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When Fidel Castro took control of Cuba in 1959, he managed to anger possibly the two most powerful organizations in the United States at the time, the U.S. government and the mafia. It seemed only natural that the two would team up to try and depose him.

The enterprise started in August of 1960. The CIA approached Beverly Hills private detective named Robert Maheu and asked him to help them with their plan to kill Castro by contacting his old friend Johnny Rosselli. Maheu was an ex-FBI agent who the CIA used to handle delicate matters where they didn’t want to have an Agency or government person get caught. Johnny Rosselli was one of the heads of the Chicago Outfit, the most powerful organized crime group in the country. He split his time between Los Angeles and Las Vegas, handling all of the Outfit’s west coast operations. For all of his criminal dealings, Rosselli was also an ardent patriot who loved his country.

Operation Pluto, as the assassination and ensuing invasion was deemed, had the heavy backing of Vice President (and presidential candidate) Richard M. Nixon. Nixon wanted the overthrow of Castro and the taking back of Cuba to happen before October of 1960 in order to give the administration a major victory before the election in November. The original plan was to use specially trained Cuban exiles to go in and kill Castro, but the administration also wanted to hire some professionals too, to make sure they got the desired results.

After being contacted by the CIA, Maheu and Rosselli met at the Brown Derby restaurant in L.A. Surrounded by Hollywood people pitching film scripts, Maheu pitched the idea of political assassination. Rosselli was initially reluctant to the idea, but after Maheu compared Castro to Hitler and talked about how the mission was necessary to protect the country, Rosselli agreed. Rosselli figured that not only was he doing he doing a service for his country, but also if his organized crime friends ever needed a little help, the government would be in their debt. Maheu was also authorized to offer the mob $150,000 to do the job, but Rosselli insisted that they would do it for free.

Rosselli took the plan back to his partners in Chicago, who tentatively OK’ed the plan. The other bosses were interested because, with Castro gone, the mob could reopen the casinos they controlled in Cuba. Sam Giancana was especially interested in the deal, reportedly declaring “We’ll have the fucking government by the ass.” Rosselli and Giancana flew to Miami where they met Maheu and officially agreed to the deal. The trio also welcomed to their inner circle Santo Trafficante, the mob boss of Miami, thanks to his contacts with anti-Castro dissidents in Cuba. The men began trolling the streets of “Little Havana” seeking Cuban exile accomplices. The mob needed to find a man that they could sneak into Cuba and poison Castro with special pills that had been provided to them by the CIA.

While all of this was going on, Rosselli and Giancana were still under constant surveillance by the FBI for their ties to organized crime. Maheu did his best to try and get rid of the agents, but he obviously couldn’t tell them that he was secretly working for the CIA, so the watching continued. Ironically, Rosselli and Giancana ended up having to use their well-honed surveillance dodging skills to try and lose their FBI watchdogs in order to meet their CIA handlers. This ended up all for naught, as FBI director J. Edgar Hoover caught wind of the operation anyway. He kept his mouth shut, but saved the information for future blackmail purposes against Allen Dulles, the director of the CIA.

As election day neared, President Eisenhower refused to green light the operation in time to help Nixon. As a result, the operation quickly lost steam and was never even attempted. The assassination plot was cancelled, but the plan for an invasion continued. After the Bay of Pigs invasion failed, Johnny Rosselli again offered his services to the CIA by helping out Operation Mongoose. He often visited the Mongoose base, where the soldiers knew him as “Colonel Rosselli.” The 57 year-old gangster also commanded speedboats across the straights to Cuba in dangerous nighttime runs, infiltrating shooters onto the island. His boats were sunk several different times by Cuban patrols, but he always found a way to make it out alive. On one occasion he drifted for days before being rescued by colleagues who had given him up for dead. Throughout all of this, Johnny Rosselli was still under investigation by the FBI for the crimes he had already committed against the United States.

The Outfit by Gus Russo

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