‘Mafia Spies’: Why mob boss Sam Giancana made Rat Pack play his Northbrook club

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Chicago Outfit boss Sam Giancana demanded Frank Sinatra and his Rat Pack buddies play the Villa Venice, the Northbrook club he secretly owned. Here, Dean Martin (from left), Sammy Davis Jr. and Sinatra perform there in 1962. | Sun-Times files

Chicago gangster Sam Giancana and his mob pal Johnny Roselli hoped their involvement with a secret CIA plan to kill Cuban leader Fidel Castro in the early 1960s would earn them a “Get out of jail free” card. But they were sorely surprised by the Kennedy administration. This is the second of three parts excerpted from the new book “Mafia Spies: The Inside Story of the CIA, Gangsters, JFK and Castro” (Skyhorse Publishing, $25.99) by Thomas Maier, a former Sun-Times reporter whose other books include “Masters of Sex,” which was made into a Showtime TV series

Villa Venice was a hit. The newly renovated supper club, secretly owned by Sam Giancana in Northbrook, opened to rave reviews and a sold-out holiday audience.

“It’s been like old times to see the crowds and the familiar faces at the Villa Venice, where Frank Sinatra, Dean Martin, and Sammy Davis Jr. are winding up their one-week stand tonight,” a Chicago newspaper observed in December 1962. “The chairs are pushed so closely together you can’t shove your way between them.”

Packing them in was the penance Giancana demanded from Sinatra, his star attraction. He blamed the singer for “disloyalty” with the Kennedys. The singer had tried, but been unable, to dissuade them from the government’s relentless investigations against the Mafia.

Giancana was furious when Johnny Roselli relayed the news of Sinatra’s failure. One Chicago wiseguy even volunteered to exterminate Sinatra and the Rat Pack.

“Let’s show ’em,” growled John Formosa, Giancana’s gargoyle-like associate. “Let’s show those a–hole Hollywood fruitcakes that they can’t get away with it as if nothing’s happened. Let’s hit Sinatra. Or I could whack out a couple of those other guys. [Peter] Lawford and that [Dean] Martin, and I could take the n—– [Sammy Davis Jr.] and put his other eye out.”

Uncharacteristically, Giancana demurred. He would bide his time and hopefully still avoid the traps set by the Justice Department.

“No,” Sam replied. “I’ve got other plans for them.”

Instead of killing Sinatra in retribution — as some grisly suggested — Sam demanded the crooner and his Rat Pack buddies perform for free at the Villa Venice.

Top mobsters and high-rollers flew in from around the country. Seated courtside were homegrown hoodlums like Joe Fishetti, Sinatra’s pal at the Fontainebleau in Miami, and Marshall Caifano, the Outfit’s man in Las Vegas when Roselli wasn’t around. “Practically all of Chicago’s top hoodlums, with the exception of Giancana, were present,” reported one FBI memo.


‘Mafia Spies,’ part 1: Chicago’s ‘Mafia Spies,’ CIA Castro plot detailed in new book by ex-Sun-Times writer

‘Mafia Spies,’ part 3: Sam Giancana is gunned down before he can be called before Senate

Regardless of whose name appeared on the Villa Venice deed, everyone seemed to know whose house it was — Sam Giancana’s. He used an alias “Mr. Flood” but made his presence felt. A week earlier, when Sinatra arranged for singer Eddie Fisher to appear, Sam was more conspicuous. He sat in the front row with girlfriend Judy Campbell.

Insisting that the Rat Pack — then America’s most celebrated entertainers — appear gratis was a clear sign of Giancana’s clout.

Dressed up in tuxedo, Martin made light of the tension. “Hold the noise down,” he instructed, pointing to a penthouse apartment overlooking the stage. “There’s a gangster sleeping up there.”

Sinatra arranged for a stream of entertainers to play the Villa Venice, which garnered big crowds. Patrons floated to their seats in Venetian boats manned by gondoliers, who steered them across a man-made canal to an 800-seat auditorium. Between shows, the big spenders shuttled back and forth to a nearby Quonset hut, where casino-like gambling tables were set up.

The roulette wheels, craps and blackjack games, all crooked, were the main enticements where Sam made his big money. Giancana and the Outfit collected an estimated $3 million from the illegal gambling and gala entertainment at the Villa Venice before it soon closed down.

Sinatra and his Rat Pack friends appeared under “what can only be termed a command performance,” the FBI reported. Agents quizzed Sammy Davis Jr., like the other reluctant performers, about his knowledge of Giancana’s gang operation.

“Baby, let me say this,” explained Davis, who lost his left eye years earlier in a car accident. “I got one eye, and that one eye sees a lot of things that my brain tells me I shouldn’t talk about. Because my brain says that, if I do, my one eye might not be seeing anything after a while.”

During a rendition of ‘The Lady Is A Tramp,” Martin worked a sly joke into the song about their situation: “I love Chicago, it’s carefree and gay; I’d even work here without any pay.”

Missing from the Chicago festivities was Peter Lawford, the president’s brother-in-law. A few months earlier, Sinatra had dumped him from the Rat Pack.

Lawford’s banishment was a jarring reversal. In the late 1950s, the actor introduced Jack Kennedy to Sinatra and his swinging entertainment world in Las Vegas and Los Angeles, a friendly alliance full of women and good times that carried through the 1960 election.

But as the Justice Department compiled an increasingly thick dossier on Giancana and his mob pal Johnny Roselli, Attorney General Robert Kennedy warned his brother to steer clear of Sinatra because of his devotion to his Mafia friends. Few knew about the CIA’s recruitment of Giancana and Roselli in a top-secret assassination plan aimed at Cuba’s Communist leader Fidel Castro.

Johnny Roselli. | Skyhorse Publishing

Johnny Roselli. | Skyhorse Publishing

Lawford tried to intervene to stop Bobby Kennedy’s anti-Mafia campaign, just as Sinatra did, but was firmly rebuffed. “You know, as much as I like Frank, I can’t go there, not while Bobby is handling this [the Giancana] investigation,” the president explained to Lawford.

The rift became deeply personal in March 1962, when the White House asked Lawford to inform Frank Sinatra that the president, during a West Coast visit, wouldn’t be staying at Sinatra’s California home as planned but rather a nearby place owned by singer Bing Crosby. Sinatra was stunned by the rebuff. He adored JFK and had built a helicopter pad for his arrival. He devoted a room in his Palm Springs house to their friendship. On a wall, there hung a framed note signed by the president: “Frank — How much can I count on the boys in Vegas? JFK.”

Lawford blamed “security” concerns for the last-minute cancellation. But the real reason was Sinatra’s connections to Giancana.

After Lawford’s call, Sinatra reached Bobby Kennedy. “What is this s–t?” Frank was heard saying. Kennedy refused to budge.

Sam Giancana. | Skyhorse Publishing

Sam Giancana. | Skyhorse Publishing

Sinatra listened for a moment, furious at the betrayal. Then he flung the phone against a wall. The singer peered out a window.

“There was an endless silence,” recalled his assistant, George Jacobs. “He stood there staring out at the desert, as if someone had told him his folks had died. It took him about five minutes before he could tell me.”

After hearing of the reaction, the president called Sinatra to emphasize the decision was made by the Secret Service. He urged him not to blame Lawford. “Frank didn’t buy that for a minute,” Lawford recalled, “and, with a few exceptions, he never spoke to me again.”

While he still admired the president, Sinatra aimed his rage at Lawford. He cut him out of all future Rat Pack activities.

To the mob, their man Sinatra had been played for a fool. The Kennedys “used him to help them raise money, then they turn around and say they’re great fighters against corruption,” complained mobster Vincent “Fat Vinnie” Teresa, in a howl picked up by FBI microphones. “They criticize other people for being with mob guys. They’re hypocrites.”

The accumulation of FBI evidence — based on telephone traces, listening devices and constant surveillance — documented numerous contacts between Sinatra and Giancana. Overall, these FBI files reflected both Hoover’s obsession with the Kennedys as well as the poor judgment of the president, whose private behavior and philandering would later disappoint his Camelot admirers.

For Roselli, it was hard to figure out the federal government’s puzzling view towards the two gangsters. The FBI’s harassing approach was directly contrary to the steady flow of compliments the CIA bestowed in their fight against Castro. On the street, he felt the constant presence of FBI agents following them.

Typically, Roselli made light of it. As he entered one building, he held open the door for the agents chasing him.

“I know, I know, you’re just doing your job,” he said with a smirk.

Author Thomas Maier, a former Chicago Sun-Times reporter whose other books include “Masters of Sex,” which became a Showtime TV series. | Provided photo

Author Thomas Maier, a former Chicago Sun-Times reporter whose other books include “Masters of Sex,” which became a Showtime TV series. | Provided photo

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