A raw December Sunday afternoon in 1915, a day more like the old century than the new among the wood-frame tenements and horse-shit- flecked cobblestones of Hoboken's Little Italy, a.k.a. Guinea Town. The air smells of coal smoke and imminent snow. The kitchen of the cold-water flat on Monroe Street is full of women, all gathered around a table, all shouting at once. On the table lies a copper- haired girl, just nineteen, hugely pregnant. She moans hoarsely: the labor has stalled. The midwife wipes the poor girl's brow and motions with her other hand. A doctor is sent for. Ten long minutes later he arrives, removes his overcoat, and with a stern look around the room- he is the lone male present-opens his black bag. From the shining metallic array inside he removes his dreaded obstetric forceps, a medieval-looking instrument, and grips the baby with it, pulling hard from the mother's womb, in the violent process fearfully tearing the left side of the child's face and neck, as well as its left ear.
The doctor cuts the cord and lays the infant-a boy, huge and blue and bleeding from his wounds, and apparently dead-by the kitchen sink, quickly shifting his efforts to saving the nearly unconscious mother's life. The women lean in, mopping the mother's pallid face, shouting advice in Italian. One at the back of the scrum-perhaps the mother's mother, perhaps someone else-looks at the inert baby and takes pity. She picks it up, runs some ice-cold water from the sink over it, and slaps its back. It starts, snuffles, and begins to howl.
Mother and child both survived, but neither ever forgot the brutality of that December day. Frank Sinatra bore the scars of his birth, both physical and psychological, to the end of his years. A bear-rug- cherubic baby picture shot a few weeks after he was born was purposely taken from his right side, since the wounds on the left side of his face and neck were still angry-looking. Throughout Sinatra's vastly documented life, he would rarely-especially if he had anything to do with it-be photographed from his left. One scar, hard to disguise (though frequently airbrushed), ran diagonally from the lower-left corner of his mouth to his jawline. His ear on that side had a bifurcated lobe-the classic cauliflower-but that was the least of it: the delicate ridges and planes of his left outer ear were mashed, giving the appearance, in early pictures, of an apricot run over by a steamroller. The only connection between the sonic world and the external auditory meatus-the ear hole-was a vertical slit. Later plastic surgery would correct the problem to some extent.
That wasn't all. In childhood, a mastoid operation would leave a thick ridge of scar tissue on his neck behind the ear's base. A severe case of cystic acne in adolescence compounded his sense of disfigurement: as an adult, he would apply Max Factor pancake makeup to his face and neck every morning and again after each of the several showers he took daily.
Sinatra later told his daughter Nancy that when he was eleven, after some playmates began to call him "Scarface," he went to the house of the physician who had delivered him, determined to give the good doctor a good beating. Fortunately, the doctor wasn't home. Even when he was in his early forties, on top of the world and in the midst of an artistic outpouring unparalleled in the history of popular music, the birth trauma-and his mother-were very much on Sinatra's mind. Once, in a moment of extraordinary emotional nakedness, the singer opened up very briefly to a lover. "They weren't thinking about me," he said bitterly. "They were just thinking about my mother. They just kind of ripped me out and tossed me aside."
He was talking to Peggy Connelly, a young singer whom he met in 1955 and who, for almost three years at the apex of his career, would be as close to him as it was possible for anyone to be. The scene was Madrid, in the spring of 1956: Sinatra was in Spain shooting a movie he had little taste for. One night in a small nightclub, as he and the twenty-four-year-old Connelly sat in the dark at the edge of the dance floor, she caressed his left cheek, but when her fingertips touched his ear, he flinched. She asked him what was wrong, and he admitted he was sensitive about his deformity.
"I really don't think I had ever noticed it, truly," Connelly said many years later. "This was early on in our relationship." Sinatra then went on to spill out the whole story of his birth: his great weight (thirteen and a half pounds), the ripping forceps, the way he'd essentially been left for dead. "There was no outburst of emotion," Connelly recalled. "There was [instead] an obvious lingering bitterness about what he felt had been a stupid neglect of his infant self to concentrate only on [his] mother, intimating that he was sort of 'ripped from her entrails' and tossed aside; otherwise his torn ear might have been tended to."
In the years immediately following the harrowing birth of her only child, Dolly Sinatra seems to have compensated in her own way: she became a midwife and sometime abortionist. For the latter activity she got a nickname ("Hatpin Dolly") and a criminal record. And while she sometimes refused to accept payment for terminating pregnancies, she could afford the generosity: her legitimate business of midwifery, at $50 per procedure, a substantial sum at the time, helped support her family in handsome fashion. Strikingly, two of her arrests, one in late 1937 and one in February 1939 (just three weeks after her son's wedding), neatly bracketed Frank Sinatra's own two arrests, in November and December 1938, for the then-criminal offenses of (in the first case) seduction and (in the second) adultery. Also remarkable is that all these Sinatra arrests were sex related-and that none of them would have occurred today.
What was happening in this family? To begin to answer the question, we have to cast ourselves back into the knockabout Italian streets of Hoboken in the 1920s and 1930s-and into the thoroughly unpsychological household of Dolly and Marty Sinatra. But while it's easy to wonder what effect growing up in such a household could have had on an exquisitely sensitive genius (which Frank Sinatra indisputably was), we must also remember that he was cut from the same cloth as his parents-especially his mother, a woman he seems to have hated and loved, avoided and sought out, in equal measures, throughout his life; a woman whose personality was uncomfortably similar to his own.
The first mystery is what brought two such disparate characters as Natalina Garaventa and Anthony Martin Sinatra together in the first place. Dolly (she acquired the nickname as a little girl, for being so pretty) was, even as a very young woman, loud, relentlessly foulmouthed, brilliant (she had a natural facility for languages), and toweringly ambitious. So-to what kind of star did she imagine she was hitching her wagon when she went after (for she must have been the aggressor in the relationship) Marty Sinatra?
For he was a lug: a sweet lug, maybe, but a lug nevertheless. Short, with an obstinate-looking underbite and an early-receding hairline. A fair bantamweight prizefighter (he billed himself as Marty O'Brien, because of the anti-Italian prejudice of the times), frequently unemployed, who sometimes moonlighted as a chauffeur to make ends meet. A little man who had his arms covered in tattoos to try to look tough. Asthmatic; illiterate all his life. And exceedingly stingy with words. In his sixties, Frank Sinatra recalled listening to his parents through the bedroom wall. "Sometimes I'd be lying awake in the dark and I'd hear them talking," he said. "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_._._._He'd just say, Eh. Eh."
It's difficult to extract much personality from the few stories told about the elder Sinatra. He seems to have had a wry and quiet sense of humor, and photographs of him as a young man appear to bear this out-it's a sweet, though dim, face. Nancy Sinatra, in Frank Sinatra, My Father, tries to paint her grandfather as a lovable practical joker: There was the time Marty gave a pal a laxative and spread glue on the outhouse toilet seat. And then there was Marty's revenge on a deadbeat barkeep who tried to pay off a debt to him with a sick horse instead of cash: her grandfather, Nancy says, walked the horse to the saloon in the middle of the night and shot it dead in the doorway, leaving the carcass as a discouragement to business.
Rough humor! The joke has a Sicilian tinge to it, and Sicily is where Marty came from, in 1903, aged nine, when he landed at Ellis Island with his mother and two little sisters to join his father, Francesco Sinatra, who-in the common practice of the day-had arrived in America three years earlier to establish himself.
Dolly Garaventa's people were from the north of Italy, near Genoa. And the ancient, deeply held social prejudice on the part of northern Italians toward southerners makes it doubly difficult to imagine what was on her mind when, at sixteen, she set her cap for the eighteen- year-old Marty. Was it irresistible attraction? Or adolescent rebellion-the chance to stick it to her parents, the lure of the bad boy? It's said that little Dolly (she was under five feet, and just ninety pounds) used to disguise herself as a boy to sneak into Marty's prizefights, her strawberry blond hair stuffed into a newsboy cap, a cigar stuck in her mouth: a sweet story, with a ring of truth about it, bespeaking her willfulness, her force. And her originality.
Against her family's outcry (and probably at her urging), the two eloped, ages seventeen and nineteen, and were married at the Jersey City city hall on Valentine's Day (a holiday that would loom large at two junctures in Frank Sinatra's first marriage) 1913. On the marriage certificate, Marty gave his occupation as athlete. In truth, he only ate regularly because his parents owned a grocery store. Soon the couple made it up with her parents, got remarried in the church, and set up housekeeping in the cold-water flat at 415 Monroe Street.
Every family is a mystery, but some are more mysterious than others. After Dolly and Marty Sinatra's only child was born, theirs was a centrifugal household. Family lore says that the birth rendered Dolly unable to have more children, but it seems equally likely she simply decided-she was a decider-she didn't want to go through that again. Besides, she had many other fish to fry. Her skill with Italian dialects and her fluency in English led her to become a facilitator for new immigrants who had court business, such as trying to get citizenship papers. Her appearances in court brought her to the attention of local Democratic politicians-the Irish bosses of Hoboken- who, impressed by the force of her personality and her connection with the community, saw in her a natural ward leader. Soon she was getting out votes, petitioning city hall (as part of a demonstration for suffrage in 1919, she chained herself to the building's fence), campaigning for candidates, collecting favors. All the while roaming the streets of Hoboken with her black midwife's bag.
It all meant she simply wasn't at home very much. In any case, home wasn't the place for Dolly: she was out, not in; she had the politician's temperament-restless, energetic, unreflective. And she had unique ideas about child rearing. Of course, to present-day sensibilities filled with the art and science of what we now call parenting, child rearing in the early twentieth century has a distinctly primitive look to it. Poor and lower-middle-class families were large, and with the parents either working or simply exhausted, the older children-or the streets-frequently raised the young.
Neither was an option for Frank Sinatra. As an only child in Hoboken in the 1920s and 1930s, he was an anomaly. His mother paid him both too much attention and too little. Having wanted a girl, she dressed him in pink baby clothes. Once he was walking, there were Little Lord Fauntleroy outfits.
He was the apple of his parents' eye and their ball and chain. Dolly had babies or votes to deliver; Marty had things to do. Italian men left the house whether they were employed or not, if only to sit somewhere and sip a beverage with pals. Late in the second decade of the twentieth century, Dolly borrowed money from her family, and she and Marty bought a bar, on the corner of Jefferson and Fourth, which they called Marty O'Brien's. While they ran the place, little Frankie was looked after by his grandmother or a cousin or, most regularly, a nice Jewish neighbor named Mrs. Golden. She taught him Yiddish.
When Dolly was with her son, she alternately coddled him-beautiful clothes continued to be a theme-and abused him. In those days it was known as discipline. The child was spirited, and so was the mother. It's a miracle the child kept his spirit. Dolly once pushed her son down a flight of stairs, knocking him unconscious. She playfully ducked his head under the ocean waves, terrifying him (remarkably, he became an expert swimmer). And most regularly, she hit him with a stick. It was a small bat, actually, something like a policeman's nightstick: it was kept behind the bar at Marty O'Brien's.
"When I would get out of hand," Sinatra told Pete Hamill, "she would give me a rap with that little club; then she'd hug me to her breast."
"She was a pisser," he recollected to Shirley MacLaine. "She scared the shit outta me. Never knew what she'd hate that I'd do."
If the primary intimacy was up for grabs, so was every subsequent relationship: Sinatra would feel ambivalent about women until the end of his days. He would show every lover something of what Dolly had shown him.
It seems straight out of a textbook: an only child, both spoiled and neglected, praised to the skies and viciously cut down when he fails to please, grows up suffering an infinite neediness, an inability to be alone, and cycles of grandiosity and bottomless depression.
"I think my dad desperately wanted to do the best he could for the people he loved," Tina Sinatra writes, "but ultimately he would do what he needed to do for himself. (In that, he was his mother's son.)"
Yet that doesn't quite tell the whole story. Yes, Frank Sinatra was born with a character (inevitably) similar to Dolly's, but nature is only half the equation. Frank Sinatra did what he needed to do for himself because he had learned from earliest childhood to trust no one-even the one in whom he should have been able to place ultimate trust.
Excerpted from Frank by James Kaplan. Copyright © 2011 by James Kaplan. Excerpted by permission of Anchor, a division of Random House, Inc. All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.