The Heroic Gangster_The Story of Monk Eastman, From the Streets of New York to the Battlefields of Europe and Back

by Neil Hanson

  Periodic economic crashes increased the sum of human misery. In the year after Monk returned from Brooklyn to the streets of Manhattan came the Great Crash of 1893—the worst economic crisis in the history of the United States, heralding a depression that lasted four years. Within twelve months two and a half million men were out of work; when an army of the unemployed marched on Washington in protest, they were arrested for walking on the grass of the Capitol lawn.

  There were soup kitchens on the streets and make-work schemes mending roads or working in parks, but many people simply starved. Joseph Pulitzer’s World newspaper set up a “Free Bread” fund, leading its rivals, the Herald and the Tribune, to establish “Free Clothing” and “Coal and Food” funds, while Fleischmann’s bakery, next to Grace Church on Broadway, began distributing a third of a loaf of bread to all comers at midnight every night, inadvertently spawning the term breadline, but such palliatives were few and far between. As in every crash, thousands of recent immigrants besieged the ports and steamer companies, hoping to return to Europe.

  Those who remained fought for whatever work they could find, but even those in full-time employment struggled to pay their bills and feed their families, with hourly wages often measured in cents. Laws protecting factory workers were weak enough—in a single year, 1904, there were fifty thousand industrial accidents in New York City alone, and twenty-seven thousand workers across the United States lost their lives as a result of their jobs—but work contracted out to tenement sweatshops bypassed even those feeble safeguards.20 The legal maximum working day in factories was ten hours, and no child under the age of fourteen was to be employed. Yet in sweatshops, children as young as four or five worked alongside their fathers, mothers, and siblings, with a working day that started at six in the morning and could continue until midnight. Many toiled for seventy or eighty hours a week, including on Saturdays and Sundays. “A sign would go up on Saturday afternoon: ‘If you don’t come in on Sunday, you need not come in on Monday’… children’s dreams of a day-off shattered. We wept, for after all, we were only children.”

  The already miserable wages could be cut without warning, and many poor families existed on little more than tea and bread, the tea boiled and reboiled to extract the last vestige of strength and flavor from it, the bread usually bought stale for a cent or two. Others bought their food from the pushcart market on Mulberry Street, even though the produce on offer was of the lowest possible quality: stale bread sold by the sackful, “tainted meat, poultry blue with age and skinny beyond belief, vegetables in every stage of wiltedness, fruit half-rotten or moldy, butter so rancid that it poisons the air, eggs broken in transit, sold by the spoonful for omelets, fish that long ago left the water.”21 Even worse were the “fragments of bread and other farinaceous food, decaying potatoes, cabbage, &c, interspersed with lifeless cats, rats and puppies, thus introduced to a post-mortem fellowship,” that ragpickers gleaned from the rubbish and resold to those unscrupulous enough to convert even this foul mixture into sausages or lobscouse. Board of Health officers repeatedly raided the Bend and dumped the contents of the entire market into the river, but by the next day, the market was once more thronged with customers. To the poor and destitute, half-rotten food for a cent or two was better than no food at all.

  For many of the inhabitants of the Lower East Side, the only employment was in ragpicking, begging, theft, or prostitution. Clouds of dust and ash billowing from cellars announced the presence of ragpickers carrying out their dismal trade, hauling in burlap sacks full of garbage and sifting it for items that could be repaired or reconditioned and for the clean paper, rags, bones, cigar stubs, bottles, and metals that, gathered together, could be sold for a few cents to junk dealers. “Paper wasn’t worth much.22 They got only a penny for ten pounds. Rags brought two cents a pound and iron, four.” Their few possessions piled to one side to allow the stinking contents of their sacks to be spread across the floor and sorted, the ragpickers were smothered from head to foot in fine dust, and moved like wraiths among the garbage they were sifting.

  An estimated six thousand beggars and ten times as many homeless men and women spent their nights on the streets of Manhattan alongside the countless thousands of barefoot, dirt-encrusted homeless children, known as “street-arabs,” “street-rats,” or “dock-rats”—the weakest were called “guttersnipes”—who found shelter in boxes or barrels or dark holes under flights of stairs. In bitter weather hundreds huddled on top of the steel gratings, where the heating mains laid throughout Lower Manhattan in 1881 sent gouts of steam billowing upward, fogging in the still, cold air.

  Almost all the newsboys were homeless. Most wore shoes only in winter, and often bought their clothes from ragpickers who had stripped them from the bodies of smallpox or typhus victims, adding yet one more hazard to the newsboys’ perilous lives. Homeless boys also worked as bootblacks or peddlers of matches or “small notions,” or they found work swill-gathering or ragpicking. Many more turned to petty crime—pilfering, theft, pickpocketing, stripping lead from roofs—and aped in their dress and mannerisms the adult gang members they sought to emulate.

  When the social reformer Jacob Riis surveyed 278 juvenile prisoners, none more than thirteen years old, he found burglars as young as four, while the charge sheets for the others included drunkenness, theft, brawling, forgery, highway robbery, arson, and assault.23 Some gambling dens, saloons, and dives catered exclusively to street-rats, selling them “frightful whiskey at three cents a glass and providing small girls for their amusement.”

  In every slum tenement and thieves’ kitchen there were children “wild as hawks and as fierce and untamable,” but there were other, even younger denizens of the streets.24 More than two hundred foundlings and more than a hundred dead infants were found by the police every year, and these were only a few of the actual numbers abandoned by poverty-stricken or unmarried mothers. Babies were often left at night outside well-to-do uptown houses, in the hope that they would be adopted and enjoy a better life than the unfortunate mother who had abandoned them there. Rarely were such hopes justified, for even those found alive had a survival rate of just 20 percent. There was “an odd coincidence” in New York: “year by year, the lives that are begun in the gutter, the little, nameless waifs whom the police pick up and the city adopts as its wards, are balanced by the even more forlorn lives that are ended in the river.25 I do not know how or why it happens, or that it is more than a mere coincidence … But there it is. Year by year, the balance is struck—a few more, a few less—substantially the same when the record is closed.”

  2

  BLACKER THAN A WOLF’S THROAT

  These mean streets of the Lower East Side were a paradise for criminals, and Monk Eastman was soon claiming his share of the spoils. He was a hulking figure, and although only five foot seven inches tall, he still towered above most of his peers—police and prison records show that the average gang member of the era was just five foot three inches tall and weighed only 120 to 135 pounds.

  In the early 1890s, a “City Missionary and Philanthropist” had an encounter on Monroe Street, Monk’s home turf, with an eighteen-year-old thug, “brutal in face and form.”1 The thug was not identified by name, but his age and physical description, and the timing and location, make it very probable that the thug was Monk. Seized by two policemen, both of who bore the look of “having come through a severe conflict,” he kept swearing and throwing punches until he took a few blows from the policemen’s clubs. Their sergeant described him as “the devil himself … Every one on the streets that he bulldozes is afraid to complain of him.”

  By now Monk was already a familiar figure to the police, but his true name and origins remained unknown to them—and to almost everyone else. They believed that he really was William Delaney, the name under which his first arrest was recorded in 1892, the year he returned to the Lower East Side from Brooklyn. “I gave my name Edward Eastman when I was arrested,” Monk later claimed, “and the officer ju
mped up and said, ‘I know him, his name is William Delaney.’2 … I says, ‘Well, if my name is William Delaney, put it down William Delaney.’ ”

  Monk used the same alias in September 1893, when he “handled” one of the professional prizefighters who were breaking state law by taking part in a boxing match at Coney Island.3 Monk’s police file remained in the name of William Delaney throughout his nearly thirty-year criminal career, and that was constantly cited as “Monk Eastman’s real name,” in police briefings and newspaper reports. The name does not appear to have had any special significance for Monk, and may simply have been protective coloration, an Irish-sounding name adopted in his early days of brawling around Cherry Hill, when the street gangs, like the police, were still Irish-dominated and the great Jewish diaspora from Russia and Germany had yet to complete the transformation of the Lower East Side.

  Monk’s first arrest had been for the relatively minor offense of stealing pigeons, and his first brushes with the law resulted in nothing worse than an occasional night in the police cells and a brief appearance before the magistrates.4 But in January 1898 he was caught carrying burglars’ tools; using another alias, William Murray, he appeared in court and was sentenced to three months on the Island. He emerged unscathed and unreformed and at once returned to “The Gap,” an area of Cherry Hill around Hamilton and Market streets, where he was already known as one of a group of particularly ruthless young thugs.

  Monk further honed his pugilistic talents by taking work as a bouncer at the Silver Dollar Saloon, famed throughout the Lower East Side for its floor inlaid with a thousand silver dollars.5 The owner of the saloon, a Jew named Charles Solomon, who operated under the more Anglo-Saxon-sounding soubriquet of Silver Dollar Smith, had close links to Tammany bosses; such political connections were of great value not just to saloon owners but also to aspiring criminals like Monk. Opposite the Essex Market Court, the saloon was the headquarters for a gang of shyster lawyers, bail bondsmen, false witnesses, and corrupt cops, who had made the court a byword for crooked justice, a place where the innocent were often convicted while the guilty walked free, and a key focus of political influence on the Lower East Side. The night court heard three to four hundred cases every night—it was claimed that during one sitting, one hundred cases had been disposed of in one hundred minutes—and it was easy for corrupt junior court officials to mislay or fabricate evidence, or to mislead judges overwhelmed by the sheer volume of court business.6

  Corrupt lawyers—“fixers” and “bellowers,” “the use of the first being silently to pervert the course of justice and of the other to cover this up by bawling a few inches away from a judge’s nose a diatribe concerning the rights of man and the oppression of the poor”—worked with “one chief purpose: the defense of the criminal.”7 They conspired to destroy or manufacture evidence or postpone cases until they could be heard by a corrupt or pliable judge, though interference in the machinery of justice could be even more overt than that. When a notorious hotel at 23 Bowery, the hangout of a band of thieves and prostitutes, was raided and its proprietors put on trial, the judges were constantly summoned from the bench to take telephone calls from Tammany politicians demanding the release of the prisoners.

  After serving his apprenticeship at the Silver Dollar Saloon, Monk graduated to the post of “sheriff”—bouncer—of a far larger and grander establishment: the New Irving Dance Hall at 214 Broome Street, “a dive notorious for its rapes and robberies.”8 It was said that when Monk walked in and asked for the job, the owner tried to turn him away, gesturing to the two massive figures he already employed. Monk then set upon the pair of them and, single-handed, left them in a bloodied heap on the floor. The owner was convinced: the two battered thugs were fired and Monk hired in their place.

  Young working-class women, immigrants or the daughters of immigrants, were the dance halls’ best customers. They ranged in age from fourteen to twenty-five, with the majority under twenty. The men were generally older. There were some genuine “dancing academies, beckoning and calling to tired and lonesome souls sweating their flower and youth away to the time of spindles and belts and foot-powered machines,” but the majority of Lower East Side dance halls were thinly disguised brothels.9 Women were usually admitted free and men either paid to dance or paid for drinks for themselves and their women companions, who were provided by the management for men who came alone. Those who failed to buy drinks often enough were thrown into the street by fearsome bouncers like Monk.

  At the larger dances, attended by as many as seven or eight hundred people, there were always men who became “boisterously drunk after midnight, and enough of the rougher class of girls to assist the men in fixing a certain obviously immoral character upon the assemblage.”10 Erotic “circuses” were often staged, with curtained back rooms or alcoves available for private shows and assignations. Dance halls where girls danced naked and took part in simulated or genuine sex acts with naked men were so common that in the late 1880s the price of admission to such performances dropped from five dollars to fifty cents. In the lowest places, like the Cremorne, “it was not unusual to see a drunk stretched unconscious on the floor while half a dozen women fought for the right to pick his pockets. A bouncer always stood patiently by, waiting for the ladies to conclude their explorations, after which the victim was dragged into the street.”

  The dances held at the New Irving were often what were known in thieves’ argot—“the foulest of all human lingoes, that dialect of sin and death, known as the Cant language, or the Flash”—as “ballum-rancums”: balls at which all the customers were criminals or prostitutes.11 The dance halls also regularly featured balls known as “tough rackets.” Ostensibly sporting, cultural, or benevolent organizations, their members, known as “hard guys,” were in fact invariably dubious characters: thugs, pickpockets, thieves, and pimps.

  Tickets to such rackets were sold to individuals and businesses on terms that often amounted to blackmail—those who declined to buy sufficient tickets would find their windows smashed or their business stock destroyed. Rackets were often used as fund-raisers by Tammany politicians and by aspiring gang leaders like Monk, particularly if a court case was looming and cash was needed for lawyers. It was easy money. “He bulldozes the merchants in the neighborhood to advertise in his ball journal.12 He disposes of his tickets in the very same way. Those who do not take tickets walk up to the box office on the night of the ball and bring with them their ‘slap down,’ which means two, three, five, ten, or sometimes twenty or twenty-five dollars.”

  Monk and his assistants, armed with clubs, presided over these gatherings and “were in the habit of quelling any disturbances … and sometimes started the trouble themselves just to demonstrate how expert they were in quieting it.”13 Monk kept order with the huge bludgeon he carried, the blackjack in his pocket, and the brass knuckles on both hands. Brass knuckles were formidable weapons; “a blow behind the ear from a strong man’s fist felled the victim like an ox.” Monk also regularly wielded his bludgeon, and every time he used it on a recalcitrant customer, he cut another notch in it. One evening he walked up to an inoffensive man drinking beer at the bar and laid him out with a blow to the head. When asked why, he pointed to his bludgeon. “Well, I had forty-nine nicks in me stick, an’ I wanted to make it an even fifty.”

  Monk was skilled with a revolver, and he wielded a beer bottle or a lead pipe “with an aptitude that was little short of genius,” but he maintained certain moral standards.14 It was his proud boast that he always removed his brass knuckles before hitting obstreperous women at the dance hall, and he never used his club on them. “I only give her a little poke, just enough to put a shanty on her glimmer [black her eye], but I always takes off me knucks first.”

  The role of dance-hall sheriff was no more than a stepping-stone for Monk. He used it to establish his reputation as the toughest of the Lower East Side’s hard men and to foster criminal and political connections that would aid his developing career a
s a strong-arm man and gang leader. His assistants from the dance hall became his first gang members. Monk continued to send out decoy pigeons trained to lure the flocks of the East Side to his premises, but he also operated as “a pimp, a thief, and a trainer and manager of young Jewish pickpockets.15 He had a staff of them, whom he sent out over the city to steal,” a task made easier by the new fashion for conspicuous consumption, with gold pocket watches, jeweled tiepins, and rings on prominent display. Each recruit learned how to take watches, extract pins from neckties, and steal pokes and scratches—wallets and rolls of bills—out of a man’s pocket. “He learns how to become a wire, an instrument, digging his hands into the man’s clothes, working as the tool for the mob who stall and jostle for him.”

  The skills of the young boys were such that one old-time pickpocket complained,

  Those little boys on the East Side have got all us old guys beaten by a city block.16 Why, they took my watch and chain the other night like I was a simple gilly from the country, and it cost me $30 to get back my stuff … Formerly when a pickpocket took your watch, he was satisfied to twist it from the ring that attached it to the chain. The East Side boys now take watch, chain, charm and whatever may be attached to the other end of the chain in your opposite waistcoat pocket. They consider the ancient system coarse work.

  As well as participating directly in crime, Monk’s gang members could also make use of his criminal and political contacts to find easy work as lookouts, runners, touts, doormen, and bodyguards at poolrooms, racetracks, saloons, gambling dens, and brothels.

  Monk’s schooling had been on the streets, not in the classroom, but he was far from inarticulate, and his lack of formal education did not mean that he was unintelligent. If his rise was based on his prowess as a street fighter, skilled with his fists and a revolver and not afraid to use either, Monk also brought an unprecedented degree of business efficiency and organization to the traditional gangland rackets. Alongside the Eastman gang’s own burgeoning enterprises, Monk was also soon seeking tribute from every other criminal operating on his turf, and from every legitimate and illegitimate business. His territory eventually extended from the Bowery to the East River, and the teeming tenements were a fecund source of recruits for his ever-growing gang of thugs and criminals.