September 25, 1960
Miami, Florida
When the CIA’s man stepped off the plane in Miami, Organized Crime was waiting at the gate in a natty pin-striped suit, ready to do America’s dirty deeds.
Robert Maheu didn’t have to wait long after his meeting with Johnny Roselli in New York. Roselli was a true-blue patriot, pleased to go to work for America. Yes, Roselli said, his boss would meet with Maheu in Miami.
Maheu booked a flight.
On the tarmac, Roselli smiled, shook Maheu’s hand, and helped him with his bags. Roselli was pumped up.
“Where are we going?” Maheu asked.
“The Fontainebleau,” he said.
That figured, Maheu thought. The place was over-the-top, a destination for upscale tourists and a hangout for gangsters. Back when Al Capone was at the height of his power, he spent his winters in Miami, and his crew followed. It made sense, with the Cuban casinos only about 230 miles south across the Caribbean.
The men made small talk on the drive to the hotel. Maheu enjoyed the views of the ocean, sky, and art deco buildings in every shade of pink. They parked at the Fontainebleau and headed inside. Roselli led his man past the tourists, bars, and gift shops and into the Boom Boom Room, a swanky restaurant with a performance stage.
Maheu smiled—he’d seen this place on television, back in the spring. Frank Sinatra had hosted Elvis Presley, who had just been discharged from the Army. It was schlock, but plenty of fun.
The mobsters clearly were out to impress.
Two men were waiting at the table. Roselli waved and headed in their direction.
The men stood to greet them, and Roselli kissed each on the cheek—the old-school way of showing respect to the boss.
Roselli introduced Maheu to Sam Giancana and Santo Trafficante Jr.
Maheu knew who they were. These two controlled almost all the rackets east of Chicago.
Trafficante was just as powerful as Giancana. With his thin build, receding hairline, and thick horn-rimmed glasses, Trafficante looked like an accountant, but he was a stone-cold killer.
When his father died quietly in 1954, Trafficante took over his Tampa-based operation. Gambling was big, but Trafficante Jr. was expanding into narcotics smuggling and distribution. He was keenly interested in killing Castro. He’d lost tens of millions when the Cuban strongman seized power.
Maheu didn’t waste any time. He sat down, ordered a drink, and pitched his idea to the bosses.
Giancana listened for a few minutes before stopping Maheu. He was “only going to be the back-up man,” he said. If they agreed to cooperate, Trafficante and Roselli would be the point men. Trafficante was fluent in Spanish, so he could serve as a translator to possible recruits.
Over lunch, they discussed the “who” of this assassination. It wouldn’t be hard to find a Cuban to kill Castro. Just about anyone in the exile community would volunteer, but they had to find someone who could get close enough to Castro to do the job. He never went anywhere without his machine-gun-toting revolutionaries.
Maheu said the CIA wanted Castro dead as soon as possible. He didn’t mention that the agency was coordinating an invasion by Cuban exiles to overthrow Castro. If the dictator was simply removed, they could scrap the expensive invasion.
Giancana knew it would take time to develop a plan and, more important, find the right person to pull it off, but it was an exciting diversion. He was in.
Roselli was ready to fly to Cuba himself and start shooting commies. He was a fiercely patriotic man, or as Giancana said, “Wave a flag and Johnny will follow you anywhere.”
Trafficante was quiet but clearly engaged.
Maheu smiled to himself. His bosses would be happy.
The mobsters had their own motivations for eliminating the dictator. Aside from revenge for their lost millions, they believed they could reopen their casinos once the revolutionary leader was out of the picture. Things would go back to where they were before.
And they also believed that cooperating with the government in such a high-risk venture would earn them a kind of “get out of jail free” card that would keep the FBI off their backs as they pursued their dark business at home.
What Roselli, Giancana, and Trafficante didn’t know was that this was a covert operation. The FBI had no clue about the CIA’s plot, so FBI surveillance of the organized crime leaders and their operations would continue.
Maheu had his own blind spots. He didn’t know Giancana was working on behalf of Kennedy’s campaign, persuading labor union associates all over the country to campaign legally—and illegally—for Kennedy.
Giancana thought things through and came to a realization. He might be an uneducated thug, but he was now in an unprecedented position to shape the 1960 election. If they killed Castro before November, it would show that the Eisenhower administration had been working behind the scenes to eliminate a communist threat—and Richard Nixon would reap all the benefits.
If they waited until after Election Day, Kennedy could claim that the administration hadn’t done anything to remove the Cuban leader from power, or stop Soviet advances in the Western Hemisphere.
The possible scenarios were mind-boggling.
Now that Maheu had successfully recruited the gangsters, they moved on to the “how.” Giancana said there was a better, more discreet way of doing the job than using a gun.
At later meetings there was discussion about the possibility that the CIA could furnish “some type of potent pill,” and they could come up with a plan to place it in Castro’s food. Giancana threw out the name of a “prospective nominee,” a former Cuban official who’d been taking kickbacks from the mob and “still had access to Castro.” The man was in financial trouble, Giancana said.
That was an interesting idea. Handlers from the CIA would be in touch with them soon, Maheu said.
With a deal in place, the former G-man rose from the table. He told the group he’d still be involved in the planning, recruitment, and execution of the plot. There was no time to waste. He had to get on the phone and talk to his bosses.
He had to get this plan underway before anyone changed their minds.