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

by Neil Hanson

  Some of his former adversaries were co-opted into Monk’s “army,” but he also recruited more and more gang members from among the dirt-poor Jewish immigrants flooding into New York, for whom crime under the protection of a gang was often the only means to put food on the table. Orthodox Jews from Poland and Russia, whose way of life had been virtually unaltered for centuries, watched in helpless horror as their children turned their backs on their beliefs and traditions. Their daughters often became prostitutes, while their sons embraced a life of drinking, gambling, womanizing, and crime. “It was an abyss of many generations; it was between parents out of the Middle Ages … and the children of the streets of New York today.”2 Some Jewish fathers disowned their errant daughters and “formally cast them off as dead; among the very orthodox, there were cases where the family went through the ancient ceremonial for the dead—slashing the lapels of their clothing and sitting out the seven days of mourning in their houses.”

  Yet Monk’s gang also provided what might be described as a public service by protecting the Jewish population of the East Side from the depredations and attacks of Italian and Irish New Yorkers, often operating with the tacit consent, encouragement, and sometimes active participation of New York’s predominantly Irish police. In an area virtually devoid of the rule of law, Monk’s gang offered the possibility of protection, restitution, and retribution to those who felt themselves threatened or wronged, and who had no one else—least of all the police—to whom they could turn. Such aid almost always came at a price, of course, but it was one that many were prepared to pay, and the Eastman gang went out “every afternoon, just like mechanics going to work.”3 In a society where the law “exactly reflected, as a pool reflects the sky, the demands and self-interest of the growing propertied classes,” even some upright citizens regarded gang activities—including theft and murder—as little worse than the wrongs daily inflicted on the poor.

  Monk had married in 1896, at the age of twenty-two. His wife, Margaret, was twenty-one, and had been born in New York, though her parents came to America from Germany. Beyond that, little is known about her. It would be surprising, though, if Monk had not picked her from among the prostitutes whom he both exploited and befriended. Neither of their first two children survived infancy, but two others were born just after the turn of the century. The 1900 U.S. census, the only one in which the adult Monk ever appeared, recorded him as living with Margaret at 101 East First Street and gave his occupation as “Salesman, birds.”4 A year or so earlier he had indeed set up a pet store on Broome Street, though the animal-loving Monk reportedly refused to sell any of the five hundred animals and birds in the shop, and the large profits generated by the business came from activities entirely unconnected with pets.

  Monk’s Broome Street premises were opposite Public School No. 110 at Cannon and Broome streets. It was a tough school, and when a new headmistress, Miss Adeline E. Simpson, took charge, she was inclined to be discouraged by the problems she faced.5 Not the least of those problems was Monk. One day he chose the school windows as “objects for target practice with his revolver. Bullets rained through the schoolrooms, and the children were in panic. Without stopping to think that he might transfer his attentions to me,” Miss Simpson later recalled, “I ran out and remonstrated with him, telling him that his own children were being endangered. He looked at me a moment, pistol in hand, and then said, ‘Yer all right. Yer a good sport f’r not callin’ th’ cops.’ And he did as I asked him.”

  Few other law-abiding citizens would have dared to emulate Miss Simpson’s bravery when facing Monk and his gang of “hard-fisted, tough-faced young bullies.”6 It was an era when gangsters not only were tough, but also were expected to look and act tough. When cartoonists drew caricatures of gangsters with broken noses, cauliflower ears, and caps pulled low over narrowed eyes, they might well have been drawn from living models. Monk was the archetype, and other gangsters strove to imitate his walk, his mannerisms, the slang words, and his “Toity-toid Street and Toid Avenue” speech. Like virtually all gang members and criminals, Monk was known only by his nickname, making the job of identification and arrest doubly difficult.

  Although one observer attributed Monk’s nickname to his “monkey-like face,” he had acquired it not because of his features or a monastic vow of silence under interrogation by the police, but in tribute to the housebreaking skills he showed in clambering up and down the sides of buildings.7 “Monk” was an abbreviation of “monkey”; despite his bulk, he was a remarkably agile and fearless climber, scaling drainpipes and walls and swinging like an ape through windows and from ledge to ledge of upper stories and lofts to carry out burglaries.

  Even if surprised by the householders, men as skilled in brawling as Monk and his street toughs had little trouble in making their escape. His gang included specialists of every type: hotel thieves, boarding-house thieves, house thieves, and sneak thieves. “Second-story” burglars would go to work when a family was on a lower floor of the house, rifling the bedrooms and then either dropping the loot out the window to accomplices in the street or brazenly descending the stairs and letting themselves out the front door. Sneak thieves pillaged houses by picking the front-door lock and sneaking through the house in rubber-soled or woolen shoes. In other houses, a servant might be bribed to produce a key, or the bolts slid from outside using a loop of wire. There were other, even more specialized thieves, like “Long John” Garvey, whose chosen field was to rob newlyweds of their wedding presents and jewels.8 He studied the wedding announcements in the newspapers, then broke into his victims’ houses while they were away on their honeymoon. Eventually he died on the job after falling through a skylight, trying to burgle a house while drunk.

  Stolen goods were disposed of through a receiver, who rarely paid more than a quarter of the value and ran few risks because he never paid out until the goods had been removed to a place unknown to the thieves. The receiver thereby avoided any risk of being double-crossed and, if the thieves were later arrested, they could not betray him by leading the police to the stolen property. Many receivers doubled as the owners of pawnshops and were often known euphemistically as “my uncle.” The typical pawnshop had a long counter and shelves overflowing with pledged goods: clocks, guns, ornaments, pictures, musical instruments, and the tools of carpenters and mechanics. More valuable and easily portable items like watches, jewelry, and silverware were stored in a vault built entirely of iron, and usually accessible only through the “office”: an iron-barred enclosure where the pawnbroker pronounced valuations and dispensed hard cash. Bulkier items were transferred to storage on an upper or lower floor by means of a chute or dumbwaiter known as “the spout,” from which developed the expression “up the spout,” meaning lost, dead, or useless.

  As Monk’s gang grew in size, wealth, and power, he was able to delegate more and more of his crimes to his lieutenants, though he admitted that he still liked to “beat up a guy once in a while.9 It keeps my hand in.” Other New York gangs hid behind soubriquets—the Five Pointers, the Whyos, the Yakey Yakes, the Gophers—but Monk’s gang members, unafraid to show their allegiance, were universally known as “the Eastmans.” Monk and his henchmen put so many people in the hospital that ambulance drivers started calling the accident ward at Bellevue “The Eastman Pavilion.”10 With its forbidding gray façade on the East River waterfront at Twenty-sixth Street, Bellevue was “the poor man’s hospital” and, along with Gouverneur near Grand Street and East Broadway, served the population of the Lower East Side.

  Monk’s growing gangland reputation—and his increasing notoriety with the police—led him to become ever more wary. He hid his identity and his true address, moving house frequently and operating his gang from a constantly shifting series of saloons and poolrooms, and even a disused graveyard. The Eastmans also hung out in two stores on Rivington Street near the East River, one at Goerck Street and one at Mangin Street.11 Monk’s expanding army of toughs were almost all young Jews from the Lowe
r East Side territories he ruled; few members of the Eastmans or any of the rival gangs were older than twenty-five. Their readiness to use violence and intimidation made Monk a powerful figure in gambling, extortion, and prostitution.

  The protection rackets that Monk set up, initially to extort money from street vendors, were the prototypes for the kinds of extortion and rackets used by later generations of gangsters, like the mafia. The East Side streets were jammed with pushcart peddlers selling the staples of life: food, clothing, crockery, and furniture. An upset cart was a disaster for its owner, and a couple of thugs could do it in seconds, one wrecking the cart while the other held back or beat up the hapless owner. A pushcart vendor had to pay the gangsters twice: first to stop the destruction of his cart and goods, and second to buy protection from the other gangs in the same line of work. Many of the most vicious gang fights grew out of disputes over this trade.

  The profits from this kind of protection racket were not vast—pushcart vendors were not wealthy individuals, and even the most ruthless gangster could not extort money when there was no more to be extorted—but they were easily obtained. Even though protection rackets were soon extended to stores, restaurants, and factories—a failure to pay was met by attacks on employees, the destruction of stock and buildings, and the wrecking of delivery vehicles—one estimate suggested that the New York gangs were exacting no more than $75,000 annually from protection.12 Nonetheless, Monk took the lion’s share of that, and also extorted money from less legitimate trades. He was “a sort of licensed bandit on the East Side,” forcing other thieves, gamblers, and the owners of whorehouses and gambling dens to pay him a share of their profits.13 Protection rackets gave Monk a useful addition to his four main sources of profit: robbery; violence on commission from individuals, organizations, and politicians; gambling; and prostitution. In return Monk could always “be appealed to by the criminal for political influence with the police or courts.”

  The operators of the stuss and crap games scattered throughout the East Side and Mulberry Bend districts also had to pay the Eastmans for protection. Kid Twist, one of Monk’s lieutenants, used to walk into a stuss or crap joint and say, “I want fifty dollars.14 What, you’re not going to cough up? I’ll shoot up your **** place.” When he got his fifty, he would say, “I’ll see you again in about a month.” In time Monk and other gang leaders took over many of the most lucrative games, and a suitable proportion of the take always found its way to Monk’s friends in the police and Tammany Hall.

  Even more than gambling, prostitution was probably the most profitable of all of Monk’s enterprises. At one time “a real gangman” would never have admitted to earning money as a pimp, though none ever hesitated about exacting protection money from brothel owners.15 In Monk’s day that stigma no longer applied; prostitution was just another—very rich—source of income, and all the criminal gangs profited from it. In the 1870s there were more than twenty thousand full-time prostitutes in New York, approximately one to every forty inhabitants, and probably a similar number of part-timers.16 Sex was on sale for as little as fifty cents, a price that remained unaltered for decades, and there were five thousand overt brothels, together with countless others that masqueraded as cider mills, cigar stores, groggeries, dance halls, and concert saloons. There were also thousands of “blind pigs”—illegal dives concealed by innocuous-looking storefronts—and speakeasies.

  The only thing that had changed in the remaining years of the century was that the number of brothels and prostitutes had increased. Brothels ranged all the way from the dismal sailors’ haunts by the East River, where “half-exposed women, often far gone in age, looks and alcoholism, sat on stoops of tenements” and would render almost any service for the price of a drink.17 There were brothels catering to male laborers, where prostitutes serviced prodigious numbers of men at rates from fifty cents to one or two dollars a time. One “Stakhanovite of sex” claimed to have serviced fifty-eight men in three hours.18 Many of the prostitutes were girls aged between ten and fifteen; in New York the age of consent was raised from ten to sixteen in 1889, and to eighteen in 1895, but that was routinely ignored by policemen on the take.

  Some brothels specialized in very young girls, and others catered to those who preferred “unnatural practices.” The prostitutes of “Soubrette Row” offered oral sex, a service few prostitutes would render because of the stigma associated with it at the time; “as a result the other girls will not associate or eat with them.”19 There were small places with one, two, or three women, like the places run by “Jennie the Factory” on Eighteenth Street or “Sadie the Chink” on Twenty-seventh Street, and at the top end of the scale, establishments like the extraordinary “Sister’s Row” in the Tenderloin, run by seven sisters in adjoining brownstone houses, where prices ranged up to a hundred dollars and “on certain days of each month, gentlemen were only admitted if they carried bouquets of flowers and wore evening clothes.” Madame Josephine Woods ran an even more exclusive brothel, where only champagne was served and the sordid topic of money was never mentioned. Her gentlemen received a monthly statement of “professional services” rendered, which they paid by check.

  In less exalted establishments, prostitution was also often a cover for robbery or fraud. Some women worked with “panel-thieves” who, while the prostitute was occupying her customer, would slide open a panel or other concealed opening and rifle the man’s jacket and trousers. In another variant, “the badger game,” the victim would be interrupted in the act by a man posing as the prostitute’s irate husband. After threatening violence and death to the victim, he would then allow himself to be pacified with cash.

  By the turn of the century, Monk’s gang had grown into a twelve-hundred-strong army of thieves, pickpockets, safecrackers, prostitutes, and thugs, ruling over the area between Monroe and Fourteenth streets and from the Bowery to the East River, including “the treasure-laden Red Light district.”20 He set up his headquarters in a dive on Chrystie Street, just off the Bowery, called The Palm. It was just one of many Lower East Side dives with evocative names: others included The Flea Bag; The Bucket of Blood; The Morgue, whose owner’s proud boast was that his liquor was equally efficacious as a drink or an embalming fluid; and McGurk’s Suicide Hall, a place notorious for the number of young women who had thrown themselves from the balconies to their deaths on the dance floor below.

  This was the heyday of the Eastmans, and Monk and his followers wore expensive clothes, drank good liquor, squired the best-looking prostitutes, and had money to burn.21 There were many other gangs, including the Whyos, the Gas House and Cherry Hill gangs, and the “Razor” Riley, “Mike the Bite,” “Kid” Gorman, “Ike” Fadinsky, and “Humpty” Jackson gangs—the latter’s acolytes met in a graveyard between Twelfth and Thirteenth streets—but they seldom went beyond brawling and petty crime. Monk’s rise heralded the emergence of large-scale organized crime, and of federations of criminal gangs uniting to further their interests or defend their territories. He was the bridge between the era when the Irish gangs had been dominant and the emergence of the mafia and organized crime as we know it today.

  Monk’s gang was less a single entity, like one of the old Irish gangs, than a series of separate but interlinked organizations. When necessary, this “Prince of Thugs” could call not only on his own army of men, but also on the allegiance of smaller gangs. These gangs all had their independence, their own territories and sources of revenue, which they policed, but all also paid tribute to the supreme commander, Monk, who along with the right to impose “taxation” also had the right to conscript their men in time of war with other gangs.

  In addition to his pet and bird store, Monk had also set up another “front”: a bicycle store. One of his principal lieutenants, “Crazy Butch,” established a gang of young criminals called the Squab Wheelmen, in homage to Monk’s twin “legitimate” trades: squabs—pigeons—and bicycles. Crazy Butch then fully justified his nickname by staging a midnight attack on the
Squab Wheelmen’s own poolroom, “by way of testing their valor and settling definitely, in event of trouble, who would stick and who would duck.”22 The results did not encourage him; there were sixty gang members in the room when he and six others ran up the stairway with pistols blazing, and almost all sixty fled in terror. “Little Kishky,” who was sitting by the open window, was so startled and terrified that he fell out the window and broke his neck. Some of those who had fled for their lives were outraged that Little Kishky’s life had been needlessly sacrificed, but the gangland consensus was that he was a weak link who deserved his fate: “If Little Kishky hadn’t been a quitter, he would never have fallen out. Butch was not only exonerated but applauded.”

  Crazy Butch had once been closer to “the heart of that grim gang captain,” Monk, than any other man, but, after serving four years in Sing Sing for a botched burglary, Butch played a much less active part in the Eastmans’ gang activities and instead began operating as a New York Fagin, with thirty boys on the streets “all trained in pocket-picking to a feather-edge.”23 Butch would mount a bicycle (no doubt rented from Monk’s store) and knock over a woman pedestrian. As Butch and the woman exchanged recriminations and accusations, a crowd of onlookers would form around them and Butch’s young pickpockets would go to work.