Dolly Sinatra was able to run that saloon because of her political connections. She was naturally gregarious, full of spirit and jokes, equipped with a bawdy sense of humor. That made her a perfect bartender. But it was her political talents that gave her the freedom to run the place itself. She spoke the natural, rushed American English of the New York area, which allowed her to communicate easily with the Irish political bosses. She had mastered a number of Italian dialects, which made her a perfect go-between in the neighborhood between baffled individuals and the agents of the state. She knew how to get a lawyer or a tax accountant or a bailbondsman. She showed up at weddings and wakes. She was generous with her personal time, repeatedly helping those neighbors who were less fortunate than the Sinatras. But she was also a realist. She had learned how the world works and looked at it clearly. Niccolò Machiavelli, the philosopher of political lucidity, would have loved Dolly Sinatra. Yes, there was a part of her that wanted the world to be better, an idealistic streak that would reach fruition during the New Deal. But in the days of Prohibition, she was more concerned with living in the world as it was. And prospering in it.
That obviously meant knowing some of the bootleggers. Not all were Italian. The Mob was not a synonym for the Mafia. It was an alliance of Jews, Italians, and a few Irishmen, some of them brilliant, who organized the supply, and often the production, of liquor during the thirteen years, ten months, and nineteen days of Prohibition. The most famous of the original Mob chieftains were Lucky Luciano, Meyer Lansky, Ben (Bugsy) Siegel, Frank Costello, and Longie Zwillman. Their alliance – sometimes called the Combination but never the Mafia – was part of the urgent process of Americanizing crime. (Sinatra, in my conversations with him, sometimes employed the word Mob when referring to the gangsters of the era but usually called them “the boys.”) The young Italians among them believed that it was foolish to abide by the old Sicilian traditions of excluding non-Sicilians in the name of honor and respect. Luciano, after all, was from Naples, not Sicily. Those traditional notions, the strict and narrow codes of men now patronizingly called Mustache Petes, were too vague, too old-fashioned, too rigid a part of la via vecchia. This was America; you worked with any nationality if it was in your common interest.
Prohibition gave them that common interest. The model for a criminal enterprise could no longer be a local racket, safely lodged within the boundaries of a neighborhood; it had to be organized like any large capitalist corporation, able to cross state lines and national frontiers. That common interest also gave the young Mob guys enormous profits, of course, and bootlegging provided capital for widening their interests into the more traditional underworld enterprises of gambling and prostitution. The overhead was high; it took a lot of money to pay off thousands of cops, Prohibition agents, and prosecutors. But it was better to make payoffs than to go around shooting guns like a bunch of cowboys. Murder had to be an absolutely last resort; wild shooting sprees would only bring down the heat. If the scene was peaceful, you only had to get the law to look the other way, and that was a simple matter of paying off the politicians.
“You know what we all thought growing up?” Sinatra said. “We thought everybody was on the take. We knew the cops were taking. They were right in front of us. But we thought the priests were on the take, the schoolteachers, the guy in the marriage license bureau, everybody. We thought if God came to New Jersey, he’d get on line to get his envelope.”
In New Jersey the most important members of this confederacy were Waxey Gordon (Irving Wexler) and Abner (Longie) Zwillman. Years later there were people in Hoboken who claimed that Gordon was a regular in Marty O’Brien’s. But Sinatra once told me, “The first time I ever saw his face was in a newspaper, when he got out of jail in the 1950s. He was an old man then.” Still, his name was known; he controlled many rackets in Philadelphia and most of the liquor supplies in Hudson and Bergen Counties, and he had even established stills around Hoboken to manufacture beer. “Sometimes the stink was unbelievable,” Sinatra remembered. “The hops, I guess. Whatever it was, it made you gag.”
Zwillman was much more important than Gordon, who always deferred to him. Tall, young (born in 1899), and tough, Zwillman affected an urbane public image. His base was Newark, where he was born and served an apprenticeship as a numbers runner. He helped set up overland routes through New Jersey, assembled a fleet of thirty ships to pick up booze in Canada for delivery along the Jersey Shore, and standardized distribution in the cities. If he needed muscle, he turned to an associate named Willie Moretti, sometimes known as Willie Moore. In the early years of Prohibition, muscle was most often needed to convince the Mustache Petes that their time was over. Some were persuaded to retire. Others were shot in the head. In New Jersey this work was usually left to Moretti and his enforcement squad of about sixty men. By the time Frank Sinatra was ten, the rackets in New Jersey had settled into a routine business. Years after the end of Prohibition, Willie Moretti would play a role in the Sinatra saga too.
III. Against the cynical backdrop of Prohibition, Frank Sinatra was on his own. On the street the most admired men were tough guys. The bootlegger could be seen as a glamorous rebel, one who reaped the rewards of fine clothes, shiny cars, and beautiful women. At the movies the heroes were often cowboys, silent men, handy with guns, who rode in and out of town alone. Each taught the lesson that one solution to perceived injustice was violence. The outlaw, the desperado, the good man who was dealt a bad hand by life: they were central to the emerging American myth, as defined and spread by the new technology of mass culture.
That culture was also forming young Frank Sinatra. In 1927, a few months before Sinatra’s twelfth birthday, the first talkie was released, The Jazz Singer, with Al Jolson. There on the screen, a man opened his mouth and you could hear him sing. The story itself was a Jewish version of the conflicts in Hoboken. Jolson played the young son of immigrants who resists his parents. They want him to sing only in synagogues; he goes out into the world and finds his way to show business, fame, and fortune. Translated into the struggles of Little Italy, it was a triumph of la via nuova over la via vecchia.
At the movies Sinatra began to dream his own American dream. Sometimes he carried those visions to school. Sometimes they were with him after school, when he was in the care of his maternal grandmother, Rosa Garavente. Old-timers from Hoboken would remember him later as a lonely boy, standing in the doorway of his grandmother’s building, watching life go by without him. In a neighborhood of large families, he was often all by himself. Meanwhile, Dolly worked and laughed at the bar of Marty O’Brien’s and combed the tenements for votes. The year 1927 was momentous: Lindbergh flew the Atlantic, Babe Ruth hit 60 home runs, Sacco and Vanzetti were executed in Massachusetts, Stalin took power in the Soviet Union, and Dolly Sinatra got her husband a job with the Hoboken fire department. Later, there were stories claiming that Dolly also had a side business: providing abortions. Like many families, the Sinatra family had its own secrets, and it’s unlikely that they were shared with their son.
“Sometimes I’d be lying awake in the dark and I’d hear them talking,” he remembered years later. “Or rather, I’d hear her talking and him listening. Mostly it was politics or some worthless neighbor. I remember her ranting about how Sacco and Vanzetti were framed. Because they were Italians. Which was probably true. All I’d hear from my father was like a grunt. They never talked about themselves. Except for things like, How could you do a thing like that? That was my mother. He’d just say, Eh. Eh.” Sinatra smiled and said to himself, “Eh.”
It was his mother he remembered most vividly. In his sixties he would remember Dolly nagging him about the dangers of tuberculosis, insisting that he stay away from kids who coughed. He remembered her fears of polio, shared by millions in those days, and her refusal to let him go to beaches or public swimming pools. (He went anyway.) He remembered how she wanted him to go on to a career as an engineer at the Stevens Institute of Technology. And he remembered how she kept a small
bat, a kind of billy club, behind the bar at Marty O’Brien’s.
“When I would get out of hand,” he said, “she would give me a rap with that little club; then she’d hug me to her breast.” He paused, and smiled: “I married the same woman every time.”
He was serious. In various ways, in spite of admirable efforts to change himself and leave behind his personal disguises, Sinatra would swing back and forth between father and mother for the rest of his life. Too often he could fall into the patterns of the mute Marty Sinatra, locking himself in cramped cages of solitude. At other times he would become a male version of the garrulous Dolly, waving her vulgarity like a flag of triumph. Across his long life those swings in mood and style would offer him little relief from the template cut in Hoboken. Always he would be driven by the solitary’s longing to be reconciled with the world.
On October 19, 1929, the world abruptly shifted again as the stock market crashed and the end came for what Westbrook Pegler later called the Era of Wonderful Nonsense. At first, nothing affected the neighborhood in Hoboken or the growing prosperity of the Sinatras. Not many people in that neighborhood had plunged hard-earned money into the stock market. Some didn’t even trust banks. For a while life went on. In 1930 the Sinatras moved to a three-bedroom apartment in a large house, and for the first time fourteen-year-old Frank had his own room. Now he had friends too, from the street and from David E. Rue Junior High School, where he was an intelligent but lazy or indifferent student. He seemed desperate to make friends, to be thought of as someone other than a spoiled skinny kid, someone other than Dolly’s, or Marty’s, son. He would play class clown. He showed a talent for drawing. (He would do much painting in the last fifteen years of his life.) He would try to buy friendship with the generous allowance money given to him by Dolly, splurging on candy, ice cream sodas, baseball gloves and bats. Contrary to the public relations myth, he was never a member of an adolescent street gang, but he did get into some fistfights. He rode a bike. He played ball. He discovered girls, developed crushes on a few, was sometimes embraced and more often rejected, with some girls making fun of the scars he’d carried from birth.
“I had some fun there,” he said later, about Hoboken. “I had some misery too.”
There was much misery in the land now, and it was spreading. Hoovervilles began appearing along the New Jersey and New York waterfronts, clusters of crude shacks that housed the Depression homeless. In 1931, with 4 million Americans now unemployed, there were reports of food riots in Oklahoma and Arkansas and a riot over jobs in Boston. Through all of this, Frank Sinatra was sitting in the dark, watching James Cagney hit Mae Clarke in the face with a grapefruit in The Public Enemy and Bela Lugosi sucking blood in Dracula. He no doubt talked with his friends about Al Capone going to prison for tax evasion and Legs Diamond being shot to death in a hotel room in Albany; his youth was lived in the great era of the tabloid newspaper. But he wasn’t sure how he fit in. Anywhere.
“I’d rather do time in Attica than be fifteen again,” he once said. “I didn’t know whether I was coming or going.”
That year of 1931 the Sinatras moved again, this time into their own home, which they bought for $13,400, a considerable sum in that Depression year. They had, at last, their piece of the American earth. No more paying rent. No more hassles with landlords. Now they had a three-story home at 841 Garden Street, complete with steam heat, a bathtub, and a finished basement. A house that rode high over the street. Dolly was more active politically than ever before, operating as the ward boss. She helped the Depression casualties as best she could, laying out spreads of food, trying to find work for those who had lost their jobs. She tried to persuade some despairing Italians that they should not go home, that Benito Mussolini had not created paradise in his Fascist Italy; some departed anyway. During this period Frank Sinatra began to invent his dream.
“I was always singing as a kid,” he said. “But it was never serious. I’d sing at the bar, you know, and get a round of applause, led by Dolly. There was a player piano in the joint, with music on a roll. I’d sing and they’d give me a hand, and sometimes a nickel or a quarter. It wasn’t that I was so great. Mainly, they cheered because I could remember the words.”
But in Dolly’s saloon the only child was discovering that he needed an audience. If his mother whacked him and then hugged him, then he would present himself to strangers. If he was good, if he could be more than just a kid who remembered the words, they certainly wouldn’t whack him. Their cheers would make him feel valuable, and connected to others. Maybe then Marty and Dolly would recognize his existence in some new way, and if they didn’t, the hell with it. In junior high school he joined the glee club. He listened constantly to the radio, bought sheet music (he never learned to read music), and memorized lyrics. He was given a ukulele by his mother and would play and sing with his friends on the street. At the movies, he saw that singers always got the girl. On the radio he heard Rudy Vallee and Russ Columbo and Dick Powell. And then he discovered Bing Crosby.
“The thing about Bing was, he made you think you could do it too,” Sinatra said, half a century later. “He was so relaxed, so casual. If he thought the words were getting too stupid or something, he just went buh-ba, buh-ba, booo. He even walked like it was no effort. He was so good, you never saw the rehearsals, the effort, the hard work. It was like Fred Astaire. Fred made you think you could dance too. I don’t mean just me. I mean millions and millions of people. You saw Fred dance, you heard Bing sing, and it was like you were doing it. After a movie you saw guys in the street dancing. You heard them singing to their girls. It was amazing, what those men did, Bing and Fred. Some people, they danced and sang right through the fucking Depression. Every time Bing sang, it was a duet, and you were the other singer.”
Young Frank Sinatra began to develop a theatrical personality to go with his singing. His mother arranged for credit at a clothing store, and he soon had so many pairs of slacks that he was nicknamed Slacksey O’Brien. He owned a phonograph and a growing collection of records. When he was sixteen, his father allowed him to use the family Chrysler, and he would take his friends for rides, often wandering as far as Atlantic City. The new house even had the ultimate luxury: a telephone. Frank Sinatra did not have a hard Depression.
“We never went hungry,” he said later. “It wasn’t luxury, but it wasn’t bad.”
He began to live a split life. On the street he donned the mask of the wise guy, an image fed by the gangster films that had taken the place of westerns in creating the myth of the American outsider. He posed like Cagney, like Edward G. Robinson. He dressed “sharp.” He jingled change in the pockets of his slacks. He cursed. He talked tough. He showed his friends he would fight if he had to, and what he lacked in street-fighting talent, he made up for with courage. On the street he was developing an act, a disguise that would protect him from the world while asserting his presence in his own small piece of that world.
Alone, he was conceiving a different vision, and it had nothing to do with the neighborhood streets of Hoboken. As a teenager, he must have realized that loneliness might be his lot, but even then he refused to accept it as inevitable. Across a lifetime he would make many attempts to relieve loneliness, submerging it in marriages and love affairs, hard-drinking camaraderie, bursts of movement and action and anger, but the only thing that ever permanently worked was the music. And when he was an adolescent, a combination of words and music began to create the vision of escape. From solitude. From obscurity. From the polarities represented by Marty and Dolly Sinatra. Sometimes he would wander down to the waterfront alone, past the Hoovervilles, past the rusting tracks of the railroad spurs, out to the edge of the piers. There, he would gaze across the harbor at New York, the spires of its skyline rising toward the sky.
THE BIRTH OF A CREATURE OF HUMAN FANTASY, A BIRTH WHICH IS A STEP ACROSS THE THRESHOLD BETWEEN NOTHING AND ETERNITY, CAN ALSO HAPPEN SUDDENLY, OCCASIONED BY SOME NECESSITY. AN IMAGINED DRAMA NEEDS A CHARACTER WHO D
OES OR SAYS A CERTAIN NECESSARY THING; ACCORDINGLY THIS CHARACTER IS BORN AND IS PRECISELY WHAT HE HAD TO BE.
– LUIGI PIRANDELLO, 1925
“WHAT THE FUCK WAS THAT?”
– BENNY GOODMAN, his back to the audience at the New York Paramount, as Frank Sinatra made his entrance and the fans roared, December 30, 1942
4
THE SONG IS YOU
HIS FINEST ACCOMPLISHMENT, of course, was the sound. The voice itself would evolve over the years from a violin to a viola to a cello, with a rich middle register and dark bottom tones. But it was a combination of voice, diction, attitude, and taste in music that produced the Sinatra sound. It remains unique. Sinatra created something that was not there before he arrived: an urban American voice. It was the voice of the sons of the immigrants in northern cities – not simply the Italian Americans, but the children of all those immigrants who had arrived on the great tide at the turn of the century. That’s why Irish and Jewish Americans listened to him in New York. That’s why the children of Poles in Chicago, along with all those other people in cities around the nation, listened to him. If they did not exactly sound like him, they wanted to sound like him. Frank Sinatra was the voice of the twentieth-century American city.
In life even the mature Sinatra would sometimes speak in the argot of the street. He could be profane, even vulgar. The word them could become dem, and those could become dose. It depended on the company. But in the songs the diction was impeccable. The children of the Italians, the Irish, and the Jews wanted to believe that they could express themselves that way, and many of them did. In my Brooklyn neighborhood, many of us understood that we were not prisoners of the Brooklyn accent, because Sinatra’s singing refused to use it. And he was like us. His diction was something that Sinatra learned early, from the movies.