At 11:30 a.m. on March 13th, 1961, a man calling himself John Rston walked into the boom boom room at the Fontlow Hotel in Miami Beach. He wasn’t alone. Across the table sat three of the most dangerous men in America. Sam Momo Jankana, boss of the Chicago outfit, Sto. Traficane Jr., Florida’s most powerful mobster.

and Johnny Rosselli, Hollywood suave fixer with ties to Vegas, the film industry, and multiple murders. What happened in that room would change American history. A CIA operative named Jim Okonnell placed an envelope on the table. Inside were poison pills, poison designed to kill Fidel Castro and 10,000 in cash. The United States government was hiring the mafia to commit murder.

But here’s where the story gets truly insane. At the exact same moment this meeting was taking place, Robert F. Kennedy, the president’s brother and US attorney general, was launching the most aggressive campaign against organized crime in American history. Prosecutions for racketeering by his organized crime section in the Justice Department rose by 300% above 1961, and convictions of organized criminals grew by 350%.

Think about that. One part of the Kennedy administration was prosecuting the mafia. Another part was paying them to kill a foreign leader. The right hand fighting what the left hand hired. If you want to understand one of the most twisted contradictions in Cold War history and how it poisoned every investigation into JFK’s assassination, please hit that like button.

It helps us share more forgotten stories like this. And please subscribe if you haven’t already. Back to March 1961. The story begins not with the Kennedys, but with Dwight Eisenhower. In 1959, Fidel Castro seized power in Cuba. He nationalized American businesses. He shut down the casinos and he turned Cuba into a Soviet ally 90 m from Florida.

For the CIA, Castro was a communist threat. For the mafia, he was something worse. He’d cost them millions. Before Castro, Havana was the jewel of organized crimes empire. The mafia had lucrative investments in Cuban casinos. Sam Gianana ran operations there. Sto. Trafocante controlled much of Havana’s underworld.

Johnny Roselli had connections throughout the Caribbean gambling scene. When Castro shut it all down, the mobsters lost fortunes. Jana had lost out on a shrimp boat operation he was trying to build, as well as on a plan to offer gambling on tourist boats traveling from Miami to Cuba. As an heir to Jana’s estate, his daughter could say that they lost everything to Fidel Castro.

The mere mention of Castro<unk>’s name in the Gianana house would make him flip his lid. The CIA recognized an opportunity. The mafia wanted Castro dead. The CIA wanted Castro dead. Why not work together? In September 1960, Momo Salvatorei Jankana, a successor of Al Capone in the Chicago outfit, and Miami syndicate leader San.

Trafocante, who were both on the FBI’s 10 most wanted list at that time, were indirectly contacted by the CIA about the possibility of Fidel Castro<unk>’s assassination. The CIA couldn’t approach the mobsters directly, too risky, too obvious. So they used an intermediary, Robert Mahu, a former FBI agent who worked for Howard Hughes.

On September 14th, 1960, Mayhew met with Rosselli in a New York City hotel and offered him 150,000 for the removal of Castro. Johnny Roselli was the perfect go-between. Roselli was known as Handsome Johnny. He was a man who dated a lot of actresses, Lana Turner, Donna Reed. He had Hollywood connections, Vegas connections, mafia connections, and he had something else.

A twisted sense of patriotism. Roselli was an Italian immigrant. He’d made his fortune in America. And 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 the efforts to keep CIA involvement a secret, the mobsters quickly figured out that CIA was involved. But they had another motive. They thought if they helped try to kill Castro for the CIA, they would get a get out of jail free card. John Connor was convinced by Frank Sinatra that JFK would go easy on them. This assumption would prove catastrophically wrong.

On March 12th, 1961, the plan moved forward. William Harvey arranged for CIA operative Jim Okonnell to meet Sam Jon Kana, Santo Trafocante, Johnny Rosselli, and Robert Mayu at the FontinBlow Hotel. Okonnell 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, someone with access to his food or drinks. Poison him. Make it look natural. It was Jana who suggested poison pills as a means to Dr. Castro’s food or drinks. Such pills were given to Jana’s nominee named Juan Orta. Jana recommended Orta as being an official in the Cuban government who had 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. Accordingly, he was laying 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 weren’t stupid. They were creating leverage, insurance. If the government ever came after them, they could threaten to expose the CIA’s role in plotting murder. And they would need that insurance because while the CIA was recruiting mobsters in Miami, Robert Kennedy was planning to destroy them in Washington.

January 20th, 1961, John F. Kennedy was inaugurated as president. His first major appointment, his 35-year-old brother Robert as attorney general. The appointment was controversial. Bobby Kennedy had never argued a case in court. He’d never tried a criminal trial. Critics called it nepotism.

But Robert Kennedy had something more important than courtroom experience. He had obsession. Previously, individual gang members had been investigated for crimes. But this was the first time the government had 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, and Kennedy had opened federal investigative bureaus in cities outside of Washington charged with gathering information on racketeers. Kennedy’s strategy was unprecedented. Kennedy was the first attorney general to encourage the government’s investigative agencies, the DOJ, the FBI, the IRS, and others 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 didn’t exist. Hoover was more interested in catching communists. He was interested in bank robberies, autothefts, things where the media made him look good when he went up to Congress for money. Kennedy forced Hoover’s hand.

He coordinated all 26 federal law enforcement agencies. He opened files on one top racketeers. He created task forces. He got wiretaps. He seized financial records and he went after specific targets. Jimmy Hafa, Teamsters Union president. Sam Jana, Chicago boss. Sto. Trafocante, Florida Don Carlos Marello, New Orleans Kingpin. The very men the CIA was working with.

In May 1961, Bobby announced his first drive to root out raketeers in Chicago with a special prosecutions unit assigned to bust an automobile theft ring allegedly involving suspected lone shark Leo Rugenorf, mob triggerman, Felix Milwaukee Phil, Aldericio and Sam Betaglia and Joseph Joe Pig Pignatello, a courier for mob under boss Sam Gianana. Think about the timing.

made on 1961. Two months after Okonnell gave Jana poison pills to kill Castro, the CIA was paying Jana, the Justice Department was investigating him. In 1961 and 1962, Congress approved seven anti-rime laws authorized by the attorney general. In the first 6 months of 1963, 171 racketeers were indicted, as against 24 in 1960.

During his term, convictions against members of organized crime rose by 800%. Bobby Kennedy wasn’t playing. This was total war, and the mafia knew it. Despite the foot dragging of FBI director J. Edgar Hoover, the Justice Department indicted a 116 members of the mob. But here’s where it gets complicated.

The FBI didn’t 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 when a technician illegally wiretapping a Las Vegas entertainer’s telephone for John Kana was arrested and sought help from the CIA.

CIA became involved and succeeded in having charges dropped, but FBI investigated the matter. As 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 US 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 John Kana or Robert Mahu then or in the future. The CIA’s secret alliance was sabotaging Bobby’s war on organized crime. The mobsters knew it and they exploited it several times and with varying degrees of success.

Jean Connor and Roselli sought to use the CIA relationship to their personal advantage. In 1963, when Sam John Kana sued the FBI to halt its surveillance, Jan Kana was required to take the witness stand and was legally subject to cross-examination. Perhaps because of Gianana’s role in the Castro matter, the Department of Justice reportedly ordered the prosecutor not to question Jon Kana.

The mobster who worked for the CIA couldn’t be questioned under oath because he might expose the plot. Meanwhile, the plot itself was failing spectacularly. Allegedly, after several unsuccessful attempts to introduce the poison into Castro’s food, Orta abruptly demanded to be led out of the mission, handing over the job to another unnamed participant.

The first poison plot failed, so 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 Johnny Roselli that Santos Trafocante and Sam Gianana had to cease involvement in the project to kill Castro. 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 Verona, who would forward the pills to a chef in a restaurant frequented by Castro. This suggestion was adopted, although the chef placed the pills in the 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. There was a lab at the CIA actually exploring ideas like exploding cigars, gadgets that could be killing devices, exploding cigars, poison diving suits, toxic pens, chemical sprays to make Castro’s beard fall out, hoping humiliation would destroy his image.

One attempt involved a chemical with comparable effects to the drug 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 while on air. All of it failed. It became like the gang that couldn’t shoot straight. According to CIA director Richard Helms, Kennedy administration officials exerted a 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 in 1960 1965. But Cuban intelligence chief Fabian Escalante had a different count. Escalante estimated the number of assassination schemes or actual attempts by the Central Intelligence Agency to be 638 and split them among US administrations as follows. Dwight D.

Eisenhower, 38. John F. Kennedy, 42. 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 Trafocante was playing both sides. Santo Trafocante Jr.

was the Florida Dawn who joined Jana and Roseli in the CIA plot, but may have been a double agent for Castro. Think about that. 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 that 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 November 22nd, 1963, Dallas, Texas, 12:30 p.m. John F. Kennedy was shot.

As the men were coming out of the meeting about the CIA Castro plot, they were given terrible news. President Kennedy had been assassinated. Minutes before hearing the shooting of John F. Kennedy RFI 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, “Did his war on organized crime get his brother killed?” On November 22nd, 1963, rumors began to circulate that Gian Kana and other gang bosses such as Santos Trafocante, Carlos Marello, and Johnny Roselli were involved in the crime.

The Warren Commission investigated. They interviewed thousands of witnesses. They examined ballistics. They analyzed Oswald’s background. But there was one thing they didn’t know. The CIA didn’t tell them. The Church Committee 1975 finally revealed this to the public, noting CIA had deliberately kept such plots from the Warren Commission.

Why? [snorts] 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 US 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, from the American people.

The secret festered. CIA director Alan 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 24th and September 22th, 1975, Rosselli testified before the US Senate Select Committee about the CIA plan to kill Castro.

Shortly before Rosselli testified, an unknown person shot and killed Jan Kana in the basement of his Illinois home. This happened just days before Django was to testify before the committee. Sam Jano was murdered on June 19th, 1975. Seven shots to the head and neck, one 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.

Junkana was silenced before he could tell Congress what he knew. Roselli testified anyway. He told the church committee about the poison pills, about the CIA meetings, about the failed attempts. Then in July 1976, Roselli disappeared. On August 3rd, Roselli was missing. On August 7th, 1976, fishermen discovered Roselli’s body stuffed in a 55gallon oil drum floating in Biscane Bay near Miami.

He had been strangled, shot, 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 beguiled 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 Omera.

Two of the three mobsters recruited by the CIA were now dead, murdered within 13 months of each other. Both killed after being called to testify about the Castro plots. One fact was indisputable. Santo Traficante was the only survivor of the three mobsters recruited by the CIA to kill Fidel Castro.

Trafocante 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 don’t 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 didn’t have to be direct to be poisonous. The CIA’s decision to hire mobsters created a situation where one, the mafia had leverage over the US government. Two, CIA operatives had to protect mob contacts from prosecution. Three, Bobby Kennedy’s war on organized crime was sabotaged by his own government.

Four, critical information was hidden from assassination investigators. Five, potential suspects couldn’t be properly investigated. The reason Castro knew that the CIA had plotted with Chicago mobster Sam Gianana and Hollywood boss John Rosselli to kill him may have influenced Cuban actions. Some theories suggest Castro ordered Kennedy’s death in retaliation, but there’s 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%.

Congress passed seven anti-rime laws. The Justice Department indicted 171 racketeers in the first 6 months of 1963. But Bobby couldn’t 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 US federal government to underworld blackmail.

That’s 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, a halftruth investigation. Critical leads unexplored, potential connections hidden.

For 12 years, Americans didn’t 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 John Kana and Roselli 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. 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’s be clear about what we know and what we don’t.

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 1963. The CIA hid the mafia connection from the Warren Commission. Sam Gianana and Johnny Roseli were both murdered after being called to testify about the plots.

The CIA’s deception undermined multiple investigations. What we don’t know whether the CIA mafia connection had any role in JFK’s assassination, why Jon Kana and Roselli were killed, mob internal politics or silencing witnesses, the full extent of what Trafocante knew and did. Whether any CIA officers genuinely believe the mobsters could have been involved in Dallas declassified documents in 2017 revealed that US Attorney General Robert Kennedy hesitated to recruit the mafia and assassination attempts on Castro due

to his push against organized crime. Bobby Kennedy knew about the plots by 1962. He objected, but he couldn’t 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, CIA and the Kosanostra 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 feray 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 didn’t 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 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’ll never know what the Warren Commission might have discovered if the CIA had told the truth. We’ll never know what leads they might have followed if they’d known about Jan Kana Roselli and Trafocante’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 didn’t create those conspiracy theories. The CIA’s decision to hide them did. If this story made you rethink what you thought you knew about the Kennedy assassination and the institutions meant to protect us, do something simple. Hit that like button. Every like helps YouTube share this investigation with people who need to understand how secret operations corrupt public truth.

Don’t forget to subscribe and turn on notifications so you never miss our next deep dive into hidden history. Every day we uncover stories buried in classified files. Tales of secret alliances, institutional deception and the price of cold war paranoia. Real documents, real conspiracies, real history. And now I want to hear from you.

Drop a comment and tell us where you’re watching from. Are you in the US, Europe, Latin America, somewhere else? Our community spans the globe and your voice matters. Share your thoughts on government secrecy and the limits of covert operations. When does national security justify alliances with criminals? Where’s the line? Let us know you’re here demanding accountability and refusing to accept easy answers.

Thank you for watching and thank you for understanding that sometimes the real conspiracy isn’t who pulled the trigger, it’s who poisoned the investigation afterward. Because history isn’t just about what happened. It’s about what we were allowed to know. And for 60 years, we weren’t allowed to know the truth about JFK’s secret war.

Did the CIA Betray RFK by Hiring the Mafia? DD

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