This was on a New York midnight in 1970. A hard spring rain had emptied Third avenue, and neon lights scribbled garishly across the glistening black asphalt. From the front window of P. J. Clarke’s saloon, you could see a few taxis cruising slowly among the spokes of ruined umbrellas and a trash basket lying on its side, its contents turning to pulp. Across the street, two old rummies huddled in the doorway of an antique store.

On this night in the rain-drowned city, we were safe and dry at an oak table in the back room of the saloon. Clarke’s was, and remains, a place out of another time, all burnished wood and chased mirrors, Irish flags and browning photos of prizefighters. A few aging men at the long, bright bar could gaze out the windows and still see the Third Avenue El, gone since 1955, or the Irish tenements that were smashed into rubble and replaced with steel-and-glass office buildings. They were each drinking alone and looked as if they remembered other nights too, evoked by the music of the jukebox.

What good is the scheming,
the planning and dreaming,
That comes with each
new love affair …

The man singing for the lonesome men at the bar was at our table. Or more precisely, we were at his table. Anytime Frank Sinatra sat down at a table, it became his table. On this night he was in town for a concert and he was in good spirits. To begin with, the hands of the clock had passed twelve, and he was in a large city, specifically the hard, wounded metropolis of New York. For decades now, Sinatra had defined the glamour of the urban night. It was both a time and a place; to inhabit the night, to be one of its restless creatures, was a small act of defiance, a shared declaration of freedom, a refusal to play by all those conventional rules that insisted on men and women rising at seven in the morning, leaving for work at eight, and falling exhausted into bed at ten o’clock that night. In his music, Sinatra gave voice to all those who believed that the most intense living begins at midnight: show people, bartenders, and sporting women; gamblers, detectives, and gangsters; small winners and big losers; artists and newspapermen. If you loved someone who did not love you back, you could always walk into a saloon, put your money on the bar, and listen to Sinatra.

Here in one of the late-night places of an all-night city, Sinatra was wearing a dark suit, a perfectly knotted red tie, a pale blue shirt, silver cuff links, and was drinking Jack Daniel’s. He was still lean then. The famous face remained an arrangement of knobs and planes that didn’t assemble into any conventional version of masculine handsomeness but had an enormous vitality; it was a face that defeated painters and seduced photographers. His eyes were bright and blue (although nobody had yet called him Old Blue Eyes), and the mouth was mobile and expressive. He had a wonderful smile. The voice, of course, was a whiskey-and-cigarettes baritone.

He sat with his back against the wall in the muted light of the room and seemed to ignore his own voice on the jukebox. He was facing Danny Lavezzo, who ran Clarke’s; William B. Williams, the disc jockey who had christened Sinatra “the Chairman of the Board”; Jilly Rizzo, who ran a saloon across town and had been one of Sinatra’s best friends for more than twenty years; two young women whose faces were too perfect; and the sportswriter Jimmy Cannon. The table was crowded with glasses, ashtrays, bowls of peanuts and pretzels. Only Cannon sipped coffee. There were about eight other people at smaller tables, and you could see the rain racing down one of the small side windows. Lavezzo made certain the other customers were kept at a distance by seating them as far from Sinatra’s table as possible without handing them umbrellas. The sound of “When Your Lover Has Gone” made Cannon turn his head toward the jukebox.

“That’s the saddest song ever written,” he said.

“It’s right up there,” Sinatra said, shaking his head and lighting an unfiltered Camel with a heavy silver lighter.

“You know where it’s from?” Cannon said. “It’s from a terrible movie called Blonde Crazy. Cagney and Joanie. 1931.”

“Joanie who?” said Jilly Rizzo, his bad eye gleaming. “Crawford?”

“Blondell, dummy,” Sinatra said. “Joan Blondell. Cannon used to go with her.”

“You’re kidding me,” Rizzo said. “You went with Joan Blondell? A busted down sportswriter went out with Joan Blondell?”

“He didn’t always look this bad,” Sinatra said. Cannon smiled in an embarrassed way. He was a small man with a long, pudgy Irish face and horn-rimmed glasses.

“It was a long time ago,” Cannon said. He looked relieved when the song ended, but its lonesome mood seemed to stain the air around him.

Rizzo turned to one of the young women. “You ever hear of Joan Blondell?”

The young woman shrugged. No.

“What about Cagney? You know, James Cagney?”

“I know him,” said the second woman brightly. “He was the guy, the captain, in that picture with Henry Fonda, right? About the navy?”

“You win a dish of strawberries, sweetheart,” Sinatra said.

“I don’t like strawberries,” she said in a baffled way. Sinatra laughed out loud. So did the rest of us, but it wasn’t until I was home, hours later, that I realized Sinatra had mixed the strawberries scene from The Caine Mutiny with the potted palm scene from Mr. Roberts. We’d all laughed with him, but the young woman was right to be baffled.

After a while Rizzo got up to take the two young women to a taxi while the conversation roamed in other directions. Somehow it arrived at writers. Was Ernest Hemingway greater than F. Scott Fitzgerald? Cannon insisted on the superiority of Hemingway. Sinatra preferred Fitzgerald.

“That Great Gatsby, come on, Jimmy, Hemingway couldn’t do that.”

“Yeah, but he could do a lot of other things,” Cannon said. “And Fitzgerald could only do that one thing.”

Rizzo returned and sat down. Cannon turned to me, the only other writer at the table: “What do you think?”

I repeated something Dizzy Gillespie once told me in an interview: “The professional is the guy that can do it twice.”

“Wow, is that true,” Sinatra said. “About everything. That’s a great line.”

“Yeah, and it’s a vote for Hemingway,” Cannon said. On the jukebox Sinatra was singing “You Make Me Feel So Young.”

“What about you, Jilly? Hemingway or Fitzgerald?”

“Hey, no contest,” Jilly said, deadpan. “Ella all the way.”

They all laughed, and then the talk shifted, and “Don’t Worry ‘Bout Me” was on the juke, and the waiter brought another round and clean ashtrays. Someone wanted to know the name of the worst living American. The nominations flowed and ebbed: Walter O’Malley, Mitch Miller, Richard Nixon (“Come on lay off,” said Sinatra, who had supported Nixon over George McGovern). But then another name was offered and in a rush of enthusiasm, the table unanimously voted the title of worst living American to the boxer Jake La Motta.

“He dumped the fight to Billy Fox, and never told his father, who bet his life savings on Jake,” Sinatra said. “Lower than low.”

And from La Motta, they moved seamlessly to Sugar Ray Robinson, another creature of the New York night. During the Depression Robinson had come down from Harlem to dance for pennies in the doorways of Times Square. Then he became a fighter of extraordinary grace and power. He had owned a couple of apartment houses in Harlem, a lavender Cadillac, a bar called Sugar Ray’s, where women arrived each night to find him, and then lost them all. An accountant took all of Robinson’s money to the racetrack, and the fighter had to go back to a sport he no longer loved. Still, he had fought La Motta six times, winning five, including a thirteenth-round knockout that gave him the middleweight championship in a brutal fight in Chicago in 1951. In the fighter’s great days, Cannon and Robinson had been close; we didn’t know it that night, but Sinatra had privately arranged to support Robinson after the old champion moved to California. They all knew him.

“He used to come in here all the time,” Lavezzo said. “He was some beautiful-looking guy.” I had seen Robinson’s fierce 1957 war with Carmen Basilio, watched him a lot in the old Stillman’s Gym, and had covered Robinson’s last sad fight, a loss to Joey Archer in 1965 when Sugar Ray was forty-four. Sinatra remembered seeing Robinson knock out Jackie Wilson in Los Angeles in 1947. “You couldn’t believe it,” he said. “The hand speed, the power, the elegance.” Jilly saw him decision Kid Gavilan in New York in 1948, and Williams and Lavezzo recalled specific rounds from two fights with Basilio and the one-punch knockout of Gene Fullmer in the spring of ‘57. They all talked with a kind of reverence.

“What was it the guy said?” Sinatra said. “There was Ray Robinson, and then there was the top ten.”

There was something else floating around in the talk about Robinson. They were all from the same generation, and Robinson symbolized that generation in the same way Sinatra did. Nobody said so at the table in Clarke’s, but they knew it. If Sinatra had not been there (for ass-kicking was not part of the style), someone would have said, There’s Sinatra, and then there’s the top ten.

Suddenly, Sinatra rose from his seat, excusing himself. A few other patrons looked at him. A woman in her forties widened her eyes and whispered across the table to her man, who turned for a glance. Lavezzo tensed; Clarke’s was not the sort of place that encouraged customers to ask for autographs. From the speakers, Sinatra’s exuberant voice was now singing “I’ve Got the World on a String.” He was telling the world that he could make the rain go.

“Hey, Danny, don’t you have anything on the jukebox besides this dago kid?” Sinatra said to Lavezzo. The saloonkeeper laughed and got up too. Sinatra led the way into a narrow passageway that opened into the front room. A large unsmiling man rose from a small table and followed them. In Clarke’s, Sinatra didn’t need directions to get to the john.

“He looks good, Jilly,” Cannon said.

“Better than ever,” Jilly said.

“I wish he’d give up the Camels,” Williams said.

“That’s like asking him to give up broads,” Jilly said.

“He should give up marrying broads,” said Cannon, a lifelong bachelor.

There was another voice on the jukebox now, Billie Holiday. She was singing “Mean to Me” in the scraped, hurt voice of her last years from the Ray Ellis album with strings, Lady in Satin.

“This album always makes me want to cry,” Williams said.

“Just don’t cry into the whiskey,” Rizzo said. “Makes it too salty.” Cannon smiled. He’d given up whiskey in the 1940s but never gave up the night shift. Whiskey was a big part of nights in that city, and he knew it was futile to deliver sermons to his friends.

“What makes you cry, Jilly?” Cannon asked.

“Poverty,” Jilly answered. And he laughed out loud.

Then Sinatra was coming back through the passageway, with the large dour man guarding his back. Two young women stared from the far end of the passage, giggling and tentative, as if having a small debate, and then turned back.

“You know what I love most about this joint?” Sinatra said. “Taking a piss. Those urinals . . . You could stand Abe Beame in one of them and have room to spare.”

“The really great thing is the ice at the bottom,” Cannon said. “It’s like drilling a tunnel.”

“That’s power,” Sinatra said, laughing, reaching for the Camels. Lavezzo returned, looking as if he’d just flown a combat mission.

“That better?” he said, gesturing toward the unseen speakers and the anguished voice of Lady Day.

“Like fine wine,” Sinatra said, allowing the smoke to leak from his mouth. I glanced at my watch. 2:25, the rain still falling. Cannon sipped his coffee. Jilly smothered a yawn. Then Billie Holiday began to sing “I’m a Fool to Want You,” a song out of Sinatra’s past. Out of 1951 and Ava Gardner and the most terrible time of his life. Everybody at the table knew the story. Sinatra stared for a beat at the bourbon in his glass. Then he shook his head.

“Time to go,” he said.

We all rose and went to the side door and followed Frank Sinatra into the night.

That night came back to me, along with a dozen others, when I heard that Frank Sinatra was dead at eighty-two. I was in the Miami airport, catching an early flight back to New York, after sitting on a panel about the future of newspapers. I had checked in and picked up my boarding pass. Then I saw about a dozen people staring up at a monitor. CNN. The announcer was looking grave. I couldn’t hear the sound. But then there were some clips and the legend “Frank Sinatra 1915-1998.” And I was like all the others in that sterile morning place, sliding into the blurred places of memory.

There was a radio on the window ledge in the kitchen of the tenement in Brooklyn. Through that window, past the radio, out across the backyards, we could see the skyline of New York to the right and the Statue of Liberty in the harbor and the low ridge of Staten Island and the gray smudge of New Jersey beyond. The harbor was thick with ships, heading off through the Narrows to the war. Sometimes the sky was dark with B-17s. At night the skyline vanished into blackness, the lights turned off, as were so many other things, for the duration. There was no television then, and so the radio served us kids as narration and sound track. From that little Philco, we heard about the invasion of North Africa and the assault on Sicily and the fighting at Anzio. The story of the war was all mixed up with the crooning of Bing Crosby and the score from Oklahoma! and the Andrews Sisters and Glenn Miller and, at some point, Frank Sinatra.

All or nothing at all . . .

On days of snow or rain, when we could not go down the three flights to the street, those words drifted through the railroad flat. They seemed thin, even trembling, unlike the confident baritone of Crosby, but there was a kind of defiance in them too. I was six when the war started in 1941, and my brother Tommy was two years younger; we were too innocent to connect Sinatra’s words to a longing for women. They seemed to be about unconditional surrender, as declared by Franklin D. Roosevelt, whose picture was up on the kitchen wall. It was as if Sinatra were saying the words to Hitler and Tojo. We’re coming to get you. And it’s all or nothing at all.

In the neighborhood we began to hear arguments among the kids just older than us. Crosby versus Sinatra arguments. They had nothing to do with the words. And it was not simply another division between the Italian American kids and the Irish American kids. Some of the Irish guys were Sinatra fans; some of the Italians went for Crosby. It was about his sound. And sometimes about other things.

There were always newspapers in our flat. The News and the Mirror, the Journal-American and the Brooklyn Eagle. And they began printing stories about Sinatra. The Voice. Swoonatra. Hysterical girls roaring at the Paramount, over in Manhattan, which we called New York. In June 1944 the Allies invaded France, heading for Berlin, and the lights went on again in the mighty skyline. For weeks after D-Day I would go up to the roof alone and stare at the skyline, glittering and impossibly beautiful, like the towers of Oz. And from the open windows of the tenements I could hear the battle between Crosby and Sinatra.

I was too young to choose sides. But my father was definitely a Crosby man. He was a good singer and could deliver pretty fair Crosby renditions at christenings or wakes or from his spot at the bar of Rattigan’s. In dinner-table discussion my mother was also a fan of Crosby. But in the Brooklyn mornings she always listened to Martin Block on WNEW, and that meant she also listened to Frank Sinatra. She would sing along with him in her light soprano voice, not judging the music but embracing it. Still, among the immigrants in the neighborhood, Crosby was generally triumphant. He was all over the radio. The few people who owned phonographs played him all the time. (We did not own one.) The jukebox in Rattigan’s Bar, across the street, was fat with Crosby 78s, and in the summer you could hear him singing through the open doors. He was sunny. He was optimistic. He was casual. He said we had to accentuate the positive, ee-liminate the negative, and not mess with mister in-between. He said that if we didn’t give a feather or a fig, we could grow up to be a pig.

In addition, Crosby had played a priest in Going My Way. A Catholic priest, for God’s sake, whose best friend was an Irishman from Ireland, an older priest played by Barry Fitzgerald. In the movie, which the whole neighborhood went to see during he summer of 1944, Father Crosby saved Father Fitzgerald’s run-down parish, St. Dominic’s, by writing songs, and the church was in a neighborhood that looked very much like ours. Ordinarily, that would have been enough for my father, who was an immigrant from Ireland, as was my mother. But there was still another factor.

The male anger against Sinatra came to a head in October, 1944, when he played the Paramount again and 30,000 mostly female fans erupted into a small riot outside the theater. When a male dissenter in the Paramount balcony fired a tomato at the stage, he had to be rescued from women who were trying to beat him to death. Breathless accounts of these events were all over the newspapers and the radio. At the same time, the first V-2 rockets were falling on London and American troops were fighting their way into Germany, taking heavy casualties. In our neighborhood, where the war was not a distant abstraction, the phenomenon of young Frank Sinatra was discussed with much heat in the bars and on the street corners and in the kitchens.

He’s not a draft dodger, my mother would say. He’s 4-F. He’s got a punctured eardrum. He tried to join three times, and they turned him down. It was in the papers.

The papers, he sneered. You believe the papers?

Flying north from Florida, I could remember all that argument and my own youthful wonder about its passion. At nine, I was too young to understand what Sinatra was doing with his music. I did know it was different. Crosby made us feel comfortable and, in some larger way, American. But there was a tension in Sinatra, an anxiety that we were too young to name but old enough to feel. During the last six months of the European war, when men were dying by the thousands in the Battle of the Bulge, it was confusing to hear songs that contained so much anguish. Or loss. Or loneliness. I would see young women pushing strollers along the avenue, their men off at war, see them pausing to look at the front pages on the newsstand, see the way their faces clenched, and I wished that Bing Crosby could sing to them and make them feel better. It took me a long while to understand that it was Frank Sinatra who was giving words and voice to the emotions of their own roiled hearts.

Years later, when I was a reporter and then a columnist for Dorothy Schiff’s New York Post, I got to know Sinatra. Cannon introduced me to him after the Floyd Patterson-Sonny Liston fight in Las Vegas in 1963. We were together on other evenings. On the surface, this seemed strange, another contradiction in the character of a man dense with contradictions. Sinatra had wasted too much of his adult life in vicious quarrels with newspapermen and gossip columnists, had punched out at least one columnist (the awful Lee Mortimer), and was continually in rumbles with paparazzi.

“Sinatra’s idea of paradise is a place where there are plenty of women and no newspapermen,” said Humphrey Bogart, who was sixteen years older than the singer and a kind of hero to the younger man. “He doesn’t know it, but he’d be better off if it were the other way around.”

Perhaps, as he moved toward sixty, Sinatra came to understand what Bogart meant. Certainly, when he was in New York, he sought out his favorite newspapermen. Cannon was his friend, while the rest of us were friendly acquaintances. Cannon was only five years older than Sinatra, a New Yorker shaped by Prohibition and the Depression, the myth of 1930s Broadway, and World War II in Europe, where he served as a correspondent for Stars and Stripes. They spoke the same language, shared passions for boxers, ballplayers, and beautiful women. Cannon brought a poetic language to his sports columns, some of which were shaped like songs, and his essentially romantic vision of that world was saved from sentimentality by a knowing New York tone. Like Sinatra, he was afflicted by insomnia and bouts of personal loneliness; he read widely and intelligently, deep into the night. Sinatra never gave up the whiskey, but he was a reader too; he and Cannon talked at all hours of the night about books, and it was Cannon who urged him to read Nelson Algren’s The Man with the Golden Arm, which was the basis of one of Sinatra’s finest movies. It didn’t matter where they were staying; insomniacs without wives can always be reached by phone.

I was twenty years younger than Sinatra, but he seemed to be comfortable when I was around. It certainly helped that Cannon and Shirley MacLaine had vouched for me, and he was impressed that I knew Kempton. There might have been one other factor: Cannon and I were both high school dropouts, as was Sinatra. (Oddly, Cannon and I had dropped out of the same institution, a great Jesuit high school called Regis.) This might have meant more to Sinatra than it did to us; in a very important way he defined success as a triumph over the odds.

“Every time they print your column,” he said to me once, “you are getting your diploma.”

I laughed. But he was serious.

Later, Sinatra had one other newspaper friend, Sidney Zion, now a fine columnist for the New York Daily News. Zion came out of Paterson, New Jersey, went to law school, worked as a prosecutor, and then became a reporter for the New York Post. Like all of us at the paper, he worshiped Kempton. But he had been shaped by the traditions and lore of urban New Jersey. The figure of Frank Sinatra was an immense part of that tradition. Zion loved the music that Sinatra loved most, the music of the hours after midnight. He loved saloons. He loved smoking and drinking (and still does). He is a wonderful storyteller.

“I got to know him around 1980, the time of the Trilogy album,” Zion told me. “I did a piece about the old music for the Times, and one thing led to another. A mutual friend introduced us, and I’d see him when he was in New York. I think he liked me because he’d never met a Jew who drank as much as I did.” Sinatra was always more cynical about the Hollywood press corps. He thought most of them were freeloaders, or on the take. “I’ve seen the bills, baby,” he said once about reporters and columnists who took money from the publicity budgets of the studios. In his early years he had cooperated with the fan magazines and other components of the Hollywood publicity machine. At some point he had even groveled to the more powerful columnists when advised to do so (although the most powerful columnist of all, Walter Winchell, never joined in the attacks on Sinatra). But from the mid-1950s until his death, he worked with the press only on his terms.

“The New York guys are different,” he said. “Maybe because there’s so much else going on around them, they don’t have to cover me. What can you say, I like their company. It’s as simple as that.”

Maybe it was, but I doubt it.

Jimmy Cannon, Murray Kempton, and William B. Williams are dead. So are Jilly Rizzo and Sugar Ray Robinson and all those others who once seemed so vividly alive that I could not imagine them leaving the world. Now Sinatra is dead too, and it’s like a thousand people have just left the room.

And yet the tale of Frank Sinatra isn’t only about Clarke’s and Hollywood and Las Vegas; the life he led in such places is part of the tale, but it would be meaningless without the art. Sinatra’s art can be experienced in the 1,307 recordings he made in studios from 1939 to 1995, in the recordings of his concerts, in his videos and movies. In the saloons of the city, you could see what Sinatra had become. But such evenings could never explain the long existential saga of a life entwined with art. He was, in some ways, as elusive and mysterious as Jay Gatsby, not simply to those who knew him but to himself. The keys to the life and the art can only be found somewhere back in the vast obscurity beyond the city.

The life and career of Frank Sinatra are inseparable from the most powerful of all modern American myths: the saga of immigration. Because he was the son of immigrants, his success thrilled millions who were the products of the same rough history. Through the power of his art and his personality, he became one of a very small group that would permanently shift the image of Italian Americans. Many aspects of his character were shaped by that immigrant experience, which often fueled his notorious volatility. More important, it infused his art.

“Of course, it meant something to me to be the son of immigrants,” Sinatra said to me once. “How could it not? How the hell could it not? I grew up for a few years thinking I was just another American kid. Then I discovered at – what? five? six? – I discovered that some people thought I was a dago. A wop. A guinea.” An angry pause. “You know, like I didn’t have a real name.” An angrier pause. “That’s why years later, when Harry [James] wanted me to change my name, I said no way, baby. The name is Sinatra.”

He grew up in a time when the wounds caused by nativism and anti-Italian bigotry were still raw. Those wounds, and the scar tissue they left behind, affected the way millions of Italian Americans lived, what they talked about, even how they chose to read the newspapers. In the years of his childhood, Sinatra was no exception.

“Growing up, I would hear the stories,” he said to me once. “Things that happened, because you were Italian . . . . I don’t mean it was the only thing people talked about. That would be a lie. But the stories were there. The warnings, the prejudice. You heard about it at home, in the barbershop, on the corner. You never heard it about it in school. But it was there. Later, I heard the same kinds of things from my Jewish friends, how they learned about the ways they could get into trouble.”

The stories were about insults, exploitation, worse. Part of the trouble was caused by the sheer numbers. From 1880 to the beginning of World War I, more than 24 million Europeans crossed the Atlantic to America. About 4.5 million were Italians, 80 percent of them fleeing the exhausted hills and emptying villages of Il Mezzogiorno, the neglected provinces of southern Italy and Sicily. Many thousands went to Brazil. Another million journeyed to Argentina and permanently transformed the character of that nation. The vast majority came to the United States. At first, the more adventurous Italians moved west, helping build thousands of miles of railroad tracks, finding jobs as fishermen on the sunny coasts of California or developing that state’s lush vineyards. Most settled in cities.

“I read a book once about how the Irish when they came to America never wanted to be farmers again,” Sinatra said. “I guess if you work on a farm and everything dies in the ground, you don’t ever trust the ground again. The Italians were like that too.”

Rural Italian and Irish immigrants shared that common grievance against the Old Country: the exhausted or poisoned land had failed them and, in a way, betrayed their faith and prayers; in the new World, they sought the solace of cities. Cement was better than hunger; a job and a lock on the door provided the only true safety. The Jews, haunted by the brutal realities of recurrent pogroms, or disenfranchised by a crippling, pervasive anti-Semitism, were drawn by the even brighter promise of freedom; no matter how terrible life might be in the slums of the Lower East Side, the Cossacks would not arrive at dawn with their sabers drawn. The Irish, Italian, and Eastern European Jewish immigrants shared a suspicion of government and the police that helped form the style of the American cities where they settled. Their children were touched, in various degrees, by their Old Country lore and their nostalgias. Many of Frank Sinatra’s attitudes came from that mixture.

But in the last years of the nineteenth century, rural Italians faced some special problems in urban America, burdens that did not afflict the Irish and the Jews in the same way. Even in the Italian language, too many immigrants could not read or write. Depending upon the year, between 50 and 70 percent of the new arrivals were illiterate. This was a severe handicap in the booming, more complex cities of the United States and forced many into manual labor or trades that did not demand book learning. Four thousand Italian immigrants found work building the New York subways. Others labored in the building trades, helping erect the soaring monument of twentieth-century New York. Many worked as barbers or seamstresses, as blacksmiths or mechanic or stonemasons. Some were chefs or bakers. Others were fruit and vegetable peddlers, bootblacks, or shoemakers. A few created an instant stereotype: the organ grinder. These small mustached men moved through many neighborhoods, equipped with hand organs, an occasional monkey, and a cup for coins. For most people the organ grinder was a passing amusement, singing “O Sole Mio” into the humid air of a Saturday morning; for many Italian Americans, the organ grinder was a humiliation, a beggar with a monkey and a voice.

Most of the time, the Italians did their work with silent courage and little public complaint. If you came from a place where there were never enough jobs, work itself was a kind of triumph. For those immigrants, there was no such thing as a meaningless job; the job itself was the meaning.

“They did whatever they had to do to put food on the table,” Sinatra told me once. “They took any kind of dumb job and you know why? So their kids wouldn’t have to do those jobs. So you wouldn’t have to do it. So I wouldn’t have to do it. They were some kind of people.”

The Italians also had to undergo another peculiarly American rite of passage: they had to endure and then confront the ferocious bigotry of those who had come before them. This was compounded by the American obsession with race. At the peak of the migration, there were millions of African Americans still alive who had lived a slaves; political compromise was leading to an iron segregation in the American South; various harebrained race theorists spent their time sniffing out hidden racial strains in individuals. Guilt over slavery, and over the partial extermination of American Indians, created self-serving notions about the inferiority of those with darker skin. Along came the Italians. The majority of Italian immigrants were Sicilians, from an island where Arab and Spanish conquerors had been dominant for centuries. The glories of those civilizations meant nothing to many older Americans; the darker complexions of the Mediterranean were suspect among those who believed that Americans were supposed to be fair skinned. The coarse, hurting language of ethnic inferiority followed, and it affected Frank Sinatra. Even in the years of his fame and power, Sinatra could not completely insulate himself from the social cruelties of that process.

“Every once in a while,” he told me, “I’d be at a party somewhere in Hollywood or New York or wherever, and it would be very civilized, you know, black tie, the best crystal, all of that. And I’d see a guy staring at me from the corner of the room, and I knew what word was in his head. The word was guinea.”

Some of this social minefield was waiting for the Italians when they got off the boat at Castle Garden or Ellis Island. In the 1890s, when Frank Sinatra’s grandparents made their separate passages from Italy, carrying with them the children who would become his parents, a renewed nativist fever was surging through the United States. It was driven, of course, by fear. A fear of Catholics, a fear of Jews, a fear of strange languages and secret societies, a fear of race, a fear of People Who Are Not Like Us. The Irish had gone through this paranoid test for the half century following the Great Famine that sent them to America. For a shorter period of time, the Jews who arrived on the same great immigrant tide as the Italians would suffer similar humiliations. Mexicans, Dominicans, and many Asians are today objects of the same collective stupidity. For the Italians and their children, this brutal ritual would last much longer than for other groups. And a hundred years ago it was not a simple matter of manners, social slights, or bigoted jokes. It could be a matter of life and death.

“Guys my age, one reason they didn’t pay much attention to school was the schools didn’t tell what we knew,” Sinatra said. “We heard what had happened in different places. We didn’t get it from school.”

One story that Sinatra heard was about an event that happened about the time his parents and grandparents arrived in the United States. In 1891 a singular atrocity took place in New Orleans that drastically altered the situation of all Italian Americans. A group of Italian immigrants were accused of murdering a corrupt police superintendent named David Hennessy. Nineteen were charged with the crime; eleven were tried for murder. There was much lurid talk in the newspapers of the day about the Black Hand, a secret gang of Sicilians dedicated to crime. Then, for the first time, many Americans heard the word Mafia. This was even bigger than the Black Hand. The Mafia myth, which conferred immense hidden powers to a relative handful of hoodlums, was born. It didn’t matter that among the 4.5 million Italian immigrants, no more than a few thousand were connected to the Honored Society; it didn’t matter that in the prisons of New York, the Italians were a tiny minority among an army of Irish lawbreakers. The myth had been spawned in New Orleans. Spreading like a stain, inflated by novels and movies and a cottage industry of hysterical politicians and prosecutors, the dark myth would affect all Italian Americans; it would directly affect the life of Frank Sinatra.

“Half the troubles I’ve had,” he told me once, “were because my name ended in a vowel. They tried to put me together with all the other stuff that happened. In wasn’t the only one. But there I was, up on a stage. I was pretty easy to see, a good target.”

In New Orleans the garish myth flowered in the imaginations of newspapermen. There were gangsters among us, the newspapers said, who were different from Irish gangsters or American gangsters; they were darker, swarthier, spoke a different language, and were bound together by blood oaths! In largely Catholic New Orleans, famous for its easy, tolerant ways, the myth had crude power; paranoia usually does. Even among some supporters of the Irish Republican Brotherhood, a secret society if there ever was one, it was believed that the Italians were different. The IRB wanted freedom for Ireland; the Mafia wanted America!

But then a strange thing happened in the New Orleans trial of the Italian immigrants for the murder of David Hennessy: the jury acquitted eight of the men and reached no verdict on the other three. The evidence simply wasn’t there. Not about this specific murder. And not about the Mafia.

That verdict did not satisfy the respectable Americans of New Orleans. They claimed the fix was in. They claimed that the shadowy Italian organization had paid off the jurors. Two days after the verdicts a mob of several thousand, led by sixty leading citizens and including a small number of African Americans, surrounded the jail where the Italians were awaiting final bureaucratic disposition of their cases. The Americans stormed the jail, dragged the Italians out of their cells, and murdered them. Two were hanged screaming from lampposts. One of them tried climbing the hangman’s rope with this free hands and was riddled with bullets. Seven were executed by firing squads in the yard of the jail. Two crawled into a prison doghouse to hide from the mob, were discovered, and were shot to pieces. It remains the worst single lynching in American history.

“When I was young,” Frank Sinatra said when he was in his sixties, “people used to ask me why I sent money to the NAACP and, you know, tried to help, in my own small way. I used to say, Because we’ve been there too, man. It wasn’t just black people hanging from the end of those ropes.”

The story of the New Orleans outrage spread swiftly through the world of the Italian immigrant in America, underlined by the decision of the Italian government to withdraw its ambassador in protest. Mainstream America didn’t express much horror. According to Professor Richard Gambino, in his book Vendetta, the lynchings were approved by the editorial writers of the New York Times, Washington Post, St. Louis Globe-Democrat, and San Francisco Chronicle, along with about 50 percent of the other newspapers in the nation. Theodore Roosevelt, one of the leading younger Republicans, said the lynchings were “a rather good thing” and bragged that he had said so at a party to “various dago diplomats.”

“Maybe that’s why so many people didn’t trust the newspapers, even if they could read them,” Sinatra said almost eighty years later. Then he laughed. “Maybe it’s why I did so many dumb things with newspapermen too.”

The message from New Orleans was clear to the immigrants. Americans didn’t like Italians. An American was supposed to be white, Anglo-Saxon, and Protestant. He was supposed to come from Northern Europe. Yes, the Americans talked about democracy and equality and the virtues of hard work; but it reality, the game was rigged. In the aftermath of the New Orleans lynchings, a grand jury couldn’t find enough evidence to indict the murderers, in spite of the presence of hundreds of eyewitnesses. Instead, the grand jurors indicted six men who worked for the defense attorneys, charging them with jury tampering. This chilling illustration of the failure of the American criminal justice system was part of a wider pattern. There were anti-Italian murders in the Midwest and barn burnings on the property of Italian farmers in the American South. Men from the drought-stricken fields of Sicily and Calabria were in awe of the rich earth of La America, but too often they were driven off that land by night riders. It was no surprise that many of those once-optimistic and naive Italians sought refuge in the cities. And no surprise that their ghettos became fortresses, who only one social unit mattered: the family. Nobody else could be trusted, up to and including the president of the United States.

In such places the Mafia did begin to establish itself, usually victimizing Italians but bringing a kind of authority to the social structure of the ghetto. If the government treated you with contempt and suspicion, if trade unions rejected you, if at last your children had a chance for an education and the teachers made fun of them, then you had to live by your own rules, or pack up and leave. In fact, hundreds of thousands of Italians did go home, many of them embittered by their American experience. For them, the promises implied by the Statue of Liberty were part of a cruel joke; more Italian immigrants returned home than any other nationality.

But millions stayed on, seeking their own means of protection within the warm fortress of the family and its extension, the ghetto. If, in the pursuit of justice or progress they could not depend upon the police or the courts, if they could not obtain loans from the banks, then they would go to the man in the white suit from Francis Ford Coppola’s version of The Godfather, the agent of the Honored Society. He could arrange for extortionary loans. He could settle disputes. He could dispense rough justice. Always at a price, of course. In cash, or in obligations. During the years before World War I, he was a parochial figure, strictly local, an exotic import, a poisonous flower unique to the closed ghetto hothouse. But he was created by an American failure. More than anything else, he emphasized how cut off many Italian immigrants were from the larger American society.

This isolation, this shared solitude, created problems that took generations to solve. Education was often sneered at; what was the use of working hard in school if you couldn’t take a diploma into a good job? “I know a guy who went to college,” I would hear from my Italian American friends growing up in Brooklyn. “He’s driving a truck.” Many would retreat into passivity, keeping their heads down, getting through a life in silence and safety. Others would try to defuse potential danger by performing the public role of caricatured Italian Americans, the organ grinder, the fruit peddler, a Mediterranean variation on the earlier role of the Stage Irishman.

“You know what radio show I hated the most?” Sinatra would say, many years later. “It was called Life with Luigi, with J. Carrol Naish – there’s a good Italian name for you – and it was all about Italians who spoke like-a-dis, and worried about ladies who squeeze-a da tomatoes on-a da fruit stand. The terrible thing was, it made me laugh. Because it did have some truth to it. We all knew guys like that growing up. But then I would hate myself for laughing.”

This is certain: many of the older people among whom Frank Sinatra grew up in Hoboken were shaped by the stark conflict between what America promised and what America delivered. Such a conflict can lead to the development of a defensive style, the adoption of masks of cynicism or irony, or some merger of both. Or it can lead to the guise of the don’t-mess-with-me tough guy. At different times Sinatra would try on all the masks.

“Sometimes with me, it was a case of if-you-got-the-name-you-might-as-well-have-the-game,” he said to me once. “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 head.”

For those Italians who stayed on in the American cities, life did have its consolations. In spite of the cold-water tenements, the hostile police, the sneers of strangers, the slurs in the newspapers, life in those cities was better than it was in the places left behind. As if to maintain continuity with the Old Country, the Italian immigrants – like the Irish before them – reproduced many of the rhythms of the old life. Sinatra grew up in world of feasts, weddings, funerals, and celebrations, with insistence on the traditions of courtship, marriage, personal honor. At the same time, he was pulled by baseball, the Fourth of July, the vistas of the American deserts that were shown in westerns at the movie house. He was forced to choose between two modes of thinking, admirably described by Richard Gambino in his study Blood of My Blood. One was la via vecchia, the old way, the rules as encoded over many centuries in the Old Country. The other was la via nuova, the new way, the American way, with its loose rules, its many freedoms, its abundance of choices. In some important ways, Sinatra was faithful to the old way: suspicious of, if not hostile to, authority; possessive of women; needy of family. Like most young people of his age, he despised informers, thought the law was hypocritical, the world a hard place. At the same time, he was a genuine product of the new way, exulting in the freedoms of the American, gambling for big stakes in life and career, seizing all opportunities.

Walking the streets of the neighborhood, listening to the grown-ups talk at kitchen tables or in barbershops, he came to understand something else. It was called power. Within the Little Italies of the American cities, there existed subtle structures of social power, most of them carried intact from the Old Country. As Luigi Barzini has written:

“Power has many sources. The first and nearest source is one’s family. In Sicily the family includes relatives as far as the third, fourth, or fifth degree, collaterals, in-laws, relatives of the in-laws, godfathers and godmothers, best men at marriages, dependents, hangers-on, servants, and vassals. They all help or must be helped, as the case may be, in times of necessity.”

In the years of his own power, Frank Sinatra would remain true to that particular vision of responsibility; he was ferocious in protecting his family (even after leaving his first wife); he often acted as if it was his duty, and his alone, to come to the aid of friends when they were in trouble. In some ways, of course, this attitude was not unique to Sicilians or to Italians in general; there was a pagan or Christian element to it, as could be seen among the Irish, and a tribal or religious element that could be witnessed among Jews who came together from many nations and accepted responsibility for one another. But this style and its underlying codes made their marks on Sinatra in Hoboken.

“When I was there, I just wanted to get the hell out,” he said. “It took me a long time to realize how much of it I took with me.”

In Hoboken, as in other places, the story was certainly not one of unrelieved misery. The core of the immigration myth is this: it was about the way people overcame misery, how they found their consolations, and, in the end, how they redeemed America in a time when America believed it was not in need of redemption. There was a spirit of patient optimism in Sinatra’s Hoboken, although he could not have imagined as a child that he would one day become one of the agents of consolation.

For millions of Italian immigrants and their children, technology would provide some of those consolations and accelerate the process of Americanization. The rapid development of the motion picture would provide one form of national unity, allowing people from every region and every ethnic group to share common emotional experiences, some of them virtually mythic. More important, when Frank Sinatra was a child, the phonograph and the radio were invented. When each became widely available, the lives of the immigrants changed in a revolutionary way. Many immigrants added wind-up Victrolas – which came on the mass market in 1915 – to their American homes. After 1921, when regular radio broadcasting began on WJZ out of Newark, those ghetto-bound immigrants who were cut off from English could listen to it at home, trying to crack its codes, while their English-speaking children were entranced. A few years later the immigrants could listen to the Italian-language radio stations and thus be informed and entertained even if they could not read or write in any language. An even greater impact was made upon their children. Frank Sinatra was part of a generation that could not remember a time when there was neither a radio nor a phonograph in the house; by the time of his first communion, he was listening to the music of America.

“The radio was like a religion,” Sinatra remembered. “They were even shaped like cathedrals.”

For the immigrants themselves, the phonograph was initially more important. For the first time, Italian immigrants could bring great music into their daily lives in ways that were impossible in the Old Country. These were people, the contadini from the countryside, who could never afford entrance to opera houses or grand concert halls. If they could buy the tickets, they could not afford the clothes that would grant them entry. Many knew the melodies of Puccini and Verdi from the singing of inspired amateurs. They had heard some of the music from the mouths of organ grinders. But now here was Caruso himself, singing in their kitchens or living rooms. After 1940 Frank Sinatra would also sing in many of those rooms.

Two immigrant couples concern us here: one from Sicily, the other from the distant north of Italy. They had a common goal but were shaped by different histories and geographies. As a nation, after all, Italy was even younger than the United States; the various city-states were not consolidated into a united Italy until 1871. To be Italian instead of Piedmontese or Sicilian required an act of the imagination so powerful that it could erase the disputes and violence of centuries. For many, that psychological unification never happened. Even in America, the old regional and city conflicts often continued, leading to snubs and feuds and rare spurts of violence; it took American bigotry to make them all feel like Italians. And by then most of them wanted to be something else: Americans. If they were not readily accepted, so be it; their children would be Americans by right of birth.

Begin with the Sicilian couple. John and Rosa Sinatra (the name, in some versions of the tale, was originally Sinestra, and “John” surely must have been baptized Giovanni) were from Agrigento, a lovely town on the southwestern coast of the island. The town was founded by the Greeks about 500 B.C. Growing up in Agrigento, the Sinatras were familiar with the extensive Greek ruins, the underground water system built by the Greeks, the secret catacombs. There were traces, too, of centuries of occupations by the Saracens, and later by the Spanish, in the language, the cuisine, and above all in the social structure with its elites at the narrow top and the broad, uneducated mass at the bottom.

From the hills around Agrigento, a man could stare off across the Mediterranean toward Africa. Or he could look west, toward America. The town’s most famous modern citizen was the novelist and playwright Luigi Pirandello (born in 1867 in a suburb appropriately called Chaos). Pirandello was almost an exact contemporary of the elder Sinatra. With their mixture of love and hate for their island, their cynicism about authority, and a need to escape and start over, many Sicilians often must have felt like characters in search of an author.

As a young man in Agrigento, John Sinatra was a grape grower, subject to the whims of wind and weather. Much of Sicily, like almost all of the “boot” of the lower mainland, had undergone across the centuries what would now be called an ecological disaster: its forests obliterated for fuel or profit. The once-rich land turned powdery in summer, hard and unforgiving in winter. In the spring, floods transformed clay into glue. The swamps were infested with mosquitoes that spread malaria. Infant mortality was high. Doctors were rare. Education did not exist.

Like millions of other immigrants, the Sinatras were seduced by the gaudy promises of shipping agents and labor contractors and made the decision to cross the ocean. John could not read or write English (and might have been illiterate in Italian), but he surely must have believed that in America, his son, Anthony Martin Sinatra, would have a better chance at a decent life than he could ever have in Sicily. The Sinatras left for America in the last decade of the nineteenth century. They settled behind the Statue of Liberty in a town called Hoboken, a once-genteel bedroom for New York City that was being swiftly transformed by the immigrant tide into an industrial workshop. The rudeness of the German longshoremen didn’t matter to the Sinatras, nor did the power of the Irish police and politicians. John soon had a job in a pencil factory, earning $11 a week. It wasn’t much, but it was enough to feed his family.

The other couple in our story was the Garaventes. Unlike the Sinatras, they were city people, from Genoa, a hard northern port that, with its drydocks and piers and buildingways, looks in old drawings and photographs like the waterfront of Brooklyn. Henry James, visiting in 1890, described the “wonderful crooked, twisting, climbing, soaring, burrowing Genoese alleys” and the “sensuous optimism” of the inhabitants. Founded several centuries before the birth of Jesus, conquered and ruled at various times by the French, the Saracens, and the Austrians, the port was known for centuries as La Superba, the proud or haughty one. When I visited there twenty years ago, the narrow alleys of the old town exuded a sense of danger, even menace; but the city also contained baroque marble palaces that whispered of vanished glories. Genoa’s connection to America began with Christopher Columbus, who was born there. After the discovery of America, the merchants of Genoa amassed huge fortunes in trade with the New World. But the city also fomented a rebellious spirit. It was the birthplace of two great heroes of revolutionary nineteenth-century Italian nationalism, the romantic Giuseppe Garibaldi (who once lived in Staten Island) and the idealistic Giuseppe Mazzini. Those names would also be saluted in places like Hoboken.

The Garaventes settled among the poor of Hoboken, protected from outside dangers by the rigid structure of the ghetto. The fairest of their children was Natalia, known as Dolly. In Genoa her father had been a skilled lithographer, was literate, and knew the value of an education. He quickly found work while his spouse became a midwife. In Hoboken the Garaventes worked very hard to make a traditional home for their children, a place of safety and manners and respect for older people. There was no reason why the values of the Old Country should not continue in this new country; those old rules were not unique, after all – they were common to all good people. Or so they believed.

The Garaventes surely did not anticipate the assimilating power of America, la via nuova, the mysterious process that combined schooling, the streets, social and political institutions, and a new set of myths, peopled by baseball players, prizefighters, and movie stars. The power of la via nuova would inevitably change their children into Americans.

This process was dramatized about 1912. At some point in that year, the young man named Anthony Martin Sinatra met the young woman named Dolly Garavente. Aside from the neighborhood in Hoboken, then had only one thing in common: each had blue eyes. Otherwise, they were very different.

Martin was quiet, shy, virtually uneducated (one account says that he was illiterate), but marked by a somber Sicilian gravity. The family narrative, constructed years later (and thus possibly suspect, as are all family narratives), tells us that, like many children of immigrants, he had turned to the prize ring, boxing 118 rounds under the name Marty O’Brien. We don’t know if this is true; so far, no records confirm it and there seem to be no photographs of him in boxing gear. But the use of the pseudonym makes it plausible. Certainly, Martin Sinatra would not have been the only immigrant to don a mask name in order to scrape out a hard living. Assuming an Irish name was not that unusual in that era of boxing; there were Jewish fighters with Irish names too; and Jim Flynn, the only man who ever knocked out Jack Dempsey, was actually named Andrea Chiariglione. One reason for the name changes is that there were not enough Irish fighters to satisfy the large number of Irish fans. The Irish were living their own American success story, moving away from the practice of the brutal sport, as doors opened politics, police work, and the law. With his blue eyes, Martin Sinatra could pass for Irish. He certainly had no major career in the ring: he suffered from chronic asthma, had easily breakable “bad hands,” and in the various Hoboken versions of this tale is usually described as a club fighter of mediocre skill.

“He could fight,” Sinatra said years later. “He 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. But he never hit me. Not once. Not ever. He was a gentle man. I think he was the kind of guy who never gave anyone any crap and walked away from most of the jerks he’d meet. But if you pushed him too far, watch out.”

There was nothing mediocre or reserved about Dolly Garavente. She was two years old when she came to America, and said later that she had no memories of Italy. With her blue eyes, strawberry blonde hair, fair complexion, and, above all, her attitude, she appeared solidly American. Her confident, freewheeling style might have caused some uneasiness for her parents, epitomizing, as she did, la via nuova. But it made her a vivid force within the family and on the street. She managed to get through the eighth grade, a considerable accomplishment for a woman in that neighborhood in those years. She was infused with “sensuous optimism” of the Genoese, but she was also tough, ambitious, capable of brassy vulgarity in two languages. She was very different from Martin Sinatra, and that was a surprise. In his great book The Italians, the writer Luigi Barzini writes:

“The private aims of southerners and northerners are, of course, more or less the same. The northerner, however, thinks that there is one practically sure way to achieve them: the acquisition of wealth, la richezza. Only wealth can, he believes, lastingly assure the defense and prosperity of the family. The southerner, on the other hand, knows this can be done only with the acquisition of power, prestige, authority, fame.”

After Dolly Garavente married Martin Sinatra, she combined the characteristics of north and south in the same person, becoming an Italian and an American. That fusion helped shape the character of her only child. She brought to motherhood a special combination of rebelliousness and will, defying many of the codes of the old way. The marriage itself was fiercely opposed by the Garaventes. From the viewpoint of haughty Genoa, marrying a Sicilian was a step down. To marry a young man who was barely literate, who was a prizefighter, who had tattoos: that could not be allowed. At the same time, the Sinatras were not enthusiastic either. They had no use for people from Genoa. Such people were snobs. They thought too much of themselves. Martin should forget about this boisterous woman with the blonde hair and marry a nice, quiet Sicilian girl. Both sets of parents forbade the marriage. The young people ignored them and the social codes to which they gave such immense value. This was, after all, America, not the Old Country. La via nuova would win out over la via vecchia. On February 14, 1913, Dolly and Martin eloped all the way to Jersey City and were married in City Hall. It was, of course, St. Valentine’s Day, the day on which Americans celebrated romance.

Romance meant little to the Sinatras and the Garaventes. Both families were outraged. A marriage in City Hall? That was no marriage. A marriage of two Catholics had to be performed by a priest! Ignoring the cold war between the Garaventes and the Sinatras, the young couple moved into a flat in an eight-family tenement at 415 Monroe Street in Hoboken. Dolly took a job in a candy shop. Marty scrambled to make a living and found work as a boilermaker in a shipyard. If necessary, they would be self-reliant; this was America. But the general unhappiness of the two families couldn’t go on. The following year, to calm their parents, Dolly and Marty got married again, this time by a priest. The second ceremony took place at home. Of course. But it was done more for the parents than for themselves, a bow to la via vecchia.

In an important way, Marty and Dolly – especially Dolly – were part of a bridge generation of Italian Americans, technically immigrants but confident enough as Americans to use their freedom to discard old-fashioned conventions. If the narrative of their parents’ lives had been permanently interrupted when they boarded the ships for La America, their own narratives would be lived out in that same America. For them, America was not a destination; it was a place of beginnings.

“One thing about Dolly,” Sinatra said later. “She never looked back very much. She was alive today and looked forward to tomorrow. That was her. The thing about my grandparents was, they never really got over leaving the Old Country.”

In 1914 their personal drama overshadowed the distant dramas of the public world. Far away in Europe, in the town of Sarajevo on the last day of July, a Serbian nationalist assassinated Archduke Ferdinand and set off the horrors of the Great War. At first, in the streets of Hoboken’s Little Italy, there was interest, some anxiety, but no obvious alarm. Italy immediately declared its neutrality and would not be sucked into the charnel house until May of the following year. The young Sinatra couple didn’t care. By that spring of 1915, Dolly was pregnant with the couple’s first child.

The tale of that birth is essential to the almost mythic structure of the Sinatra saga. Frank Sinatra was born at home on Monroe Street on December 12, 1915. Dolly’s mother was present, but her skills as a midwife were simply not sophisticated enough to manage the breech birth. A doctor was summoned. He was nervous and panicky. He used forceps to extract the baby’s head, but his technique was so clumsy that the boy was permanently scarred on the face, neck, and ears. Scars were a minor concern; the immediate problem was death itself. In the midst of all the blood and pain, it first appeared that the baby was dead. He was immense – thirteen and a half pounds – but he was not breathing. Dolly’s mother, Rosa, moved faster than the despairing doctor. She took the baby in her hands and held him under the cold water tap in the sink. The shocked baby began to howl. Frank Sinatra was born.

Later, he would have no memory of World War I, except its ending. “People started running around banging pots and pans and shouting and singing and then drinking and feasting in the streets,” he remembered. “It was one great big party.”

But the years of the war and its immediate aftermath would also affect Frank Sinatra and other Italian-Americans. As it grew clearer that the United States would be sucked into the great European conflict, there was much debate about the potential loyalties of so many foreign-born citizens and residents. Every immigrant was suspect. Would the immigrants and their children fight for the United States in a European war? Would the Irish fight on the side of England against Germany? Would German Americans fight against Germany? Nativism revived, now equipped with crackpot theories about the genetic inferiority of southern Europeans, and Congress passed the first of many laws that would bring an end to immigration. D. W. Griffith’s The Birth of a Nation was released in the summer before Sinatra’s birth; it was a brilliant artistic triumph, establishing much of the syntax of the feature film, but its racism was vile and served as a powerful recruiting device for the Ku Klux Klan. The Klan in those days was not simply the enemy of blacks; it hated Jews and Catholics too, and all those immigrants from southern Europe.

The paranoid American imagination was inflamed by news of revolutions in Mexico, Ireland, and, most spooky of all, Russia. By October 1917 the Bolsheviks had taken power. In the United States, fear of communism and anarchism was added to the existing fear and contempt of the foreigner. Both communism and anarchism, after all, were “foreign” ideologies. Both were organized in secrecy and believed in the use of violence. Hadn’t an Italian anarchist from Paterson, New Jersey, assassinated King Umberto of Italy in 1900? Weren’t Italian anarchists causing labor unrest in silk factories and textile mills and allying themselves with the revolutionaries of the International Workers of the World? A new version of the “dual loyalty” debate was born; were these immigrants primarily loyal to the United States or to their un-American ideologies?

Patriotism was soon redefined. It was no longer enough to love the United States; to prove your American identity, you also had to hate other countries and “foreign” ideologies. In its preparations for war, the administration of Woodrow Wilson had organized a brilliant propaganda campaign whose intention was to meld various nationalities into one. The first enemy was the Hun; the second was the Red. The Hun bayoneted babies. He executed nurses. He was the enemy of democracy everywhere, and the British and the French were its defenders (this was news to millions who lived in their colonies, of course, but logic was an early casualty of the war). Tin Pan Alley was enlisted for the duration, under the command of George M. Cohan, who created the patriotic music that is still played to this day. When the United States declared war on April 6, 1917, there was an orgy of flag-waving celebration, rallies, and parades. Even Enrico Caruso made a recording of Cohan’s “Over There.” There were no songs about chasing Reds.

Frank Sinatra would remember nothing 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.