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When the American government asked the Mafia for a favor: The assassination of Cuban leader Fidel Castro

By David Amoruso

Politics is a dirty game. Always has been, always will be. But most of the dirt is kept hidden from view. Skeletons stay in the closet. Sometimes, however, the dirt comes out because it is so mind-blowing, it cannot be kept secret. Like the time the United States government recruited the American Mafia to kill Cuban leader Fidel Castro. It was a favor too good to refuse, but also a secret too useful to keep silent.

The year was 1959 and the world was gripped by the Cold War. The United States were battling the Soviet Union for the title of most powerful nation on earth. Both countries had arisen victorious from World War II and were looking to expand their influence on the globe.

Governments were bribed and bought by both sides. Billions in money, weapons, and food flowed from the United States and Soviet Union to countries across the planet. Leaders of nations no one had ever heard about suddenly found themselves flush with riches and surrounded by praise and requests for loyalty.

Soon, these leaders found they could get away with true horrors as long as they stayed loyal to one of these two entities. Citizens in countries in Africa and South America paid for this loyalty in blood and with their lives.

Gamblers of the Caribbean

But things weren’t bad for everyone. In Cuba, out there in the Caribbean, drinking rum, surrounded by beautiful ladies, placing high stakes bets at the most luxurious casinos the world had ever seen, life was good. Each year, planes ferried tons of Americans from New York and Miami into Havana, Cuba, to enjoy the pleasant climate and exotic nightlife.

The whole place was built and run by organized crime. Mobsters from around the United States had invested heavily in Cuba’s casino business and were making money hand over fist. It was considered their playground. They were friendly with Fulgencio Batista, the nation’s president, and, effectively, had a license to get away with anything, including murder.

As tourists gambled their earnings away and enjoyed the countless parties, Batista was doing his own fair share of killing while he was hard at work keeping his citizens under his thumb. Uprisings were frequent and were beginning to erode his grip on power. Who needed the backing of his people, he must’ve thought, when he was backed by the military might of the United States?

Presidente Fidel

A rebellion led by Fidel Castro was getting ever closer to overthrowing Batista’s government and establishing his own. Castro had been fighting for almost a decade now. His violent actions against the Batista government earned him a 15-year prison sentence of which he only served 2 years. After his release from jail in 1955, Castro was seen as the face of the rebellion and continued to use bombs and other violent acts to undermine Batista’s regime. By 1958, Castro and his ragtag crew of revolutionaries were marching on Havana.

The United States knew they could no longer support Batista and maintain their grip on Cuba, so they ousted him in favor of another man who would continue to do their bidding. They were happy with any man but Castro. They feared he was a socialist and would side with the Soviet Union.

Unfortunately for them, Castro had become a powerful and beloved figure among a large percentage of the population which had suffered under Batista’s rule. Castro officially assumed power on February 16, 1959, when he was sworn in as Prime Minister of Cuba.

Kicking out the Mafia

The American Mafia had played it less strict than the U.S. government, opting to support both Batista and Castro in a bid to hedge its bets. This proved futile when Castro made it known he intended to put an end to the mob’s booming casino business in Cuba. Brothels and casinos were shut down and the new regime quickly made it known it had no intention of working with the Mafia.

Tampa Mafia boss Santo Trafficante Jr. was in Havana, Cuba, during the early days of Castro’s reign. He testified the following about that time: “Well, even before Castro reached Havana […] and he had a walkathon […] from the mountains to Havana […] he kept saying the casinos would close, statements to that effect, the casinos close without even being notified officially to close. Everything was in turmoil. There was people all over the streets, breaking into homes, there was complete enmity and the only thing at that time was to try and stay alive.”

Trafficante was doing a bit more than just staying alive. He decided to stay in Havana to oversee his casinos and vast interests there and keep business going. Most of his underworld colleagues had already left for their U.S. hometowns. It turned out they made the right choice as those that stayed behind found out soon enough. Castro’s forces imprisoned Trafficante, gambling boss Dino Cellini, and Meyer Lansky’s brother Jake on various trumped up charges. The message was clear: They were not welcome anymore.

The enemy of my enemy is my friend

By kicking the mob out of Cuba, Castro could add one more ruthless enemy to his long list of groups and people that wanted him dead. Nothing unusual there. He would not lose any sleep over a bunch of gangsters wanting his head. He now operated on another level, with a Navy and an Army, an entire country at his command. Why worry about the mob when he had much more dangerous enemies?

Indeed. But the biggest threat did not come from the American Mafia, but from the American government. With his actions, he effectively brought the United States government and Mafia closer together. They now shared a common enemy. Though the United States was known to bribe its way to power and influence, it wasn’t averse to more severe tactics if the financial incentive proved insufficient. Assassination was deemed a proper and necessary tool by many in the government if it meant it kept Americans safe from harm.

Of course, executing an assassination is one thing, but being known for it around the world would end up doing the country more harm than good. And thus, the U.S. government and its CIA began planning ways to take out Castro without the murder leading back to them.

An offer they couldn’t refuse

Fidel Castro needed to die. Both the United States government and the American Mafia agreed on that part without even having discussed the matter. From a political standpoint, the U.S. faced a new front in the war against communism right on its own doorstep. For the mob bosses involved in the matter it was much simpler: Castro fucked them over and they wanted revenge.

One should realize, that these mobsters were not like those that operate the streets of New York and Chicago today, rather they had power and wealth at levels comparable to that of Mexican drug cartel kingpins operating nowadays in Sinaloa and Juarez. They had politicians and judges in their back pocket, police commissioners and officers on their payroll. An army of hundreds of violent men at their beck and call. The American Mafia back then was at the height of its power and a force to be reckoned with.

Robert Maheu was all well aware of this. Once a member of the FBI and also a former CIA collaborator, Maheu had a large network of contacts on both sides of the law. He now worked as a man who could get things done for a wide variety of people. He was known as the ultimate fixer.

Still, it must’ve been weird when Jim O’Connell, an official at the Security Office, contacted him on behalf of deputy CIA director Richard M. Bissell, and asked him a simple, yet mindboggling question: Which mobster would he recommend for the killing of Fidel Castro?

“Johnny Rosselli,” Maheu answered without skipping a beat.

“Then we’ll give him the job,” O’Connell replied.

Johnny Rosselli the enterprising hitman

Johnny Rosselli (left) was a well-known hoodlum at the time. He was a close friend of Chicago mob boss Al Capone, who sent him to the West Coast to represent the crime family’s interests there. He settled in Los Angeles where he became close to local mob boss Jack Dragna.

The move was typical of Rosselli’s career as he had been moving around his entire life. Born in 1905 as Filippo Sacco in Italy, his parents took him to the United States in 1911 where they found a home in Boston. Sacco was a troubled teenager and when his criminal activities brought too much unwanted attention from the cops he fled to New York City. The change of scenery helped alleviate the pressure from law enforcement, but did little to stop his criminal behavior and - under the assumed name of John Stewart - he made a reputation as a capable gangster amongst his peers.

By the time he reached 18, he was working for Al Capone as a driver and bodyguard. His new boss did not like his name though, preferring something more Italian. Thus, Johnny Rosselli was born. Handpicked by Sacco himself as the latest change to his adventurous life.

When Maheu dropped Rosselli’s name as the preferred man to whack Castro he based his decision on Rosselli’s reputation for murder, his nationwide connections, and his prominent position in the American Mafia. He was a longstanding powerful figure in the Chicago Outfit with influence in several other families around the country and someone who himself had had some illegal interests in Cuba. Rosselli was the man you needed to put this whole thing in play.

The meeting between the Mafia and the CIA

At first, Rosselli was reluctant to get involved. With such a request he must’ve had a feeling it might be some weird set-up. Maheu told him that his “clients” were willing to pay the mob $150,000 for Castro’s death. When the mobster asked who was behind the plot, Maheu answered that it was an American corporation that had suffered losses in Cuba.

Unsatisfied with the response, Rosselli replied: “Well, if it isn’t an official matter, I’m not going to offer my services.”

With negotiations at a standstill, Maheu got O’Connell to join him on a trip to New York City. On September 14, 1960, Maheu introduced the government official to Rosselli and things finally got moving again. He refused to take any money, though. Known for his patriotic feelings, the mob killer felt it was his duty to his country.

With Rosselli on board, the ball began rolling. As a member of the Chicago Outfit, Rosselli was obligated to notify his boss Sam Giancana about the offer. Even if he wasn’t, this was something he knew Giancana would want in on. As well as another powerful mob leader, Santo Trafficante from Tampa, Florida.

Giancana, Rosselli, and Trafficante all had had considerable business interests in Cuba before Castro’s rise to power. A mix of legal and illegal activities made them a boatload of cash. And though they had lost their businesses on the island, they still maintained in contact with scores of associates that stayed behind. Men and women who might be willing to help them with their deadly plan.  

Three American mobsters plotting the murder of a foreign president

Confronted with the request to have Castro murdered, the three criminal masterminds went to work. First, they began plotting and thinking out various ways to kill him. The CIA suggested a street corner ambush in Havana in which a machine-gunner would execute the Cuban leader in an onslaught of bullets. This sounded like a pretty good idea until they realized Castro’s security system would make such an ambush impossible. Giancana (right) had told them beforehand it would be impossible to recruit anyone for the job as the chance of survival would be close to zero.

Rosselli then thought of a way to execute the murder while still giving the assassin time to make his getaway: poison pills. Giancana also preferred this method. The head of the CIA’s laboratories then created such a poisonous capsule, which would leave no traces. Once the deadly pills were finished, Rosselli took them to Trafficante in Florida in March of 1961, who would pass them on to a Cuban associate who would see to it that someone close to Castro would put them in his drink.

Then, they waited. And waited. They waited for a perfect moment that never came.

On April 17, 1961, Brigade 2506, a counter-revolutionary paramilitary group made up of Cuban exiles trained and funded by the CIA launched an invasion into Cuba. With the backing of the United States government the group felt empowered as they stormed the beaches. But Castro’s forces proved too well-prepared for such an attack. After three days of intense fighting, Brigade 2506 was defeated. Over a hundred of their men had been killed by Castro’s military.

After the Bay of Pigs fiasco the mood sobered down. The United States had fired its best shot so far using all its bells and whistles and had failed miserably. But despite the failure, the CIA and Rosselli never quite quit their plotting.

“I flushed them down the toilet”

Suspicions arose about the willingness of Giancana and Trafficante (left) to execute the murder plot. Giancana was angry at the Kennedys for increased pressure from the Justice Department on the Outfit. Figuring that if they were screwing him, he’d screw them right back, he simply played along with the CIA plotters without ever getting anything done.

Trafficante also decided to play along and simply smile and nod at the CIA officers. “Those crazy people,” he allegedly told his lawyer. “They gave me some pills to kill Castro. I just flushed them down the toilet. Nothing ever came of it.”

Other reports have surfaced indicating that Trafficante not only blocked the plot to assassinate Castro, but actively worked with him in order to continue gambling operations in Havana – CIA documents support this theory.

What Giancana and Trafficante lacked in loyalty to the cause, Rosselli had in abundance. And when the CIA came knocking on his door to go a second round, he was eagerly awaiting.

Colonel Rosselli

William Harvey had taken up where his colleagues had left off. On April 8, 1962, he met with Rosselli and told him that this time he was to leave Giancana and Trafficante out of the plot. Once more Rosselli was given several poison pills to pass on to a Cuban exile.

Both men immediately grew a strong bond. They shared a patriotic love for their country and both would do anything to protect it against enemies from abroad. Rosselli would have dinner with Harvey’s family, bringing gifts for his children.

Harvey trusted the mob hitman. He took him onto the CIA base in Miami and introduced him to other CIA agents there. One of them noted that Harvey bragged about his friendship with Rosselli. He would say things like: “These were guys that got things done,” the CIA operative is quoted as saying in Gus Russo’s The Outfit. Rosselli’s presence was so common that he was given the nickname “Colonel Rosselli.” He truly became a part of the team, CIA operatives said.

Despite their efforts, Harvey and Rosselli never came close to killing Castro. None of their pills ever reached Castro’s glass of wine or bowl of soup. Before the year was up, Harvey and Rosselli moved on to other projects, bringing an end to the cooperation between the Mafia and the CIA.

End Games

This unholy alliance between the CIA and a bunch of notorious mob bosses proved too juicy to be kept secret. As the FBI cracked down hard on La Cosa Nostra and its various top hoodlums, those involved in the Cuban Project, also known as Operation Mongoose, became agitated. First the government asked for their help and now they want to take us down? First they need our violent skillset and now we are being sent to prison for it?

It was a hypocrisy that could not remain hidden.

Out of spite, Rosselli leaked the story to columnist Jack Anderson under the provision that he not use any of the names. It was the first time this story was published for the public and it made members of the government very nervous. He didn’t care. It was the story of a lifetime and one he was willing to sell to Hollywood as well.

By the 1970s, much of the tale became known after journalists began to dig deeper and deeper into the American government’s dirty operations and the Church Committee began holding hearings on various related matters.

Johnny Rosselli testified before the Committee on June 24 and September 22 in 1975 about his involvement in the CIA plan to kill Castro. Giancana was called to testify as well, but days before he was to answer questions an unknown assassin shot and killed the fallen mob boss in the basement of his home. It is believed Giancana trusted his killer as no signs of a break-in were found.

The writing was on the wall and Rosselli and his pals knew it. After a dinner with Los Angeles mobster Jimmy Fratianno in May of 1976, his friend warned him. “Be careful, will you? This thing of ours is treacherous. You never know when you’re going to make the hit list. Don’t let Trafficante or [Chicago mob boss Jackie] Cerone set you up,” he told Rosselli.

Two months later, the 71-year-old mobster borrowed his sister’s car and drove off for a round of golf. He was never seen alive again. Sometime later, an oil drum washed ashore on the Florida coast. Inside, they found Rosselli’s dismembered body. Investigators concluded he had been strangled to death.

Where are they now?

  • Robert Maheu: Before and during his work for the CIA, Maheu worked for eccentric billionaire Howard Hughes. This story was the focus of his 1992 autobiography entitled Next to Hughes: Behind the Power and Tragic Downfall of Howard Hughes by His Closest Advisor. Maheu died of natural causes in 2008 at the age of 90 in Las Vegas.
  • William Harvey: After quitting Operation Mongoose, Harvey took to booze. As he drank more and more, his health deteriorated. He retired from the CIA in 1969. He returned to the days of the Cuban Project when he testified before the Church Committee in 1975. On June 9, 1976, he passed away of natural causes at the age of 60.
  • Santo Trafficante Jr.: Despite a life of crime atop the Florida underworld and connections to Mafia families throughout the United States, Trafficante was never convicted. He died on March 17, 1987 at the age of 72.
  • Fidel Castro: In a weird twist, Castro outlived all of the participants in this Mafia-CIA plot to murder him. Though the cause of death was never disclosed, Cuban state television announced that he had died on the night of November 25, 2016, at the age of 90.

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