Why Sinatra Matters (8 page)

“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.