vanished or they wanted to punish his relatives for his misdeeds, perhaps his violation of omerta.
Two of the three mobsters recruited by the CIA were now dead, murdered within 13 months of each other. Both were killed after being called to testify about the Castro plots.
One fact was indisputable. Santo Trafficante was the only survivor of the three mobsters recruited by the CIA to kill Fidel Castro. Trafficante lived until 1987. He died of natural causes. He never revealed what he knew.
In 2007, the CIA finally released the "family jewels," internal documents detailing decades of illegal activities. The declassified documents showed that in September 1960, the CIA recruited mobsters in exchange for Castro's head. The documents confirmed what conspiracy theorists had claimed for years. The CIA had hired the mafia. They had lied about it to investigators. They had concealed it from the Warren Commission.
But the documents still do not answer the fundamental questions. Did the CIA-mafia connection have anything to do with JFK's assassination? No credible evidence supports that theory. Nothing substantial has ever linked the CIA's plotting against Castro to the Kennedy assassination.
But the connection did not have to be direct to be poisonous. The CIA's decision to hire mobsters created a situation where the mafia had leverage over the U.S. government, CIA operatives had to protect mob contacts from prosecution, Bobby Kennedy's war on organized crime was sabotaged by his own government, critical information was hidden from assassination investigators, and potential suspects could not be properly investigated.
The reason Castro knew that the CIA had plotted with Giancana and Roselli to kill him may have influenced Cuban actions. Some theories suggest Castro ordered Kennedy's death in retaliation, but there is a simpler explanation for why the CIA-mafia connection matters.
It shows how secret operations corrupt legitimate government functions. It shows how intelligence agencies create conflicts of interest that undermine justice. It shows how classified programs poison investigations that need transparency.
Robert Kennedy spent three years prosecuting organized crime. Convictions rose by 800 percent. Congress passed seven anti-crime laws. The Justice Department indicted 171 racketeers in the first six months of 1963. But Bobby could not fully prosecute the men most deeply involved in criminal enterprises because those same men were assets of the CIA.
The FBI warned that any CIA-mafia arrangement could subject the U.S. federal government to underworld blackmail. That is exactly what happened. When the Warren Commission investigated Kennedy's assassination, the CIA withheld information not because the CIA killed Kennedy, but because revealing the mafia connection would expose illegal operations.
The result was a half-truth investigation. Critical leads went unexplored. Potential connections were hidden. For 12 years, Americans did not know the CIA had hired the mafia. For 12 years, conspiracy theories flourished in the absence of truth. And when the truth finally emerged in 1975, it only fueled more suspicion. Because if the CIA had lied about hiring the mafia, what else were they lying about?
The JFK files suggest Giancana and Roselli believed that cooperating with the government in such a high-risk venture as Castro's assassination would earn them a get-out-of-jail-free card that would keep the feds off their backs as they pursued criminal activity at home. For a time, their arrangement seemed to work. The mobsters were right. Their CIA connection did protect them for a while. But in the end, their arrangement with the government got two of them killed and it poisoned American history.
Let us be clear about what we know and what we do not. What we know: the CIA recruited mafia leaders to kill Castro starting in September 1960. The plots continued through 1963 with Kennedy administration knowledge and pressure. Robert Kennedy waged an unprecedented war on organized crime from 1961 to 1963. The CIA hid the mafia connection from the Warren Commission. Sam Giancana and Johnny Roselli were both murdered after being called to testify about the plots. The CIA's deception undermined multiple investigations.
What we do not know: whether the CIA-mafia connection had any role in JFK's assassination, why Giancana and Roselli were killed, whether it was mob internal politics or silencing witnesses, the full extent of what Trafficante knew and did, and whether any CIA officers genuinely believed the mobsters could have been involved in Dallas.
Declassified documents in 2017 revealed that U.S. Attorney General Robert Kennedy hesitated to recruit the mafia for assassination attempts on Castro due to his push against organized crime. Bobby Kennedy knew about the plots by 1962. He objected, but he could not stop them. The operations had been authorized before he became attorney general. The Cold War demanded Castro's removal, and Bobby's own brother, the president, wanted results.
So the attorney general, who built his career fighting the mafia, had to tolerate his government hiring them. The paradox is perfect. The same administration that declared war on organized crime also made organized crime a partner in covert operations.
One historian put it simply: the CIA and the Cosa Nostra were different sides of the same coin. Both operated in secrecy. Both used violence. Both considered themselves above the law. The only difference was which flag they claimed to serve.
Through the prism of these two mobsters, a much larger portrait emerges of America's top spying agency spinning out of control when the nation most needed its vigilance. The CIA built a secret camp next door to the Miami Zoo for anti-Castro operations. They developed James Bond-like killing devices. They conducted midnight boat raids from Florida with Cuban exiles carrying bombs and long-range rifles.
Historically, the CIA's murder plot against Castro marked America's first foray into the assassination business. And they did it all while lying to Congress, deceiving the attorney general, and compromising criminal investigations.
The CIA-mafia alliance did not kill John F. Kennedy. Lee Harvey Oswald did that. But the alliance killed something else: the ability to fully investigate Kennedy's murder, because the government that should have been searching for truth was too busy hiding its own crimes.
The Church Committee noted that the CIA had deliberately kept such plots from the Warren Commission, hinting at the possibility that CIA know-how or assets could have intersected with mafia networks. We will never know what the Warren Commission might have discovered if the CIA had told the truth. We will never know what leads they might have followed if they had known about Giancana, Roselli, and Trafficante's government connections.
Instead, we have 60 years of conspiracy theories, reasonable skepticism about official narratives, and justified mistrust of institutions that lied. The CIA-mafia plots did not create those conspiracy theories. The CIA's decision to hide them did.
Sometimes the real conspiracy is not who pulled the trigger. It is who poisoned the investigation afterward. Because history is not just about what happened. It is about what we were allowed to know. And for 60 years, we were not allowed to know the truth about JFK's secret war.