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.

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.