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

by Neil Hanson

  The fight began with Monk charging at Kelly, throwing roundhouse punches, while Kelly used his speed to avoid Monk’s rushes, ducking and weaving but still landing some jolting shots. The shouts and the thunder of applause and stamping feet at each blow or knockdown set dust and straw cascading from the worm-eaten rafters above. Each round continued until one of the fighters was knocked down. Both men had a cornerman with a sponge and a bucket of dingy-looking water to sponge his man’s cuts and splash his face between rounds, and he had one minute to revive his fighter. If his fighter had not “come up to scratch”—the line scraped in the dirt at the center of the ring—when the timekeeper rang the bell for the next round, the other man would be awarded the fight.

  Kelly and Monk both went down several times, but each time they hauled themselves back to the mark for the next round. They fought for well over an hour, without either managing to land the knockout blow, and so indomitable were their wills that even after they had both collapsed to the barn floor with exhaustion they continued to aim increasingly feeble blows at each other’s heads until at last their followers pulled them apart and the fight was declared a draw. There were some who suggested that, at Tammany’s insistence, the fight had been fixed from the start, an honorable draw being the only way to ensure that the loser’s men would not start another war to gain their revenge, but the cuts and bruises the two fighters bore were genuine enough.

  It was almost two in the morning when the crowd began to straggle back toward the city. When they came across a trolley car there was a mad rush to get aboard, though few of them showed any inclination to pay the fare. After it had traveled about a mile the motorman brought the car to a halt and the conductor hailed three patrolling policemen, who threatened to arrest all the passengers unless the fares were paid. One of the sports who had won money betting on the fight magnanimously came to the rescue, giving the conductor fifty cents, and the car resumed its journey.

  They reached 161st Street and Willis Avenue at half past two in the morning and got into the El car going downtown.41 Most got off at Fourteenth Street and, while the sports and supporters melted away into the night, the two battered and bloodied gang leaders returned to their headquarters to lick their wounds, knowing that the turf war remained unresolved and that it would be only a matter of time before hostilities between the gangs resumed.

  9

  THE TOMBS

  The decisive moment in the war between Monk and Paul Kelly came in the early hours of February 2, 1904. Monk, still wearing a mourning band after the death of his mother the day before Thanksgiving, was with a sidekick, Chris Wallace, and they were well north of the Fourteenth Street dead-line. They had made their way to Sixth Avenue and Forty-second Street either to blackjack a man who had crossed one of Monk’s clients, as one source alleged, or just to have a few drinks, according to Monk and his cohorts.1 A little before three in the morning they saw a well-dressed young man, the worse for drink, staggering out of Jack’s All-Night Restaurant. He lurched around the corner, then stood in a doorway, took his money out of his pocket, and started counting it.

  Just behind him, lurking in the shadows, were two roughly dressed men whom Monk and Wallace took to be “lush workers” waiting to rob the drunk of his wallet.2 Never one to look a gift horse in the mouth, Monk and Wallace promptly held up the young man themselves. As they were relieving him of his wallet, the other men—John Rogers and George Bryan of the Pinkerton Detective Agency—emerged from the shadows. They had been hired to protect “the wayward son of a man prominent in national affairs,” and as the son was “on a debauch,” he was being kept under surveillance.3

  Following the traditional Pinkerton method of “shoot first and then ask questions,” they at once began shooting at Monk and Wallace, who returned fire.4 After firing nearly all the shots in their guns, Monk and Wallace took to their heels and made a wild dash along Forty-second Street. The Pinkerton men kept up an intermittent fire, and their quarry paused from time to time to aim additional shots at them.

  Bryan later testified that, despite the attempts of some of Monk’s other companions to trip him up, he was able to overtake Wallace, whom he used as a shield, turning him from side to side to keep Wallace between them while Monk tried to get a clear shot.5 After firing his last shot, Monk threw his empty revolver at Bryan’s head, but the Pinkerton man ducked, and it smashed through a store window, where it fell into a tea set. Despite all the shooting, the only damage done by either side was to that seventy-five-dollar plate-glass window, and to another window in a trunk store. The revolver, which police stated belonged to Monk, was found in the store window with all its chambers empty.

  Police Officer Sheehan, who was standing outside the Knicker-bocker Hotel at the corner of Forty-second and Broadway, had heard the shots, and as Monk sprinted around the corner, Sheehan swung his nightstick and laid him out cold. Aided by the two Pinkerton men and two detectives who had been keeping watch on nearby gambling houses, Sheehan arrested Wallace and the unconscious Monk. When his head cleared, Monk found himself on the cold stone floor of a cell in the West Forty-seventh Street police station.

  At first Monk treated the police and the prospect of criminal charges with his customary indifference. He gave his address as 2060 Second Avenue and his name as William Delaney—as usual, both were false.6 Since his one term of imprisonment on the Island, Monk had always managed to get out of trouble, but this time the police were confident that the charges against him would stick.

  Monk sat back to await the arrival of Tammany’s lawyers and bail bondsmen, but the involvement of “incorruptible” Pinkerton agents in the case made Monk’s position far more precarious than he at first realized.7 Recalcitrant policemen who tried to testify against gang leaders could be transferred to the Goats, but a Pinkerton Agency operative could reputedly be neither threatened nor bought. For once Monk had overplayed his luck and would have to suffer the consequences.

  His notoriety was also making him a dubious asset to Tammany. Although he was still useful, it soon became clear that his value had strict cash limits. While Monk languished in his cell, two Tammany politicians approached Assistant District Attorney Elder and offered fifteen hundred dollars’s bail, saying that they needed Monk, “one of the best men we have for registration and election day work.8 We cannot afford to lose his services this year.” When Elder told them that he would try to have the bail fixed at twenty-five hundred dollars, they said Monk wasn’t worth that much to them. Elder protested that they were effectively saying that they knew Monk would jump bail, to which they replied, “Of course. You don’t suppose he’ll stay to be sent to jail, do you? That’s why we don’t want to go as far as $2,500. Won’t you let him out on $1,500 bail? That’s a fair amount.” The furious Elder then said that he now wouldn’t even consent to ten thousand dollars’ bail, and bade them good day.

  Recorder Goff eventually fixed bail at seventy-five hundred dollars to cover two indictments, but no one was willing to pay that much, and Monk remained in custody. When arraigned, he described himself as a newspaper speculator and again gave his address as 2060 Second Avenue. His lawyer said his client was willing to plead guilty to a charge of disorderly conduct, but the magistrate refused the offer and Monk was eventually indicted on three counts: attempted murder, first degree, and assault, first and second degree. It was charged that he had attempted “willfully, feloniously and of his malice aforethought, and with deliberate and premeditated design to effect the death of … George Bryan with … a certain pistol then and there charged with gunpowder and one leaden bullet.”9

  Monk also faced a further indictment after an old adversary—Inspector McClusky of the detective bureau, still smarting over the failure of the Lamar case in New Jersey—claimed that Monk had attempted to kill a young man named Harry Lewis two weeks before at First Street and Second Avenue. Lewis confirmed the story before the grand jury, and Monk was charged with that offense. Monk told reporters that the police were intent on send
ing him “up the river”—to Sing Sing—but with the help of a good lawyer, he was confident of beating them.10

  He was transferred to the Tombs to await his trial at the general sessions court. Officially known as the Manhattan House of Detention for Men, the Tombs stood on a site that had once been the Collect Pond, the source of New York’s original drinking-water supply; by the early nineteenth century, it had become a dumping ground and a malarial swamp. A canal (subsequently filled in and renamed Canal Street) was then built to drain it, extending to east and west, and the site of the Collect Pond was filled and leveled with rubble and rubbish, but it remained waterlogged and mosquito-ridden.

  A massive granite building, 253 feet long by 200 feet deep, was erected there, based on a steel engraving of an Egyptian tomb. A broad flight of dark stone steps led up to the entrance on Centre Street, dominated by a huge and forbidding portico, supported by four massive stone columns. The low-lying site made it barely visible from Broadway, only a hundred yards distant, and the ground was so marshy that despite the building’s having much deeper foundations than normal, subsidence made it sink even lower, warping the cells and causing cracks through which water seeped, forming pools on the stone floors. Popular mythology even claimed that the building rose and fell with the tides.

  Stonemasons were forever repairing and shoring up the building, which was condemned by more than one grand jury as unhealthy and unfit although it remained in use until 1902, when it was pulled down and replaced by a massive gray stone structure. The nickname was less easy to demolish and is still being used today. Conditions inside remained medieval. Although built to accommodate only two hundred prisoners, at least twice that number were routinely incarcerated there; fifty thousand prisoners passed through its portals every year.

  Beyond the forbidding entrance of the Tombs was a large courtyard surrounding the male prison, which was connected with the outer building only by the “Bridge of Sighs,” over which all condemned prisoners made their final walk, the gallows set up in the courtyard “meeting their eyes as they passed out into daylight.”11 The four tiers of cells opened off a high but narrow iron-galleried hall. Prisoners were compelled to walk around the gallery for an hour every day, the only time when they were not locked in their cells. There was no running water, no heating, no mains drainage—prisoners used metal buckets, making the lack of adequate ventilation even less pleasant—and minimal natural light. The only way to measure the passing hours was by the gradual, almost imperceptible lightening and darkening of the gray-black light. No lights were allowed in the cells at night. In winter, prisoners spent two-thirds of their time shivering in darkness and silence; in summer they sweltered.

  The remaining buildings of the Tombs, separated from the male prison by the courtyard, included “Bummer’s Hall,” housing the tramps, vagrants, and drunks pulled off the streets every day. Each morning they were taken out, tried, and convicted—few were ever discharged—and sent to the Island on a six-month sentence, but by the following night Bummer’s Hall would again be full. There were separate buildings for women prisoners and juveniles. The latter, incarcerated on the Centre Street side of the jail, often completed their criminal education while imprisoned there, for prisons like the Tombs were seminaries of crime.

  The Centre Street buildings also housed the warden’s office and quarters, the police court, and the court of special sessions. Six large cells directly over the entrance were reserved for those able to pay for them. They did not wait long before coming to trial; more criminals daily passed before the recorder in the Tombs police court than in any other court in the world, and the justice dispensed there was brisk. Under the eyes of half a dozen policemen, the defendants were herded together in the “prison pens,” surrounded by ranks of friends, witnesses, or mere curious spectators, on the wooden benches lining the room. Shyster lawyers always stood around the courtroom, looking for any defendant who might be willing or able to pay a fee of as little as fifty cents to as much as fifty dollars.12

  Monk had been languishing in the Tombs for a month when, in early March 1904, he was brought before Recorder Goff, a man “cold-hearted, humorless and so short as to appear stunted,” who once famously asked for the shades to be drawn because there was “not enough gloom in this courtroom.”13 The court was packed with East Side toughs who saw Monk as a hero, and for their benefit he made loud, derogatory remarks about the physique of some of the court officers, joked with his friends, and whispered to them that he was too lucky not to get out of his latest trouble.14

  Monk’s counsel, George W. Hurlbut, had made an application to the state supreme court for a change of venue, claiming that an attempt was being made to railroad his client and arguing that because of Monk’s notoriety, it was impossible for him to get a fair trial in that county. He submitted a bundle of newspaper clippings and supporting affidavits, but the supreme court justice was unmoved and the trial went ahead in the original venue after another month’s delay. Monk had been bailed pending the supreme court judgment—either the cost of bail had come down or his value to Tammany had risen—but he was at once rearrested by police, along with five companions. Monk was discharged by magistrates the next morning, but his chances of an acquittal in the looming trial were not improved when The New York Times ran an article claiming that fifteen of his gang members had been employed to “do up” some members of a synagogue with brass knuckles and iron bars.15 Their fee was said to be ten dollars for wounding a man and fifteen dollars for killing him.

  Ten days later there was further damaging publicity when police reserves were called out to a fight involving a crowd of Eastmans.16 The police could not find out what the brawl had been about, and the victim was said to be too frightened to make a complaint against any of his assailants.

  Those latest newspaper reports could hardly have been worse timed, appearing on the very morning, April 12, 1904, that Monk’s trial opened at the court of general sessions. Only those members of Monk’s gang under subpoena to appear were admitted to the courtroom; the rest gathered outside in the corridors. Monk’s sisters were in court, and at the end of the day’s hearing, he kissed them before returning to his cell.17

  Monk was dressed better than any of the jurymen who were to pass judgment upon him, but his relaxed and affable demeanor was tested when the Pinkerton agent gave evidence.18 When he claimed that Monk had shouted out, “Let go of him you God damned son of a bitch, or I’ll kill you,” Monk half-rose from his seat, but his counsel persuaded him to sit down again. When he was called to the stand, speaking in a voice “like the bark of a dog,” Monk told the court, “My real name is Edward Eastman. I am twenty-eight years old, and unmarried and I live on Ward Street, Richmond Hill. I know nothing about this holdup.” He also described himself as a dealer in pigeons. Only the first of those six statements was true: in fact, he was thirty and still married to Margaret, and Ward Street was his mother’s old house, where his sisters Lizzie and Francine, were still living.

  Assistant District Attorney William Rand’s attempts under cross-examination to elicit Monk’s true name, address, occupation, and marital state occupy eleven pages of the trial transcript, and at the end of it neither the prosecution, the judge, nor the jury were much, if any, the wiser.19 Rand began by asking Monk what address he had given to the police.

  A: 2060 Second Avenue.

  Q: Did you live there?

  A: Well …

  Q: Did you live there?

  A: I did live there, yes.

  Q: When did you move down to Richmond Hill?

  A: I live up there still, and I live with private people and they sent me a letter since I have moved to Third Avenue and asking me not to disgrace them. That is why I didn’t want to give that number any more.

  Q: What number?

  A: 2060 Second Avenue.

  Q: But you did give it in the police station?

  A: Yes, sir.

  Q: And you said you lived in Richmond Hill, too?

  A
: Yes, sir.

  Q: That was not true?

  A: Yes, well, my sister lived there.

  Q: I didn’t ask if your sister lived there; don’t let us drag your sister into this. Do you live there?

  A: Not exactly live there. I go over there.

  Q: Is that your residence?

  A: Any time I want to go there, I can, and live there.

  Q: Oh, I hope your sister is glad to see you. But where do you live?

  A: In New York.

  Q: Whereabouts? I don’t know whether you live in New York or Pekin. Where do you live; what is the address?

  A: Where I am living now?

  Q: I know where you are living now.

  A: I am living over in the Tombs.

  Q: Yes, I know where you are living now. Where were you living when you were arrested, before you were put in the Tombs?

  A: I was living in Thirteenth Street … or Tenth Street.

  Q: What number Tenth Street?

  A: I don’t know the number.

  Q: When did you move from Tenth Street to 2060 Second Avenue?

  A: About a couple of days before I got arrested.

  Q: Did you ever live at Richmond Hill?

  A: Yes, sir.

  Q: When?

  A: I lived there last summer.

  Q: How long?