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  Clothes and toys, of course, were no substitute for affection. “Aunt Dolly was always busy,” recalled one of the cousins, John Tredy. “I think Frankie was always underfoot a bit. He was always alone.” Relatives and neighbors remembered a solitary figure, sitting forlornly on his tricycle on the sidewalk, hanging around outside his grandmother’s front door.

  When Dolly was at home, Marty and Frank could not relax. She whisked away her husband’s ashtray every couple of minutes. She washed her son, in cold water with a scrub brush, far more than was necessary. Even as a grown man and a heavy smoker, Sinatra himself could not stand to see an ashtray filled with butts. He was forever washing his hands, a habit that fellow musicians mocked as his “Lady Macbeth bit,” and was, a friend said, “a fanatic about his nails.” The paper money in his pocket had to be in clean, brand-new bills. “I can’t stand bureau drawers slightly open, knives and forks out of line, books in untidy heaps,” Sinatra would say at the age of thirty. In restaurants, the glasses in front of him always had to be lined up just so.

  Dolly had no patience with childhood fears. “We were on the beach,” Frank remembered. “The waves leaping high terrified me. I kept crying: ‘No! No!’ but my mother laughed. I can still feel the cold fright that choked me when she ducked me under the water.”

  Dolly “always expected more of him,” Frank’s first wife, Nancy, would say, “it was never enough. . . . It was difficult to please her.” When Frank failed to please, the punishments were severe—he was beaten, as he himself confirmed. Once, when he stood up on a horse at a merry-go-round, he got his head caught in the roof structure and was extracted only with difficulty. Far from being sympathetic, he recalled, “Dad took it out of my hide.”

  It was his mother, though, whose beatings he feared. The once petite Dolly had grown stout and intimidating, and her punishments were fearsome and sometimes unfair. She once punished him, according to family lore, for falling down stairs. As her granddaughter Tina heard it, it was a blow from Dolly that made Frank fall in the first place, and he was knocked unconscious. Dolly then fussed around her son for days afterward, “like a chastened mother hen.”

  “She used to beat Frankie up a lot,” recalled Rose, the niece who lived across the hall. “He used to run into my mother’s apartment and go under the table and cry—she had those long tablecloths that touched the floor—so he could hide. He’d say: ‘Lala Nanina’—that was my mother’s nickname, sort of like ‘Little Auntie’—‘she’s got a baseball bat, she’s gonna kill me.’ ”

  It was sometimes difficult to distinguish between Dolly’s rage and her affection. She would “give me a rap with that little club,” Frank remembered, “then she’d hug me to her breast. . . . When she came close, I never knew whether I was going to get hugged or hit.”

  Dolly inspired a mix of obedience and resentment in her only child until well into his middle age. “Yes, mama. No, mama,” people would hear him saying into the telephone. And wearily, when she was still ordering him around as late as the 1970s, he was heard to say, “Okay, mom, if you think so, mom.”

  The singer Peggy Connelly, one of Sinatra’s lovers, remembered him “avoiding his mother like the plague. She was a pain in the neck and he found her embarrassing.” “She was a pisser,” Frank told the actress Shirley MacLaine after Dolly’s death, “but she scared the shit outta me. Never knew what she’d hate that I’d do.” All the same, he would be devastated by her passing.

  Frank’s upbringing fits a familiar pattern. Parents who cannot have more children classically spoil the child they have, exaggerate the importance of the child’s mistakes, demand perfection. Only children, studies show, may turn out overaggressive, socially inept, and less successful in sustaining relationships. Or, with careful parenting and good luck, they may turn out just fine. Frank Sinatra, however, was not only prone to the problems of an only child. He grew up surrounded by law-breakers in a time of lawlessness.

  WORLD WAR I CHANGED both Hoboken and the lives of the Sinatra family. Troopships replaced passenger liners on the waterfront. “Heaven, Hell, or Hoboken by Christmas!” became the catchphrase of the million or more soldiers who embarked for Europe. In 1917, three years before Prohibition became law nationwide, the town’s many bars were ordered to close in the interests of military propriety. A vain hope.

  Hoboken became an entry point for shipments of foreign liquor, and bars sprang up everywhere. With the local administration failing to enforce the law, there would soon be 250 of them in the little town’s square mile.

  Marty and Dolly ran one such tavern. Using money borrowed from Dolly’s mother, they opened a “bar and grill” on the corner of Fourth Street and Jefferson. They called it Marty O’Brien’s—using the name Marty employed in the ring—which made good commercial sense in Irish-dominated Hoboken. As an Italian touch, they served pasta and sandwiches along with the booze.

  A little of what went on at the bar has become family lore: Dolly helping to bounce drunks, wielding a billy club she kept behind the bar; Marty taking macabre revenge on a fellow saloonkeeper who tried to settle a $200 cash debt by delivering a horse. When Marty saw that the beast was on its last legs, he walked it to the door of the other man’s bar one night and shot it dead. The carcass was found the following morning, blocking the doorway. Marty was “a quiet, gentle guy until you backed him into a corner,” said a friend, “then he became the street guy that he was.”

  There was another, much more serious, side to the bar business. The Sinatras needed liquor and they needed protection, services only gangsters could supply. Prohibition meant a bonanza for the Italian and Jewish mobsters who would eventually join forces and control organized crime in America. The first big-name mobsters were now making fortunes and fighting bloody battles for territory: Meyer Lansky, Bugsy Siegel, Joe Adonis, Johnny Torrio, Longy Zwillman, Willie Moretti, Waxey Gordon, Dutch Schultz, Frank Costello—and Lucky Luciano.

  Prohibition was “a whole new ball game,” Costello recalled, “and we owned the ball.” The gangsters were exceptionally active in New Jersey. The Hoboken docks were a key transit point for booze shipments, and Marty Sinatra was one local Italian who got involved. “He aided in bootlegging,” his son would admit years later. “His job was to follow the trucks with the booze so they weren’t hijacked. . . . I remember in the middle of the night—I was only three or four years old—I heard sobs, terrible crying and wailing. I think my old man was a little slow and he got hit on the head. And he came home and he was bleeding all over the kitchen. My mother was hysterical.”

  Frank admitted that his father’s bootlegging activity was on behalf of “one of the tough guys” of the day. He did not say which tough guy, but in 1995 his daughter Nancy—in one of the books she wrote with her father’s help—said her grandparents had been obliged to “rub elbows” with major criminals. One of them, she specified, was the bootlegger Waxey Gordon, who did business with Luciano. According to the writer Pete Hamill, who had rare access to Frank many years later, the story in Hoboken was that Gordon had been “a regular” at the Sinatras’ bar.

  Young Frank spent a good deal of time in the bar during Prohibition—he often did his homework there in the evenings. His parents’ customers were among the first ever to hear him sing. “There was a player piano in the joint,” he recalled, “a nickelodeon—put a nickel in, and the roller would play. I was about eleven years old or so. . . . Some of the guys would put me up on the piano, and I would sing along with the piano, and they’d give me a dime. . . . I had a voice like a siren—way up there. And I remember the song was called ‘Honest and Truly.’ ” “Honest and truly,” the little boy sang, “I’m in love with you. . . .” As a grown man he would say he remembered thinking, even then, “What a great racket this is!”

  Dolly was close to her brothers Dominick and Lawrence, both of whom got into serious trouble during Prohibition. Lawrence’s criminal record began with an arrest for selling liquor to soldiers. By 1921, when he was twenty and ou
t on bail facing charges of murdering an American Express driver, he was wanted by police in connection with two New Jersey holdups and another murder. In 1922, he was arrested after yet another holdup in which a policeman was shot dead. Before dying, the policeman named as his killer a prominent associate of Waxey Gordon.

  When Lawrence stood trial in the American Express case, Dolly appeared in court masquerading as his wife, carrying a baby borrowed for the occasion and sobbing. When he received a long jail sentence, she loudly denounced the judge as “an S.O.B. bastard.” She visited Lawrence in prison regularly, then took him into her home when he was released. He lived with the Sinatras for several years, and Frank adored him.

  Lawrence was arrested yet again in 1931, as was his brother Dominick, following a shootout in the street. In the aftermath, police cordoned off part of Hoboken in search of a car registered in the name Marty Sinatra used, O’Brien. Lawrence abandoned his own car, with a bullet hole in the windshield, on Madison Street two doors away from the home of his and Dolly’s sister Josie Monaco. Frank had seen a lot of his aunt Josie, for her house backed onto the Sinatras’ first apartment. Her father-in-law, who also lived on Madison, had been a defendant in a liquor violations case, and a gangster was gunned down outside Josie’s house during fighting between rival bootleggers.

  Lawrence, like Frank’s father, was involved with a powerful bootlegger. “He was a hijacker with Dutch Schultz with the whiskey and stuff,” Josie’s son said, “and I think he got himself in a swindle by hijacking from Dutch Schultz.” Schultz used Italians as hired guns and, like Waxey Gordon at one stage, did business with Lucky Luciano. As Tina Sinatra has said, “My dad grew up with gangsters next door. . . . They were his personal friends.”

  A family named Fischetti lived near the Sinatras on Monroe Street during Prohibition, and one of the Fischetti children was close to Frank. Members of the family, according to police sources, were truck operators involved in organized crime and in touch with the notorious Fischetti brothers associated both with Chicago’s Al Capone and with Lucky Luciano. The brothers, Rocco, Charlie, and Joseph, lived in the New York area before relocating to the Midwest. They served Capone initially as bodyguards, but later rose high in his organization. The younger sibling, Joseph, Joe “Stingy,” would eventually be categorized by the FBI as a “top hoodlum.” He would specialize in the entertainment industry and become a close companion and associate of Frank Sinatra, whom he said he had known since they were “youngsters.”

  “Jimmy Blue Eyes” Alo, Meyer Lansky’s right-hand man, kept a photograph of Marty and Dolly Sinatra on his coffee table as late as 2001. “I knew Frank Sinatra from when he was a kid,” he said before his death. “He always wanted to be a gangster, this phony bastard.”

  BY THE TIME Frank turned twelve, in 1927, the Sinatras had accumulated enough money to move up in the world. They left Monroe Street and the Italian section and took a three-bedroom apartment in a German-Irish neighborhood. Marty, at thirty-three no longer fit enough to box or work on the docks, managed to get a job as a firefighter, work normally barred to Italians. It was Dolly who fixed that, reportedly by using her pull with the mayor himself. The joke in those days was that it took a bribe of $200 to get onto the police force and $300 to join the fire department—“because firemen get to sleep a lot.”

  The Sinatras kept Marty O’Brien’s bar going, ensuring that they remained fairly well off when the Depression came. The family owned a radio—Americans had been enjoying that magical invention since 1920—and Frank got one of his own, a contraption that “looked like a small grand piano.” It brought him what he would remember as the “blending saxophones and tightly knit brass” of the big bands, Guy Lombardo and Wayne King, the foot-stomping jazz of Louis Armstrong, the “serious” jazz of George Gershwin, the genius of Irving Berlin. And the crooners, too—the “tantalizing tonsils” of Rudy Vallee, “Prisoner of Love” Russ Columbo, and, solo on CBS as of 1931, a mellow Bing Crosby.

  Marty’s mother had died in 1925, her passing recalled long afterward because of the earth tremor that sent her coffin sliding across the room while relatives were viewing the body. His father, Francesco “Pops” Sinatra, lived on into the 1940s to be remembered fondly by Frank as a “sweet old gent with long curly mustachios” who offered exhortations in fractured English. “How are you going to grow up to be healthy man?” he would ask, as he cooked up a pot of spaghetti. “You gotta eat! Eat plenty! So your bones won’t stick out!” Frank and his young friends, said Lee Bartletta, who was always in and out of the house, were now “Pops’s whole life.”

  Dolly continued to buy her son fancy clothes, which attracted the envy and mockery of other children. At ten he sported a fedora. At twelve he was photographed, outlandishly, in jodhpurs. By the time Frank went to high school he had more than a dozen sports jackets, and so many pairs of pants that friends called him “Slacksey.” He sometimes gave clothes away, even bought clothing for poorer kids—and Dolly paid. He let others use his pass to the swimming pool and bought movie tickets for groups of pals. He was to be bountiful in that way all his life. “Frank doesn’t know how to express friendship,” the comedian Phil Silvers said thirty years later. “He does it with expensive gifts.”

  Astonishingly, when her son was fifteen, Dolly spent $35 to buy him a car—a secondhand Chrysler convertible. It made him “the prince of the neighborhood,” recalled Nick Sevano, a younger Hoboken contemporary. Academically, however, he was no prince. At David E. Rue Junior High School, Frank had been in constant trouble. His report cards were bad, made worse by the fact that his cousin Sam across the hall brought home good ones. Frank got a certificate showing he had completed junior high, but that was his last graduation.

  At Demarest High, he enraged his teachers. “A lazy boy,” the math teacher called him years later, “absolutely no ambition at all.” “No talent for anything,” said the principal, and Frank’s record card noted only his name, none of the usual information on his academic progress. “School was very uninteresting,” he would say later. “Homework we never bothered with, and the few times we attended school we were rowdy.” Frank frequently sneaked off with pals into New York City to visit the Hudson Burlesque House on 38th Street. After just over a year, depending on which source one accepts, he either dropped out of school or was expelled.

  The expulsion, if that is what it was, was predictable. Frank had started with pranks, complicated ones that earned him another nickname, “Angles.” He released pigeons in the school auditorium during assembly, caused a commotion by taking a cat into a movie theater and shooting it in the backside with a BB pistol, set off firecrackers under a manhole cover. In adult life, he would enjoy scaring people with cherry bombs.

  Frank also did some petty stealing. He spoke later of a time when “a bunch of us decided to raid a fruit stand. We waited until it got pretty dark, then struck out across the street. When the old fruit man had his back turned we charged the stand with loud whoops. Then we grabbed anything we could lay our hands on.” He told other stories—too numerous and too lurid to be entirely credible—of pocketing candy in stores, snatching change from cash registers, stealing bicycles. “All I knew,” he said, “was tough kids on street corners, gang fights, and parents too busy trying to make enough money for food, rent, clothing. . . . The kids in the Irish, Negro, and Jewish neighborhoods ganged together . . . we found a release from our loneliness in vicious race wars.”

  The neighborhood wars of his childhood, Frank suggested, made him a lifelong champion of racial equality. While playing in undergrowth near the Hudson River, he said, he and friends once managed to eavesdrop on a Ku Klux Klan meeting. They ran home to tell their fathers, who rushed to attack the bigots with baseball bats. “I would hear the stories,” he said, “things that happened because you were Italian. . . . I skirted some areas of town because the cry would go up: ‘Kill the dago!’ I heard the same kinds of things from my Jewish friends.” Once, he recalled, “A big kid called me a wop.
But a Jew kid and me creamed him.”

  Frank painted a lurid picture of “bitter, bloody block fights,” of a childhood in which “everyone carried a twelve-inch pipe—and they weren’t all studying to be plumbers.” He bragged of his own pugnacity. “Sometimes with me it was a matter of if-you-got-the-name-you-might-as-well-have-the-game. You think I’m just some wop wise guy off the street? All right, I’ll be a wop wise guy off the street and break your fucking head.”

  His boyhood buck teeth had been straightened, he said, not by the dentist but in a fistfight. A scar over his nose was the legacy of “a Coke bottle blow in a street fight,” inflicted when he was nine. Another story suggested that it was a crack on the head with a bicycle chain that punctured his eardrum—not, as generally accepted, the forceps used to wrench him from the womb. “I was hit,” he said, “more times than a fender in a parking lot.”

  His uncle Dominick witnessed one such encounter, after his nephew ran into another boy on his bike. “Pretty soon four or five kids were whacking the tar out of him. He just stood up to them and traded punches and never backed down. He had lots of fights as a kid, because he had a temper.” With three onetime professional fighters in the family, Frank was taught early on how to use his fists.

  His father, he recalled, “used to show me in the yard, you know, how to jab, how to throw a left hook, set your feet, that kind of thing. . . . I was five years old when I got my first pair of boxing gloves.” In an era when heavyweights like Jack Dempsey and Gene Tunney stirred worldwide fervor, the young Sinatra became a lifelong enthusiast. “My favorite exercise is boxing,” he told an early interviewer, and it was even reported that he had fought as a semipro in Hoboken clubs. He had publicity photographs taken showing him clad in trunks and wearing boxing gloves. In his early singing days, it would be said, he worked out backstage with gloves and a punching bag, or visited gyms to watch professional boxers sparring. He went on to share “ownership” of two heavyweights, Tami Mauriello and Chuck Crowell, as well as a welterweight, Ray Brown.