Why Sinatra Matters (7 page)

Frank Sinatra would remember none of this. All he remembered was the victory parades. But the immense slaughter of the Great
War had broken many things in the world. The United States would assume much greater powers, acquire more swagger, and in
the eyes of many be riddled with greater hypocrisies. The Golden Door, which had welcomed so many millions of immigrants,
would slam shut. Those who believed in the old way would receive no reinforcements. Now there was only the new way. And Frank
Sinatra would be part of it.

F
OR HOW DOES ANY MAN KEEP STRAIGHT WITH HIMSELF IF HE HAS NO ONE WITH WHOM TO BE STRAIGHT?

–N
ELSON
A
LGREN
,
The Man with the Golden Arm

A
s 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.