“Did I know those guys?” he said to me once. “Sure, I knew some of those guys. I spent a lot of time working in saloons. And saloons are not run by the Christian Brothers. There were a lot of guys around, and they came out of Prohibition, and they ran pretty good saloons. I was a kid. I worked in the places that were open. They paid you, and the checks didn’t bounce. I didn’t meet any Nobel Prize winners in saloons. But if Francis of Assisi was a singer and worked in saloons, he would’ye met the same guys. That doesn’t make him part of something. They said hello, you said hello. They came backstage. They thanked you. You offered them a drink. That was it.”
He paused. “And it doesn’t matter anymore, does it? Most of the guys I knew, or met, are dead.”
One of them was Salvatore Giancana, sometimes known as Momo, or Mooney. A graduate of Joliet prison, he ducked World War II by doing a crazy act for the draft board, which labeled him “a constitutional psychopath.” He rose through the wartime rackets to the leadership of the Chicago mob in the 1950s. During that period he and Sinatra became friends and were seen in various places together. The star-struck Momo later began a long love affair with singer Phyllis McGuire, and the friendship deepened. In 1962 Sinatra, Dean Martin, and Sammy Davis played a special engagement at a Giancana joint called the Villa Venice, northwest of Chicago. When the FBI questioned the performers, Sinatra said he did it for a boyhood friend named Leo Olsen, who fronted the place for Momo. Sammy Davis was more to the point.
“Baby, let me say this,” he told an FBI man. “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.”
Sinatra’s friendship with Sam Giancana was most severely tested in 1963, when the Nevada Gaming Control Board charged that the Chicago hoodlum had been a week-long guest at Sinatra’s Cal-Neva Lodge in Lake Tahoe. His mere presence was enough to revoke the casino’s gambling license, and Sinatra first said he would fight the charge. When Edward A. Olsen, then chairman of the gambling board, said that he didn’t want to talk to Sinatra until he subpoenaed him, Olsen claims Sinatra shouted over the phone, “You subpoena me and you’re going to get a big, fat, f surprise.”
But when the crunch came two weeks later, Sinatra chose not to fight the revocation order. Apparently his friendship with Giancana was more important than his investment in Nevada, and he sold his interests for $3.5 million. In 1975 Giancana was shot to death in the basement of his Chicago home. Phyllis McGuire went to the funeral, but Sinatra didn’t. Sinatra is again trying to get a gambling license in Nevada.
“It’s ridiculous to think Sinatra’s in the mob,” said one New Yorker who has watched gangsters collect around Sinatra for more than 30 years. “He’s too visible. He’s too hot. But he likes them. He thinks they’re funny. In some way he admires them. For him it’s like they were characters in some movie.”
That might be the key. Some people who know Sinatra believe that his attraction to gangsters — and their attraction to him — is sheer romanticism. The year that Sinatra was fifteen, Hollywood released W. R. Burnett’s Little Caesar; more than 50 gangster films followed in the next eighteen months. And their view of gangsters was decidedly romantic: The hoodlums weren’t cretins peddling heroin to children; they were Robin Hoods defying the unjust laws of Prohibition. Robert Warshow defined the type in his essay “The Gangster as Tragic Hero”:
The gangster is the man of the city, with the city’s language and knowledge, with its queer and dishonest skills and its terrible daring, carrying his life in his hands like a placard, like a club. For everyone else, there is at least the theoretical possibility of another world — in that happier American culture which the gangster denies, the city does not really exist; it is only a more crowded and more brightly lit country — but for the gangster there is only the city; he must inhabit it in order to personify it: the real city, but that dangerous and sad city of the imagination which is so much more important, which is the modern world.
That is almost a perfect description of Frank Sinatra, who still carries his life in his hands like a placard, or like a club. His novel might be a very simple one indeed: a symmetrical story about life imitating art.
III.
“My son is like me. You cross him, he never forgets.”
Somewhere deep within Frank Sinatra, there must still exist a scared little boy. He is standing alone on a street in Hoboken. His parents are nowhere to be seen. His father, Anthony Martin, is probably at the bar he runs when he is not working for the fire department; the father is a blue-eyed Sicilian, close-mouthed, passive, and, in his own way, tough. He once boxed as “Marty O’Brien” in the years when the Irish ran northern New Jersey. The boy’s mother, Natalie, is not around either. The neighbors call her Dolly, and she sometimes works at the bar, which was bought with a loan from her mother, Rosa Garaventi, who runs a grocery store. Dolly Sinatra is also a Democratic ward leader. She has places to go, duties to perform, favors to deny or dispense. She has little time for traditional maternal duties. And besides, she didn’t want a boy anyway.
“I wanted a girl and bought a lot of pink clothes,” she once said. “When Frank was born, I didn’t care. I dressed him in pink anyway. Later, I got my mother to make him Lord Fauntleroy suits.”
Did the other kids laugh at the boy in the Lord Fauntleroy suits? Probably. It was a tough, working-class neighborhood. Working-class. Not poor. His mother, born in Genoa, raised in Hoboken, believed in work and education. When she wasn’t around, the boy was taken care of by his grandmother Garaventi, or by Mrs. Goldberg, who lived on the block. “I’ll never forget that kid,” a neighbor said, “leaning against his grandmother’s front door, staring into space. …”
Later the press agents would try to pass him off as a slum kid. Perhaps the most important thing to know about him is that he was an only child. Of Italian parents. And they spoiled him. From the beginning, the only child had money. He had a charge account at a local department store and a wardrobe so fancy that his friends called him “Slacksey.” He had a secondhand car at fifteen. And in the depths of the Depression, after dropping out of high school, he had the ultimate luxury: a job unloading trucks at the Jersey Observer.
Such things were not enough; the boy also had fancy dreams. And the parents didn’t approve. When he told his mother that he wanted to be a singer, she threw a shoe at him. “In your teens,” he said later, “there’s always someone to spit on your dreams.” Still, the only child got what he wanted; eventually his mother bought him a $65 portable public-address system, complete with loudspeaker and microphone. She thus gave him his musical instrument and his life.
She also gave him some of her values. At home she dominated his father; in the streets she dominated the neighborhood through the uses of Democratic patronage. From adolescence on, Sinatra understood patronage. He could give his friends clothes, passes to Palisades Park, rides in his car, and they could give him friendship and loyalty. Power was all. And that insight lifted him above so many other talented performers of his generation. Vic Damone might have better pipes, Tony Bennett a more certain musical taste, but Sinatra had power.
Power attracts and repels; it functions as aphrodisiac and blackjack. Men of power recognize it in others; Sinatra has spent time with Franklin Roosevelt, Adlai Stevenson, Jack Kennedy, Richard Nixon, Spiro Agnew, Walter Annenberg, Hugh Carey, Ronald Reagan; all wanted his approval, and he wanted, and obtained, theirs. He could raise millions for them at fund raisers; they would always take his calls. And the politicians had a lot of company. On the stage at Caesars Palace, or at an elegant East Side dinner party, Sinatra emanates power. Certainly the dark side of the legend accounts for some of that effect; the myth of the Mafia, after all, is not a myth of evil, but a myth of power.