September 14, 1960
New York City
“Handsome Johnny” Roselli stared at the man across the table at the Plaza Hotel restaurant. In his line of business, he didn’t often meet men as well dressed as he was, but Robert Maheu, a former FBI agent, was a fixer these days, a man with big connections. Both men apparently knew it paid to look sharp.
Maheu was a freelancer, currently the middleman between the CIA and an assortment of mob kingpins. And at lunch, Maheu made Roselli an offer that he knew the gangster couldn’t refuse.
Maheu said he was working for a client who represented several “international business firms which were suffering heavy financial losses in Cuba as a result of Castro’s actions.”
His client was “convinced that Castro’s removal was the answer to their problem” and was willing to “pay a price of $150,000 [over $1.5 million today] for its successful accomplishment.”
Roselli moved his head a little closer. Had he heard the guy right? “Removal” of a foreign leader? Christ! Kill Castro. For a lot of dough.
Was this a setup? It sounded really risky.
His gut reaction was not to get involved.
But Maheu was persuasive—one of the reasons the CIA’s Office of Security had called on him. He wouldn’t give up until he had Roselli on board.
Maheu was smart as a whip and a master salesman, a natural for black ops. Born in Maine, he joined the FBI in 1940, a year before the United States entered World War II.
During the war, he posed as a Nazi-sympathizing Canadian and infiltrated New York’s German American Bund, passing disinformation to spies who were eventually arrested.
In 1947, Maheu left the FBI to become a private detective. The CIA was his principal client, giving him steady work on clear-cut assignments—dirty work the agency could not officially be involved in.
The CIA work won him contracts with billionaire Howard Hughes, an aviation giant and Hollywood mogul who had gone into luxurious seclusion, mostly in Las Vegas. In the late 1950s, Maheu worked for Hughes, intimidating blackmailers, tailing men who romanced Hughes’s actress girlfriend, and collecting information on business rivals.
Maheu had met Roselli, the Chicago mob’s front man in Las Vegas, through Howard Hughes. An impeccably well-dressed ladies’ man, Roselli had a long history with organized crime.
Roselli was like a character from a mob movie. His family emigrated from Italy to the United States when he was six years old.
Roselli dropped out of junior high and drifted to New York and then Chicago, where he fell in with bootleggers and mafiosi. He gained their trust. They sent him to Los Angeles in the 1930s to help develop the Chicago family’s gambling and labor rackets.
He was a good-looking guy who dressed like a movie star, with his slicked-back hair, tailored suits, and sunglasses. But he was no actor. Roselli was a real-life gangster in Hollywood. And his mob credentials gave him a shady cachet; he moved easily among the Los Angeles social set.
But he pushed his luck, and in 1943 he was convicted of extorting money from movie studios and theater chains. He spent four years in prison. Once free, he started over in Las Vegas, just then emerging as a gambling mecca.
Eventually Roselli became Chicago’s head fixer in Las Vegas, but his bosses lost confidence in him. They sent him back to L.A. to do lesser work.
That’s where he was when Maheu called.
Roselli knew Maheu had some kind of special contract with the CIA. And Maheu knew Roselli had deep ties to the mob.
When senior CIA officer Richard Bissell, who had developed the U-2 spy plane program, put together a “sensitive mission requiring gangster-type action,” he knew where to find real gangsters for the job.
The Mafia could fulfill the mission and provide the CIA with a credible cover story. Castro had closed down their profitable Cuban brothels and casinos. If things went wrong and the assassins were killed or captured, the media would accept that the Mafia was acting on its own.
The CIA brass gave Bissell’s plan the go-ahead, according to since-released CIA files, and Maheu was hired to organize the plot. Maheu told CIA officials he knew someone he thought was a “high-ranking member of the ‘syndicate’ ”: Roselli. Maheu said if Roselli was in fact a member of the mob, “he undoubtedly had connections leading into the Cuban gambling interests.”
Bissell asked Maheu to put the plan in motion.
That’s why these two “businessmen” were lunching in the hotel restaurant, apparently negotiating important matters. But things were at an impasse. Roselli’s body language said he didn’t want any part of this deal.
According to a CIA memo among the released files, Maheu pressed him, saying it was Roselli’s “patriotic duty” to help get rid of the communist dictator.
Roselli thought about it for a moment. Maybe this job could get him back into the good graces of the bosses in Chicago—and one boss in particular.
“I have to run it by somebody first,” Roselli said.
“Who?”
A man named Sam, he said, “who knows the Cuban crowd.”
Maheu nodded.
“One thing,” Roselli said. “I don’t want any money. I don’t think my people would want money for this, either.”
Maheu smiled to himself. He’d hooked his fish.
This was a top secret operation, he told Roselli, and they needed to move quickly. As they rose to leave the restaurant, Maheu had one more thing to say, the most important thing: “The U.S. government is not involved.”
Roselli nodded. He understood the significance. And so would his boss.