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  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.

  And then there is the larger environment in which Sinatra grew up, those knockabout streets of Hoboken during Prohibition and the Depression.

  By some accounts, the Square Mile City was a pretty mobbed-up place in those days. Some say even Marty O’Brien’s little tavern was a hotbed of crime. We hear about big Mob names like Meyer Lansky and Bugsy Siegel and Joe Adonis and Johnny Torrio and the Fischetti brothers and Longy Zwillman and Willie Moretti and Dutch Schultz and Frank Costello and—of course—Lucky Luciano, who, as fate would have it, was born in the same Sicilian village as Frank Sinatra’s grandfather, Lercara Friddi.

  What business could all these big cheeses of organized crime possibly have had with the small-time Sinatras of Hoboken? It all had to do (we’re told) with liquor. The Mob made millions from rum-running; Dolly and Marty Sinatra bought illegal booze from their lieutenants, or the lieutenants’ lieutenants. Poor Marty, it seems, once got hit, knocked unconscious, when he tried to make some pin money riding shotgun for a liquor shipment. The big-time bootlegger Waxey Gordon (identified in Nancy Sinatra’s book as “Sicilian-born,” which must mean a very odd neighborhood in Sicily, for he was born Irving Wexler) was said to be a regular at Marty O’Brien’s.

  Meanwhile, by his own later account, little Frankie also hung out at the bar, doing his homework and, now and then at the urging of the clientele, climbing up on top of the player piano to sing a song of the day for nickels and quarters: Honest and truly, I’m in love with you …

  It appears that Dolly’s brothers Dominick and Lawrence were both involved in shady activity. Both had criminal records; Lawrence, a welterweight boxer under the name Babe Sieger, dabbled in crime, sort of. “He was a hijacker with Dutch Schultz with the whiskey and stuff,” Dolly’s sister’s son recalled, somewhat vaguely. And, of course, Dutch Schultz did business with Lucky Luciano, and we can fill in the blanks from there.

  But to understand the effect of organized crime on the evolving psyche of young Frank, we need look no further than Dolly herself—at least if we consider the writings of Mario Puzo.

  In 1964, Puzo published his second novel, the highly autobiographical The Fortunate Pilgrim. Critics hailed it as a minor classic—much as they had hailed his first book, a World War II novel called The Dark Arena. After those two books, Puzo, unable to make a living from his writing, decided he was tired of creating minor classics. And so he wrote The Godfather.

  The Fortunate Pilgrim is a beautiful, harrowing story, depicting the travails of an Italian-American family living in Hell’s Kitchen in the depths of the Depression. When the father, the family’s breadwinner, has a breakdown and is institutionalized, the mother, Lucia Santa Angeluzzi-Corbo, takes matters into her own hands, deciding she will not let her six children go hungry or be farmed out to other households. She learns how to earn a living; she holds the family together by the sheer force of her will.

  The book was based on Puzo’s own childhood, and he would later make an amazing admission: he had based the character of Vito Corleone, the Godfather, on the very same person who had been the model for Lucia Santa Angeluzzi-Corbo—his own mother. Just like Lucia Santa and Don Corleone, Mother Puzo had been benevolent but calculating, slow to anger but quick to decide: the ultimate strategist.

  Like Lucia Santa Angeluzzi-Corbo, Dolly Sinatra managed, by sheer force of will, to make a life for her little family in the years leading up to, and into the teeth of, the Depression. It wasn’t easy.

  She was a politician and a master strategist: endlessly ambitious, fiercely determined, utterly pragmatic. She was also abusive, violent, and vengeful. It was quite a different version of the godfather from Mario Puzo’s. But it was a cogent version nonetheless. Frank Sinatra may have grown up with Fischettis down the street, Dutch Schultz around the corner, Waxey Gordon on the next bar stool at Marty O’Brien’s, but he had his own model for a Mafia chief right inside his house. Small wonder that when he eventually met the real thing, he felt a shot of recognition, an instant pull. And small wonder that when the real mafiosi met Sinatra, they smiled as they shook his hand. It wasn’t just his celebrity; celebrities were a dime a dozen. It was that part of Dolly that her son always carried with him: his own inner godfather. He both wanted to be one of them and—in spirit and in part—really was.1

  A heavy hand. “She scared the shit outta me,” Sinatra recollected to Shirley MacLaine. “Never knew what she’d hate that I’d do.” Frank and Dolly on a trip to the Catskills, circa 1926. (photo credit 1.2)

  2

  First Communion, 1924. (photo credit 2.1)

  Even with Dolly’s Napoleonic drive, moving up from Guinea Town was no simple matter. She and Marty endured 415 Monroe Street for fourteen years, Frankie, almost twelve. A long time.

  Toward the end of their tenure there, another joined them.

  It was a strange little ménage, the precise sleeping arrangements lost to history: Dolly and Marty in one bed, Frankie in another, and somewhere Marty’s cousin from the Old Country, one Vincent Mazzola. In her memoir, Tina Sinatra remembers “Uncle Vincent, a tiny, darling man with a severe limp from World War I, where he’d earned a Purple Heart. With no family of his own, he’d lived with my grandparents since the late thirties.”

  In fact, according to a family friend, it was a dozen years earlier, around 1926, when Vincent Mazzola moved into the little flat with Dolly and Marty and Frankie. Mazzola’s mysterious nickname was Chit-U. Nobody seems to know what it meant, but one wonders if it was in any way related to citrullo, an Italian word for simpleton, or fool. (Or a crude joke—shit-you-pants?) In any event, Chit-U seems not to have had much going on upstairs. In all likelihood he was shell-shocked.

  His arrival at Monroe Street came at a particularly inopportune moment for the family: Marty could no longer box, having broken both wrists in the ring,1 and had lost his job as a boilermaker because of his asthma. Between the fees she earned from midwifery and abortion and a weekend job dipping chocolates in a candy store, Dolly was holding the Sinatras’ fortunes together. Imagine her delight at having to take in a slow-witted cripple.

  But she pulled up her socks and put Chit-U to work, using her political influence in the Third Ward to get him a job on the docks. Every week, he meekly handed his paycheck to her. She also took out a life-insurance policy on the little man, listing herself as the beneficiary.

  And not long after setting Cousin Vincent to work, she got busy with Marty, marching to city hall and calling in some Democratic Party chits to demand for her husband a coveted spot in the Hoboken Fire Department. Since the HFD (a) was predominantly Irish and (b) required a written test of all applicants, and since Marty Sinatra was (a) Irish in nickname only and (b) illiterate, one would imagine his chances to have been slim. But no, to Dolly Sinatra, was an inaudible syllable. Presto, Marty was a fireman! And now, with her husband established in a rock-solid and well-paying (and as a bonus, not excessively labor-intensive) position, and Chit-U’s income from the docks added to Marty’s pay and Dolly’s own, escape from Guinea Town was at long last possible.

  He was a lonely boy, by turns timid and overassertive. He desperately wanted to be “in”—part of a gang or group of any sort. Pampered and overprivileged, he used the money Dolly gave him to try to buy friendship with gifts, with treats. Still, as in the early Hal Roach Our Gang films in which the prissily dressed stock character of the rich boy is pushed into mud puddles, he was mocked: for his outfits, his oddity.

  And his emotionalism. He would never be one of the cool kids—he was hot, and his anger and laughter and tears came too easily.

  Yet this was not the rich boy in Our Gang. The damaged left ear was clearl
y visible, as was a scar at the top of the philtrum. This was a face to be reckoned with—a startling face, not least because of the similarity to what it would become; but also in itself: serene, mischievous, beautiful. Late in life Sinatra told a friend that as a child he had heard the music of the spheres.

  He may have been timid and babyish and spoiled; he may even, as some accounts suggest, have played with dolls as late as age twelve. But he seems from early years to have had the strong sense that he was Someone—a sense that would have been encouraged by the material things lavished on him, and undercut by the attention that was denied. Not to mention the billy club.

  Still, if there’s any truth to the idea of victims’ identifying with the oppressor, it can be found in young Frank Sinatra’s face. Dolly wanted and expected things: things material and immaterial, possessions and power. She wanted the world. Her son may have been uncertain of the ground he walked on where she was concerned, but if there was one thing he was absolutely sure of, it was that he had big things coming to him.

  And in early adolescence (just as his family was beginning to bootstrap itself out of the ghetto) he began to dress the part. Frankie had a charge account at the local department store, Geismar’s, and a wardrobe so fabulous that he acquired a new nickname: “Slacksey O’Brien.” A lesser boy might have become just a well-tailored layabout, a Hoboken vitellone, but young Frank’s splendor was much more than skin-deep. And his large sense of himself derived not only from his identification with Dolly’s voracious sense of entitlement but also from the Secret he entertained, the sounds he heard in his head.

  In September 1927 the Sinatras made their big move east, from Monroe Street across the super-significant border of Willow Avenue and into a three-bedroom apartment, at $65 a month, in a German-Irish neighborhood on the tony-sounding Park Avenue.2 Later in life, Frank Sinatra liked to foster the impression that he’d led a pretty rough-and-tumble boyhood among the street gangs of Hoboken. More likely, he spent his early years dodging the gibes and brickbats of the tougher boys of Guinea Town. Now, however, he and his family had crossed a crucial line, into their new life in the high-rent district: every morning, Marty went off to the firehouse to roll up his sleeves (revealing those impressively tattooed arms) and play pinochle; Dolly roamed Hoboken with her black bag; Chit-U limped off to the docks (in his spare time, he limped around the new apartment, mopping and dusting); and Frankie, once school was done for the day (thank God—he hated every minute of it), dreamed by the radio.

  It was the centerpiece of any bourgeois or aspiring-bourgeois household in the mid-1920s: the more elaborate and fine-furniture-like, the better. And the Sinatras owned not just one radio but two. For eleven-year-old Frankie had his own bedroom (at a time when entire families in Hoboken slept in a single room) and his very own Atwater Kent, an instrument he would later recall resembling “a small grand piano.”

  Radio was just coming into its own as a medium. The linkage of local transmitters by telephone lines had led, in 1926 and 1927, to the formation of the first two networks, NBC and CBS. Suddenly a wondrous world of faraway news, drama, and sports opened up, emanating from the magical cabinet. Alone in his bedroom, young Frankie would have listened hungrily, passionately. But to his ears, the most miraculous sounds of all were musical: the operatic voices of Lauritz Melchior and Lily Pons and Amelita Galli-Curci; the jazz rhythms of the Roger Wolfe Kahn and Ted Fio Rito and Paul Whiteman orchestras.

  And then there were the crooners.

  The recent perfection of the electronic microphone had led to a sea change in the art of popular singing. Music had been recorded since the 1870s and broadcast since 1920, but prior to 1924 singers had to project through megaphones or into acoustical microphones that provided scarcely greater amplification than cardboard cones. The art of popular singing had therefore been an art of projection, and higher voices—female or tenor—simply carried better.

  Now with the modern microphones came a new generation of baritones, men who leaned in and sang softly, intimately, to millions of listeners. There was Gene Austin and Art Gillham and Cliff “Ukulele Ike” Edwards (later the voice of Jiminy Cricket) and Rudy Vallée and Russ Columbo. But most startlingly, there was Bing Crosby.

  Crosby, out of Spokane, Washington, had come up through vaudeville, singing as part of a trio called the Rhythm Boys, first with Paul Whiteman, then with the Gus Arnheim Orchestra. But Crosby quickly overshadowed his singing partners—and then even the orchestras that accompanied him—by bringing something entirely new to the art of the popular song: himself.

  Prior to the age of the new microphone, popular singing had been, of necessity, a declamatory art: singers literally had to reach the back rows. Crosby’s idol, Al Jolson, electrified the Jazz Age with his overpowering pipes and incandescent theatricality. Artifice was an essential part of show business.

  The new crooners were more laid-back, but equally artificial. Under the old show-business conventions, a certain remove from the audience, in the form of “classiness,” as exemplified by heightened diction, was a quality to be cultivated. Bing Crosby captured America’s heart as no entertainer had ever done before by removing the remove, by seeming the most common of men.

  Of course he wasn’t that by a long shot. He was a one-of-a-kind phenomenon, a single figure as transforming of the American cultural landscape as Jolson had been, and as Frank Sinatra himself—or Elvis Presley, or Bob Dylan—would be in decades to come. Crosby was, first and foremost, a musical genius, a quality that underlay all his other contradictions, which were plentiful. He was a Jesuit-educated intellectual and a ne’er-do-well; he was at once lovably warm and unreachably cool. He was, with his English-Irish background and ice blue eyes, the whitest of white men and, with his fondness for hard liquor (and, now and then, marijuana) and his incomparable talents for melodic and rhythmic improvisation, a great jazz musician to the core of his being. As Artie Shaw memorably put it: “The thing you have to understand about Bing Crosby is that he was the first hip white person born in the United States.”

  In other words, Crosby came along (as Elvis would a quarter century later) at precisely the tick of time when the vast white music-listening audience of the United States was primed for hipness—as long as it came in white form. As Gary Giddins reminds us in his superb biography of Bing, A Pocketful of Dreams, the definition of jazz in the Jazz Age was far looser than it would come to be later: witness the above-mentioned Kahn, Fio Rito, and Whiteman orchestras, which were stately and lily-white but agreeably peppy.

  Meanwhile, truly transformational musicians, both black and white—the likes of Fletcher Henderson, Bix Beiderbecke, Duke Ellington, Bubber Miley, Chick Webb, and Benny Goodman—were creating genuine jazz. It was an age of intense cross-fertilization in popular music, and an age of great excitement, when anyone who was paying attention could hear new and wonderful things.

  And Bing Crosby had big ears, literally and figuratively. He heard jazz, and for a few years at the beginning of his career he projected something earthshakingly new through the speakers of those Zeniths and Crosleys and Philcos, something that set him quite apart from all the other crooners.

  First came the voice itself, deep and rich and masculine, though not ostentatiously so. Crosby was also pitch-perfect and wonderfully adventurous rhythmically—but again, these are the last things most listeners would have noticed. What was most thrilling about Bing Crosby’s voice to radio listeners of the 1920s and 1930s was its warmth and directness: unlike other singers, who seemed to be contriving a character as they vocalized, Crosby appeared to be himself, speaking straight to the listener in the most casual possible way. It sounded almost as if he were making up the song on the spot.

  How did he accomplish this? Remarkably, his Jesuit education had much to do with it. Crosby had been born with a gift for language and a love for words, qualities that were especially encouraged at Spokane’s Gonzaga High and Gonzaga University. Giddins writes: “Bing Crosby is the only major singer in A
merican popular music to enjoy the virtues of a classical education … Classes in elocution, in which he excelled, taught him not only to enunciate a lyric but to analyze its meaning. At Gonzaga High, education was idealized in the phrase eloquentia perfecta (perfect eloquence). Students coached in literature were expected to attain rhetorical mastery as well.”

  Crosby did well in his studies; at the same time, he was a deeply ambivalent student who, lured by popular music’s siren call, dropped out of his pre-law course at Gonzaga in his senior year to go on the road—for the rest of his life, as it turned out. His intellectual half-heartedness forever saved him from pedantry and lent a sense of playfulness to his verbal theatrics.

  That he was smart and funny on his own terms raised him above the pack. The popular music of Crosby’s early career was a very mixed bag, containing both great standards that would endure the test of time and some of the schmaltziest tunes ever written. As Bing approached the peak of his movie success in the 1930s, he would have the power and the good sense to simply command his songwriters to leave out the schmaltz. Early on, though, he had to sing plenty of it. This is where his fabled coolness stood him in good stead: Crosby possessed the unique ability to make a number like “Just One More Chance” (“I’ve learned the meaning of repentance/Now you’re the jury at my trial”) work by sounding wholehearted and ever so slightly skeptical at the same time.

  The effect was electric. To women, he sounded romantic, vulnerable, and faintly mysterious; to men, he conveyed emotions without going overboard. He was one of them: a man, not some brilliantined eunuch. And the seeming casualness of his vocal style made every man feel he could sing like Bing.

  Little Frankie was no exception. But he came by the idea honestly: as it happened, both his parents could also sing. Marty had wooed Dolly by serenading her with an old-fashioned number called “You Remind Me of the Girl Who Used to Go to School with Me.” For her part, Dolly used to love to gussy herself up on Saturday nights, bounce around to Hoboken’s many political meetings, get loaded on beer, and warble “When Irish Eyes Are Smiling” over and over and over again. No wonder Frankie got up on the piano at the bar.