Crime Library: Criminal Minds and Methods

Frank Sinatra and The Mob

The Night Life

On November 9, 1962, the roster of entertainers playing the Villa Venice Supper Club was beyond belief. Crooner Eddie Fisher was the opening act. Sammy Davis Jr. took the stage next, wowing the crowd with his song-and-dance routines. Then came Dean Martin, and finally the headliner, Frank Sinatra. At the end of the evening, the performers all came out and sang together, kibitzing with one another between numbers and generally hanging loose, letting the audience in on their private party. The crowd ate it up, cheering and applauding wildly. It was a performance that people would talk about for years to come, the kind of impromptu extravaganza that happened only in Las Vegas.

Except this wasn't Vegas. It was Wheeling, Illinois.

The Villa Venice Supper Club, just outside Chicago, had first opened its doors in 1960. Most of its business came from private functions—weddings, bar mitzvahs, retirement parties, and the like. But in the summer of 1962 it underwent a major renovation. Canals were constructed on the eight-acre property and stocked with gondolas, each one manned by a gondolier and in most cases a prostitute. For those who didn't care for water sports, there was the newly built Quonset Hut two blocks away, a clandestine and illegal gambling casino. Buses and limousines shuttled customers back and forth between the club and the casino all night long. Undoubtedly most of the people who flocked to the Villa Venice that opening week came for the entertainment, but a large enough percentage of the customers spilled over to the other attractions, wandering out of the club to try their luck at the gaming tables or take a little boat ride with a young lady for hire. This was exactly how the silent owner of the Villa Venice, Sam Giancana, had envisioned it. Sinatra and his pals were the lure for the more lucrative illegal delights at the Villa Venice. And the best part was that it was almost pure profit for Giancana because he wasn't paying the talent. They were all working gratis as a favor to Sinatra who had arranged it for his old pal Momo. After all, from Giancana's point of view, Sinatra owed him for his failure to deliver President Kennedy.

The FBI was paying close attention to the goings on at the Villa Venice, and special agents interviewed each of the performers. Eddie Fisher insisted that he had appeared there as a favor to his close friend Frank Sinatra. Sinatra said that he'd put it all together as a favor to his old friend Leo Olsen, who was in fact Giancana's front man. But Sammy Davis Jr., who had lost his left eye in a car accident, was a little more forthcoming regarding the Villa Venice engagement. When asked why he had performed without pay, he responded, "...I have to say it's for my man Francis."

Did he do it for anyone else? the agents wanted to know. Like Sam Giancana perhaps?

"By all means," Davis said.

When the agents asked him to explain, he said, "Baby, let me say this. 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."

Actor Peter Lawford, who was President Kennedy's brother-in-law, elaborated on Sinatra's relationship with Giancana: "I couldn't stand him [Giancana], but Frank idolized him because he was the Mafia's top gun. Frank loved to talk about 'hits' and guys getting 'rubbed out.' And you better believe that when the word got out around town [Hollywood] that Frank was a pal of Sam Giancana, nobody but nobody ever messed with Frank Sinatra. They were too scared...."

But Sinatra's association with Giancana proved to be a major liability for the star in the fall of 1963. Sinatra owned nine percent of the Sands Hotel in Las Vegas, where he performed regularly, earning more than $100,000 a week. To own a stake in a Nevada gambling establishment, an individual had to have a state gambling license, which Sinatra had obtained in 1954. This license later allowed him to buy into the Cal-Neva Lodge in Lake Tahoe, which sat on a piece of property that was half in California and half in Nevada. The gambling casino was, of course, on the Nevada side. The state of Nevada maintained what was called the Nevada Black Book, which contained the names, photographs and criminal records of 11 men who were forbidden from entering any casino in the state. Casino owners who allowed any of these people into their establishments risked losing their licenses. Sam Giancana was one of the 11.

Sinatra was in no position to be inhospitable to Giancana in Nevada or any place else. Giancana had pulled strings to get Sinatra a $1.75 million loan to refurbish the Cal-Neva Lodge. And though Giancana never expressed his half-hearted feelings for Sinatra to the singer's face, Sinatra always hosted Giancana lavishly at his homes and hotels. Whenever he was in Nevada, Giancana was always careful to stay out of the casinos, knowing that federal agents kept a close watch on them, and at the Cal-Neva Lodge, Sinatra made sure that Giancana was kept out of sight in luxury. This arrangement worked so well, Giancana became a frequent visitor to the state where he was officially persona non grata.

The McGuire Sisters (AP)
The McGuire Sisters (AP)

In July 1963 while Giancana was staying at the Cal-Neva, he had gotten into a public shouting match with a man named Victor Collins who was the road manager for the McGuire Sisters, a popular singing trio. Giancana's longtime lover was one of the singers, Phyllis McGuire. The argument grew more heated, and someone threw a punch, igniting an all-out brawl. Witnesses recognized the Chicago mob boss, and the incident came to the attention of the Nevada Gaming Control Board. The board launched an investigation, and employees of the Cal-Neva unwisely attempted to bribe the investigator. At a hearing Sinatra allegedly used "highly insulting language" with the chairman. The board gave Sinatra an ultimatum: he had until October 7 to present evidence that would disprove the charges that he had willingly allowed an outlawed person into his establishment. The date arrived, but Sinatra failed to respond. As a result he lost his gambling license and was forced to sell his interests in both the Cal-Neva Lodge and the Sands Hotel.

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