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

by Neil Hanson

  In an observation that would have astounded the officers of the New York City Police Department, Captain Conrow also noted that Monk was “a quiet, disciplined soldier, who never gave any trouble … He bears an excellent reputation in the company for soldierliness and bore himself admirably under fire.6 Toward all comrades he evinced the greatest kindness and devotion.” After describing Monk’s heroism in battle, Lieutenant Kerrigan noted that Monk’s conduct had also been exemplary and he had never been reported for absence without leave or any other offense. He had given Monk an excellent character on his discharge and believed that he “should be rewarded for the wonderful work done by him in the line and his honest and faithful service since his enlistment.”

  MONK EASTMAN WINS NEW SOUL, the Tribune proclaimed in its frontpage report on the petition.7 After sober consideration, on May 8, 1919, Governor Smith duly restored citizenship to the “one time ‘bad man’ of the East Side, survivor of a hundred gun fights, political ward heeler, repeater at the polls and finally convict … because of his exceptional record in the army overseas.” As Monk confided to a friend, “Army life has made me over. I’m going to stick. If a fellow makes good wearing the uniform, his work is appreciated.” The New York Times noted that “his own testimony on that score might not be readily taken, were it not backed up enthusiastically by those above him, [but] every man with human instincts will be glad to extend his hand to ‘Monk’ Eastman, the bad boy who had something in him.”

  However, questions still remained about the true extent of citizen Eastman’s reform and redemption, and he refused to reveal to reporters where he was going to live or the nature of the work he had been offered. In fact, using the qualification as a motor mechanic he had gained in the army, Monk found work with Charley Jones, an old friend and former member of his gang who had gone straight and built an auto repair business on East Twentieth Street. For several months Monk appeared genuine in his desire to go straight, but a new and formidable temptation had emerged: Prohibition—“the father of the modern gangster.”8

  The Great War had provided firm evidence that the United States had replaced Britain as the world’s dominant power. The U.S. economy was already by far the most dynamic since well before the turn of the century, and now U.S. industrial output exceeded the combined production of Europe’s three richest countries—Britain, Germany, and France—and by 1913 accounted for 35 percent of the world’s total industrial production.9 America’s political influence and military power had not reflected that economic strength, but now the United States had flexed its muscles. The nation that at the time of the declaration of war with Germany in April 1917 ranked equal with Finland in the size of its armed forces had armed, equipped, trained, and shipped to France two million soldiers by the time of the Armistice, barely eighteen months later. Although isolationism would remain a potent force in domestic politics, the United States was now the major figure on the world stage, and a perverse demonstration of that fact came when the American refusal to join the League of Nations rendered that organization impotent from the very start.

  If the balance of world power was shifting toward America, her greatest city, New York, was also undergoing another seismic shift. The criminal gangs that had been driven to the point of extinction were now rising again as a direct consequence of the imposition of Prohibition, and the profits to be made dwarfed by far those that Monk had been able to achieve. Even at the peak of his powers, his annual returns from his criminal enterprises were probably counted in tens or, at most, hundreds of thousands of dollars; the major gang leaders of the Prohibition era would soon be calculating theirs in tens of millions.

  The strength of the temperance movement in rural America had produced enough votes for the Eighteenth Amendment, prohibiting intoxicating beverages, to be ratified in January 1919, but it was believed to be unenforceable without further legislation, and in October 1919 Congress accordingly passed the National Prohibition Act, more widely known as the “Volstead Act” after its Republican sponsor, Representative Andrew J. Volstead from Minnesota. President Woodrow Wilson at once vetoed the measure, but Congress overrode the veto the next day. Distracted by the great issues of war and peace, the Spanish flu epidemic, and the increasing incapacity through ill health of President Wilson, the American electorate had now allowed a rump of almost exclusively rural and Protestant voters to turn the entire nation “dry.”

  The Volstead Act came into effect on January 16, 1920; nationwide prohibition was now in force. The act established penalties, including a search-and-seizure clause, against establishments selling liquor, while perversely continuing the taxation of alcoholic beverages. Private stocks of liquor bought before the act went into effect could be retained, and beer manufacture was permitted to continue, but only if brewers reduced the alcoholic content to 0.5 percent or less.

  However, the principal consequence of Prohibition was not to turn the population of the United States into teetotalers overnight, as its proponents had hoped, but to secure the dramatic rebirth and regrowth of the previously moribund gang culture, and the fight to control bootlegging was more ferocious in New York than in any other American city—even Chicago.10 In a truly bizarre reversal, the once vilified gangsters would also acquire—albeit temporarily—the mythic status of folk heroes and community servants, American Robin Hoods committing “victimless crimes” to bring succor to a thirsty nation.

  Much of the legitimate alcohol for medical or industrial use, housed in bonded warehouses on the Manhattan and Brooklyn waterfronts, found its way into bootleggers’ hands through theft or forged medicinal withdrawal permits.11 A Brooklyn man, Edward J. Donegan, was said to have made more than two million dollars in two years after acquiring a set of blank permits and a rubber-stamp facsimile of the liquor administrator’s signature. Bootleggers also loaded cargo ships with alcohol legally purchased in Europe. The ships were met in international waters just outside the three-mile U.S. territorial limit by fleets of fast speedboats that ran the contraband into coves and jetties the length of Long Island Sound. One of the leading rumrunners was Monk’s old adversary Paul Kelly. Garbage scows operated by the members of his Scow Trimmers Union went out to sea to dump New York’s garbage every day, and it was easy for the scows to rendezvous with rum ships while out in the harbor. Booze was also trucked from Canada while many excisemen, like their counterparts in the Coast Guard, took bribes and looked the other way. Illicit breweries and distilleries within the United States also churned out everything from fine bourbon to rotgut hooch and sold it at a huge profit to speakeasies, clubs, restaurants, bars, brothels, and backstreet dives.

  Police departments from which at least some of the corruption and criminality had been driven now found themselves again riddled with policemen on the take. Prohibition also put millions of ordinary, normally law-abiding citizens on the wrong side of the law, either as consumers or producers of illicit booze. Within months of the Volstead Act being passed, thousands of homes throughout the United States were being transformed into small-scale distilleries and breweries. In North Tarrytown, New York, the sewer inspector was forced to ask the town’s inhabitants not to flush prune pits, grain, potato peelings, and other detritus from the stills, because they were clogging the drains.12 Mrs. Viola M. Anglin, deputy chief probation officer for New York City, testified that in each of the districts of her sixteen probation officers there were between one and two hundred stills, and not just in cigar stores, delicatessens, and other commercial premises, but “in the homes of the people who live in the tenements … any child in New York who knows anything about the city at all, can point out a still in his own neighborhood—can point out a speakeasy.”

  The gangs were now back on the streets of the Lower East Side, albeit in far lesser numbers than in Monk’s prime, and bootleg alcohol was sold to bar, brothel, and speakeasy owners from “curbside markets” on Kenmare, Broome, Grand, and Elizabeth streets, only a stone’s throw from police headquarters.13 When Monk disappeared fr
om his old haunts and failed to appear at the garage for several weeks, police at once suspected that he had tired of honest toil and slipped back into criminality, though friends hinted that he had grown tired of New York and left the city to make a fresh start in a place where there would be less temptation to return to his old criminal ways. Some felt that he had at last fulfilled his pledge to go West and had joined Worthy in the Big Bend area of Texas. However, police treated those claims with derision, insisting Monk “couldn’t be any further from the Bowery and Chrystie Street than the police would take him.” Their cynicism soon seemed justified. If he really had gone West, it proved a short-lived move, and within weeks he was on a rampage around his old haunts and was seen drunk in a Brooklyn saloon at Broadway and Driggs Avenue.14

  He did not return to work at the garage, but instead took another job obtained for him by a Democratic politician in Brooklyn. In company with another reformed East Side gangster, he worked as a loading foreman and was paid in cash per load by the truckmen. At the end of each week the two men shared the profits and started a “booze party” that might last all weekend. However, there were rumors that Monk was once more active in racketeering, and according to one criminal, he was certainly involved in car theft.15 It was claimed that in May 1920, Monk and three other men stole a Cadillac, a shiny blue landaulet “with nickel plate a-plenty, sparkling like a bridal gift,” parked outside Big Tom Foley’s speakeasy, in plain sight of the criminal courts building. Although the thieves were unaware of the fact, the car belonged to Fanny Brice, star of the Ziegfeld Follies on Broadway and wife of one of Arnold Rothstein’s henchmen, Julius “Nicky” Arnstein. Rothstein, who in his early days as a loan shark had hired Monk and his gang as “muscle,” was one of the most feared of the new wave of gangsters, the real-life model for Meyer Wolfsheim in The Great Gatsby and Hyman Roth in The Godfather. Although he denied it, Rothstein was widely believed to be the brains and the money behind the 1919 “Black Sox” baseball scandal—the fixing of the World Series of America’s national pastime.

  After the theft of the Cadillac, word was put out on the streets by a henchman of Big Tom Foley that if the car was not returned at once, there would be fatal consequences for those involved. It was said that within half an hour, Monk drove up in the Cadillac, offering profuse apologies for the error.16 “It’s a good thing we got word in time,” Monk was purported to have said. “Half an hour more and nobody would have recognized it.”

  Such stories were flatly contradicted by Charley Jones, who claimed that, having been given the chance to live clean after his war service, Monk had turned his back on his old ways. When Jones heard that Monk was going on the level, he had taken him into his automobile business, and although Monk had soon tired of the business, Jones claimed that it was because he was finding even that too lively for his tastes and perhaps too fraught with temptations to resume the old sort of life. Monk had then crossed the bridge, said Jones, and gone back to Brooklyn, taking a furnished room at 801 Driggs Avenue—an ordinary rooming house in an ordinary neighborhood, “within a biscuit toss of the Williamsburg Bridge and within the shadow of the Williamsburg police court.”17 He had opened a pet store on Broadway specializing in birds and settled down to live “the quietest life a man could live.” However, Monk’s Polish landlady at Driggs Avenue, where he had indeed lived for seven months, said that though he kept pretty much to himself, he spent most of the daylight hours asleep and his evenings out, which hardly sounded like the typical daily routine of a pet-shop owner.

  Brooklyn police said Monk was working as a bouncer in a crap joint near Flushing Avenue and Broadway.18 New York police went further, claiming that there was already reason to believe that Monk’s reformation had been much less genuine than many people believed.

  Whatever the truth, even if he really had reformed, Monk still could not escape his past, and the very qualities that had made him such an admired and inspiring comrade in the army—candor, openness, patriotism, courage in the face of danger, and a willingness to risk his own life for the greater good—might also have made him a perceived threat to some elements of the underworld. The governor’s pardon and the press portrayals of Monk as a reformed good citizen might on their own have been enough to start questions forming and rumors circulating in gangland circles. Perhaps, too, someone remembered the curious incident ten years earlier when, while recovering from a stomach operation in an Albany hospital, Monk had been given a round-the-clock police guard.

  On the evening of Christmas Day 1920, Monk went to an all-night restaurant, the Court Cafe, at the corner of Broadway and Driggs Avenue in Williamsburg, where he was seen talking to two girls and a tall thin man carrying a traveling bag.19 Soon after midnight, he left in the company of some friends and was driven to a Manhattan basement cabaret, the Blue Bird Cafe, on the corner of Fourth Avenue and Fourteenth Street, “the northern boundary of the asphalted domain which once he ruled by right of might.” Long known as Pabst’s Rathskeller, the Blue Bird had been taken over and renamed the Café Chateau-Thierry—though no one but the owner used the name—by Willie Lewis, a prizefighter turned soldier who had owned it long enough to have gotten himself badly shot there.

  Monk, who was in the habit of going to the Blue Bird every Saturday night, was with friends, several of them members of his old gang whom it was said he had continued to see regularly.20 The party gathered at a big table and had plenty to drink. They chatted in low tones, turned now and then to greet friends, and appeared to be having a good time, though Monk was getting drunker and drunker. According to other accounts the party was boisterous and there was considerable singing, with Monk taking the lead. When a woman cabaret singer came in with a party of friends, the two groups joined forces and more singing and drinking followed. Monk was said to have talked a great deal about his record as a gang leader and a war hero and been very boastful. “Do you know who I am?” he was said to have asked. “I’m Monk Eastman, the gang leader who made good; the guy that went over there and came back a hero and was made a good citizen by Governor Smith.” The cabaret singer and her companions eventually departed after “a hilarious time.”

  Later, “always likely to be quarrelsome, self-assertive and domineering,” according to police, Monk was said to have gotten into an altercation, and other members of the party had to separate the disputants.22 Angry and outraged, Monk left the place almost at once. He staggered into the street at about 3:45 and apparently started for the downtown subway station, probably intending to go home to Brooklyn, but as he reached the subway entrance on the south side of Fourteenth Street he was shot five times with a .32-caliber pistol.21 “He crumpled up on the sidewalk. A trickle of blood ran along the cement.”

  Monk was found by two patrolmen. They bent over him and, despite the bullet wounds he had suffered, they were able to detect a faint heartbeat.23 However, he had suffered bullet wounds to the left chest, heart, stomach, pancreas, and second lumbar vertebrae and, although a taxicab took him to St. Vincent’s Hospital, he was dead when taken to the operating room. One bullet had pierced his heart, passed through his stomach, and embedded itself in his backbone. That wound was cited as the direct cause of death. Another shot had hit his right arm, and two more shots hit his left arm—suggesting that Monk had tried to shield himself with his arms as the gunman fired at him. The fifth shot apparently struck something else and then ricocheted, lodging in Monk’s overcoat with insufficient force to pierce the cloth. A bullet hole in the coat, near his heart, was two inches in diameter and covered with powder marks, showing that the fatal shot had been fired at point-blank range.

  23

  DRAPED IN BLACK CLOTH

  Monk’s body was taken to the morgue and docketed as that of an unidentified man. Bodies in the holding rooms lay on a zinc table, and in hot weather a spray of cold water fell constantly from a shower-head and was carried away by a drain beneath the table; in the depths of winter, the biting cold was enough to delay decomposition until the coroners a
nd undertakers had done their work. A postmortem examination revealed a good deal of grain alcohol in Monk’s stomach.1 The body of the man whose face was once familiar to every detective lay unrecognized for two hours before it was identified by two old-timers—policemen who had known Monk in his heyday.2

  A label on the inside coat pocket of the good suit of clothes he had been wearing when shot was marked E. EASTMAN. OCT. 22 1910. NO 17434. W.B.3 That identified the suit’s makers as Witty Brothers of 50 Eldridge Street, and Henry Witty confirmed that he had made the suit for Monk. “We have made clothes for him for nineteen years. The last suit we made for him was delivered October 21 this year.” Still not completely satisfied with that identification, detectives took fingerprints from the body and compared them with those held at police headquarters, definitively establishing his identity.

  Contrary to a lurid and entirely fictional newspaper report of Monk shooting back in his last moments, he had been unarmed when he was killed. “That fact, even more than the mystery of his murder, was the talk of the Lower East Side last night.4 The Monk was killed while unarmed.” John A. Ayres, a printer, was the only witness to come forward, even though he said that Monk had been killed in the sight of ten or more people, several of them within fifteen or twenty feet. Ayres was in a restaurant on the other side of the street, and when he heard the first shot he rushed outside and saw a man lying on the sidewalk across the street with his arms over his face. “A man was standing over him,” Ayres said, “and as we reached the window, we saw him fire four more shots into the man on the sidewalk.”5 The murderer “bent over his victim a moment, presumably to make sure he was dead,” then ran to a taxicab moving slowly up Fourth Avenue. “He ran out as if he expected it,” Ayres said. The taxi slowed and the killer jumped onto the running board. Ayres saw the man throw something out of the window as he got into the taxi. Someone shouted, “Stop him!” but the taxi drove off. Ayres said that he was warned by one of the men who had been in the restaurant, “If you try to mix in this, you’ll get killed,” so he had stayed where he was for fifteen minutes and then caught a cab home.