WHEN ABE RELES and his gang went to war with the Shapiros, it was a rite of passage—for the Italians, it was making your bones; for the Jews, it was a kind of underworld bar mitzvah, like becoming a man. And it was yet another installment in the long history of gang warfare in New York City, which stretches clear back to the eighteenth century, when a bad night out meant drinking knockout drops, getting blackjacked and rolled, then waking, hours later, on a broken-down ship bound for China, the captain saying, “Work or swim.”
Each kid who makes his way in the city’s underworld, whatever his background, inherits this tradition as even the lowliest bush league baseball player inherits the mantle of Gehrig and Ruth. It’s why Reles named himself after Kid Twist Zweibach, a gangster who was killed one night in 1908 by Louis the Lump in Coney Island; why, in the 1920s, Arthur Flegenheimer, a Jewish kid from the Bronx, called himself Dutch Schultz after a German gangster from a century before.
For living gangsters, the stories of dead gangsters, their exploits and failures, the way they died, is the only history that really amounts to much. It’s a story that most ambitious gangsters are trying to make themselves a part of, a story that begins over two hundred years ago in the Five Points and the Bowery, the toughest, most storied slums in New York, and follows the great gangs that dwelled there: the Bowery Boys, who fought just north of Grand Street, on Bunker Hill; the Dead Rabbits, who were sometimes joined by Hell-Cat Maggie, a ferocious female gangster who filed her teeth to points; the True Blue Americans, who wore stovepipe hats and ankle-length frock coats; the Daybreak Boys, who worked the docks, killing vagrants and nightwatchmen, pillaging ships and warehouses; the Plug Uglies, who wore oversize plug hats, which, before fighting, they filled with wool and leather, fashioning an early version of the sports helmet; the Buckoos; the Hookers; the Swamp Angels; the American Guards; the Slaughter Housers; the Short Tails; the Shirt Tails; the Patsy Conroys; the Border Gang; the O’Connel Guards; the Atlantic Guards; the Forty Thieves; the Roach Guards.
And later: the White Hands, a Brooklyn gang that stole across the Brooklyn Bridge each night, terrorizing downtown neighborhoods; the Whyos; the Hudson Dusters; the Gophers; the Potashes; the Chichesters; and the Stable Gang, who hung out in a barn on Washington Street in Greenwich Village, just a few blocks from where I now live.
Going back through police files, or the pages of old books, you can find pictures of many of the early century gangsters. They have names like Red Rocks Farrell, Slops Connolly, Big Josh Hines, and Googy Corcoran. Their faces are dark and tight, their features pressed like fingers in a fist. They probably did not have what we would today call a balanced diet. They were surprisingly small: a hundred years ago the average New York gangster was not more than five feet three or heavier than 135 pounds.
If you go back further, to the time of President Ulysses S. Grant and the Tweed ring, the pictures give way to police drawings. Looking at these hastily made sketches—a line here, a shadow there—it’s hard to believe in the actual, day-to-day life of such men. They look like characters in a fairy tale.
And going back before that, to the decades preceding the Civil War, you are left with only a few legends—the creation myths of New York’s underworld, stories as mysterious and full of portent as those in Genesis. The characters in such stories stand forever behind reputation-minded criminals like Reles and Goldstein, a backdrop against which their most daring crimes are cast.
In his 1927 book, The Gangs of New York, which is really the Old Testament of the New York underworld, Herbert Asbury wrote about one of these early gangsters:
The greatest of the Bowery Boys, the most imposing figure in all the history of the New York gangs, was a leader who flourished in the 40s, and captained the gangsters in the most important of their punitive and marauding expeditions into the Five Points. His identity remains unknown, and there is excellent reason to believe that he may be a myth, but vasty tales of his prowess and of his valor in the fights against the Dead Rabbits and the Plug Uglies have come down through the years, gaining incident and momentum as they came. Under the simple sobrique of Mose he has become a legendary figure of truly heroic proportions, at once the Samson, the Achilles and the Paul Bunyon of the Bowery. And beside him, in the lore of the street, marches the diminutive figure of his faithful friend and counselor, by the name Syksey, who is said to have coined the phrase, “hold the butt,” an impressive plea for the remains of a dead cigar.
When Jews began arriving in New York in numbers in the middle of last century, they at once found themselves among the gangs. On the Lower East Side, in rickety tenements, on narrow streets, in brick alleys and crowded warrens, they came face-to-face with Irish thugs. Late at night, when the only light came from the moon or a flickering gas lamp, the streets would fill with toughs who moved among the newcomers. Some preyed on immigrants, Italians and Jews, who could often be tricked out of what little they had; those who could not be tricked could be bullied; those who could not be bullied or tricked could be killed. In those days, before the spread of handguns, an old immigrant would often be found in some dark alley, his skull smashed, his pockets turned out, a timesaving message to scavengers: Nothing more here.
To some Jews still trying to find their way through the streets, this was just a continuation of the past, more of the same harassment they had known in Europe. There was a real anti-Semitism in the air, a hatred often dressed as civic pride. Frank Moss, who worked with the preacher William Pankhurst, claimed he was trying to clean up the city when he wrote of his visit to the Jewish slums:
Ignorance, prejudice, stubborn refusal to yield to American ideas, religious habits and requirements, clannishness and hatred and distrust of Christians; these combine to hinder any device for raising the condition of the poor of the great Jewish district . . . there is no part of the world in which human parasites can be found in more overpowering numbers. . . . The criminal instincts that are so often found naturally in the Russian and Polish Jews come to the surface in such ways as to warrant the opinion that these people are the worst element in the entire makeup of New York City.
The strongest of the immigrants took such words as a challenge. Jews were bullied in America, but in America Jews could fight back. They were not confined, in a legal sense anyway, to any particular place or profession—they were free to be criminals. And they had an advantage that Irish gangsters, many of whom were born in the United States, did not quite understand: the Jews had little to lose. Nearly two million of them left Eastern Europe in the last two decades of the nineteenth century, washing up here like driftwood, with nothing but a few names, a few riddles. How the hell do we get out of the Lower East Side?
And the pogroms of Europe had taught them something. Some it taught how to die; others it taught how not to die. When he was an old man, Meyer Lansky, who came to the Lower East Side in 1911, talked to Uri Dan, an Israeli reporter, about the pogroms that swept through his hometown of Grodno, Poland. Lansky talked about those who threw up their hands, who saw the situation as hopeless, a punishment from God; but he talked about others, too, a new generation determined to fight back.
“One man—I don’t remember his name, but I wish I did—held a meeting in my grandfather’s house,” said Lansky. “ ‘Jews,’ he shouted. ‘Why do you just stand around like stupid sheep and let them come and kill you, steal your money, kill your sons, and rape your daughters? Aren’t you ashamed? You must stand up and fight. You are men like other men. A Jew can fight. We have no arms, but it doesn’t matter. We can use sticks and stones. Fight back! Don’t be frightened. Hit them and they’ll run. If you’re going to die, then die fighting.’
“This speech is burned in my memory,” Lansky went on. “I carried the words with me when I finally traveled with my mother to America and the Lower East Side. I remembered those words when I fought back at the Irish as a boy on the East Side. They were like flaming arrows in my head.”
By the time many Jewish immigrants reached New York, they too were ready to fight back. Some because they had to—for their wives and children. Others because they had to, but also because they wanted to. And still others, who came from middle-class families and did not have to, because they would rather fight than go to school or work. They fought for sport. The most skillful of them became gangsters, mastering things like stealing and killing, which Jews are not supposed to master.
Unlike the gangsters who came later—gangsters truly of the twentieth century, men like Crazy Joe Gallo and John Gotti—these early figures, who often went straight from the boat to the street, were not going into a family business, not following a blazed path. Their fathers were peddlers or tailors, butchers or merchants, and here were their sons, good Jewish boys, going into crime, which to their fathers must have seemed as strange and exotic as investment banking or advertising might seem to the Gallos or Gottis today. Like many Americans of the first generation, these gangsters were taking on the hard task of reinventing themselves, of creating a new identity for a new country.
“They were tough because they had to be tough,” said John Cusack, formerly an agent for the Federal Bureau of Narcotics, now the head of drug enforcement in the Bahamas. In the fifties, Cusack testified on organized crime before the McClellan Rackets Committee. “If these men had grown up in another place, in another time, who knows? But they were playing what was dealt. They were just trying to survive on the streets where the wind had brought them.”
Though there were many accomplished Jewish gangsters in the years before 1900, the first truly famous one was Monk Eastman. His real name was Edward Osterman. He was born in Williamsburg, Brooklyn, around 1873. His father was solidly middle-class, a restaurant owner. Before Monk was twenty his old man gave him a store to run, a pet shop on Broome Street in Manhattan. Monk sold the store and went instead to work as a bouncer at New Irving Hall, a nightclub on East Eleventh Street, where he became renowned and feared for the easy manner in which he dispatched drunkards, defeating men twice his size with a few sharp blows. Like the hero of a calypso song, he whipped every man and loved every woman.
Monk was ugly in a way you don’t see anymore—nineteenth-century ugly. His face, the aftermath of smallpox and brawls, looked like a stretch of Carolina landscape after a hurricane has blown over, with boats in the middle of town, cars overturned, cows hooked on flagpoles. You know what his face looked like? Like an art class sculpture by an eight-year-old: his ears cauliflowered, his nose really just the suggestion of a nose, his mouth a dark gash. His hair was parted neatly—an odd, dandified touch, like a hat on a horse. He was around five feet five and weighed 150 pounds. Coming down a dark downtown street, he must have looked like death itself.
By the time Monk was in his early twenties, he had gathered around him most of the East Side Jewish thugs. The Eastmans, as he called the gang, hung out in a clubroom on Chrystie Street near the Bowery. Monk could call out over a thousand soldiers. These men mostly fought an Italian gang headed by Paolo Vaccarelli, a former prizefighter who called himself Paul Kelly. One night the gang leaders fought, one on one, for supremacy. Eastman and Kelly brawled under klieg lights for two hours, until each man, bruised and battered, had to be carried off by his troops.
The Eastmans were not tightly organized. There was no schedule of events, no newsletter. They were either fighting or not fighting. When soldiers were needed for a fight, the call was shouted in the streets, whispered in the dives—in Gluckow’s Odessa Tea House on Broome Street, in Sam Boeske’s Hop Joint on Stanton Street, in Dora Gold’s candy store on First Street. The Eastmans fought wars inconceivable today: all-day gunfights with hostile gangs, passersby falling here and there; pitched battles with entire police divisions. Barricades were erected, stones hurled. Though they sometimes had guns, most of these battles were fought with clubs or blackjacks or pipes. Raiding the Eastmans’ clubhouse, the police came away with two cartloads of slungshots.
When not fighting, the gangsters were left to make their living—robbing, looting, stealing. Mostly they dressed like river rats, in tattered shirts and mothy jackets, fingerless gloves and broken-brimmed hats. At night they drank blue ruin, the cheapest rotgut whiskey, chased girls, started fights. The victims were found in the East River the next morning. This was New York’s Wild West era, when the most important gangsters were really just street thugs. The underworld had not yet made the transition to the twentieth century. Parts of lower Manhattan made Tombstone, Arizona, look like a sleepy border town.
In 1904 Monk bungled a holdup, shooting at a Pinkerton detective in the process. He was sent to Sing Sing. In his absence, a succession of Jewish gang leaders rose and fell, passing like picture cards in a fast shuffled deck: Kid Twist Zweibach, who died in a fight over a girl; Big Jack Zelig, a broad-shouldered, arrogant young man whom enemies called the Big Yid (“Where’s that Big Yid?” an Italian assassin asked one night. “I gotta cook me that Big Yid”); Dopey Benny Fein, the sleepy-eyed trailblazer who led the way to labor racketeering; Kid Dropper, who was shot while in police custody in front of the Essex Street courthouse by a mysterious figure who said his name was Louis Cohen; Little Augie Fein, who was killed in 1927 by Louis Lepke and Gurrah Shapiro at Norfolk and Delancey Streets as his bodyguard, Legs Diamond, looked on.
Monk Eastman was released from prison in 1916. All of a sudden the word was out: Monk is back! But things had changed. The old gangsters had died or gone straight; the young gangsters were different. No longer did people fight for the sheer joy of it. Monk could not raise an army. Not yet thirty, he was an old man, a relic. He worked as a sneak thief, a pickpocket, a dope peddler. After a half dozen small-time arrests and short stints in prison, he decided to go where there was sure to be fighting. In the spring of 1917, Monk Eastman joined the U.S. Army. At the enlistment, when he was stripped and examined, the doctors, noting the dozen or so knife wounds on his torso, asked, “What wars have you served in?”
“Just a lot of little wars around New York,” said Monk.
He was sent to France. I like to think of him arriving in Paris not too many years after the Dreyfus affair—this big, ugly, broken-nosed, backbreaking Jew. How could the French, with their ideas about Jews—what they looked like, what they did—deal with a man like Monk Eastman?
On the battlefields of France Monk was a hero. He led charges, gave orders. He did things, courageous things, in the face of enemy fire. It probably reminded him of the old days on Chrystie Street. In New York a year later, he was rewarded for the same behavior that once sent him to Sing Sing. On May 3, 1919, Governor Al Smith signed an executive order restoring Monk to full citizenship.
The police helped him find a job, but how could they help him settle down? When most people see extravagant window displays, they think: Wait until I get my paycheck! When Monk saw extravagant window displays, he probably thought: Where’s a rock? At night he went for long walks by the river—the hero back from the war, realizing he is still not home. Monk was soon mixing with criminals. On December 26, 1920, he was found dead in front of the Bluebird Cafe on Fourteenth Street. He had been shot five times. He was buried with military honors.
The death of Monk Eastman marked the end of the old-time gangster, whose world had been one of brute force and blunt instrument, whose money had come in dribs and drabs. Already, in the first years of the century, there were hints of the future, when gangsterism would at last become Americanism—as much about remaking yourself as about striking it rich. Monk actually spotted this future years before, in a seedy gambling house downtown. Here was this skinny kid (thin hands, thin wrists) leaning over the crap table, throwing dice. “Who the hell is that?” asked Monk.
“That’s Rothstein,” someone said.
Though Arnold Rothstein was just a boy—fifteen, sixteen years old—there was already something great about him, something just coming into focus. Monk sensed it right away. Not only was Rothstein the future of Jewish crime in New York, he was the future of all crime everywhere. In the coming decades, this skinny kid, who was probably losing that night at craps, would find that perfect mix of grace and violence, bluff and bravado, sophistication and brutality, that would become the modern American gangster. “Look out for number one,” Rothstein told a reporter years later. “If you don’t, no one else will. If a man is dumb, someone is going to get the best of him, so why not you? If you don’t, you’re as dumb as he is.”
Arnold Rothstein was a rich man’s son. He grew up in a town house on the Upper East Side. His father, Abraham Rothstein, owned a dry goods store and a cotton processing plant. Abraham had one of those dark, haunted Jewish faces that seemed to disappear with the last century, or else survived just long enough to die in Treblinka or Auschwitz. He had a beard, a nose, eyes. By certain friends he was called Abe the Just. A dinner given in his honor in 1919 was attended by Governor Al Smith and Judge Louis Brandeis. Whenever a Protestant politician had trouble with the poor, downtown Jews, they sought the advice of Abe the Just. From an early age, Arnold must have known he would disappoint his father, that he was not very much interested in his father’s sense of justice.
When he was around fifteen Arnold began slipping away from his father’s house and heading downtown. Though just a few minutes by train, it was like crossing into another country. He walked along flaring streets, jostled by drunken men and mysterious women, surrounded by accents, shouts, the clang of buoys, the cry of gulls. Running together, these sounds built to a roar—the song of the slum. Arnold sought ghetto life the way white teenagers later sought black music—jazz, rock ’n’ roll, rap. Here was a world beyond the humorless conventions of middle-class society. Arnold went to the Lower East Side the way Teddy Roosevelt went to Africa—in search of big game.
What he loved most were the card and dice games being played on every corner. When Rothstein first threw a pair of dice, something magical must have happened, a flash illuminating the next twenty years: smoky rooms, late nights, laughter, bluffs, tells, codes, straights, guns, bootleggers, casinos, horses, showgirls, Saratoga, Miami, bets won, bets lost, more bets lost. Though Rothstein would eventually tire of most things—friends, cities, states, styles, girls—he never lost his interest in gambling. It built him in the beginning and destroyed him in the end. From the day he first went below Fourteenth Street, his life was an endless succession of bets.
Gambling put a distance between Arnold and his father. If you could come away from a card game rich and fulfilled, if a seamless bluff brought respect and money, what did that say about the old morality? Was hard work really the way to the good life, or was it just a path for suckers? But despite that first rush, Arnold intended to come home. He would quit slumming, go into the family business, attend shul. He always wanted to be the good son. So what happened? The same thing that always happens. Arnold Rothstein met a girl.
When Arnold brought his girl home to meet his father, when Abe the Just hobbled downstairs, tugged his beard, straightened his yarmulke, when he heard his boy out, the plans to get married, when the girl told the old man no, she was not Jewish, and no, she would not convert, the old man shook his head and said, “Well, I hope you’ll be happy.” And after the wedding, when the old man pronounced his boy dead, when he covered the mirrors and read the Kaddish, it was a great development in American crime. It set Arnold free.
For Rothstein this was the decisive break, an excuse to turn his back on the old laws, subjecting himself instead to the rule of the street—a father/son split that was mirrored throughout Jewish America. “We saw it everywhere,” wrote reporter Lincoln Steffens. “Responding to a reported suicide, we would pass a synagogue where a score or more of boys were sitting hatless in their old clothes, smoking cigarettes on the stoops outside, and their fathers, all dressed in black, with their high hats, uncut beards and temple curls, were going into the synagogue, tearing their hair and rending their garments. . . . Their sons were rebels against the law of Moses; they were lost souls; lost to God, to the family and to the Israel of old.”
Rothstein was darkly handsome, with a high forehead, sloping nose, downturned eyes, thin lips, and a mole on his left cheek. Every line in his face, every crevice, seemed as carefully placed as war paint on a Sioux, each mark declaring his dread intent: to win every bet, whip every foe, meet every challenge, take every sucker. In rooms where other men wore cloth jackets or shabby suits, he wore tuxedos and top hats. “I had no idea he was a gambler,” said Carolyn Greene, his showgirl girlfriend. “He looked like a successful young businessman or lawyer.”
In the early 1900s Rothstein was making his way in the small gaming houses and pool halls of the Bowery. He changed this world as he passed through it, showing the young hoods how a gentleman carries himself. In the way that every great stylistic invention seems a convergence of high and low, a cultural cross-pollination, Rothstein was taking his uptown sophistication to the Jews downtown. He had more influence on the look of American criminals than Jackie O had on middle-class American housewives. Jackie brought hats, gloves, big sunglasses. Arnold brought wing-tip shoes, silk suits, expensive hats. He kept his money, his bankroll, in his front pocket. Whenever a friend needed a loan, he whipped out the entire roll, which, thanks to winning hands and gutsy bets, was getting fatter all the time. “No problem,” he would say, tearing off a few bills. “How much do you need?”
Like most great men, Rothstein can be judged as much by his enemies as by his friends. In 1911 some of these enemies—sour old gamblers—decided to teach him a lesson. Arnold thinks he’s great at pool? Well, let’s get a real shark in here and show him he’s wrong. So they got Jack Conway up from Philadelphia, a pool prodigy. They took Conway to Jack’s, a popular bar with the Broadway crowd, where he struck up a conversation with Rothstein. “I hear you play pool,” Conway said. “Maybe you think you can beat me. What do you say? Do you want to play some pool?”
Before Rothstein sensed all those gamblers smirking in the dark, he had accepted the bet. And then it was too late. Once you’re in, you’re in. Okay, said Rothstein. First man to one hundred points wins.
Since Conway was the challenger, Arnold got to choose the pool hall. Easy. John McGraw’s Billiard Parlor, next to the Herald Building. McGraw was then the manager of the New York Giants. One of the great baseball men of all time, he was one of the great sports of his time. He followed the races, the fights. On off days he could be seen at the track, leaning on the rail. He was friendly with all the big New York gamblers. For Rothstein, McGraw’s was home court.
Arnold took the first break early Thursday evening, the sky already more black than blue. The only light in the room came from lamps that hung over the tables. The light showed only the felt of the tables and the lay of the balls. When Rothstein leaned to shoot, you would see his face and veined hands. Standing around the table, or watching from the bleachers along the wall, the other men in the room were just shadows or the glow of cigarettes.
When the balls crashed, the shadows shifted, the voices murmured. The room was full of voices. Every important New York gambler and gangster was in the room that night. The men who brought Conway up from Philly were there, betting anyone fool enough to believe in Arnold—who, by the way, was betting on himself, which he would do up to the very end.
Conway reached a hundred points first. “Nice game,” said Arnold. “What do you say, do you want to play some more pool?”
“All right,” said Conway. “Let’s play.”
Arnold won the second game, and the third. Over time, he wore Conway down. By sunrise Rothstein was up three thousand dollars. “That’s fine pool,” said Conway. “Let’s play some more.”
So they kept at it, the big hand circling the clock like a device in an old movie. The sun came and went. The shadows lengthened and shortened. The noise in the street changed. Daytime noises: kids, dogs, crowds. Nighttime noises: rain, laughter, footsteps. A hat was filled with money for the kids racking the balls and keeping score. Black coffee was served on silver trays. When the sky paled Saturday morning, the gamblers backing Conway were down more than ten grand. Conway, who had yet to win a single best-of-three series, shook Arnold’s hand. “Nice shooting,” he said. “What do you say, do you want to play some pool?”
Before Arnold could answer, John McGraw stepped in. “That’s it,” he said. “If I let you go on, I’ll have you dead on my hands.”
Rothstein put his hand on Conway’s arm. He thanked him. They must have been in that region of exhaustion where every word is a joke and every joke is unnecessary. As the spectators—some happy, some not—went off into the morning, Rothstein took Conway downtown to the Turkish baths.
By evening the news had made the rounds: Arnold Rothstein had pulled off a great feat in an era of great feats—he had prevailed in an epic encounter, an underworld spectacle. It was a triumph of will. Even in hour forty, when every eye in the room was itchy and crying for sleep, when the balls moved in trails across the table, when the outside world was just a blur beyond the glass, Rothstein stayed cool. He did not rattle or break.
The underworld was now open to Rothstein. Each night he wandered as far north as Harlem, as far south as Delancey Street. If you went out to a Manhattan nightclub in those years, a dark place at the bottom of some stone stairs or maybe a casino hidden in back of a tall office building, you would have seen gangsters in parrot-colored shirts and hats, backs and shoulders, faces. If, in a corner of one of these rooms, you saw a well-tailored young man with a curled lip and downturned eyes, surrounded by other men fighting for his attention, this was Arnold Rothstein making the rounds. Athletes, starlets, tycoons—they sought him out. They wanted to shake his hand, collect the encounter.
It was around this time that Rothstein was befriended by Big Tim Sullivan, the great Irish political boss of the Lower East Side. Throwing an arm around Arnold, Sullivan would say, “This is one of my smart young Jew boys.”
Wondering about Sullivan’s new protégé, a ward leader once asked, “How can you tell what a Jew’s thinking? They’re different from us.”
“Rothstein’s a good boy,” said Sullivan. “You stick with him and you’ll make a lot of money.”
With Sullivan’s protection—from gangsters, from cops—Rothstein took the next step, opening an opulent midtown casino. In addition to money, the casino, which brought in about ten grand a week, gave Rothstein stature. He was now the house, the establishment, the meeter and greeter who accepts or does not accept markers, who sees people in their true nature, how they act in the wee hours when the table is just a sea of chips. His regular customers included Charles Gates, the son of John W. “Bet-a-Million” Gates; Julius Fleischmann, the yeast king, whose family would later found The New Yorker magazine; Joseph Seagram, the Canadian whiskey baron whose heirs now run MCA; Harry Sinclair, the oil magnate. For lots of wealthy New Yorkers, Arnold Rothstein was a door to the kind of fun that could not be had legally.
One night, Percival H. Hill, the president of the American Tobacco Company, lost $250,000 in Rothstein’s casino. Hill left Arnold a marker, which he said could be redeemed from a Mr. Sylvester the next day at the American Tobacco Company.
When Rothstein showed up with the IOU, Mr. Sylvester shook his head and said, “A gambling debt, I presume?”
Rothstein was not only getting rich—he now had more money than his father—he was climbing the underworld ladder from brash young gambler to elder statesman. Coming out of his own casino, he was less the smart young Jew boy than the Brain, the Bankroll—names he answered to on Broadway. To those who never met him he was A.R. the way James Pierpont Morgan was J.P. Biographer Gene Fowler compared him to “a mouse standing in a doorway, waiting for his cheese.”
When Arnold had enough money, he went still further, becoming the financier of the underworld, backing any shady project that caught his fancy. He was involved in the drug trade, raised horses, fixed fights. To downtown Jews he was the Jew with money, “the Man Uptown.” They called him Ph.G.: Pappa has gelt—the old man has cash. He could be found each night at Lindy’s, a diner on Broadway and Forty-fourth Street, hearing get-rich-quick schemes. It was here that he was first approached about fixing the 1919 World Series. Though Rothstein turned down the members of the Chicago White Sox who approached him—“You’d get lynched if it ever came out,” he told them—popular imagination has fastened this piece of corruption to his legend.
In his 1925 book The Great Gatsby, F. Scott Fitzgerald based the character Meyer Wolfshiem on Rothstein:
“He’s quite a character around New York—a denizen of Broadway,” Gatsby tells narrator Nick Carraway.
“Who is he anyhow—an actor?” asks Nick.
“No.”
“A dentist?”
“Meyer Wolfshiem? No, he’s a gambler.” Gatsby hesitated, then added coolly: “He’s the man who fixed the World’s Series back in 1919.”
Fitzgerald had already described Wolfshiem: “A small flat-nosed Jew raised his large head and regarded me with two fine growths of hair which luxuriated in either nostril. After a moment I discovered his tiny eyes in the half darkness.”
Of course, in the real world, Arnold Rothstein was just as smart and well put together as F. Scott Fitzgerald. (If they had nose-hair clippers in the twenties, you can bet Rothstein owned a pair.) And that was the point. There was no easy way (reptilian eyes, Jew nose) to tell Rothstein from the other successful businessmen skulking around Manhattan. He was a businessman just like so many of those fathers who, returning each day from the city, disappear into neat suburban homes—whose wives, when all is said and done, have no idea what their husbands do. He had broken through the traditional confines of the underworld and come out in a place where the line between the criminal and the commendable is vague and unreal. He worked the underworld the way a great aristocrat works the upper world: moving gracefully through rooms and thresholds.
In the fall of 1920 Arnold Rothstein was approached by Irving Wexler, a small-time dope peddler and sneak thief whom everyone called Waxey Gordon. Waxey and his partner, Big Maxie Greenberg, who had just arrived from Detroit, had come up with a way around the Volstead Act, which enforced the Eighteenth Amendment, which made the sale or transport of alcoholic beverages illegal. Waxey and Maxie would speedboat cases of whiskey across Lake Michigan from Canada to Detroit. The whiskey would then be smuggled and sold across the country. Simple. Only thing: Waxey and Maxie needed $175,000 to get it going. A.R. was the only gangster anyone knew with that kind of money. After meeting with Maxie the next day on a bench in Central Park, Rothstein said he would think it over.
The best gangsters act like the best businessmen: it’s not their job to come up with the great discovery, the flash of inspiration. Their task is instead to recognize the great idea in others. See it, back it. Sometime in the next few days, as Rothstein considered Waxey’s plan, he must have realized that here was a key to the future: that by banning alcohol, the U.S. government was turning a legitimate, multimillion-dollar business over to criminals, like walking into an abandoned factory and everything clean and shiny and ready to go; that young thugs who would have once gone straight would now stay in crime, at last having an illegal business to grow up in; that this new business would demand a new type of criminal, men with enough polish to move in the upper world, enough muscle to move in the lower, who could kill but could also intimidate, corrupt; that, if things went well, organized crime would soon change from an urban menace to a great moneymaking American industry, like steel or oil; and that he, Rothstein, was perhaps the only gangster in New York with the connections, money, sophistication, and smarts to turn East Side street punks into an army of business thugs.
The thing in Rothstein that recognized this, that saw beyond the patterns organized crime had followed until then (street brawls, gambling) to a glimmering world of gangster statesmen, is what separates old-timers like Monk Eastman from moderns like A. R. Rothstein was to the back alley what the money baron was to the boardroom: he pushed the barriers, bent the rules. He understood the truths of early century capitalism (hypocrisy, exclusion, greed) and came to dominate them. When a friend was in trouble, Rothstein offered the use of his lawyer. The lawyer told A.R.’s pal to refuse to answer questions, saying he might incriminate himself—that is, stand on the Fifth Amendment of the U.S. Constitution. This had never before been tried, and the lawyer went clear to the Supreme Court to make it law. So, in a way, A.R. created even this—taking the Fifth, a tactic that would come to define the American gangster. If the world of organized crime were a university, this alone would assure Arnold Rothstein tenure.
When A.R. again met Waxey and Big Maxie, he told them yes, he would back their plan—only he wanted some changes. Instead of A.R. financing Gordon and Greenberg, he would hire them. He would become the first big-time American bootlegger and they his employees. Another thing: Instead of bringing cases of alcohol on boats from Canada, which struck A.R. as small-minded, they would bring in a shipload of whiskey from England. After crossing the Atlantic—a hard, dangerous crossing—the ship would sit just outside American waters, about three miles off the coast of Montauk, Long Island, where it would be met by cutters fast enough to outrun Coast Guard boats. Rothstein bought six speedboats, each to carry ashore between seven hundred and one thousand cases of whiskey. The alcohol would then be trucked to a warehouse in Manhattan, from where it would be sold and shipped to speakeasies and clubs throughout the city.
In 1920 Montauk was just a sandy, unprotected, windblown point. Lighthouse. Shacks. Rock. I like to think of A.R.’s boys meeting the cutters on the beach out there, city men in black city suits, lugging heavy cases of whiskey across the dark sand in black city shoes; starting the truck and heading east down an empty ocean road, leaving in their wake a trail of sand and dust, the road a black ribbon beneath a black sky. They drove through a darkness composed of farms and fields, towns, houses, church spires, railroad platforms. City crime making its first groping contacts with a world beyond the last city light, the sticks, where everyone is assumed to be a sucker.
Rothstein had paid off cops all along the way. When the truck went barreling through some lonely crossroads, the patrolman just looked the other way. Or maybe he pulled the truck over, made small talk, then asked for a bottle. “Just something to keep me going,” the cop might say. No, the problem wasn’t the cops or the locals. It was the other gangsters. Coming out of nowhere, in dark sedans and coupes, bandannas below their dark eyes, guns flashing, these hijackers would stop the truck, hold up the drivers, and make off with a few dozen cases. And who could protect A.R.’s product? When a smuggler is robbed, can he go to the cops? No, not really. What Rothstein needed were his own criminals, men tougher and smarter than those robbing him. In the future, each of his trucks would head out with a driver up front and two soldiers in back, riding shotgun, like heroes of the Old West protecting the mail from bandits or Apaches.
These recruits came from the Lower East Side. They were Jewish and Italian—but mostly Jewish. If A.R. didn’t find them, then they found A.R. (Meyer Lansky met Rothstein at a bar mitzvah.) This was a generation miles removed from gangs like the Eastmans. Many of these men came here as boys from Italy or Poland or Russia, but already they were Americans. Already they had the pragmatism of the new world—Jews and Italians who saw that they were more alike than different, that old rivalries meant less than new money. When Irish gangs came down to beat up immigrants, young Italians and Jews fought them off together. It was the beginning of an alliance that, for many Jews, was a great part of the American experience. “When Lucky Luciano was deported from America and was living in Italy, you know what he talked about missing?” John Cusack asked me. “Jewish corned beef, pastrami, rye bread. He said just thinking about it made his mouth water.”
And these men, growing up on the same streets, learned the same lessons: that in America it isn’t enough to be strong, you also have to be smart; that in America it isn’t enough to be strong and smart, you also have to play a role, making others feel that you are really just like them, only younger or older or from a different place; that in America people help you only when they are convinced they are really helping themselves, either through a mutual interest or through identification, a belief that by helping you, they are actually helping themselves in some other incarnation.
Rothstein picked out the best of these young thugs, those he could train, who shared his views, who got it. In the first years of Prohibition, riding shotgun for A.R. was like fighting for the Mujahdeen—it taught you, hardened you, marked you for life. The men Rothstein hired included Lansky, Siegel, Luciano, Frank Costello, Legs Diamond, Waxey Gordon, Dutch Schultz, Louis Lepke, Gurrah Shapiro—men who would eventually turn A.R.’s lessons into a national obsession and would themselves become the most notorious criminals of the twentieth century. “Meyer Lansky went on to become the king of illegal casino gambling,” a retired New York detective named Ralph Salerno told me. “I think the first time he ever saw the green felt of a crap table was in Rothstein’s place. Arnold taught Lansky about style. He was maybe the first guy to take craps off the street and put it indoors, up on a table.”
As far as I’m concerned, Arnold Rothstein was the Moses of the underworld: he led the next generation to the promised land but himself could not enter. He was shot in the stomach on November 4, 1928. A Sunday night. Earlier that evening he had received a phone call at Lindy’s. He was asked to come to the Park Central Hotel on Fifty-sixth Street to discuss a debt. Having lost at cards some weeks before (fifty grand in a single hand), he now owed a California gambler a few hundred thousand dollars. Small change. But A.R. refused to pay, saying he had been cheated. “I don’t pay off on fixed poker,” he told a waitress. The same thing that gave Rothstein the strength to play pool for forty-five hours would not let him pay off that chicken-shit marker. Leaving Lindy’s, he gave his gun to a friend. Weapons were not allowed at such meetings. Rothstein was found an hour later, slumped over a banister in the lobby of the hotel. “Call me a taxi,” he told the doorman. “I’ve been shot.” Later, at the Polyclinic Hospital, when the cops asked Arnold who shot him, he waved them off, saying, “I’ll take care of it.”
Though Rothstein had seen dozens of underworld figures fall—Louie the Lump, Monk Eastman, Kid Twist Zweibach, Dopey Benny, Little Augie—he could not believe in his own death. He spent the next few days promising to recover as he dissolved into delirium. Slipping away, his hospital window showing nothing but river and sky, he must have felt less like an underworld genius than a lost son, a boy who has disappointed his father.
A few years before, Arnold heard his father was in trouble. The cotton market had collapsed. Abraham Rothstein’s cotton processing plant was worthless, creditors were after him, he couldn’t get a loan. Arnold learned of this from his kid brother, Jack. “He needs a lot of money,” said Jack. “More than two hundred thousand.”
“Why doesn’t he just ask me?” asked Arnold.
“You know he wouldn’t do that.”
“Okay,” said Arnold. “Tell him to go to the main office of the Bank of the United States tomorrow and ask for a loan.”
“He’s been there,” said Jack. “They refused him.”
“I’ll see to it that they change their minds,” said Arnold, who then went to the bank and gave the president $300,000 in Liberty bonds—enough to secure the loan. “When my father comes in, give him his loan,” said Rothstein. “My father is not to know that I was here.”
Rothstein was no longer an observing Jew, but here he was living the Jewish experience—giving anonymously. No one but Arnold and God would know of this gift. No matter the bad things Rothstein did, I like to think this act carried weight with God. Rothstein was looking after his father long after his father stopped looking after him.
One afternoon Rothstein’s estranged wife came to see him in the hospital. “I want to go home,” he told her. “All I do is sleep here. I can sleep home.” He died a few hours later. The funeral was overrun by sharks and gamblers, superstitious men hoping to take away some part of A.R.’s magic. In front of the crowd stood Abraham Rothstein, old man in prayer shawl, saying Kaddish a second time for his son.
For the most part, Rothstein’s legacy would be carried on by the young criminals he had influenced. “He taught me how to dress,” Lucky Luciano recalled years later. “He taught me how to not wear loud things, how to have good taste. If Arnold had lived longer, he could have made me pretty elegant; he was the best etiquette teacher a guy could have—real smooth.”
A.R.’s legacy was powerful, finding its way even to those who never met him, who would not make their names until much later. The connection between Rothstein and the Jewish hoods of later generations like Abe Reles and Buggsy Goldstein was tenuous but real—like the relation of a photograph to a copy made from a copy made from that photograph. Though years had passed and the image had blurred, some of the original features—a hint of style, a dash of color—could still be made out. To this day, every gangster in America, in ways they probably don’t even understand, is imitating Arnold Rothstein.
The time of Rothstein’s death was an in-between time for organized crime in America. Rothstein had left disciples behind, a cadre of young criminals determined to carry the word forward: Money is money, everything else is bullshit. But the streets were still in the grip of the last generation, traditional Italian gangsters whom A.R.’s boys disdainfully called “Mustache Petes.” These were old world criminals with thick mustaches, dark eyes, creased brows, heavy hands, strong loyalties, ancient hatreds, deep suspicions. The Petes traced their roots to the Black Hand of Sicily, secret societies, vendettas, stylish symbolic killings: shoot out the eyes, stealing the last sight accorded even the dead; cut out the tongue, telling the world, “Here lies a squealer.”
These men were bothered by what they saw as the corruption of the new world, where promising young thugs like Charles Luciano consorted with Jews like Meyer Lansky. When Frank Costello introduced Vito Genovese to Bugsy Siegel and Meyer Lansky, Genovese said, “What are you trying to do? Load us with a bunch of Hebes?”
“Take it easy, Don Vitone,” said Costello. “You’re nothin’ but a fuckin’ foreigner yourself.”
The Mustache Petes were small-minded, parochial men who really belonged to the past. And soon the past would come looking for them. The resulting fight—the Castellammarese war—would be perhaps the most important battle in underworld history. It was to organized crime what the Civil War was to the United States: a battle of ideas, economies, vision: Do we go forward, do we go back? It was a war in which Jewish gangsters would play a decisive role.
By 1930 everything seemed settled, with the underworld, the Italian part of it, at least, run by those men—Costello, Luciano, Anastasia, Gambino—loyal to Joe Masseria.
Masseria had come to the Lower East Side from Sicily—where he was wanted for murder—in 1903. He was a short, roly-poly guy a shade above five feet, but something in his eyes, some steadiness, froze people. As a young man he had a reputation for athleticism, an agility that defied his physical appearance. Once, when an enemy came after him on Second Avenue, he literally dodged the bullets. After killing Masseria’s bodyguards, the assassin fired several shots at Masseria, who bobbed and weaved, the bullets lodging in the wall behind.
In the coming years, Masseria rose to power. Behind this rise, as behind the rise of all powerful men, stood a troop of shattered friends and rivals: Lupo the Wolf, Peter Morello, Ciro Terranova. By the late twenties, Masseria, having defeated his enemies and tricked his friends, declared himself capo di tutti capi, boss of bosses. To those working for him, he was simply Joe the Boss.
Masseria was not a popular leader. He was disliked even by his own lieutenants, especially those who had worked for Rothstein. Costello and Luciano distrusted the boss, his love of ritual, his prejudice. “When I started hanging around with Jewish guys like Meyer and Bugsy and Dutch, Masseria used to beef me about it,” Luciano later wrote. “He said someday the Jews were going to make me join a synagogue.”
But what could Luciano do? Masseria was the power on the street. What he lacked in foresight he made up in guns. A well-armed past can, for a time, hold off even the most prosperous future. Joe the Boss would be Joe the Boss until someone took that title away. And it wasn’t going to be Luciano or Costello or Lansky or Siegel. Not yet, anyway. In the meantime, Luciano would just have to wait, all the while playing the role of top man behind the boss.
All things in the world are connected. Throw a switch here, a light goes on over there; break a promise here, make an enemy over there. In 1926, when Benito Mussolini began cracking down on the Mafia in Sicily, he probably did not think it would affect life over there, in New York, but it did. Soon after the dictator pushed the crime bosses out of Italy, they began turning up in Manhattan. They came mostly from the area around the Bay of Castellammare, a rugged country of squat white houses running over scrubby hills to the sea. Some of these men—Joseph Bonanno, Joseph Profaci—would later become powerful gangsters. Arriving on the East Side, though, they were just hungry exiles. And they were a threat to Joe the Boss. The newcomers did not respect the current order. Why should they? They ran things in Sicily. Why not run them here, too?
These men were led by Salvatore Maranzano, who in 1927 settled in America with his old world ways. A thug who met Maranzano later wrote: “When we arrived, it was very dark. We were brought before Maranzano, who seemed absolutely majestic, with his two pistols stuck in his waist and about ninety boys who were also armed to the teeth surrounding him. I thought I was in the presence of Pancho Villa.”
Setting up headquarters in an office tower near Grand Central Station, surrounding himself with lieutenants, Maranzano went to war with Joe the Boss. All over Manhattan, in blue smoky rooms and underground clubs, in pool halls and all-night diners, gangsters took sides. They fired from moving cars, rooftops, doorways. Pistol shots punctuated the night. In the morning the cops came for the bodies. Between 1927 and 1930 at least fifty men fell. Luciano spoke to young soldiers on both sides, telling them the war was a waste, how nothing would come of it, how it was costing everyone money, how here was another example of old generals fighting with young lives.
Charlie Luciano had come to New York from Sicily in 1906. He had a dark fleshy face, curly hair, and a quality smile. On a fall night in 1929, four thugs dragged him from the West Side docks, where he was unloading a shipment of heroin, and into a car. As the sedan ghosted through Brooklyn, Charlie was beaten, blackjacked, pistol-whipped, ice picked, cut across the throat and face, then left for dead on Huguenot Beach in Staten Island. At dawn he was found by a cop and rushed to the hospital. Later, when he was asked who attacked him, he shook his head, saying, “I’m pals with everybody. Nobody’s after me. Everybody likes me.”
Gangsters suffer the same setbacks as everyone else, only their losses can be more easily seen. Luciano’s defeat could be seen in the scars that ran across his face. The muscles below his cheek had been severed. As a result, his left eye drooped, giving him a sinister aspect. Women in his world found this attractive. “I never liked a pretty man,” an old gangster doll I met in Miami told me. “I like a man that’s been marked up.” On the street, Luciano was now called Charlie Lucky—the only man lucky enough to be taken for a ride and survive. The very term “going for a ride” was really just code, another way of talking about death, the way American soldiers in Vietnam would later talk about “buying the farm.” Charlie was a religious man. He must have believed God had saved him for a reason, that there was still work to be done.
Whenever he could get away, Luciano went down to Delancey Street, a crowded little delicatessen—silverware ringing, voices chattering—for breakfast with Meyer Lansky. Luciano first met Lansky years before, on a January afternoon at the beginning of the century. Meyer, a scrawny immigrant kid with huge features, was walking alone through the snow on Hester Street. Looking up, he saw he was surrounded by young Italians. “If you wanna keep alive, Jew boy, you gotta pay us five cents a week protection money,” said the leader, Charlie Luciano.
Meyer looked up. Two sharp eyes met two sharp eyes. They saw something in each other, something familiar. “Go fuck yourself,” said Lansky.
It was one of those moments—Mick Jagger meeting Keith Richards; Otto von Bismarck meeting Kaiser Wilhelm—that would have consequences. “He stood there, this little punk,” Luciano later recalled. “I was five years or so older than him and could have smashed him to pieces. But he just stood there staring me straight in the face, telling me to stick my protection up my ass. He was ready to fight. His fists were clenched.”
Luciano respected the kid’s nerve. He hit him with some small, face-saving insult, then walked away. Later he came back alone, looking for an ally—someone who would fight with everything he had. In the coming years the boys looked after each other, protected each other. Crossing one was crossing both. Gangster arithmetic. They forged one of the great friendships in criminal history. “We had a kind of instant understanding,” Luciano later said. “It was something that never left us. We didn’t have to explain things to each other. It may sound crazy, but if anybody wants to use the expression ‘blood brothers,’ then surely Meyer and I were like that, even though we had come from totally different backgrounds.”
Here was an example of gangsters living ahead of their time. In an era when much of the country was hyper-aware of background and religion, Lansky and Luciano got beyond that. They believed that in America your brother can be born to any parents, in any house. “Gangsters who never made it out of high school broke social barriers thirty years before anyone else got near them,” Ralph Salerno told me. “Much more than people in other parts of society, gangsters are pragmatic and realistic. Why the affinity between Italians and Jews?” he went on. “It was a marriage of convenience. They were in the slums at the same time; they went against Prohibition at the same time. It was a marriage of the three M’s: moxie, muscle, money. The Jews put up the moxie, the Italians supplied the muscle, and together they split the money.”
Whenever Luciano talked about the war between the Mustache Petes, Lansky urged caution. Wait this thing out. Let the bosses kill each other off. But by 1931 both men had tired of waiting. Too many people had died; too much money had been lost. Something had to be done.
That spring Luciano went to see Maranzano in his headquarters, a real estate office in the Eagle Building at 230 Park Avenue. Lucky spent an hour in the office, nodded at the bodyguards in the outer room, took the elevator down, and disappeared into midtown. At that point, only one person other than Lucky knew what would happen next—Meyer Lansky. Whatever happened, some of Meyer’s boys would be involved. After all, the future Lucky and Meyer were planning was Italian and Jewish—so Jews and Italians should ring it in together.
On April 15, 1931, Luciano asked Masseria to lunch. “We’ll go over to Scarpato’s,” Lucky told the boss. “Scarpato fixes sauce like in the old country, with the clams and good olive oil.”
They took Masseria’s steel-plated, bulletproof limousine. From the East Side it was a short drive through lazy red brick Brooklyn, alleys and stoops tumbling past the window. Now and then a kid stood watching the car go by, dark windows, mystery.
They drove along the harbor, schooners and sloops stretching to the horizon, masts making lines against the sky. The restaurant was on West Fifteenth Street in Coney Island—one of those run-down Italian joints by the boardwalk. You can still go there today. The restaurant is gone, but the building is there. It’s now the General Iron Corporation, but it looks pretty much the same: narrow facade, slender columns, arched windows. The street runs under stunted city trees down to the ocean. Standing out front, clouds moving fast on the horizon, you think: This is how it must have felt in 1931, only less carefree, less picturesque, less sinister; romantic now only in the way of a ruin, a place where something important happened long ago.
That afternoon, Luciano and Masseria took a table in back. They had the kind of long, leisurely lunch known only to the very rich and the very poor. Masseria probably talked about the war, how it was going, how he still hoped to win. Maybe he talked about the Jews, again telling Charlie how a man can only trust his own. They drank Chianti. Plates were cleared. A waiter brought a deck of cards. They played poker. At around three P.M. Luciano excused himself, saying he had to go to the toilet.
A moment later the restaurant’s front door flew open. In came a ragtag collection of killers: Ben Siegel, Albert Anastasia, Joe Adonis, Red Levine. They walked to the back room and began shooting. Twenty shots. When the killers returned to their car, Adonis got behind the wheel. He was shaking so, he couldn’t turn the key. Siegel pushed him aside, started the engine, and drove off.
When Luciano returned from the bathroom, he saw panicky waiters, Masseria slumped on the table, holes in the wall, holes in the boss, an end (to some) of his problems. In newspaper photos the only thing visible is Masseria’s bloody hand, palm up, holding the ace of diamonds. Among gangsters, that card was ever after cursed. Receiving an ace of diamonds by messenger was another way of learning of your own death.
When cops later asked Luciano where he had been during the shooting, he said, “In the can taking a leak.” He thought a minute, then added, “I always take a long leak.”
That night, when Maranzano heard about the killing, he declared himself the victor of the Castellammarese war. He got a message to Luciano: Thank you. Lucky was named Maranzano’s first lieutenant, perhaps the second most powerful job in the underworld.
A few weeks later Maranzano called a meeting. Just about every Italian gangster in New York was there, a huge warehouse in the Bronx, a few blocks from the Harlem River. The doors were patrolled by armed guards, the roof by sharpshooters. Like at the Congress of Vienna, which followed the defeat of Napoleon, or the Yalta Conference, which followed the defeat of Hitler, the survivors were meeting to redraw the maps. Standing before the boisterous crowd, with his guns and bodyguards, Maranzano laid out a blueprint for the next generation. The Italian underworld would now be divided into five criminal families. Each family, which was really just an affiliation of like-minded thugs, would operate like a trade union. Low-level members of a family, soldiers, would pay the boss a percentage of their earnings, a tribute. In return, the soldier is protected—from other criminals, from cops. If a soldier from one family is wronged by a soldier from another family, he has someone to go to—his capo, a neighborhood leader, who may then bring the matter to a lieutenant, who may then bring it to the boss, who may then bring it to the boss of the rival family, quietly settling what might once have led to a bloody war. And if a soldier is arrested on family business, the family posts bail, hires a lawyer, fixes a judge. If a judge cannot be fixed, the soldier’s wife and kids are taken care of while the soldier does his time. It was a good system.
Maranzano named bosses to run each family. The selections were not random. Maranzano was not betting hunches. These were already powerful underworld leaders. Each man gave his family his name: the Lucky Luciano family; the Albert Anastasia family; the Tommy Luchese family; the Joseph Profaci family; the Joseph Bonanno family. For the most part, these families still exist today, operating on the same basic principles Maranzano set up in the warehouse in the Bronx, running restaurants, stores, guns, bakeries, trucking companies, hotels, resorts, drugs, whatever. When most successful, their operation is as fluid and invisible as the wind.
Over the years, as bosses have been killed or jailed or deported, new bosses have risen to take their place, giving the families new names. When Albert Anastasia was shot dead in midtown, his family became the Carlo Gambino family and was still called that when it was being run by John Gotti. When Lucky Luciano was deported to Italy, his family became the Frank Costello family, then the Vito Genovese family, then, when Genovese was wanted for murder and was hiding in Sicily, it again became the Frank Costello family. When Genovese came back to New York and realized Costello would not relinquish power, he organized a coup. As Costello passed through the lobby of his Upper West Side apartment building, a hulking youth stepped from the shadows and shot him. Though Costello survived, he surrendered power. When Genovese died, family leadership went to the kid who allegedly shot Costello—Vincent “the Chin” Gigante, who is said to still run the family, even though he was convicted in 1997 of racketeering and conspiring to kill John Gotti. Since Maranzano first set up the families, underworld politics have supplied more intrigue, color, and drama than even the most backward state in the Balkans.
As far as the younger generation saw it, Maranzano made only one mistake. He placed himself above the family bosses, making himself the boss of the bosses. So, after all that, after the gunfights and stabbings, here was yet another would-be dictator, another cappo di tutti capi. Maranzano must have known his decision was not popular, that downtown clubrooms were filled with young men who would not bow to absolute rule, who were determined to make the underworld a republic, who in every important way were more American than Sicilian. Maranzano could call himself whatever he wanted—boss of bosses, boss of the universe—but it wouldn’t mean a thing until he dealt with these young men, who were led by Luciano and his friends. That’s why Maranzano made Charlie his chief lieutenant—keeping Lucky close was a way of controlling him. And when it was time to kill Lucky, he wouldn’t have to go far looking for him.
Luciano knew the truth—that he was an obstacle, something in the way. And if he didn’t know it, he had only to ask the Jewish gangsters, who were sufficiently removed from the Sicilian underworld to see the pattern. Luciano was being warned, not only by Lansky, but also by Louis Lepke, who was the first gangster to come into real conflict with Maranzano after the war.
In the summer of 1931, during a season of strikes, one of the most important garment workers’ unions, the Amalgamated Clothing Workers, splintered into factions. One faction, run by Phillip Orlofsky, was allied with Lepke, who supplied protection. The other was led by the union president, Sidney Hillman, who would later serve on Franklin Roosevelt’s kitchen cabinet. When relations between the factions turned ugly, Hillman went with money to Luciano, asking for help. Though Lucky said he would like to help (money is money), he couldn’t. Lepke was his pal. How can you go against your pal? So Hillman instead went to Maranzano, who took the job. Maranzano told Luciano not to worry. He knew he and Lepke were pals. There would be no fighting. This was just about the money. A few weeks later, though, Maranzano’s men opened fire, killing a few of Lepke’s soldiers. “Don’t you see?” Lepke told Luciano. “He’s not just shooting my men. By going after me, he’s going after you.”
September 10, 1931. Sometime that morning, the phone rang in Luciano’s clubhouse. It was Maranzano. He wanted to talk business. Could Lucky come up to the office? And could he bring along his friends Frank Costello and Vito Genovese?
To Luciano, Maranzano’s call was a warning bell—it said, “You’re about to be killed.” Just a few weeks before, Lucky had learned of the plan, probably from Tommy Luchese, a Maranzano confidant who was secretly working with Luciano. Maranzano had drawn up a list of men to be killed: Luciano, Costello, Genovese, Willie Morretti, Joe Adonis, Dutch Schultz (the only Jew to make the list), and, in Chicago, Al Capone. The killings would start that afternoon with the murder of Luciano, Costello, and Genovese. They were to be shot dead by the Irish gangster Vincent “Mad Dog” Coll, whom Maranzano hired special for the job.
Coll was a gawky Irish kid, twenty-two years old, with a big toothy grin, blue eyes, freckles. He looked less like a killer than someone you see leaning on a wall at a country club social, hoping to God no one asks him to dance. In the twenties he worked for Dutch Schultz. The men later had a falling-out, which turned violent. While trying to shoot the Dutchman, Coll accidentally killed a five-year-old boy. Though never convicted, Coll was ever after reviled. By hiring him, Maranzano was hiring the most hated gunman in town.
When he got off the phone with Maranzano, Luciano called Lansky. It was time to set in motion a plan they had arranged weeks before. The killers could not be Italian—Maranzano would recognize them. And they could not be Jewish gangsters of too much prominence. He would recognize them, too. No, the killers had to be strangers to Maranzano, men who could walk by all his guns and bodyguards the way a jet can fly under radar. So Lansky went to work, assembling a team of Jewish gunmen from across the country. This group included Red Levine, from Toledo, Ohio, an Orthodox Jew who would not kill on the Sabbath; and Bo Weinberg, a top Dutch Schultz lieutenant.
To me, these killers seem about as skillful as the Israeli commandos who slipped into Entebbe, freeing Jews held hostage at the airport in Uganda. These were men hand-picked by Lansky for their cool. Posing as federal alcohol agents, they went into Maranzano’s headquarters, said something about a raid, flashed badges, and lined the bodyguards against the wall. As two men covered the guards, the others went with Maranzano into his office. As he pleaded his case—“There is no liquor here!”—Red Levine stabbed him. He stabbed him six times. When Maranzano, wild-eyed and dying, lunged at the killers, they shot him four times. The killers then ran through the office and into the hall. I like to think of them out there, the sound their shoes made on the floor, sliding around corners, wheels spinning.
Years later, Dixie Davis, Bo Weinberg’s lawyer, talked about Weinberg’s involvement in the killing, which he said Weinberg had confessed to him. Davis talked about Weinberg’s escape, how the killers made a wrong turn and wound up in a ladies’ room; how they saw Mad Dog Coll waiting for the elevator in the lobby. “Beat it,” one of the killers said. “The cops are on their way.” How they ran into the street, flushed, heart pounding, crowds, traffic, horns, colors, sirens; how they scattered, some down side streets, some into getaway cars; how Weinberg, finding himself in the rush-hour crush of Grand Central Station, smoothly slipped his pistol into the pocket of an unsuspecting commuter.
Some historians talk of a purge that followed the killing: the slaughter of the Sicilian vespers, in which forty Mustache Petes were executed across the country. Many scholars say this never happened, that it’s an underworld myth. But even if it didn’t happen, the fact that gangsters tell the story—Joseph Valachi, who was one of Maranzano’s bodyguards, told it to prosecutors when he turned state’s evidence—is itself of interest. The slaughter of the Sicilian vespers is a kind of underworld Bible story, like the story of Noah and the Flood, that marks the destruction of one world, the birth of another. The world of the Petes was gone—what survived was a generation raised by Rothstein, Prohibition, the twenties, the slums. For them violence was not the end—it was a way of getting there; it filled the void between wanting and having. They were Americans.
Over the next few months, these leaders created new rules. The five families would still exist, only now they could work closely with Jewish gangsters, as the Luciano family did. “The Italian gangs with Jewish friends did better than the others,” Ralph Salerno told me. “The Genovese family, the Gambino family, they had Jewish friends and prospered. What did they care about a guy’s religion? Do you like him? Do you trust him? Can you make money with him? That’s all that matters.”
And there would be no boss of bosses. The system would instead run like a corporation, with a board of directors voting in policy. The members of the board included Lansky, Luciano, Lepke, Anastasia, Siegel, Costello. Together these men and the troops they commanded were called the Mob or the Syndicate or the Combination; it was the birth of modern organized crime; it was the disciples of Rothstein putting the teachings into practice. Before anyone could be killed anywhere, the Syndicate had to okay it. In hotel rooms across the country, these men held court, questioned witnesses, passed judgment. If some family member had to die, the board hired the killers. Since having killers from one family kill wrongdoers from another family could lead to a war, Lansky and Luciano decided to create an enforcement wing, a group of gunmen who would kill just for the Syndicate. They looked for these gunmen mostly in Brooklyn. Since the Williamsburg Bridge went up in 1903 and the Manhattan Bridge in 1909, the slums had moved with the subway to the end of the line. The Lower East Side was melting away. Brooklyn was the place for young criminal talent.
Then somebody (Anastasia? Lepke?) remembered the kids making their way in Brownsville, the young toughs Louis Capone was always talking about. Maybe their names were mentioned: Abe Reles, Buggsy Goldstein, Happy Maione, Frank Abbandando, Harry Strauss. Lansky must have remembered them, too. Maybe, turning to Ben Siegel, he said, “Didn’t we supply them with slot machines?” And someone probably mentioned the feud between Reles and the Shapiro brothers. What was going on out there? There had already been shooting. Who was coming out ahead? If anyone could test the Reles gang, it was Meyer Shapiro. If the Brownsville Boys could handle the Shapiros, they were probably the gunmen the Syndicate was looking for.
So, as the new era began, all eyes were trained on a few ragged streets in Brownsville, where Kid Twist, Buggsy, Pittsburgh Phil, Happy, and the Dasher were set for the fight of their lives.