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

by Neil Hanson

  A: I raised my pigeons out there.

  Q: I didn’t ask that. How long did you live there?

  A: I go over there and sleep there.

  Q: Off and on?

  A: Yes.

  Q: Visit your sister?

  A: Yes.

  Q: When did you stop living there last summer?

  A: Well, I stopped … I didn’t stop living there. I go over there and when I go over there, I sleep there.

  Q: Let us be frank about this. Has Richmond Hill ever been your residence?

  A: Not mine exactly, no.

  Q: All right, not yours exactly.

  A: No, sir.

  Had the police been able to establish his real address, they would immediately have raided the building and would undoubtedly have found his tools of trade—weapons and burglary equipment, and very probably some of the proceeds of his crimes and rackets. Even if the cash disappeared straight into policemen’s pockets, the weapons and robber’s tools alone would have been enough to earn him another trial and a long spell in jail.

  Monk’s defense rested on his claims that he and Wallace had merely been drinking with friends, first at McDermott’s gin mill in the Bowery near Stanton Street, and then at Sig Cohen’s on Forty-second Street. By the time they left there at two or half past two in the morning, they had been drinking for six to seven hours. By then Monk had “twenty glasses of lager” in him, though he still claimed he was not drunk.20 He said that as they came out onto the sidewalk there was a scuffle and they “started to rumble around … and I says, ‘There will be some trouble,’ so I kept a-going and a-going; and when I got a little ways, I looked up and saw a crowd gather and heard two shots fired.” He said he was walking toward Broadway when “Wallace came running past me, and I ran too. I wanted to get away in the excitement and when I went to run down [into the subway], I slipped downstairs and an officer was after me and picked me up, and I says, ‘What is the matter?’ and there was a lot of them there and a lot of citizens and they started to hit me there.”

  Monk claimed that he had run only because he did not want to be caught in a fight, as the police were always persecuting him. He denied that he ever carried, drew, fired, or threw a pistol at any time that night, or that he was ever closer than twenty feet to Bryan. He also denied shouting at Bryan, “Let go of him, you God damned son of a bitch, or I will kill you.” Having already claimed not to have seen anything of the shooting until Wallace came running past him, Monk then appeared to forget his earlier testimony when trying to exonerate Wallace: he claimed that Bryan had put his gun under Wallace’s arm and “held Wallace in front of him and kept shooting in the crowd.”21

  The trial lasted three days. Summing up for the defense, George W. Hurlbut said that Monk did not want sympathy but mercy, and told the jury that they must “wonder at the nerve of the district attorney in not producing ‘the wayward son of a man prominent in national affairs’ who had caused all the trouble … Better that he should have been produced and suffer humiliation than that an innocent man should be sent to prison.”22 Hurlbut claimed that there was a police conspiracy to send Monk to prison and that there had been no drunken youth, as the prosecution had claimed.

  Rand countered that the sole reason for not producing “the wayward son” was that he had been so drunk that night he did not even know he was being robbed and would have been useless as a witness. Summing up for the prosecution, Rand declared, “Never in my experience have I known of such a scoundrel, burglar, thug and self-confessed perjurer as this Eastman.”23 An ugly light gleamed in Monk’s eyes as he listened to this, but he looked away as Rand turned and pointed at him.

  The jury spent two hours deliberating over their verdict, and on the three ballots that were taken, eleven were in favor of a conviction on the more serious charge of attempted murder in the first degree. However, one juror refused to assent to the verdict, since it carried a possible sentence of twenty-five years’ imprisonment. He insisted he would not change his mind no matter how long his fellow jurors argued, and after two hours, they filed back into court. Monk searched their faces for some clue to his fate; most of them avoided his gaze.24 The foreman then delivered their compromise verdict: guilty of assault in the first degree. Monk looked stunned; “in the language of his friends, he was ‘all out.’ ” However, as he was being led back across the Bridge of Sighs to the prison at the Tombs, he managed a show of bravado for the police and the prison wardens. He stopped suddenly as he heard the music from an Italian funeral, pulled off his hat, and said, “Thanks gents, for this flatterin’ serenade. De tune, ‘Nearer My God to Thee,’ is almost as ‘pro-priate as if I was going to de chair.”

  At the request of Monk’s counsel, Recorder Goff delayed sentencing for five days because Monk “had some property interests which he wished to settle before he went to prison”; it was as close as the famously tight-lipped Monk ever came to revealing the extent of his wealth. When Monk returned to court for sentencing on April 19, 1904, his counsel made no attempt to enter any plea in mitigation, instead telling the court, “I have ordered the defendant to serve whatever sentence your honor may impose as a warning to others … The defendant Eastman is not a well man.25 The life he has led has undermined his health but I hope he will be able to serve his sentence and when he comes out, he will be a better man.”

  Recorder Goff said that “the circumstances of the case and the need of conserving the public interests and deterring others of Eastman’s stamp” had led him to impose the maximum punishment the law allowed: ten years in Sing Sing.26 This time Monk remained impassive. Whether he’d been railroaded, as his defense counsel had claimed, or was rightly convicted was no longer of any consequence; as one newspaper reporter scathingly remarked, “Nobody begrudged the Monk the ten-year sentence he received, whether he went to Sing Sing by railroad or otherwise.”27

  Monk’s prime concern was allegedly neither his property nor his business interests, nor even his own fate, but that of his beloved pigeons, and he asked the court to allow him to remain in the Tombs for another week so that he could find someone to tend his five hundred pigeons. Despite his plea, Monk was due to be sent to Sing Sing that same day, along with a convict named George Coan and four other notorious thugs.28 At the last moment, when he and Coan had already been handcuffed together, the warden of the Tombs received a telephone call from the sheriff’s office, informing him that someone wanted Monk to remain a few days longer in the Tombs. It was difficult to imagine any other convicted prisoner being given such leeway; this suggests that Tammany, in its anxiety to ensure the loyalty of Monk’s successor, was engaged in last-minute negotiations with Monk himself.

  On the morning of April 22, 1904, with the gray stone walls above them still in deep shadow, two deputy sheriffs and three assistants led Monk and three other prisoners out of the Tombs. Smoking a big black cigar, Monk waved to the group of spectators and reporters watching as he entered the police van. “Well, I’m going now,” he said.29 “This is the last you’ll hear of Monk for a while.” They were driven to Grand Central Terminal, where a crowd that police estimated at five thousand people was waiting to bid farewell to the notorious Monk Eastman. As he was led from the van handcuffed to another prisoner, twenty or thirty plainclothes policemen were sent out to mingle with the crowd, while armed police formed a cordon around Monk in case of a last desperate attempt by the Eastmans to free their leader. By now, Monk’s mood had changed and his customary bravado seemed to desert him as he realized where his life’s path had led him. He glowered at the crowd, and in contrast to his earlier ebullience, refused even to acknowledge the smiles, waves, and shouts of the friends who had walked from the Lower East Side to the station just to catch his eye. As Monk stood silent, his fellow prisoner, handcuffed to him, stared at the throng of people surrounding them. “Holy smokes!” he said. “Gee, but don’t they give ye an awful weighin’ up when the jig’s over?”

  Monk and his fellow prisoners were put aboard the 2:06 trai
n, which would take them up the Hudson Valley to Sing Sing. As a contemporary remarked, “That hour goin’ up the river was the toughest I’d ever come to.”30 A few reporters made the journey as well, one noting that although Monk “buried his face in a newspaper, it is said that he cannot read.” When the train reached Ossining, Monk and his fellow prisoners began the slow, shackled walk along the road toward the main gate, past groups of prisoners breaking rocks on the hillside above them. At 3:15 that afternoon, beneath the watchtower like a squat lighthouse, manned by armed guards with rifles, the great gates of Sing Sing clanged shut behind Monk.

  The sprawl of gray granite prison buildings was set on a promontory surrounded on three sides by the river. Clutching at any straw of distinction for the dismal institution he ran, one of Sing Sing’s governors claimed the smokestack rising high above the prison was one of the highest prison smokestacks in the country. The four-story redbrick-and-steel prison hospital stood on a bluff above the prison, and “were it not for the iron bars that betray its purpose, this hospital would be the proud possession of any normal community.”31 In its foyer was the Latin inscription Nihil Humani Probis Alienum—“Nothing that is human is foreign to us.” From the heights around the hospital, just inside the perimeter wall, the wide sweep of the Hudson was visible for miles.

  Monk handed over his money and other valuables and was assigned a prison number: 54,863. His pedigree was then taken by the prison clerk. Monk gave his parents’ names, his date and place of birth, his religion, his occupation, the crime for which he was sent to Sing Sing, and the cause of it; “experienced cons answered ‘bad association.’ ”32 He was described on the record of admission as a tar and tin roofer who kept a bird store.33 He was married, his habits were intemperate, he indulged in tobacco but not religion, and he said he could not read or write.

  His next of kin was listed as his sister Lizzie Reynolds, living in the Richmond Hill house that Monk had bought for his mother. She was a puzzling choice, given that Monk was a married man, and perhaps suggests that his marriage to Margaret was already failing. His description ran to a dozen lines of the clerk’s spidery copperplate handwriting, as he tried to include as many as possible of Monk’s innumerable distinguishing features, scars, and bullet wounds:

  Complexion dark, Weight 167 pounds, Hair dark brown … good-sized head, 7 ⅛ hat, 7 ½ shoes. Several small scars on back head. An angle-shaped scar near rear of crown. Scar at crown, several small scars on left [?] side of head. Scars above right ear. Large diagonal scar, also a large scar shaped as a figure 9, back from upper rt angle of forehead. Large ears. Flat-sided head. Med. forehead. Good eyebrows. Short thick nose and broken. Two upper front middle teeth capped with gold. One tooth absent. Tough featured. Scar near left eye. Part faded cut [?] between index and forefinger each hand. Large, long ragged scar on right side of abdomen.

  Even then, the clerk missed some of the most prominent marks, including the two bullet holes in Monk’s stomach.

  Monk then got the usual bath, haircut, and shave, and donned a suit of prison clothes—shirt and trousers and a small round cap that must have sat on his large head like a frog on a lily pad.34 He was then interrogated by a representative of the Department of Correction and informed of the only two legal rights enjoyed by prisoners at Sing Sing: to attend whatever religious worship accorded with his beliefs and conscience, and to receive a specific food allowance. Everything else, including fresh air and exercise in the prison yard, writing or receiving letters, having visits, smoking, and all forms of amusement were privileges that could be awarded or withheld at the whim of the wardens.

  Sing Sing was the most notorious prison in America, a byword for brutality and corruption. Like the other eight hundred inmates, Monk was confined in a cell only seven feet long, three feet wide, and six feet seven inches high. Those cells, unimproved in eighty years, were “unfit for the housing of animals, much less human beings.”35 The cell block was so damp that one head warden said that when he rubbed his hand on the first-tier walls, seven feet above the water level, it came away damp. The cells smelled horrific and were infested with rats, cockroaches, and lice. Prisoners were locked in their cells with a latrine bucket from 5:30 p.m. until the following morning. On weekends and holidays they were locked up for twenty-one hours at a time. In such a restricted and poorly ventilated space the stink from the bucket was terrible at any time, and unbearable in hot weather. When the tiny cell was occupied by two people, as was often the case, the stench was doubled. Drinking water was also kept in a bucket in the cell and was subject to contamination. The conditions caused inmates to suffer chronic rheumatism and sometimes fatal heart disease, and many of them, serving sentences of from one to twenty years, left the prison permanently crippled.

  A grand jury found that the warden and head guard regularly put inmates who were “repugnant and dangerous to each other” in the same cell.36 Physically or mentally ill prisoners, including those with advanced tuberculosis or syphilis, were often paired with healthy men, and first offenders and young boys were condemned to share cells with habitual criminals or men who made a practice of sodomy.

  Inmates were also subjected to a prison regimen of a brutality matching the worst aspects of the society beyond the prison walls. “The whole system under which this institution is conducted … is pernicious … the prisoners are not reformed, they are merely penalized, and in the worst way.”37 Any breach of prison rules was punishable by solitary confinement in “the Cooler”—one of two padded cells or one of eight pitch-black, airless dungeons. In the Cooler, the inmate’s mattress was removed by day, and he could rest only on the stone floor or on his latrine bucket. Once every twenty-four hours he received a slice of bread and eight ounces of water; a 150-pound man requires a minimum of fifty ounces daily. As a grand jury reported, “This situation is as deplorable and pitiful as any we have found.38 So desperate is their condition that they have been known to drink their own urine, as well as the disinfectant placed in the cell buckets. As a result, some are driven insane, others attempt suicide.” A prison physician claimed that one of his main duties was to knock on the doors of the dark cells every day to discover if any of the occupants had succumbed to disease or madness.

  In theory any infraction of the rules, however minor, led to a spell in the Cooler, but the removal of men from the labor force reduced the profits from the prison workshops, so physical punishment was often substituted. There was no standard code of punishment, and the duration of beatings was simply left to the whim of the guards. Many went undocumented, but the prison records still contain a staggering catalog of whippings, “water cures,” stocks, “stretchers,” and “sweatboxes,” which continued well into the twentieth century.39

  The water cure, also known as “the bath,” was used for decades at Sing Sing to cow and terrify the inmates. In the worst variant of the punishment—a direct antecedent of waterboarding—the prisoner was hung up by his arms so that he was at full stretch, standing on tiptoes. A leather collar was placed around his neck like a noose and a torrent of water was then unleashed onto his head. Battered, half-drowned, and often unconscious, the man was then revived, but might face the punishment again and again, until the guards, sated, chose to cut him down. “It’s the leather collar that holds an’ galls you, an’ you strapped up by the arms with your toes just touchin’ the floor; an’ it’s the shower-bath that leaves you in a dead faint till another dash brings you out.”40 Prison records showed that 170 men received this brutal punishment in 1852; half a century later, there had been little diminution in its use.

  Even in 1920, when the reforming governor, Lewis E. Lawes, took over Sing Sing, he unearthed a catalog of brutality and abuses stretching back decades. Thirty-three male and twenty female prisoners had simply gone missing, presumably after bribing their guards to allow them to escape, and more than thirty thousand dollars in cash had been stolen from prison bank accounts.41 Swindles at Sing Sing and other jails, involving the substitution of n
ear inedible food for the meals paid for by the state, also netted the perpetrators several million dollars. Since food was scarce and of such appalling quality, inmates were often debilitated and prey to disease, and any man sent up the river to Sing Sing was aware that he might not survive.

  On the Monday morning after his induction, Monk experienced the full prison regimen for the first time. At 6:30 a.m. a strident bell sounded the start of the prison day. The night staff had already made a head count of prisoners, and this tally was checked by the morning shift. At seven a second bell signaled the moment when the brakes controlling all the iron-barred cell doors on each gallery were released. The prisoners at once stepped out and marched to breakfast—cornmeal, milk, bread, and coffee, ladled into bowls as the men passed the counter.

  At eight a steam whistle sounded, summoning them to work. Monk now began the grueling regimen of hard labor that made Sing Sing notorious. The first inmates had been compelled to build the jail that would confine them, shaping and laying blocks of Ossining granite. Convicts under punishment still broke rocks every day in the quarry, endlessly pounding with sledgehammers, reducing boulders to blocks, gravel, and rock dust, labor that broke men’s spirits as it drained their bodies. Some “trusties” were sent outside the prison on road gangs. The other inmates worked long hours in the prison “shops,” producing, among other things, highway signs, brushes, mattresses, pillows, government forms, letterheads, envelopes, socks, vests, shirts, straitjackets, pajamas, mittens, aprons, shoes, cans, and scrapers.42 These goods were sold to offset the costs of the prisoners’ incarceration.

  At ten to noon, the steam whistle blew again, summoning the prisoners to “noon mess.” They formed up in pairs and, in step to loud martial music played by the prison band, marched the length of the courtyard, around the death house, through the old south gate, up the hill, through the chapel, and along a corridor to the mess hall. There they ate lunch of a small piece of gray meat of doubtful provenance, mashed potatoes, turnips and brown gravy, bread and cocoa, and corn-starch pudding. Thirty minutes’ recreation was allowed in the prison courtyard after lunch, “an endless line of marchers, treading unending circles around the flower beds and the large fountain.”43 At ten to one the steam whistle summoned them back to work, where another head count was taken.