War in Brownsville

IN THE SPRING of 1931, the war came to Brownsville. It was one of the first springs of the Depression, and the corners were full of young jobless men. Vendors huddled pushcarts along curbstones, warming their hands over red charcoal fires. The butcher shops were full of meat no one could afford to buy, and the wind carried the sweet smell from bakery ovens into the sky, where old women in windows sat stitching seams for the great middle class. At night Brownsville was like Manhattan in negative: empty alleys, tumbledown facades, dark windows. No glamour. And then the intriguing, too close sound of gunfire, where killers were doing business.

Abraham Reles and Buggsy Goldstein were busy each night with the Shapiros, hunting the brothers like game. Kid Twist didn’t like fair fights; they were something he worked to avoid. He preferred taking enemies by surprise. If surprise was impossible, he overwhelmed them with numbers. If he had neither numbers nor surprise, he used all kinds of sly tricks. Reles thought he was the smartest man around and was forever trying to figure it from the other guy’s point of view. When he thought he knew what the other guy was likely to do, no matter how low-down or cheap, he would do it first himself. And though he tricked the Shapiros many times that spring, his luck was bad, and his dream of killing Meyer must have sometimes seemed as impossible as the American dreams of all those poor out-of-work men on the corners.

Reles and Goldstein shot at Meyer maybe ten times that spring—in alleys, streets, garages, hallways—and not a single bullet found its target. The bullets instead lodged in walls or skipped off concrete floors or sailed harmlessly into the dark. And the screech of tires taking Meyer away. It must have become a neighborhood joke: Reles can’t hit the side of a barn; Meyer has the power of the hex. Who knows? Maybe the Shapiros had access to some old Sioux war cry that turns bullets to water in midair?

In April Reles paid some neighborhood punk a few bucks to lead the brothers out of their clubhouse and into a trap. While the punk was in there, saying whatever, Reles was crouched in an alley around the corner. When the punk, followed by Meyer Shapiro, came into the alley, he looked at Reles, nodded, ran. The scene was probably still arranging itself in Meyer’s head as Reles stepped forward and fired. Meyer felt his arm—warm with blood. He had been hit at last, only it was a nothing flesh wound. Meyer fled to his clubhouse.

Reles and Buggsy ran to the candy store on Livonia and Pitkin, where they had their headquarters. They called the Italians in Ocean Hill; someone from the Italian gang could always be found drinking in Sally’s Bar. Sitting in the back room of the candy store, Reles explained the situation, how Meyer had been wounded and would now be even more dangerous. The war was entering a phase of dark images running across a small screen. Cars driving up out of gloomy garages, rumbling down blue streets, spent weapons being tossed into turbid rivers. Sometimes there were two or three sets of killers on the street, trailing Meyer. What the Shapiros were doing just then is hard to know. It’s a clear case of history being written by the winners. In the coming years, Meyer would not be around to tell his story to police or reporters or friends. The Shapiros were on their way out, so their significance comes only in moments of conflict with Reles and his gang. When the Shapiros appear in the Kid’s world, they are on our map. Otherwise they are off screen, somewhere in the wings, conducting affairs in those parts of the past that contribute nothing to the present.

Meyer came back on screen one afternoon in May, when Reles and some friends were hanging out at Buggsy Goldstein’s pool hall. It was one of those middle-of-the-day middle-of-the-week nothing doing afternoons that, in small towns and on the outskirts of big cities, comes to even the most important men. And then it was gone. Maybe someone heard the car, or maybe the first thing they heard was glass shattering and gunshot peppering the walls. Maybe a stray bullet struck the eight ball, rolling it across the table and into the corner pocket. Probably not. The Kid crawled to the window. He could see Meyer shooting from the rumble seat of a dark sedan. His brothers fired from the back. The man at the wheel was a stranger: a handsome, sad-faced rich boy looking straight ahead, like a hack unconcerned with the behavior of his fare. The shooting stopped and the car drove on.

No one was hurt. Not a scratch. And the attack was over. It had to come, and now it was over. And it was a good thing. The attack was Meyer’s way of acknowledging the corner he was in. Reles must have known that by joining the battle, Meyer was accepting his vulnerability. He was just another soldier now, and soldiers die all the time.

In June Reles and the boys cornered the Shapiros on Sheffield Avenue, outside the City Democratic Club. Caught by surprise, the brothers made a break for it, each running a different direction. Pep, Happy, and Dasher gave chase, leaping fences and running through backyards, a kind of youthful suburban race from danger. Reles and Buggsy instead went to one of the apartments the Shapiros kept. Like great athletes, they were playing the ball where it would be, not where it was. They walked to the fifth floor, where the Shapiros had a two-bedroom place. After wrapping a handkerchief around his hand, Reles unscrewed the hall light bulb. He and Goldstein then crouched in the dark. They waited ten minutes, twenty minutes, an hour. They heard someone on the stairs. When the man stepped to the door, Reles got him from behind. It was Irving Shapiro. Reles dragged Irving outside, pushed him against a wall, and shot him eighteen times, twice in the face.

It was like the domino theory. After the first brother fell, the others went just like that. Reles caught up with Meyer on a deserted street a few days later. Pep and Dasher were there, too, but they let the Kid take care of it. Reles shot Meyer only once. Maybe he wanted to show the neighborhood that Meyer was not Rasputin, that the life in him could be snuffed out as it could be snuffed out of any living thing. He shot Meyer through the ear. When they found Meyer he looked just fine, except for the blood coming from his ear.

A few days later Reles and Happy trapped Joey Silver. Joey was the kid who betrayed Reles and Goldstein, leading them into an ambush. Backing him against a tree, Reles blew Silver’s head off.

After each killing, a squad car would answer the call, coasting down some deserted Brownsville streets (Pitkin, Van Sicklen, Livonia), a dashboard searchlight sweeping the pavement for evidence, illuminating a piece of ground: concrete, cobblestone, glassy puddles. After a killing, the gangsters would often leave their weapons at the scene. The guns they used were wiped clean of serial numbers and fingerprints. The only way a weapon would ever be tied to the criminal was if it was found on him. So the best way to dispose of a gun was to leave it at the scene. This was also a way to tell the cops to give it up, that they were dealing with professionals.

Sol Bernstein worked for the Shapiros. Against him there were no grudges. No one wanted him dead. He was just an order taker, a piece that could fit into any machine. But really, it was up to Bernstein. Could he accept the death of his boss? Would he seek revenge? About a week after Meyer was killed, Bernstein came to the corner by the candy store, asking after his boss. “You mean Meyer Shapiro?” said Pep, scratching his head. Pep had one of those faces you see all the time on the subway. A city face—sly, concealing, waiting for something even he knows will never come. “I don’t know what happened to Meyer,” he said. “Come to think of it, I haven’t seen him around.”

Bernstein then went to a bar at 161 Rockaway Avenue where the Shapiros hung out. Meyer wasn’t there, either. As he walked out, Bernstein was surrounded by maybe fifteen men. Happy and Dasher were in the crowd. “What do you want?” asked Bernstein.

“We want you to drink,” someone said.

They stayed at the bar through the afternoon and into the night, making Bernstein drink whiskey until he could barely stand. The Dasher then led Bernstein to the candy store, where he was seated at a table with Reles, Goldstein, and Pittsburgh Phil. As neighborhood kids milled around up front, Reles spoke softly in back, telling Bernstein, detail by detail, how he killed Irving, Meyer, and Joey Silver, how he would kill still more.

Telling the story this way—when Bernstein was drunk enough to spin the walls—Reles was making sure Bernstein’s guard was down, that his feelings could not be easily hidden. Alcohol as truth serum, something that brings out honest emotions. Telling Bernstein this way might also soften the blow, making it all blurry and unreal—as if the Kid had entered Bernstein’s dream and were telling him there. The faces at the table turned to Bernstein, seeing how he would take the news. “Listen,” said Pep. “We know you, and we just took care of your friend. Go home and don’t worry about nothing.”

The Dasher followed Bernstein home.

The next day a kid came up to Bernstein on the street. “Pep wants to see you,” he said.

“Who is Pep?” asked Bernstein.

“Harry Strauss.”

Bernstein went to the candy store, where Pep was waiting. “What is going on?” said Pep. “Anything important happen lately?”

“Nothing,” said Bernstein. “Nothing at all.”

And that was it. Bernstein was a civilian.

Willie Shapiro wore silk gloves and cashmere scarves. When his brothers died, he must have felt alone. Probably he never felt so alone in his life. The fight in him, whatever it was that made him a threat to the Kid, was gone—a light that went out with the bulb Reles unscrewed before killing Irving. And though there was no rush to kill Willie, it had to be done. A sentence passed must be carried out.

Willie was killed a few years later in a bar in East New York. Reles killed him with a garrote, strangling Willie until his time ran out on the floor. Then, just in case some part of Willie was still alive, Pep tied him up, put him in a laundry bag, dumped him in a car, and buried him inCanarsie. A few years later, when he was dug up and autopsied, a coroner found dirt where Willie’s lungs had been. He had been buried alive.

Something about Reles’s nature is mysterious; it runs away from me like mercury. The reason is, until he fought the Shapiros, he gave no indication of just how deep within him the violence ran. Before he got mixed up with Meyer, I don’t even think he was that violent. He probably could have gone on and lived a life like other people—got a job, raised a family, not killed handfuls of men. But the way he was treated by the Shapiros—abused, humiliated, threatened, shot, girlfriend raped—turned him into a killer. I’m not saying he was just like everyone else. He surely had a tendency to violence. Something in his makeup or upbringing made killing something he could deal with, a direction in which he could go. But the Shapiros, together with his neighborhood and the nature of his times—the twenties, the Depression—revealed in Reles what might otherwise have remained hidden.

In the course of the war, Reles and Harry Strauss emerged as partners. Their personalities, taken together, were bittersweet and could at once repel and attract. While Reles moved on impulse, Strauss lived in a deeply moral world. His views—on punishment, responsibility, covenant—were, in many ways, Jewish views. For Strauss, God was present in every move, gesture, act. If you were associated with him, you would, sooner or later, cross a line, defy his code. And when you did, he was there, beyond hearing but within view. He sometimes couldn’t tell where his authority ended and that of the world began. He was like the God of the Old Testament, seeing, judging, punishing. Punishing was more fun than forgiving. Forgiving meant a sit-down, coffee, a handshake. Punishing meant a rope, an ice pick, a fire. His world was like one of those early Puritan communities where suspicion is guilt, where being seen coming from the wrong building—the Shapiros’ clubhouse, say—is enough to be declared a witch, hunted, hounded, burned. It was a world where, though killing might not be a sin, talking behind the back of a friend usually is; where murder is better than cowardice; where the rules of loyalty are fluid and complicated; where the word “rat” is as indelible and damning as a concentration camp tattoo. You never knew just how things would look through his eyes and what he would declare a sin.

The war had also remade the other members of the troop—from mercenaries to nationalists. The gang members were now less in it for themselves than for honor, fame, each other. You can see it in pictures taken at the time. In mug shots the gangsters look as different from each other as you would expect men with different parents to look. They are tall or short, fat or thin, dark or fair, with sharp or wide noses, blond or brown or black or red hair, curly or straight, or else no hair at all. What they have in common is in their eyes. Not the color of their eyes, which are brown or black or gray or green or blue, but something beneath the color, a kind of icy calm, like something seen at the bottom of a river. After my grandmother met Strauss in her family’s diner, what she talked about were his eyes, which she said were disturbing and beautiful. On their own, these men were dangerous. Together they were something new in Brownsville—a crew of killers at once predictable and mysterious: You will die, but where? When?

And slowly, word of the gang—their success, how they handled the Shapiros—made it back to Manhattan, to ballrooms and suites where Charlie Luciano and Meyer Lansky were planning the future of crime. The Brownsville gang passed the test! It would be hard to find a more effective, artistic, single-minded band of killers anywhere in the underworld. “We were good before all this happened,” Reles later said. “But when we added Pep, it was like putting on a whole new troop.”

The winter and spring slipped by in a haze, a blur of late nights in tumbledown local bars or seedy nightclubs and dance halls or else the smoky back room of the candy store, playing cards, making plans, wondering who will next come through the door. When Meyer Shapiro was killed, the candy store became a capital of crime. Like London after the Spanish Armada was sunk, it was a new seat of power, where dreamy locals went with their best ideas. Sometimes, if a gangster wanted to leave a gun or bullets or an ice pick or rope for another gangster, he would stash it under the toilet in the back of the store. A few hours later the other killer would say, “Jeez, I gotta take a leak,” go back, and retrieve the package. Young toughs stood on the corner in front of the store all day, the way longshoremen stand on docks, hoping someone will call them to work.

The store was run by Rose Gold, a cantankerous, tough-talking sixty-something immigrant who could neither read nor write English. To gang members she was Midnight Rose, partly because her store stayed open all night, partly because she reached her true magnificence only in the small hours, when her light was the only thing going in Brownsville. Over time, Rose became godmother of the troop. When one of the boys was arrested, she bailed him out. In the late thirties hundreds of thousands of dollars went from her account to the state and back again. Later, when she was arrested, she chose jail over telling on her boys. When at last she came to trial and a lawyer asked, “Why do you let so many criminals frequent your store?” she said, “Why don’t the police keep them out?”

The store was on Saratoga Avenue directly under the elevated tracks of the number two train. On summer afternoons the sun came through the rails, leaving shadows on the brick facade. On winter evenings the store’s yellow light could be seen for blocks. It sometimes seemed the whole neighborhood was in there, the slosh of galoshes across warped wood floors: old men in shirtsleeves with cigars and stories; young machinists and dockworkers getting a free read of the World Telegram or the Brooklyn Eagle or the Forward; long-skirted lady garment workers stopping in for a soda or a date; kids wide-eyed before cases gleaming with licorice, ring-dings, sourballs, lemon drops. A few times each hour, when the pay phone rang, Rose sent one of these kids out to find the man or woman being called. Few people could afford a phone in those days, so they took calls at the local candy store. After completing the call, this man or woman would give Rose some money—a nickel, usually—that the kid could redeem in candy. A nickel could buy a lot of ring-dings. And always, from the back room, the low, mysterious murmur of gangsters being gangsters. For many kids, the first image of adulthood—other than their parents, who never count much anyway—was that secret laughter in back of the candy store.

As summer approached, Reles and the boys must have heard the distant rumblings of armies over larger landscapes, as Lansky and Luciano remade the underworld. Maybe they could even hear the echo of other wars in other cities—Detroit, where the Purple Mob was fighting the Little Jewish Navy; Cleveland, where Moe Dalitz and the Cleveland Four were cementing control; Chicago, where Al Capone was fighting the remnants of the Bugs Moran gang. But mostly the Reles troop was too busy being bosses of Brownsville to worry about much else. Like politics, all crime is local. The troop hosted crap games, loaned slot machines, muscled merchants, hounded rivals, shylocked.

Why live this way? Well, as far as Reles was concerned, it was the only way to live. It was the other guys—who went to work, came home, went to work, came home, went to work—who were hard to figure. The nine-to-fivers were fools. The men in back of the candy store were wiseguys. Wiseguy, a term that appeared around this time, refers to any crook hooked up with the rackets. By nature a wiseguy should be realistic, worldly, not a kvetcher, not sentimental about women, family, or cars, not eager, naive, or romantic. “There was nothing special about what we did,” Reles said later. “We just did what we could to turn a dollar.”

Late that year, when the snow covered Brownsville in drifts, things began to change. The first call probably came to the candy store, where Rose would have sent a boy to the back room. “Mr. Reles,” the boy would say, “there’s a man for you on the phone.”

“Uh-huh,” Reles would say, setting down his cards.

It was Louis Capone. He had a piece of work for the boys. A few weeks later there was another call, another piece of work. Then another. After each killing, Capone got word back to the boys: You boys done a real good job. Real good! Maybe he even let slip a few names: Luciano, Lansky, Lepke. Reles would have known how important these names were. He was not a dumb man. At this time, though, similar pieces of work were being farmed out to other wiseguys in other neighborhoods. It was like an open call—the Syndicate casting heavies. And it was not until a few years later, when the Brownsville troop had clearly emerged as the best killers, that Reles went to Manhattan to meet Louis Lepke.

Louis Buchalter was born in Williamsburg, Brooklyn, in 1897. He was one of fourteen children. His parents were Russian-born Jews. His mother called him Lepkeleh, a Yiddish way of saying Little Louis, which friends shortened to Lepke. His father, Burton, owned a hardware store on the Lower East Side, one of those dreary little shops with a bell above the door. Burton sometimes took his son to work. They would walk across the Williamsburg Bridge, over the East River and the rooftops of Chinatown. Whenever he had the chance, Louis would slip from his father’s sight into the narrow immigrant streets.

Louis was one of those reckless kids who spring from large middle-class families, the youngest brother, out of reach, who for parents come as a last piece of busywork at the end of a long semester; a wild kid who everyone says can go either good or bad, but almost always goes bad; a kid on Ritalin; a kid you either want to like but don’t, or want to hate but can’t; a kid who makes some teachers believe in God: If something is this bad, there must be something somewhere just as good.

Lepke was abandoned when he was thirteen: first by his father, who died of a heart attack; then by his mother, who, after the death of her husband, moved to Colorado, leaving her son in the charge of an older sister. Father dead, mother gone—the law had run out of his life in an instant. And he must have been angry: at his sister, who thought she was his mother; at his mother, who was off with the Buttes and Indians while he was left to find his way here. Skipping school, he would cross the bridge, losing himself in the streets. Walking from the Bowery to the mansions along Fifth Avenue, taking it all in, a thoughtful, narrow-shouldered adolescent. He had a dimple, which did not make him cute; it just highlighted his toughness, like a blue sky above a graffiti-covered wall.

He fell in with a group of older men—gangsters who had worked for Big Jack Zelig and Dopey Benny Fein—who taught him the old tricks: how to pick a pocket, roll a drunk, wield a slungshot, spot a nose (a spy working for the cops). This was a primitive society of deals in dark cellars, a world far removed from the one being staked out by Arnold Rothstein. And though Lepke would grow into the epitome of the modern gangster, he would always carry this world with him. Whenever he was in a jam, instinct would tell him to revert, to take care of it the old way, as his first heroes would, with a gun and a shovel.

On those streets, Lepke met other young Jews—Lansky and Siegel, but also Joseph “Doc” Stacher, who smoked huge cigars behind which his face was a planet in eclipse; Louis “Shadows” Kravits; Hyman “Curly” Holtz; Phil “Little Farvel” Kovolick. These young men made up an elite youth group: Jews not afraid of parents or cops, who would keep on until they were knocked down. For such kids, life would unfold as an unending effort to get up more times than they were knocked down.

Lepke was first knocked down in the winter of 1915. Caught robbing a store, he was sent to live with an uncle in Bridgeport, Connecticut, where he was knocked down again, this time for stealing a salesman’s sample case. Sent to a reformatory in Cheshire, he must have again felt abandoned, lost to a world that had pushed him to the margins. He was not yet sixteen. In future years, as childhood trauma hardened to middle-age neuroses, Lepke’s fear of abandonment would prove deadly to those he was convinced would betray him. But that was much later, when all that remained of the kid in the reformatory was the dimple and the fear.

When he got back to the Lower East Side, Lepke made his way stealing from pushcarts. One day he robbed a pushcart that was just then being robbed by someone else. When the thieves ran off in the same direction, they began talking and Lepke soon realized who this other thug was: Jacob Shapiro, already a notorious downtown figure.

Shapiro was known to most people as Gurrah. He was always walking around with hunched shoulders, telling people, “Get outta here!” And somehow, when he said it, because of his gruff voice and thick accent, it came out as one word—Gurrah. “Hey, what are you doing here? I thought I told you to beat it! For the last time, Gurrah!” I have tried to say “Get outta here” again and again, with all kinds of fake accents, yet it never sounds anything like “Gurrah.” I guess that’s just another thing lost in the translation of the years, the way, no matter how hard I try, I cannot make Yiddish words sound as sensible or elegant as my grandmother can.

Shapiro and Lepke formed a great partnership. Where Lepke was reserved, Shapiro was out front, every emotion crossing his face like a weather system. Two years older than Lepke, Shapiro had a sidewise way of talking that made people think, Gangster! On the street he could be seen coming from a long way off, tacking toward you, like a yacht. With thick, gangly arms and a powerful circus strongman torso, he was the exclamation point at the end of Lepke’s every sentence. He had come to New York as a boy from Odessa, Russia, home of the brutal, farcical Jewish gangsters immortalized in Odessa Stories by Isaac Babel, whose descriptions could apply as well to the Jewish hoods of New York as to those of Russia. “Tartakovsky has the soul of a murderer, but he is one of us,” Babel wrote in “How It Was Done in Odessa.” “He has come from us. He is our blood. He is our flesh, as though born of the same mother. Half Odessa works in his shops.”

Lepke and Gurrah were soon accepting tributes from vendors all over the East Side. But they were really still small-timers, running big risks for nothing prizes. In 1918 Louis was caught robbing a loft downtown. He was sent first to the Tombs, a jail his old gangster friends called City College. He was then sent for postgraduate study to the state university at Sing Sing.

On the road between the East Side and Sing Sing he left behind the person he had once been, the reckless energy, the small-time glee that drove his first felonies. When he got back to the city in 1923, he already had the face he would carry with him to the death house: spaniel eyes, sad mouth. He was famous for his reserve, a man who never lost his temper. Yet his exterior hinted at some desperation within; his eyes could cloud over in an instant. And all around him, like an overcast sky, hung a threat of violence. He was twenty-five years old.

Soon after prison, when he got some money, he took himself for clothes, changing his outside to reflect the changes within. He now wore dark suits, conservative ties, loafers, cuff links, wing-tips, fedoras. He tried to dress like a businessman, just another trader on his way home from work, but never got it quite right. If he was standing in a crowd of white-collar boys, something in him, some pride or defiance, would jump out at you.

Lepke and Gurrah, back together, climbed from pushcart vendors to merchants, theft to extortion. People called them the Gorilla Boys. They told strangers they were in the bakery business. While others supplied flour, pots, pans, they supplied protection. “Please get your boss,” Lepke might say, showing up at some bakery. “Please tell him Mr. Buchalter and Mr. Shapiro are here on business.”

As Shapiro walked the kitchen, smelling this, touching that, Lepke wound through a speech, a lecture on the city, the sorry state of things, immigrants and how they had brought along bad habits, a lack of respect, a disregard for property; he would talk about business and how, no matter how meticulously you build, someone always comes along to destroy; about man, how he is driven by dark forces, vanity, greed, ambition, and how these flaws lead him to do wildly brutal things. Maybe he would let his eyes move around the room, then say, “Why this should be, who knows?”

If a baker asked if there was a point to all this, Lepke might shake his head and say something like “No, not really. Most of the important things in life, they have no point. They’re just like a crossroads, and you go one way or the other. I’m here to protect you from going the wrong way, which can lead to problems. With my help, that won’t happen. Crazy immigrants won’t come burn your store.”

Such protection went for a monthly rate, a fee Lepke based on the requirements of a particular job. If the head man said yes, he could use such protection, the details were worked out there and then. If the head man said no, then a few days later crazy immigrants really would burn the store.

Though Lepke and Gurrah would go into many fields, travel the country, make millions, bakeries would always hold a special place. Over the years they extorted money from the biggest bakeries in New York: Gottfried’s, Levy’s, Fink’s, California Pies, Rockwell’s, Dugans. By the mid-thirties Lepke and Gurrah were receiving about a million a year in tribute from the industry.

Arnold Rothstein was always on the lookout for smart young Jew boys. And who was smarter, younger, more of a Jew boy, than Louis Lepke? So sometime in the mid-twenties Rothstein gave Lepke the call; getting the call from A.R. was like getting called to the majors. Lepke started riding shotgun on liquor runs; he also did odd jobs, like baptizing the whiskey—watering it down. Later, when all hell broke loose in the garment industry, Lepke and Gurrah went to work in the labor wars.

Jewish gangsters first went into the garment industry for the same reason wealthy Jews later went to Miami Beach—because that’s where the other Jews were. The men who owned clothing factories and sweatshops were mostly uptown German Jews; their employees were mostly downtown Jews from Eastern Europe. Among these men were the future leaders of the American labor movement, ideologues every bit as tough as the thugs leading gangs on the Bowery. One of the first unions in New York was the United Hebrew Trade Union.

In 1897, when garment workers first went on strike, the bosses took their problems to the Jewish gang leaders. Jews seeking help from Jews. One employer hired Monk Eastman to drive the strikers back to work. Monk and his boys attacked the strike leaders on Allen Street. While breaking strikes, gangsters often beat workers with a length of metal pipe wrapped in newspaper. They called this schlamming. In the coming years, as the nation was rocked by strikes, even the most down-on-his-luck hood could get work as a schlammer, the way even a blacklisted actor could later get work at one of the resorts in the Catskills.

Over the years, as factory owners complained about labor, how hoodlums lurked on the edge of every strike, it was good to remember this: It was the bosses who first brought in the gangsters. Union leaders then followed their employers to the clubhouses; how else could they protect themselves? It was Arnold Rothstein who eventually agreed to help the unions, assembling (for a fee) a counterforce, schlammers to schlamm the schlammers. These men were paid $7.50 a day; their leaders were put on the union payroll, at about fifty bucks a week. One of these leaders was Little Augie Orgen, an experienced gangster who had worked for Dopey Benny Fein, one of the first schlammers.

The thugs went to work for the unions, protecting strikers and also taking it to the bosses: setting fires, lobbing rocks, throwing bombs. Gangsters had learned lessons labor leaders were just beginning to grasp: that a bad deed unpunished is another way of asking for it; that noble sentiments, without muscle, are about as useful as get-well cards; that an enemy will make peace only when he has felt the sting of battle.

It was only natural that some gangsters identified with the workers—they came from the same streets as the workers, the same neighborhoods. They too descended from the Jews of Eastern Europe; they too resented the bosses, German Jews who looked down on Eastern Europeans, acting as if they were members of an inferior race, as if this were something more than a dice game, what happens when a distant ancestor, on the long road from Zion, takes a right instead of a left. Now, because they had been in America longer, because they had more money, were better educated and more assimilated, the Germans had lost the very otherness that makes a Jew a Jew. As bad as the gangsters were, as far outside the law as they lived, they thought they were, in some way, more in touch with Jewish experience than uptown Jews like the Schiffs. The gangsters were out where the Jews had always been, living by their wits, where the difference between living and dying is a single bad decision. The gangsters only wondered why the workers weren’t more like them. Why did they suffer? Why did they take it?

“You say labor unions hire dynamiters and sluggers,” a racketeer told a reporter. “Well, I may be a low-down criminal pervert, but I don’t think there’s anything the matter with that. How do the capitalists treat labor? Is it worse to dynamite a building than to turn out of work, in the middle of the winter, thousands of men whose families live hand to mouth? Why isn’t there more dynamiting? If there were, I’d get a little more respect for the working class. Now, to hell with them. These goddamn stiffs, with their docile suffering, make me sick.”

The real problems began when the strikes ended, when the union leaders came to the gangsters and said, “Thank you very much. Your services are no longer needed.” The gangsters didn’t want the war to be over. Yes, they liked the steady paycheck, but it was more than that. Working in the labor movement gave the thugs a cause. It also gave them something to tell people at parties. “Me? I work in garments. I’m a furrier!” And at some point, as Little Augie was figuring what to do next, the question fell on him like a light: Why not run the union? Collect the dues? Call the strikes? Be the boss?

This question came to Augie in that moment where all corrupt generals realize that they don’t have to take orders, that they can head the parades, declare the wars, be the president. When Augie went with this alternative to the union leaders, there was not much they could do. Behind the leaders stood experience, philosophy, dreams. Behind Augie stood a few hundred armed thugs. Over the years, the few labor leaders who did resist racketeers turned up dead in lots or were buried beneath grain elevators or crushed in freak accidents on the docks or else disappeared only to wash up weeks later on some weedy Staten Island beach.

For some gangsters, labor racketeering offered one way out of the twenties, out of the speakeasies and into the factories. A steady income, a title, an office. With labor racketeering began the long run of euphemistic job titles, wiseguys describing themselves as organizers, overseers, fixers. As the power behind a union, a gangster would not only have access to dues—that went without saying. He could also take kickbacks from workers—cash in exchange for jobs or promotions. But the real money would come from the factory owners. Just like a holdup: Give us what we want or your employees walk. And it was good work, like a real job, with an office and a secretary. All they needed was a telephone and the threat of violence, which danced between their words, as abstract and real as sunlight on water.

A few years later, when federal officers tapped phones in a racketeer’s office, they captured how this part of the job was done:

(Phone rings.)

Moe: Hello. Moe speaking.

Racketeer: I have something to tell you. You won’t like to hear it. I am sending you an extra man.

Moe: No good. I have enough men now. I know Sam is the best man in the flour business, but I can’t use him.

Racketeer: Listen, Moe. Don’t be tough over the phone, then come down here and you’re like a kitten. Talk to your delegate. Listen to reason.

Moe: Listen. I am going to run my own business.

Racketeer: No, Moe. I’ll run your business for you. If that man don’t go to work, somebody will suffer.

The bosses and union leaders had invited in the gangsters, and now they couldn’t get rid of them. It would take the federal government years to do that. Meanwhile the factory owners passed their additional costs on to consumers. During the Depression, for every two hundred dollars spent in New York, an additional twenty-three went to mobsters; it was a gangster tax.

Within a few years, battles between labor and management no longer mattered much. In many cases the boundaries of those relationships had been drawn. What mattered now were struggles within the unions, as racketeers fought for control with honest labor leaders or else with other racketeers. Soon after they joined the struggle, Lepke and Gurrah were called in by their new boss. Little Augie, who was about ten years older than Lepke, had big doe eyes and a soft mouth.

Augie wanted the Gorilla Boys to take care of Dopey Benny Fein, who was clawing his way back into the union game. Lepke and Gurrah cornered Dopey Benny in a bar on the Bowery. The old gangster got off several rounds before slipping into the night. Looking around, Lepke saw Gurrah was down, blood spreading beneath him. Shapiro had been shot in the back and spent several weeks in the hospital. A few months later, the bullets Lepke had fired that night finally found Dopey Benny. He was killed in front of the Essex Street courthouse by Louis Cohen, a mysterious figure who slipped out of a crowd and shot the gangster where he sat, in the back of a squad car between two cops.

The underworld has no peaceful way of bringing the next generation to power, no way, other than killing, to ring in the future. So, in 1927, when Lepke and Gurrah seized on some petty issue to split with their boss, everyone knew it was really about succession. Who could know this better than Little Augie himself, who for so long had been the next generation, the kid feared by old-timers? It was only a year before that he had tried to have Dopey Benny killed. Now he was the old man. (Things happen so fast in the underworld, time there should be gauged in dog years.) And even if Augie wanted to step down, even if he said, “Fuck it; I retire,” Lepke wouldn’t let him. Lepke had to kill Augie for the same reason Lenin had to kill all the Romanovs: because even a retired Augie was a challenge. Besides, killing Augie was the only sure way Lepke could secure power. Power flows from a dead gangster to his killer as through an IV. The only thing Augie could do was play the part of the incumbent: wait and see where the attack will come.

He hired himself a new bodyguard: Jack “Legs” Diamond, a freewheeling gunman who scared even the scariest men in town. Legs once guarded Arnold Rothstein. Though still in his early twenties, Legs was already a glamorous nighttime figure whose very name conjured images of hotel rooms with ice buckets and champagne, limousines, starlets, showgirls, all-night cabarets where the singer is interrupted by gunfire and shattering glass, or a small hotel upstate, his wife in one room, his mistress in another down the hall. Legs was a great dancer. He had slender shoulders and a thin, tapered bullfighter’s waist. He was handsome, but his head was weirdly small, with sunken, emaciated cheeks, like something you imagine at the end of a cannibal’s stick. Having Legs Diamond on his side must have made Augie feel better, but it was a desperate act, like piling sandbags before a flood; a defensive, already defeated maneuver that any dedicated foe would easily find a way around.

On October 15, 1927, Little Augie was standing in front of his clubhouse on the corner of Norfolk Street near Delancey—a narrow street running between wooden facades, doorways along the street low and uneven, something built for a smaller race of men. From above, the neighborhood was just roofs and chimneys. Augie was talking to Legs on the sidewalk. Everyone on the street (men working, kids playing) must have been aware of the gangsters (where they stood, how they held themselves), so they probably saw what happened next.

A sedan came very fast around the corner. Before it stopped, two men jumped out: Lepke and Gurrah. “Get back,” Gurrah yelled at Legs. He yelled the way parents yell at kids standing too close to the train tracks. Lepke then walked up to his old boss, close enough to read the time off his watch, shot him four times, got back in the car with Gurrah, sped off. Legs fired at the car, probably for appearance’ sake. Gurrah returned fire, grazing Legs. In the future, when people talked about the legend of Legs Diamond, his amazing power of survival, they usually cited his escape from harm on Norfolk Street.

The next morning, Lepke and Gurrah went to the police station and surrendered. They knew the cops were looking for them. They also knew the cops would have no reason to keep them. Suspicions, yes. Evidence, no. They presented themselves like a pair of overdue books: Buchalter and Shapiro for questioning. A few hours later, when the police were through interrogating the suspects, they hesitated. They didn’t want to just let these men go. As soon as Lepke and Gurrah walked out the door, they figured some trigger-happy Little Augie loyalist would shoot them dead. The last thing the police wanted was a repeat of the Dopey Benny thing—a killer killed leaving the police station.

The police decided to make sure Lepke and Gurrah stayed safe, seeing them home under guard. The Gorilla Boys came out of the station behind an army of cops. They walked through the streets. It was like a parade. Two East Side Jews behind a blue wall of Irish cops. Merchants watched from doorways, kids from stoops. A man, darting between parked cars, snapped a picture. The next day, when the photo appeared in the newspaper, it looked as though the cops worked for Lepke and Gurrah. The police, without realizing it, had crowned the Gorilla Boys. They killed Augie and got a police escort home. Besides, no one wanted to avenge Augie anyway. Gangsters are realists. Augie was dead. No use feeling bad about it. It was part of history. The thing now was to figure out who the next power would be, and the picture in the paper answered that. Lepke was the new king of the labor rackets—Gurrah his lieutenant.

What Augie built, that was just a starting point for Louis. He raised an army: 250 men. He was soon moving factory to factory, picking up unions like properties on a Monopoly board. He went after entire industries. In each field he targeted the key union, the piece on which all else hung. In the garment industry, for example, he went after the cutters, a small, easily controlled union. The cutters cut the fabric that made every garment in New York. If the cutters went on strike, the entire garment industry would be crippled. Following the old formula, Lepke presented himself to the union as a savior, someone with the muscle to take on the bosses. To arenas of cutthroat competition and undependable paychecks, he quickly brought a prized stability. You were paid on time; you were promoted as promised; if injured, you were compensated; scabs did not cross your picket lines; the boss kept his promises because now the boss had something to fear. Even enemies said Lepke succeeded where government regulators had failed.

And all the while, as he was raising salaries and securing benefits, he was taking over. Though he never made himself president of a union—he was, after all, a notorious criminal—he put people loyal to him in power. When he took control of the cutters, for example, he put Philip Orlofsky in charge. It was Orlofsky who later fought for union control with Sidney Hillman, the fight that led to a shooting war with Salvatore Maranzano, then to Maranzano’s death.

Lepke and Gurrah had joined Little Augie in the winter of 1925. In those first years they were small-time hoods, out there with the workingman, on picket lines in nights so cold they must have cracked apart in their fingers. By the early thirties, when Lepke asked Abe Reles to his office, he controlled thousands of workers through unions of truckers, motion picture operators, and painters. He and Gurrah were adding about $1.5 million of yearly costs to the flour end of the trucking business. They also acquired interests in legitimate businesses: Raleigh Manufacturing, the Pioneer Coat Factory, Greenberg & Shapiro. Each took home about a million dollars a year. No one called them the Gorilla Boys anymore; they were now the Gold Dust Twins. In 1933 the U.S. Subcommittee on Racketeering suggested officials fighting racketeers consider “martial law or renewal of the public whipping post.”

Different gangsters bought different things with their money. Some bought apartments or cars or girls. Many bought their way out of the old neighborhoods, into the best rooms of the best hotels. In the twenties Lucky Luciano lived in the Waldorf-Astoria, and so did Ben Siegel and Frank Costello. It was a kind of gangster dorm, a stop on the way from the East Side to Vegas or Cuba or the suburbs. While Gurrah stayed in Brooklyn, moving to Flatbush, Lepke bought a place on the Upper West Side: lobby, doorman, park view. He lived with his new wife, Betty Wasserman, the daughter of a London barber. Lepke was not one of the glamorous gangsters. He did not go to bars or date showgirls. He did not dance in clubs. He was in it not for the girls, but for the money, the power. He was also in it for the long haul and knew publicity, especially good publicity, is just the worst thing for a gangster. A gangster’s name in the paper is an advertisement telling cops and DAs: “Make your name here!”

To people in his building, Lepke was just another businessman. I see him riding the elevator up to his apartment, nodding to other riders, cringing at the sight of his name in a stranger’s Herald-Tribune. When his home phone rang, he would answer only to the name Murphy. Code. A way of avoiding enemies. And the phone rang all the time. Lepke was now sought after in the underworld, his advice prized. To fellow gangsters he was Judge Louis. When people talked about back-room deals, about men powerful men fear, they were talking about Lepke. J. Edgar Hoover said he was “the most dangerous criminal in America.”

By the early thirties Lepke was actually living the life of a businessman. Each morning, after breakfast and a nod to the doorman, a private car took him to his Fifth Avenue office. There were phone calls, accountants, negotiations. There were several meetings before lunch and several more after. So the meeting he had one morning in 1933 probably just seemed like something on a schedule. How could Lepke know it would turn out to be one of the most important of his career, that it would bring someone new into his life, someone who would help him realize his worst fears.