by Neil Hanson
Despite the harshness of the regimen and the totality of surveillance under which they lived, inmates at Sing Sing, as at every other prison, showed enormous ingenuity in producing rotgut alcohol, which made its “odiferous appearance” despite the most stringent regulation and supervision.44 Those found in possession of alcohol or under its influence had a further ninety days added to their minimum term, but this had little deterrent effect. There were also other soporifics; a Jewish chaplain, Rabbi S. Braverman, was dismissed after he confessed to smuggling opium into the prison and selling it to inmates. Three guards were also fired for smuggling money to prisoners from their friends and relatives; some of that had no doubt found its way to the rabbi.
The electric chair had been introduced to Sing Sing as early as 1891—four prisoners were executed by that method on July 7 of that year—but the legend that the lights would dim when the electric chair was switched on was apocryphal; the power for executions was generated solely for that purpose.45 In the gallows humor of the jail, inmates called the execution block “The Dance Hall” because the night before an execution, guards played the condemned man’s choice of music on a phonograph.
Conditions at Sing Sing were so grim that after visiting the prison, Sir Arthur Conan Doyle’s recommendation was brief and to the point: “Burn it down! The buildings are absolutely antiquated and it is nothing less than a disgrace for a State so great and wealthy as New York to have a prison which is a hundred years behind the times.”46
With Monk rotting in Sing Sing, his gang was now literally beyond his control, and at once the Eastmans began to disintegrate into rival factions fighting for dominance. Within four days of Monk’s journey up the river, two aspiring young leaders of the gang, Otto Bennett and Morris Rothschild, met in a vacant lot at Second Avenue and First Street and fought what began as a street brawl but was finished under Queensberry rules. They had fought three rounds, and the succession to the powers of Monk was still in doubt, when “some alarmed and unsportsmanlike citizen” telephoned police headquarters.47
Captain McDermott left the police station in such a hurry that he forgot to take his hat. Three detectives followed him, running the four blocks to the scene of the fight, with a dozen reserves chasing after them, as soon as they had grabbed their coats and nightsticks. Even this sizable force had difficulty pushing its way through the mob surrounding the combatants, and as soon as they did, the fighters and their seconds turned on them. Rothschild attacked Detective Wasserman, and in the process of subduing him, Wasserman “did some fist work himself; as Rothschild’s face bore witness when he was arraigned at the station.”48
As well as young bloods like Bennett and Rothschild, Monk’s chief lieutenants, Kid Twist and Richie “Kid” Fitzpatrick, inevitably fell out over the division of the spoils from Monk’s empire. Fitzpatrick had just had an altercation that left Thomas McCauley in Gouverneur Hospital with a bullet in his hip when Kid Twist issued an invitation to a meeting to settle their differences in the back room of a Chrystie Street dive—probably The Palm. Fitzpatrick was naïve enough to accept the invitation. One of Twist’s hatchetmen, Harris Stahl, was lying in wait, and Fitzpatrick was shot in the heart.49 He sank to the sidewalk unconscious and died before he reached Gouverneur Hospital. Twist then had five more of Fitzpatrick’s men killed within a week.
As usual, hostilities were suspended while the November elections were in progress and, even without their jailed leader, the Eastmans showed they had lost none of their abilities as sluggers and repeaters. “Old-timers … rubbed their hands with glee,” claiming that it was just like an election from the old days, as gang members intimidated and attacked voters and police who tried to intervene.50 “Florrie” Sullivan, Big Tim’s cousin and Tammany protégé, made the breathtakingly disingenuous claim that one of the Republican district captains had hired the gang in return from a promise from Governor Odell that he would pardon Eastman after the election, which drew a withering rejoinder from Judge Otto Rosalsky: “Then how does it happen that only Republican voters and workers are assaulted?”
With the election over and his chief rivals killed or intimidated, Kid Twist set about consolidating his power. Bringing an even more ruthless efficiency to the operations and rackets that Monk had established, Twist extracted more money from the districts he controlled. One of his new scams was to force all the small refreshment and confectionery stores to buy a so-called celery tonic from him at a suitably inflated price.51 He wrecked the premises of anyone foolish enough to refuse to stock the tonic, and some store owners were murdered as a warning to others. Twist was also implicated in the murders of a Five Pointer, Dick Fitzgerald, and “Big Butch,” a poolroom hanger-on, and at least two other murders on the East Side were widely assumed to have been carried out on his orders. He was arrested for both murders and for dozens of other offenses, but he was always discharged.
Kid Twist lasted four years as undisputed ruler of the Eastmans, but on May 14, 1908, a Five Pointer named Louie “The Lump” Pioggi shot Twist dead, along with his lieutenant Samuel Pletch, a professional wrestler and circus strongman also known as “Bat Lewis” or “Cyclone Louie,” as they were dining with two women at the South Brooklyn Hotel at Coney Island. One of the women, Carroll Terry, a singer in the Imperial Music Hall in the Bowery, had been living with Pioggi but was now Twist’s girl.52 According to one account, Twist had taunted Pioggi about her earlier that evening, then drew a gun and forced him to jump from a second-story window. Backed by a group of Five Pointers, Pioggi returned two hours later, limping on a damaged ankle, to claim his revenge.
The crowds thronging Oceanic Walk on that warm spring evening heard nine pistol shots, followed by the screams of a woman. An instant later, Kid Twist and Bat Lewis staggered through the swinging doors of the barroom and fell dead on the floor, beneath a huge floral horseshoe presented to the proprietor to commemorate the opening of the hotel the previous day. Kid Twist had been killed by a single shot behind the ear; Bat Lewis’s body “held six bullets in his left arm, groin, and hand, and in his right arm and breast, as well as another behind his ear.”53 The source of the dispute, Carroll Terry, was also shot in the arm. “I wouldn’t have anything to do with him [Pioggi],” Terry told police as she recovered in the hospital, “and he got angry. I suppose he must have been following me today, for when we all left the restaurant he was standing in the doorway. He struck me with his fist and knocked me down, and then he drew the gun. He fired at the men and I saw them fall, and then he shot me.”
Pioggi was arrested, convicted of the shooting, and sent to Elmira prison for at least a year, though in an era when drunkenness or vagrancy could be enough to earn a six-month stretch on Blackwell’s Island, twelve months for a double murder seemed a curiously lenient sentence. After his release, Pioggi was arrested for carrying a concealed revolver. Facing another prison term, he was released on a four-thousand-dollar surety put up by a prominent Tammany alderman and promptly jumped bail. “The spectacle of a thug hurdling a four-thousand-dollar bankroll to liberty gives a true idea of the lush days in which the New York gangster now lives.”54 An even truer idea was given when it was revealed that Kid Twist—a man who had never held an honest job in his life—had left a fortune of fifty to a hundred thousand dollars.55
Although the Eastmans were in decline and riven by internecine warfare, Paul Kelly largely failed to profit from his rivals’ turmoil. Kelly’s Five Pointers had staged a show of force in the summer of 1905, smashing plate-glass windows, robbing a bar, a fruit stand, and a coffeehouse, and beating and intimidating passersby within fifty yards of the police headquarters on Mott Street; “evidently the gang wanted to make the police understand that it could operate right under their noses.”56 But it was a hollow gesture, and Kelly himself was a marked man. During the course of that year there were two attempts to kill him. In the first, a man hiding in a doorway plunged a stiletto into his back. He was taken to Gouverneur Hospital and survived, unlike his bodyguard, “Jack�
�� McManus, also known as “Eat ’Em Up” and “The Brute,” who was hit on the head with an iron bar and died in Bellevue Hospital.
Kelly had barely recovered when, in November 1905, “Biff” Ellison—reputed to be able to kill a man with a single blow of his fist—“Razor” Riley, and another man, a prizefighter, raided Kelly’s headquarters at Little Naples, a saloon down the street from the New Brighton Dance Hall. Kelly took three bullets, but despite his wounds, he was “last reported as running down the Bowery, hatless, in the direction of the Occidental Hotel”—Big Tim Sullivan’s saloon.57 One of Kelly’s gang members was killed in the attack, and when a patrolman passed on his rounds in the early hours, he found Kelly’s bar—usually full of light and noise—dark and deserted. The mahogany bar bore the scars from large-caliber bullets, and the brass rail at the foot of the bar was bent and broken; the dead man’s legs were protruding from a closet and the only signs of life were “a lurking cat, a loud ticking clock, and the usual huge portrait of The Big Feller—Big Tim Sullivan.”
Kelly was hurried to the hospital, and though he again survived the attack, he came under increasing pressure from the police, who were now being forced to act against the gangs. The Great Jones Street saloon was closed down on the personal orders of Commissioner of Police William McAdoo, and the Five Pointers went into decline. Seeing the writing on the wall, Kelly’s gang migrated from Five Points to the neighborhood of Seventh Avenue and Forty-first Street, and Kelly himself moved his operations even farther uptown, to a house on East 116th Street owned by Ciro Terranova and members of the Morello family.58 In the less actively policed districts of Harlem and Brooklyn, Kelly then established himself as a labor-union organizer. He brought together some previously ununionized workers in the Garbage Scow Trimmers’ Union, and used that power base to gain the vice presidency of the International Longshoremen’s Association. Although Kelly changed his name back to Vaccarelli and liked to portray himself as a reformed character and a respectable union man, he kept his underworld links and his gang methods, maintaining a link between organized crime and some branches of organized labor that continues to this day.
10
A NAPOLEON RETURNED FROM ELBA
Although Monk was still behind bars, his former Tammany protectors had not given up hope of obtaining the release of the best man they ever had at the polls.1 They made continuing efforts to free him, but his release, when it eventually came, was not the result of Tammany influence. Instead, it was a new law that made any first-time prisoner—no matter how many offenses he might actually have committed—eligible for parole after completing half his sentence. After five years in Sing Sing, Monk was accordingly granted early release by the State Board of Parole. He would have been granted remission of one-third of his sentence for good behavior, anyway—he was described by the prison governor as a model prisoner—but the new law brought him his liberty even quicker than that.
Announcing the decision to free him, Judge George A. Lewis, who chaired the meeting of the parole board, conceded that Monk had lived a notoriously rough life before being sent to Sing Sing, but in prison he had “conducted himself admirably.2 Monk is a man of intelligence and of great force for either good or bad … He would have got his liberty in thirteen months anyway, so why not let him earn his living outside of prison? If he makes a mis-step, back he goes to Sing Sing, and he knows that.”
However, Lewis added that men of Monk’s type rarely became parole violators, as “one of his intelligence and marked individuality [a polite reference to his memorable physiognomy] would find ultimate escape too improbable and difficult, and existence in the role of runaway convict intolerable.” Lewis also cleared up the mystery of Monk’s origins, stating that he was of Anglo–New England stock, not an Irishman as had been stated in the press, nor a Jew as many others had believed, but for whatever reason, the New York City police continued to regard Monk as an Irishman whose real name was William Delaney.
When the great gates of Sing Sing opened to release Monk into the hot, still air of a June morning in 1909, there were no wife and children waiting to greet him. What had become of Margaret Eastman is unclear. Unless she had access to at least some of the proceeds of Monk’s criminal activities, her financial position would have been dire after he was sent to Sing Sing. Her husband cannot have been the easiest of marriage partners, and it is possible that she either tired of waiting for him or seized the chance offered by his incarceration to make a new start for herself and her children elsewhere, or she might even have died. Whatever happened, she left no trace of her movements, and she and her children disappeared completely from Monk’s life. They were neither seen nor heard of in the Lower East Side again, and their fate remains a matter of speculation.
None of Monk’s old acolytes had made the journey to Sing Sing to greet him, either, and instead he was met by his new employer, a farmer who had offered work, which Monk was willing to accept. The terms of his parole required him to report to the local police in Albany for more than a year, during which time Monk was supposed to be working on the farm in Dutchess County. However, after an abdominal operation while in prison, he was no longer very robust, and in September 1909 he walked into Harlem Hospital and asked to be operated on immediately for “some internal trouble which was causing him agony.”3 Doctors put him on a diet to build up his strength enough to face the ordeal of an operation. The surgeon examined Monk before the operation and was astonished by his patient’s forest of scars, stab and bullet wounds, and “a wound under the right eye evidently made by some blunt instrument.” He asked Monk how he had come by them.
“Oh, I’ve been in war,” Monk said.
“The Spanish war?”
“Oh, no. Half a dozen wars down on the East Side. I’m Monk Eastman.”
While Monk recovered from the operation, plainclothes policemen stood guard outside the hospital, though none of them would say why they were posted there. Such round-the-clock police protection was normally given only to important witnesses or police informers, and it raised tantalizing questions about their presence. They may have been responding to a threat against him, or trying to pressure him to become an informer. If so, they were putting his life at more, not less, risk. If word reached Monk’s former gangland associates that he was under police protection, the mere suspicion that he might be informing would be enough to ensure a contract on his life. In any event, the police guard ceased without explanation as soon as Monk was discharged from the hospital. He did not return to the farm and instead found less physically taxing work in Albany, living under an assumed name.
At the end of his parole period, on October 21, 1910, Monk told the chief of the Albany police that he was going to New York to see some of his old companions and then intended to go to “the wild and wooly West.”4 Whether that was his true intention is dubious: it was hard to believe that Monk would have left his Tammany backers on the eve of an important election. The police were unsurprised when they learned a few weeks later that Monk was again active around Chrystie Street and the Bowery, “a Napoleon returned from Elba.”
However, if Monk planned to resume his gang activities, he found a different New York awaiting him. Gang leaders sentenced to a long stretch in prison often emerged “stone broke, with the remnants of their little world toppling about their ears,” and when Monk reached the Lower East Side there were few friends or gang members to acclaim his return or flock to his standard.5 As the head of the detective bureau remarked, “Most of his old mob is gone and all those gangs are under the table now.”6
Although there were reports that Monk had set up an opium joint, a trade he was said to have learned as a “lobbygow” in Chinatown, police took his return to the city with apparent equanimity.7 “He won’t want to show his face around here for a while,” one said, “and when he does, he’ll behave—he’s had his lesson. The first cop that sees him will pick him up on general principles, so the new men can take a peep at him. They’ll need only one look—he�
�s got a face you won’t forget.” Police also warned that if Monk went back to his old gangland ways, he wouldn’t be handled with kid gloves.
Meanwhile, there were new political and gang bosses on the streets, and new gangsters like Nathan “Kid Dropper” Kaplan—who used a can opener to “carve guys up.”8 There were new ways of doing things, too; it was reported that some members of the Eastmans and other gangs had become chauffeurs who, when off-duty, used their automobiles for quick getaways after robberies and shootings.
Many of Monk’s former lieutenants were in jail or dead.9 Jack “Eat ’Em Up” McManus, Kid Twist, and “Red” Harrington had all died; “Humpty” Jackson was in jail; and those who remained, like “Big Jack” Zelig, no longer owed any fealty to Monk. Zelig now controlled a faction of the Eastmans, enforcing his rule through a group of killers who were vicious even by the standards of that era. “Lefty” Louis Rosenberg, “Dago” Frank Cirofici, and “Whitey” Lewis were all cold-blooded, but even they paled beside Harry “Gyp the Blood” Horowitz, whose horrific party trick, often performed for no other reason than to win a couple of dollars in bets, was to break the back of a hapless victim across his knees, leaving him flopping on the floor, gasping out his last breaths like a fish out of water.
Monk was also a less imposing figure than in his heyday. He was now almost thirty-seven, an old man in gang terms; very few gangsters, pimps, and prostitutes were in their thirties, and virtually none were in their forties.10 Five years of hard labor, bad food, and bad conditions in Sing Sing and the stomach complaint that had caused him to have two operations had left their mark on him. According to one report, he had also begun using opium, further weakening him, and when a gangster lost his strength and his reputation as a “hard man,” he lost his principal business asset.
