by Neil Hanson
In comparison to the dapper Kelly, Monk was a crude, clumsy-looking figure and, even before his face was scarred and battered in street brawls, his own mother would have struggled to describe him as handsome. His suits were expensive and hand-tailored, but looked ill-fitting on his ungainly frame. He often went shirtless or collarless, and his looks were not improved by his habit of wearing a narrow-brimmed derby hat several sizes too small for him, perched on top of his shock of bristling, unruly hair.12 The effect must have been comical, but few would have risked laughter. Yet it was the bruising, scowling Monk, not the flashy Kelly or “the flabby and epicene Capone,” who was the model for the typical gunman depicted in Hollywood movies, and it was said that the actor Louis Wolheim regularly portrayed gangsters mainly because his coarse, fleshy features reminded people of “the deplorable Monk Eastman.”
Yet if outsiders saw him as a daunting, even terrifying, figure, Monk inspired great loyalty and affection in his gang members. “Monk hadn’t a real personal enemy that I knew of,” one contemporary said.13 “Most of his acquaintance with the police was due to troubles of others that he took up because he was leader of the gang.” Even his greatest rival, Paul Kelly, had only good words for Monk, calling him “a soft easy-going fellow,” but with “a gang of cowards behind him, second-story men, yeggs, flat-robbers and moll-buzzers.”
Like other leading gangsters, Monk and Kelly delighted in squiring the most beautiful or feisty prostitutes, and battles—sometimes to the death—were fought over their affections. Monk was far from handsome, but he possessed two potent aphrodisiac properties: he was famous, and he had money to burn. In addition to his two wives—the second one possibly acquired without the formality of a divorce from the first—there would have been no shortage of brief couplings with the prostitutes he controlled, but his life, as far as women are concerned, was something of a mystery, even to his friends.
Monk and Kelly were by far the most powerful gang leaders in New York and were bitter rivals, apart from during elections, when their followers worked alongside one another to turn out the Tammany vote. There had already been trouble between the gangs when at midnight on April 13, 1901, two members of the Five Points Gang—the brothers “Peggy” and James Donovan, a Bowery saloonkeeper and an ex-convict—walked into a saloon where Monk was drinking.14 According to Monk’s later account, “Peggy Donovan, without warning, pulled his revolver and fired at me.”15 The bullet missed Monk and struck eighteen-year-old Samuel Frankel in the guts, but it was stopped by his watch and he was only slightly wounded. Monk ran into the street, but the Donovans pursued him, shouting “Stop, thief!”
Monk ran to Grand and Orchard streets, where, he later said, “Two men grabbed me, thinking I was a thief.16 Peggy Donovan reached me first. He pulled his revolver, pressed it against my stomach and fired [twice] into my abdomen. I fell to the sidewalk. Then the other brother shot me behind the ear as I lay on the walk.” James Donovan was cornered by police and fired twice at Policeman Hogan of the Eldridge Street station before he was overpowered, but Peggy Donovan escaped.
The Donovans had left Monk for dead but, as he was often later to boast, he got to his feet, dazed and badly bloodied, plugged the bullet holes in his stomach with his fingers, and staggered to Gouverneur Hospital. He was taken first to the receiving room, where the examining surgeon made a swift inspection of the wounds and assigned Monk to one of the surgical wards. The orderlies sponged him with warm water, then laid him in bed and reported him ready. After he underwent an operation in the surgical amphitheater to remove the bullets and staunch the bleeding, a nurse in a starched white cap and apron brought him a liquid opiate in a glass, carried on a wooden tray.
Monk had lost pints of blood. Told that he was not expected to survive, he made an antemortem statement to the coroner, naming his attackers and offering a motive for the shooting: “The Donovans were heard to say they intended to kill the gang that hung out in Silver Dollar’s place, as it was made up of ‘stool pigeons.’ ”17 Two days later, The New York Times reported that Edward Eastman of 101 First Street had “died in the Gouverneur Hospital yesterday.” The report was wrong. Although he remained on the critical list for several weeks, Monk survived. When he realized that he would live, he reverted to the gangland code, withdrew his earlier deathbed statement, and refused to testify against his assailants, preferring to bide his time and exact his own brand of justice. Within a week of Monk being discharged from the hospital, a Five Pointer was decoyed out of a bar by a woman and then shot dead at the corner of Grand and Chrystie streets.18 No one was ever arrested for the crime, but the police said “Monk got his man.”
In later years the incident in which Monk was gut-shot became mythologized by Herbert Asbury. He described Monk in the summer of 1901, venturing alone into Chatham Square—“a jagged confluence of streets over which clatter two old elevated lines,” which converged at the square and briefly ran double-decked.19 There, said Asbury, Monk was set upon by half a dozen Five Pointers, but laid out three of his assailants with his brass knuckles and slungshot before another of them shot him twice in the guts. However, the chances of Monk having been hospitalized with two gunshot wounds to the stomach twice within three or four months are slim, and Asbury’s version and timing of events are unsupported by any independent evidence. Much of The Gangs of New York drew on Asbury’s conversations with reporters and police contacts, years and sometimes decades after the events in question, and his account of the shooting is one of several stories in the book that perhaps have more of the flavor of half-remembered hearsay and police department gossip than of hard fact.
However, it was indisputable that there was constant fighting between the Eastmans and the Five Pointers. In the previous era, the street fights for supremacy had been between the Cherry Hill and Five Point gangs, but those ancient foes were now united, as Kelly’s gang and the Old Irish Yakey Yakes and their allies fought against the might of the Eastmans. It was a vicious fight for supremacy, “a veritable Wild West reign of terror … the greatest and most bloody of a generation in the three lowest wards of the city.”20 Cherry Hill, Chinatown, and the old red-light district around Chrystie, Allen, Stanton, and Forsyth streets were the battlegrounds, and several lives had already been sacrificed in the blood feud.
Since the turn of the century, the Eastmans and Five Pointers had been fighting a brutal turf war for control of a strip of disputed territory between the Bowery and a dive called Nigger Mike’s on Pell Street, a dismal thoroughfare lined with opium dens, in an area colonized by Chinese immigrants.21 Chinese criminal gangs had yet to establish themselves in New York, and Monk and Kelly both sent regular patrols of their men into this disputed territory with instructions to beat, blackjack, or shoot any member of the rival gang they encountered.22 This turf war may have been behind a killing in April 1902, when Thomas Cominsky shot and killed Isidor Zucker in Silver Dollar Smith’s saloon.23 He then fled to a place owned by Monk on Ninth Street, where he hoped to hide out, but armed police went to the third-floor room and, though Cominsky made a run for it, he was cornered in the cellar and arrested.
In late September 1902 the small-scale killings erupted into a full-scale battle. The trouble began when a Five Points gang member, the son of a Mulberry Street saloonkeeper, was robbed and beaten senseless in Doyers Street. The following night Isidore Foster, “said to be of the Eastman crowd,” was beaten so badly in Broome Street that he died in Gouverneur Hospital.24 The next night Chinatown echoed with the sound of shots. The rioting started about nine o’clock, when the Eastmans, about sixty strong, invaded Chinatown. They divided into two groups, one going through Doyers Street and the other along Walker Street, “looking for the enemy. Pistols were the general weapons, but some of the men carried long knives and murderous ‘slung-shots.’ ” The first confrontation took place on the corner of White and Walker streets. As the Chinese inhabitants and bystanders dove for cover, bullets and bricks filled the air. The gangs fought their way along Wa
lker Street to Broadway, where police armed with clubs and revolvers quelled the riot and took four prisoners. Fighting then flared up again at Centre and White streets, where another thirteen prisoners, thirteen revolvers, six knives, and three blackjacks were seized. Police reserves patrolling in squads of five men eventually quelled the riot, “pouncing on the knots of fighters at every opportunity and sending them to prison in groups.”25
Five days later, hostilities broke out again when thirty-five members of the Five Points Gang, heavily armed and looking for revenge, burst into one of the Eastmans’ hangouts, a poolroom on Suffolk Street.26 Taken by surprise, the Eastmans were rallied by Monk, who was in the room at the time, and for ten minutes there was a ferocious battle during which three men jumped or were pushed out of windows. One of them, Samuel Levinson, an Eastman gang member, fractured his skull and died at Gouverneur Hospital. A loaded revolver was found in his clothing.
Once more the police had to summon reserves before confronting the gangs. Twenty-nine arrests were made, and a dozen loaded and half-loaded revolvers were found on the floor of the poolroom. All twenty-nine men, most of them Eastmans and including Monk himself, were arraigned the following morning before the Essex Market Court, where they heard their gang described as “a disgrace to the city” but, ably defended by ex-assemblyman Isidor Cohn, who countered that they were all just “innocent boys … arrested without cause,” all were discharged.27
Ignoring the classic military dictum of never waging war simultaneously on two fronts, Monk was also trying to achieve the final elimination of Yakey Yake Brady’s gang and the small gang led by “Big Dave” Bernstein.28 The declining Irish Yakey Yakes had once ruled the area around Water, Roosevelt, and Cherry streets, but their territory was now a dying ward. The fighting went on throughout the winter of 1902–1903, and by March the hostility between the two gangs grew so strong that there was almost a nightly pitched battle and an exchange of shots. Police were powerless to stem the fighting or bring the culprits to justice, as shooters and victims alike remained closemouthed. An Eastman gang member, Louis Karp, refused to reveal who had shot him in the leg, but not long afterward, Big Dave Bernstein was severely wounded. A familiar figure in the Bowery, he was shot a few minutes after he had been seen talking to Monk. When taken to the hospital, he swore that Monk was not the man who had shot him, but then added, “Anyway, I’ll settle my own scores.”
However, the Eastmans learned of his intentions and, shortly after midnight, four of them went to Houston Street. Standing on the sidewalk, they poured a fusillade of shots into Bernstein’s saloon, though “no one knows how many revolvers were used and who used them.”29 John “Mugsy” Bayard, a member of Bernstein’s gang, was one of two seriously wounded men and was unable to fulfill his threat to “get even,” as he died that night in Gouverneur Hospital. A thin, hatchet-faced member of Monk’s gang, the nineteen-year-old Max Zwerbach, also known as Kid Twist or Joe Fox, was arrested for the killing, but claimed he had acted in self-defense after Bayard began shooting up the place. With no witnesses coming forward to dispute his version of events, Twist was eventually released.
As the feuding continued, Patrick Shea, “a friend of Monk Eastman … known among his peculiar following as ‘Paddy the Snake,’ ” was badly beaten by the members of a gang headed by a small-time gangster called William “Billy Argument” McMahon, and taken to Gouverneur Hospital.30 Once more, Shea would say only, “I ain’t no squealer, not me. When I get out of the hospital, I will attend to this matter myself and maybe I won’t do a little six-shooting.” Released from the hospital two days later, Shea went straight to McMahon’s house in Hamilton Street—“the wickedest street in New York”—and lay in wait. When McMahon emerged, Shea “pressed a revolver to the base of his skull and blew the top of his head off.”
According to one report, the conflict began over a woman, but reporters looking to add color or glamour to their accounts of gang warfare often overstated the role of an East Side femme fatale.31 Fights over women were by no means unknown, but they were often not crimes of passion but feuds over the control of prostitutes, gangland turf, or rackets. The subject of this dispute was said to be an Italian girl, originally employed by a paper-box manufacturer but more recently a prostitute in a Chinatown dive, who had been the girlfriend of one of the Yakey Yakes until one of the Eastmans took her over. That night, he was leading a waltz with her at the New Irving Hall, surrounded by some of his admiring comrades, when a dozen Yakey Yakes burst in with drawn revolvers, “laid violent hands on the maiden and departed in triumph to Cherry Hill, leaving behind them sore hearts and sorer heads.” In revenge for this humiliation in their own stronghold, the Eastmans shot a Yakey Yake a few nights later; a week after that an Eastman was in turn left dying on a Cherry Street sidewalk.
In an attempt to control, or at least moderate, the intergang violence, police made a series of ax and sledgehammer raids on poolrooms used as gang hangouts. Thirty-three men in various stages of fright were rounded up after police smashed their way into “Biff” Ellison’s poolroom at 231 East Fourteenth Street; so many were arrested that the patrol wagon had to make seven trips to transport them all to the police station.32
Another force, led by Inspector George McClusky, raided a poolroom in a cellar on West Third Street. After arresting the lookouts and smashing their way through armored doors and steel bars, they were confronted by “a labyrinth so cunningly arranged” that they could not tell whether they were moving toward or away from the poolroom. They found themselves in a small anteroom with three doors, and when a detective smashed through the first of those with an ax, he only entered another anteroom with three more doors. He retraced his steps and attacked the second of the doors in the original anteroom but again found himself in another anteroom, faced with three more doors. When he attacked the oak partition next to the doors with his ax he merely broke through into yet another anteroom with yet another set of three doors. A detective eventually “cut the Gordian knot” by retreating to a room that he knew to be over the poolroom. He smashed through the floor with his ax and dropped down almost on the heads of a startled crowd of men.
The police raids had little effect on the levels of gang violence, but Tammany politicians now intervened. The one factor that they feared was that the often bloody rivalry between the gangs would spill into open war, rousing even New York’s soporific or indifferent electorate, and the fighting had now reached the point where Tammany bosses felt compelled to take action. Kelly and Monk were summoned to separate meetings with Big Tom Foley, who laid down the law to them individually and then arranged a conference between delegations from the two clubs at the downtown Tammany headquarters, with Foley acting as chairman and arbitrator of disputes.33 There he again warned them that while an occasional beating or murder might be just part of doing business, open warfare that terrorized whole city blocks was counterproductive for everyone. Foley then delivered an ultimatum, phrased in the starkest possible terms: either the fighting ceased or Tammany would withdraw its protection and the gangs and their leaders would be hounded to extinction. It is not clear whether he could actually have delivered on the threat, or even whether he would have wanted to, given the gangs’ central role in ensuring his reelection, but it was enough to persuade Monk and Kelly to at least make a show of settling their differences.
In language more appropriate to a schoolteacher separating fighting infants than a Tammany boss dealing with two warring gangs, Foley then felt able to tell reporters that “the representatives of these rival factions have given their words that they will never more be bad, thus obviating the necessity of calling out the police reserves to quell riots and disperse gangs armed with pistols, clubs and other weapons.”34 Foley sealed the peace treaty with a chowder at New Dorp, Staten Island, attended by Monk, Kelly, and almost all of their followers. Food and drink flowed freely, and if the day passed peacefully, it ended in predictable fashion. Returning to New York by ferry at midnight, and led th
rough the streets from South Ferry by a brass band also supplied by Foley, six hundred Five Pointers began firing revolvers in the air as they marched up Broadway. Turning onto Franklin Street, “the gang reached the old Five Points stamping ground, and awoke the echoes vociferously.” Fifteen policemen attempting to restore order were badly beaten and were “able to bring but two of their assailants to the Tombs Police Court” the next morning.
7
THE WOLF OF WALL STREET
Even while the gang feuds and police raids were taking place, Monk’s normal gangland activity continued. His fame had spread far beyond the Lower East Side; accompanied by one of his men, Joseph Brown, he now accepted a lucrative mission in Long Branch, New Jersey, where “The Wolf of Wall Street,” financier and fraudster David Lamar, was about to face trial, charged with assault. The charges arose from an altercation between Lamar and his coachman, Joseph McMahon, who while taking Lamar’s wife for a drive refused to chase after her pet dog when it jumped from the carriage and ran off. When Mrs. Lamar ordered McMahon to bring the dog back, he said, “I’m paid for driving horses, not for catching dogs.1 If you want the dog, get him yourself.” After Lamar was told of this, he allegedly struck McMahon in the face with his cane. Lamar also stood accused of attacking McMahon’s wife and driving her out of her home with an iron bar.
Lamar was anxious that the coachman should not testify against him and recruited Monk to ensure McMahon’s silence, though Lamar claimed that he had merely hired Monk to guard his house. He said that Monk had not even wanted money but had taken the job as a favor to a friend, in return for nothing more than the promise of a few drinks.2 Intimidating witnesses was the sort of job that was meat and drink to a gangster, but Monk’s rival, Paul Kelly, would have delegated the job to a couple of his men. Whether out of hubris or his desire to “keep his hand in” by beating up a guy once in a while, Monk elected to carry out the job himself.
