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

by Neil Hanson

  Butch even trained his dog Rabbi—inevitably, he had stolen it—to retrieve women’s bags and purses. When Butch saw a promising purse, he drew it to “the rascal notice of Rabbi” and left the dog to seize it in its jaws, wrest it away from its owner, and race off through the streets before delivering “the touch” to Butch at the corner of Willett and Stanton streets.

  As well as Butch’s Squab Wheelmen, Monk could also draw on the ranks of juvenile gangs like the Junior Eastmans, boys from as young as seven or eight up to sixteen or seventeen who tried to emulate their heroes in dress, speech, and deed, in the hope of one day winning admission to the adult ranks. If all Monk’s smaller affiliates and juniors were added to his strength, he could put a private army of somewhere near two thousand in the field. They were also formidably well-armed. When police—perhaps angered that their customary slice of the action had not been paid—staged a raid on Monk’s headquarters at The Palm, they removed two wagonloads of brass knuckles, slungshots (a rock or other dense object in a thick, close-woven net), blackjacks, knives, pistols, and other weapons.

  Despite the rough-and-ready nature of his enterprises, Monk was sufficiently businesslike—even at the risk of providing evidence that might be used against him—to require his lieutenants to compile written reports of the crimes they were commissioned to carry out; one of his most efficient blackjackers always handed in a formal, typewritten document.24 Monk was also “the first of the gangsters to exploit the labor field.” In 1897 he accepted a commission to break up a union action in the garment industry and beat up two of the ringleaders. After that, Monk found regular work during labor disputes, and he was more than willing to take money from either side.

  Profound social changes were beginning to sweep America, and the dominance of the capitalist robber barons was threatened by the emergence of organized labor. Strikes meant long hours on duty and hard work for the police. As a result, they were instinctively hostile to strikers and “not tender” in handling them.25 While suppressing strikes, they often found themselves in unofficial alliance with Monk. However, when not strikebreaking and intimidating or assaulting union pickets on behalf of the employers, Monk and other gang leaders were also often placed on union payrolls, earning twenty-five to fifty dollars a week as a retainer, and taking a 25 percent slice of the ten dollars a day each of their thugs was paid for threatening and blackjacking strike-breakers. During the strikes arising from attempts to unionize the garment trades on the Lower East Side, groups of Monk’s shtarkes (sluggers) were simultaneously assaulting strikers on behalf of the Jewish manufacturers and attacking scabs for the union organizers.

  As his powers grew, Monk began to do criminal business with “respectable” New Yorkers and operate beyond the confines of his Lower East Side domain. He hired out small gangs of strong-arm men to private individuals to collect debts, pursue personal vendettas, frighten off business or sexual competitors, or ensure the silence or nonattendance of court witnesses. One of the individuals who made use of Monk’s services was a ruthless young criminal called Arnold Rothstein.26 Just eighteen at the turn of the century, Rothstein was already running his own card games, and soon branched out into loan-sharking, employing Monk’s gang members to pressure or beat up his more recalcitrant clients.

  Monk’s terms were the same for either side in a dispute, or for any other prospective customer. One of his more fearsome lieutenants, “Big Jack” Zelig, had a comprehensive list of charges:27

  Slash on cheek with knife: $1–$10

  Shot in leg: $1–$25

  Shot in arm: $5–$25

  Throwing a bomb: $5–$50

  Murder: $10–$100.

  The bargain rates, even for murder, reflected not only the general poverty of the Lower East Side and the power of competition to drive down prices, but also, perhaps, the low level of risk attached to even bombing and murder in a city policed with such rampant incompetence and corruption.

  Monk and his men went about their business with something close to impunity, as was illustrated when two members of his gang were charged in 1903 after Monk was hired by “a blonde of striking appearance.”28 Seeking to be rid of her husband, a wealthy dentist, she allegedly paid Monk three hundred dollars to throw acid in his face or kill him. However, when the case came before the Essex Market Court, Magistrate Pool dismissed all charges against the wife and Monk’s men, and even claimed that the witnesses’ affidavits branded them as perjurers: “the conspiracy in the case was on the other side.”

  Police claimed to have traced a score of murders to the areas in which Monk and his fellow gangsters were operating, but no convictions ever followed.29 He was arrested dozens of times, often for serious assault and once for murder, but he was never brought to justice. “In the three years I was over there,” a policeman said, after his transfer from the Lower East Side to the City Hall Squad, “Monk Eastman was arrested thirty times, but we never got him dead to rights, and had to let him go.”

  4

  A MODERN ROBIN HOOD

  The leader of the first primarily Jewish criminal gang, Monk had now become the dominant figure in New York’s criminal underworld, and his power and influence grew with the steady expansion of his domain as the Eastmans eroded the territories of the old Irish gangs, ousted, defeated, or co-opted their gang members, and adopted their techniques. From rival gangs like the Irish Whyos and Yakey Yakes, the Eastmans learned the use of strong-arm methods, and from the Italian Five Pointers they appropriated a method of terrifying the patrons of poolrooms by playing a game of pool using revolvers instead of cues.1

  Monk’s gang operated from a string of other hangouts apart from his headquarters at The Palm, including a barbershop on Allen Street, a place at the back of a hat store on Delancey Street, and around New Irving Hall, on Broome Street. He was also spreading his operations from the relatively lean pickings in the Jewish districts and into the riches of the Sixth Avenue shopping area and the Tenderloin—Midtown from Twenty-third to Forty-second streets between Fifth and Seventh avenues. Year by year, the Eastmans had moved westward toward the Bowery, “that mecca of all criminals. Ten years ago they were at Goerck Street, three years ago they had reached Allen Street and in their migration had changed character and race.”

  Allen Street was lined with brothels, and the junior members of Monk’s gang soon realized that the “cadet” business—pimping and procuring women to work as prostitutes—was easier, more profitable, and much less risky than picking pockets. Every prostitute a cadet pimped was “a hostage to fortune always on the street” because she was vulnerable to the depredations of other gangs, and cadets who were not gang members themselves had to pay the gangs for protection for their women and their beats.2 As a result, prostitution and gangsterism went hand in hand. Their political connections helped cadets to control their prostitutes, “secure their hard-and ill-earned money,” and, with the aid of professional false witnesses, send any women who stepped out of line to the Island.

  Monk’s men were now thoroughly professional criminals, and the organization of the gang had also been refined and perfected over the years.3 Just like a corporation, Monk had a legal counsel on retainer and set aside a percentage of his earnings to pay the court expenses for himself and his gang members. He also had a regular “fence”—a receiver of stolen goods—though much of the property the gang stole went through the hands of another fence, “who receives propositions on the sidewalk of Delancey Street and offers the best prices.” Even if his uncle, Thomas McSpedon, had not already introduced him to Tammany politicians, as the de facto boss of his teeming district, Monk would soon have come to their attention, and a symbiotic relationship developed between them: “the gang needed the politician, and the politician must have the gang,” because politicians profited from graft and corruption on an epic scale.4

  Thomas F. “Big Tom” Foley of the Second Assembly District was bull-necked and bald as a billiard ball, with a boozer’s flush to his features, and looked like wha
t he was: a bruiser. Like Monk, he had been a bouncer in saloons and dance halls, and was the owner of a Brooklyn dive before he fell afoul of the law and found it prudent to move across the East River to Manhattan. There he established a string of bars and dives, including his headquarters, a saloon on Franklin Street near the Tombs prison. “The swellest ginmill below the line [Fourteenth Street],” it became one of the most famous saloons in New York, patronized by politicians, prizefighters, prosecutors, and defense lawyers.5

  Timothy D. “Big Tim” Sullivan was an even more powerful figure. A former bootblack and newsboy who “never tastes tobacco, never touches liquor, never breaks his word,” he became a saloonkeeper, theater and nickelodeon owner, and Tammany boss of the Bowery.6 As wide as a door, over six feet tall and weighing 250 pounds, with a piercing stare from his pale blue eyes, Big Tim was a controversial figure, but hugely popular in the slum districts that composed his power base. “The political boss of downtown New York” and “The King of the Underworld,” Sullivan epitomized the “Tammany Man”: “Politically he is corrupt; personally he is good—richly good.”

  Big Tim’s first headquarters was a saloon on Doyers Street, just off the Bowery, a narrow, filthy thoroughfare that even by day was “repulsive enough to keep anybody from trying to penetrate its mysteries,” and was “the scene of more murders than any other place in New York.”7 Later he moved his chief base of operations to another saloon, the Occidental, with a famed erotic fresco on the ceiling. Opposite the Tombs police court, it was well patronized by police and court officials.

  Big Tim had Irish roots, but as the ethnic makeup of the Lower East Side changed, he took care to cultivate both the Italian and Jewish immigrant populations, becoming an honorary member of the Paul Kelly Association. Purporting to be a sports and social club, it was the front for Kelly’s largely Italian Five Points Gang. Big Tim was also vice president of the Max Hochstim Association—“the society of politicians, pimps and thieves,” named in honor of a Tammany ward heeler—the leading social and political organization in the Jewish districts.8

  Big Tim was always content to allow others the appearance and trappings of power. He saw few people and did business only by word of mouth, but though Charles F. Murphy was the ostensible leader of Tammany Hall, no one in Tammany—or in New York—could be in any doubt where the real power lay in the city: Big Tim’s “word is law to thousands.”9 He dispensed largesse like a medieval monarch, but also used intimidation and thuggery at the ballot box to build the most cynical and effective political organization in the country. Tammany supporters on the Lower East Side would tie brooms to their railings the night before an election, in a public show of support for a Tammany sweep the next day, though such demonstrations were scarcely necessary since in Big Tim’s kingdom, nothing was left to chance. In the 1892 presidential election, Sullivan’s Lower East Side assembly district voted 395 to 4 for the Tammany-backed candidate, Grover Cleveland, but Big Tim felt compelled to apologize to “Boss” Croker: “Harrison got one more vote than I expected, but I’ll find that feller.”

  The extent of Big Tim’s wealth was artfully concealed. He had sixteen paid employees, whose duties included disbursing cash in response to the scores of begging letters Big Tim received daily; he counted those dollars well spent if they bought him the loyalty—and the votes—of a few more electors. He also made frequent flamboyant charitable gestures, giving away forty-five hundred pairs of shoes and socks to shoeless constituents during one harsh winter, and every year he provided a free Christmas dinner with turkey and plum duff, limitless beer and tobacco, and a pair of buckskin gloves for each of the six thousand people who turned up, at a cost estimated at ten thousand dollars.10 There were also glittering ballum-rancums at the New Irving Dance Hall, where, in “the great dancing hall, stuffed to the doors with painted women and lean-faced men,” Big Tim held court from a box “in the name of a young Jewish friend”—possibly Monk, whom many believed to be Jewish. A judge of the general sessions court sat at the rear of Big Tim’s box, and another city judge “leads through the happy mazes of the grand march a thousand pimps and thieves and prostitutes, to the blatant crying of the band: ‘Sullivan, Sullivan, a damned fine Irishman!’ ”

  Big Tim also staged an annual chowder at which a horde of his constituents and associates were treated to a daylong festival of music, sports, entertainment, food, and drink, capped off with a fireworks display at night. Heralded by as many as three brass bands, Big Tim led his army of supporters down to the South Street waterfront, where chartered paddle steamers were waiting. Lubricated by free beer, whiskey, and cigars for the men, and ice creams, candies, and entertainment for the women and children, the throngs spent the day at College Point or Coney Island, where at least some of the costs of the day were recouped from the stuss games and the gambling on boxing bouts and sports that the inebriated East Siders took to with enthusiasm. They returned late at night in a drunken, brawling cavalcade through the Lower East Side.

  Sullivan supported a score of indigent families, donated money to hospitals and orphanages, and, wherever he went, he paid the bills of all who shared his company. The cost of all this largesse was stupendous, but despite all the money he gave away—“Not a splinter under three hundred thousand dollars a year”—by the time he was in his forties, his worth was estimated at more than two million dollars.11

  Big Tim had business interests, particularly in the field of popular entertainment, promoting boxing, horse racing, and operating chains of burlesque houses, vaudeville theaters, and nickelodeons, but even his most fervent admirers would have struggled to claim that all his wealth came by such legitimate or semi-legitimate means. Big Tim barely troubled to deny the huge income he enjoyed from gambling dens, though he fervently denied profiting from prostitution.

  Like Big Tim, Tammany’s other power brokers made only cursory attempts to conceal the source of their wealth, though “Boss” Croker offered an ingenious justification of the Tammany system:

  Think of the hundreds of thousands of foreigners dumped into our city … Not a Mugwump [do-gooder] in the city would shake hands with them … Tammany looks after them for the sake of their vote, grafts them upon the Republic, makes citizens of them, in short; and although you may not like our motives or our methods, what other agency is there by which so long a row could have been hoed so quickly or so well?12 If we go down into the gutter it is because there are men in the gutter, and you have got to go down where they are if you are to do anything with them.

  One estimate put the cost of this Tammany “citizenship” program of graft at two fifths of New York’s annual budget. Controller Metz, in an appendix to a 1909 report on New York’s chaotic public finances, claimed that from a quarter to half of the city’s annual payroll of $80 million was useless—skimmed off in supposed wages to names padding the city payroll—and in that year, New York’s actual debt topped $800 million.13 Other skimmings, scams, bribes, and kickbacks took the total figure lost by graft even higher; one estimate put it at $80 million a year. Thousands shared in the proceeds, but there was no doubt that Sullivan took the lion’s share.

  State Senator and Tammany sachem George Washington Plunkitt also found his elected position no obstacle to accruing substantial wealth. Despite being a millionaire contractor and real-estate operator, his HQ and only office was his shoeshine stand in the New York County Courthouse.14 The first man—publicly at least—to draw the distinction between the honest graft that he practiced and the dishonest graft practiced by others, Plunkitt’s motto was said to have been “I seen my opportunities and I took them.”

  Politicians like these stood to profit both from Monk’s criminal enterprises and from his ability to get out the vote—both genuine and bogus—on primary and election days, using his army of gang members. Deals were done, and henceforth Monk’s gang members spent election days working as “guerillas” (or “gorillas”) stealing ballot boxes, and acting as repeaters who voted early and often and “slugger
s,” persuading others of the wisdom of voting the Tammany ticket, while frightening off those intent on voting for a rival candidate.15 “Any political wavering to Monk’s philosophy meant a busted head,” and his gang was particularly effective at intimidating “the nervous Hebrews, who could not be depended upon to ‘vote right.’ ”16

  In return, Tammany could offer Monk the one thing a gangster craved above all others: Monk’s gorillas had effective immunity from the law not just on election days but on every other day of the year as well.17 That immunity made the gangs even more daring, so that “youths who, alone and unaided, would run from the blue uniform of the greenest and rawest policeman, carry pistols, hold up decent citizens, and defy the law and the police in conjunction.”

  Tammany politicians displayed great skill in publicly denouncing organized crime while actually profiting from and building alliances with it. This was particularly true in the area of prostitution; many of the cadets who procured and pimped young women also formed a significant part of the army of repeaters and sluggers during voter registration and elections.18

  The shifting balance of power in the Lower East Side gangland was vividly demonstrated in the elections in the fall of 1901, when “word was sent out to all the criminal population of the East Side that ‘Monk’ Eastman was the sole leader of the election ‘repeaters,’ that every criminal was expected to be out early on election day and do his part, and that in return the politicians would stand for ‘anything but murder’ from the criminals.”19

  In addition to the repeaters provided by Monk’s gang, the poorer lodging houses in the Lower East Side were used for the “colonization” of voters, with prodigious numbers of tramps and other homeless derelicts registered at each address. In return for booze money, or sometimes their freedom from jail, these lodging-house voters duly came out “strong on the side of the political boss” at election times, and especially in presidential elections.20 After a raid on stale beer dives had rounded up 275 tramps who were routinely sentenced to six months on the Island for vagrancy, one policeman noted with an air more of resignation than outrage that at election times he had “more than once seen the same tramp sent to Blackwell’s Island twice in twenty-four hours for six months at a time.” Protected by Big Tim and the other Tammany bosses, few lodging-house owners were ever prosecuted for voter fraud, no matter how implausible the numbers purportedly living in their premises. The graveyards were another fruitful source of votes; the names of the deceased were registered, and large numbers rose from the grave to vote on election day.