Why Sinatra Matters

3 LONELY TOWN

As an artist, Sinatra had only one basic subject: loneliness. His ballads are all strategies for dealing with loneliness; his up-tempo performances are expressions of release from that loneliness. The former are almost all fueled by abandonment, odes to the girl who got away. The up-tempo tunes embrace the girl who has just arrived. Across his long career, Sinatra did many variations on this basic theme, but he got into real trouble only when he strayed from that essentially urban feeling of being the lone man in the crowded city. He is at his most ludicrous in the film clip where he sings “Ol’ Man River” in a white tuxedo; he is at his most self-parodic in the part of the Trilogy album when he addresses a hymn to himself while a celestial background choir chants, “Sinatra! Sinatra!” Like all great stars, he was susceptible to the twin temptations of flattery and mythomania. But in the end, his finest work takes place at the midnight hour, when he tells the bartender that it’s a quarter to three and there’s no one in the place except you and me.

There could have been no other subject, of course, if Sinatra was to draw, like any major artist, on the emotions that he felt most deeply. Frank Sinatra was the first and only child of Dolly Sinatra. After the panic, horror, and physical damage of her son’s birth, she was unable to bear any more children. So Frank grew up as a lone child in a neighborhood of large families. That special condition was to mark his psyche as surely as the doctor’s forceps marked his face.

“I used to wish I had an older brother that could help me when I needed him,” he said. “I wished I had a younger sister I could protect. But I didn’t. It was Dolly, Marty, and me.”

The first child in immigrant families is also the first American, the one who truly begins the American part of the family saga. But an only child is in a position of greater isolation than most such children; he or she has no older brothers and sisters who can serve as guides; there are no younger siblings who can benefit from hard-earned knowledge. The American child is forced to tell what he knows to strangers. That is, he must go beyond the older people in his life, and find an audience. And he (or she) must find ways to deal with the deepest loneliness: the hours after the audience is gone and the boy closes the door to his room.

“There’s nothing worse when you are a kid than lying there in the dark,” he said to me once. “You got a million things in your head and nobody to tell them to.”

Frank Sinatra’s personal solitude was compounded by the nature of his parents. His father lived much of his life in a dark pool of silence. “He was a nice guy,” Sinatra said later. “I loved him. But the man was the loneliest guy I ever knew.” The boy also must have been uneasy trying to separate his father, Marty Sinatra, from the public person called Marty O’Brien. A private Italian and a public Irishman. A man who was alone at a kitchen table but known publicly to dozens of people on the street. In those days it would not have been strange for a boy to believe that the man was ashamed of being Italian. His father’s split identity surely explains, at least in part, Sinatra’s later vehemence about keeping his own name when Harry James wanted to change it.

“He wanted me to call myself Frankie Satin!” he remembered many decades later, chuckling as he spoke. “Can you imagine? Is that a name or is that a name? Now playing in the lounge, ladies and gennulmen, the one an’ only Frankie Satin. … If I’d’ve done that, I’d be working cruise ships today.” He laughed, and then turned serious. “Besides, one fake name in the family was enough.”

The boy (who was, by the way, christened Frank, not Francis Albert, at St. Francis Roman Catholic Church in Hoboken on April 2, 1916) also had to deal with the absence of Dolly Sinatra. She lived at home and was house proud, but she was gone throughout most of the day, working at a chocolate shop, leaving the boy Frank in the care of his grandmother, Rosa Garavente. In the evenings Dolly’s energies were increasingly absorbed by the duties and rewards of local politics.

She was a Democrat, of course, because the Republicans then, as now, were believed to be anti-immigrant but also because in that part of New Jersey, Democrats had power. She eventually became the leader of the Third Ward in Hoboken’s Ninth District, able to deliver a minimum of six hundred votes to the Hudson County machine run by Boss Hague. To such political activists, ideology was much less important than the practical benefits that came from belonging to a powerful group. You could reward your friends. You could punish your enemies. Or at least hold them back. For many Italians and their children, holding off enemies was a serious matter. By the time Frank Sinatra was ten, there were millions of Ku Klux Klan members across the nation, 40,000 in New Jersey alone; a Klan branch even operated in Hoboken, under the leadership of King Kleagle George P. Apgar, and the haters in the white sheets made no secret of their contempt for Italians. Through politics, Dolly could enlist the law on the side of the Italians in her ward. But even before issues of common defense, she was absorbed with the more mundane concerns of her vocation: the granting of favors. I mentioned once to Sinatra the saying of Boss Tweed: “It’s better to know the judge than to know the law.”

“That could’ve been my mother talking,” he said, and shook his head in a fond way. Alas, knowing the judge didn’t help Dolly when one of her brothers was arrested in 1921 for his part in an armed robbery that left a Railway Express worker dead. He wasn’t the shooter, but he drove the getaway car and was sentenced to ten to fifteen years at hard labor. It could have been worse; he could have been executed.

Even though she was seldom around, Dolly would be a permanent force in her son’s life. As a very young child, Sinatra was often dressed as a girl; Dolly had wanted a girl, bought clothes for a girl, and wasn’t going to waste them. As he grew older, she dressed him with pretensions toward elegance. It was necessary to honor the tradition of la bella figura, dressing as a form of show. There is a studio photograph of the boy at about age five, in full formal dress, with a four-in-hand white bow tie and a carnation pinned to his lapel. He is holding a top hat, one hand resting casually on the seat of a studio chair. His face is both intelligent and tentative, absorbed in the process of the photograph, looking warily at something, or someone, slightly to the left of the photographer. Probably it was Dolly Sinatra. Probably she was giving him stage directions. The photograph, after all, was not for him. It was for her.

II. It should never be forgotten that Sinatra came to consciousness during Prohibition. He was four years old when the Eighteenth Amendment went into effect at midnight on January 16, 1920. The weather in the New York area was bitterly cold, the temperatures down to six degrees above zero. Many saloons arranged farewell parties, with black-bordered invitations reading “Last rites and ceremonies attending the departure of our spirited friend, John Barleycorn.” The Noble Experiment was about to change life in America, but not in ways its bluenosed adherents suspected.

“Prohibition was the dumbest law in American history,” Sinatra said one night. “It was never gonna work, not ever. But what it did was create the Mob. These dummies with their books and their investigations, they think the Mob was invented by a bunch of Sicilians in some smoky room someplace. Probably in Palermo. Bullshit. The Mob was invented by all those self-righteous bastards who gave us Prohibition. It was invented by ministers, by Southern politicians, by all the usual goddamned idiots who think they can tell people how to live. I know what I’m talking about on this one. I was there.”

Yes, he was. From ages four to eighteen, Sinatra watched the story of Prohibition unfold all around him, most clearly within his own family. In his own kitchen he heard the justifications and rationalizations for breaking what was perceived to be an unjust law. It is no accident that he later became a fan of The Great Gatsby, which was driven by the romantic image of the bootlegger. In Hoboken (as in other immigrant communities), one of the specific rationalizations was that the Eighteenth Amendment was a betrayal of the men who fought World War I. The timing of its passage was all wrong. The Great War had succeeded in making many young Italians feel more like Americans. The draft took them out of the ghettos and allowed them to meet young men from all over the country. Some were treated harshly by isolated bigots. Most forged friendships that lasted a lifetime. There is nothing like fighting in a foreign war to erode parochialism. Italian Americans had died for their country — the United States of America. They had been wounded. They had been gassed. They had earned the right to be called Americans.

Back home, in all the Hobokens of America, those who did not become warriors succumbed to the immensely successful propaganda campaign designed by the Wilson administration to convince immigrants and their children to fight in a European war. The nativist cliché about divided loyalties made life miserable for German Americans but didn’t apply to the Italian kids. In that war, Italy was an ally of the United States, and its armies fought bravely, even after the disastrous defeat at Caporetto in 1917 (one casualty on the Italian side in that fierce battle was a young American volunteer ambulance driver named Ernest Hemingway). At home, there was a prolonged fever of flag-waving, drum-beating patriotism, and Sinatra remembered hearing Caruso’s recording of “Over There.”

“In the parade, when the war ended, there were guys from the block, from the neighborhood,” Sinatra remembered later. “They were wearing American uniforms, not Italian uniforms. When Caruso sang ‘Over There,’ he could have been them.”

The young men of Hoboken came home with all the other Americans to find that their country was less free than when they had departed. Suspect immigrants were being rounded up and deported as the result of the Red Scare, the first of the recurrent waves of hysteria over “foreign” ideologies. Worse, the Eighteenth Amendment had been passed while the soldiers were gone. The temperance forces were triumphant, a strange alliance of Bible-whacking fundamentalists, addled nativists, women suffragists, old line WASPs. Some, as always, had good intentions but did not see that their chosen path would lead to just another kind of hell. On the street level, the Noble Experiment was widely perceived as an additional attempt to tame, or cage, the immigrants and their children; most Prohibitionists also supported harsh new restrictions on immigration, some of them (against Asians) plainly racist, the rest directed at the people of southern Europe. This was all part of a wide national reaction against the teeming American cities, which were perceived as centers of vice and immorality, filling up with too many foreigners, too many Catholics and Jews.

There were intelligent voices raised against Prohibition, saying that it was a restriction on personal liberty, which it was, and doomed to lead to widespread corruption, which it did. Many agreed with the New York madam Polly Adler, who said about enforcing these invincibly stupid laws: “They might as well try to dry up the Atlantic with a post office blotter.” Madams, alas, know more about human nature than do ministers. In New York City on the eve of Prohibition, there were 15,000 places where a man could get legally drunk; within a few years there were 32,000 speakeasies providing the same service in defiance of the law. The same phenomenon was true in New Jersey. And Dolly Sinatra was to open her own speakeasy on the corner of Fourth Street and Jefferson in Hoboken. She called it Marty O’Brien’s.

“It was supposed to be a restaurant,” Sinatra remembered. “And you could get some pasta there, or a sandwich. But it was really a saloon. She didn’t call it Mama Sinatra’s, remember; she called it Marty O’Brien’s. You’re Irish: would you go to a place called Marty O’Brien’s for the food?”

Years later, while delivering the Libby Zion lecture at Yale Law School, Sinatra remembered that his father worked for a while for the early bootleggers, who made their runs north to Canada to pick up shipments of whiskey. (My father took a few similar runs himself, to the depots of Lake George.) As a prizefighter, even a mediocre one, Marty Sinatra would be a natural form of muscle.

“He was one of the tough guys,” Sinatra recalled. “His job was to follow trucks with booze so that they weren’t hijacked. I was only three or four, but I remember in the middle of the night I heard sounds, crying and wailing. I think my old man was a little slow, and he got hit on the head. Somebody opened up his head, and he came home and was bleeding all over the kitchen floor. My mother was hysterical. After that, he got out of that business. They opened a saloon.”

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.