by Mike Dash
All this meant that Bald Jack had a broader experience of life than did most downtown gamblers, including Rosenthal himself. But he might have remained simply another East Side ne’er-do-well had it not been for the fantastical appearance that made him unforgettable. Without the hat that he habitually wore to disguise his bizarre features, Rose looked disconcertingly vampiric, with a long and narrow skull, tightly wrapped in the chalk white skin of a New York nightbird, a sharp nose, and vivid, bloodred lips. His slitted eyes were a mesmerizing amber color and—set deep in a snakelike face—conveyed the impression of intense cunning. As for that uncompromising nickname,
it involved no hyperbole. As a result of a childhood illness,*37 he had no eyebrows, no eyelashes and not a hair on his head. One of his subsidiary nicknames was Billiard Ball Jack. To cut down the shine, he wore his poll thickly dusted with jasmine-scented talcum powder.
Rose had one obvious reason for hating Rosenthal: He had lost his job when Herman’s faro club was closed. But there was more to his antipathy than that. For one thing, Lillian Rosenthal was in the habit of insulting Bald Jack’s wife, who had once worked as a prostitute; whenever the gambler complained of being short of money, she was wont to snap, “Why doesn’t Hattie go back to her old business?” For another, Rose was a man of amorphous loyalties, who had run a stuss house on Second Avenue in partnership with Beansey Rosenfeld and was friends with Bridgey Webber. Perhaps most significantly of all, however, Herman’s onetime employee was also a known stool pigeon—a police informant—who had long passed tips to the cops. He was recognized in the downtown precincts as a man ready to protect his own business interests by “ratting” on other fellow gamblers. And it was in this capacity that Rose had met Lieutenant Becker.
According to Bald Jack’s own account, he had first encountered the head of the Special Squad in August 1911, when a club of which he was part-owner was raided. The next day, Rose drew Becker aside at the Exeter Market Court and offered to become an informant if the policeman would agree to throw out two unexecuted warrants against the club, which could otherwise have been used to raid the place again at any time. Becker agreed, and he also arranged to have the case that he was bringing against the gambler thrown out in exchange for a bribe of $200.
After that, Rose said, “We grew quite chummy,” and it was not long before Bald Jack was coopted as one of three collectors Becker kept hard at work, doing the rounds of gambling houses and gathering protection payments that he could not be seen to solicit himself. Bridgey Webber helped out, too, Rose claimed, and their “customers” included Sam Paul—who paid $300 a month—and another downtown gambler known as “Dollar John” (“a sneaky little rat—sharp eyed—and a framer”), who parted with the same. If Becker paid his collectors at the going rate, Rose would have retained as much as 25 percent of the cash he gathered, a sum that might have amounted to nearly $20,000. Whatever the truth, the gambler could certainly afford to move, at about this time, from his old apartment on East Seventh Street up to 110th Street in Harlem, which in those days was one of the most genteel addresses in Manhattan.
“All was going along smoothly,” Bald Jack’s account continued, until Becker met Herman Rosenthal and decided to go into business with him. When Becker needed a trusted man to watch over his investment in Herman’s faro house, he arranged for Rose to be installed as manager, and the gambler kept watch to ensure that his boss received a fair cut of the revenues. But this arrangement ended with the closure of the club. By then, Rose concluded, “Herman was growing desperate; he began threatening to tell what he knew.”
It is easy to see how, from the Bald Jack’s point of view, Rosenthal’s story might prove lethally embarrassing. For one thing, Rose might go to jail for the part that he had played in organizing Becker’s vast extortion ring. For another, Herman knew enough about Bald Jack’s sideline as an informant to plunge his sometime enemy into trouble with some wronged and unforgiving men.
Rose was for the most part a cool, clear-thinking opportunist. He had stayed in business by steering clear of trouble and seizing his chances as they arose. Had it not been for his own heavy involvement in the Rosenthal affair, he might have perceived that Herman’s threats were mostly bluster and recognized that his old boss had no evidence to prove his allegations.
But Rose was involved, and for once he failed to think things through. The prospect of exposure, jail, and ruin panicked him. Sometime toward the end of June, he went to see Jack Zelig.
Zelig was one of the great men of the New York underworld. Though only twenty-four years old, he was an influential figure on the East Side, thanks in part to his prowess as a fighter and in part to his considerable ruthlessness. The Zelig gang controlled a swath of territory along Second Avenue and was heavily involved in numerous rackets, including the collection of protection money from stuss houses and pool rooms. Like most of the hoodlums of the day, they felt more at home flitting between the tenements downtown than they did amid the tawdry glamour of Satan’s Circus. But they could be hired, by those with the appropriate connections, to act as enforcers anywhere in the city. To an East Side man like Bald Jack Rose, they seemed the obvious solution to the problem posed by Herman Rosenthal.
Gangsters of Zelig’s type had appeared in New York only recently. True, street gangs had been a feature of the city since at least the 1820s, when bands of thugs with names such as the Chichesters and the Roche Guard coalesced in the Five Points. These gangs and their great rivals, the Bowery Boys, became notorious south of Fourteenth Street, though they attracted little notice elsewhere in the city until a daylong battle fought between the warring factions in 1857 left twelve men dead and was ended only—after several fruitless police charges—by the intervention of two full regiments of infantry. But, violent as they were, these early hooligans were rarely professional criminals. Most of the Bowery Boys, and many of the Five Pointers, worked for a living, perhaps as carters, printers, or saloonkeepers, and the crimes they did commit were seldom serious. The slum gangs were also avowedly political, gathering at saloons controlled by district bosses, owing allegiance to one or another of the factions of the day, and intimidating opposition voters at election time. Most came into existence to help defend a neighborhood against external threats, whether posed by rival thugs or the police. They were organized along national or religious lines and spent a good deal more time fighting one another than they did preying on ordinary citizens.
It was not until sometime in the 1870s that gangsters, in the modern sense, appeared in Manhattan. The first group to consist principally of full-time criminals may well have been the Whyos, who congregated at Big Tim Sullivan’s saloon on Chrystie Street and were Democratic partisans at election time. Unlike their notorious predecessors, however, few Whyos had conventional jobs. Those who worked did so as “dive owners, and brothel and panel-house keepers.” The remainder made a living as pickpockets and thieves.
The Whyos faded from view around 1895 and were succeeded by a pair of gangs headquartered off the Bowery. To the west of the old street lurked the Five Pointers, who were predominantly Italian (Paul Kelly, their brainy, Irish-sounding leader, had been born Paolo Vaccarelli). To the east lived Jewish gangsters led by Edward Osterman, a muscular street tough better known by the anglicized version of his name, Monk Eastman. Kelly, the abler of the two, was good-looking and personable, spoke three languages, looked like a prosperous bank clerk, and was clever enough to take no active part in his gang’s more thuggish activities. Eastman, on the other hand, was slow and “so crude in appearance that he could model for the stereotypical crook who has continued to show up in cartoons down to the present day.” The gangster had “a bullet-shaped head, a broken nose, cauliflower ears, prominently throbbing veins,…pendulous jowls, and a bull neck,” and his body bore the scars of so many knife and gunshot wounds that a doctor who once examined him inquired whether he had seen action in the Spanish-American War. (“No,” grinned Monk. “Just half a dozen little wars down on the
East Side.”) Viewed from this perspective, Eastman—all brawn and little brain—can be seen as the last of New York’s old-style gang leaders and Kelly as the first of a new breed of smaller, brighter, faster-thinking hoodlums who combined at least a degree of restraint with better long-term planning. It came as no surprise to those familiar with both men that Monk ended up in jail, serving ten years for a botched street robbery, while his rival retired gracefully to Harlem, dying, in 1936, as a respected citizen.
It was in Monk Eastman’s day that gangsters first began to make big money in Manhattan. They ran dance halls and beer dives, worked as pimps and procurers, organized downmarket stuss games, and extorted protection payments from more respectable gamblers. A few sold drugs. And as workers throughout the city unionized and began to fight for improved conditions and wages, Paul Kelly and a Jewish counterpart known as “Dopey Benny” Fein perfected the art of labor racketeering, organizing new unions, infiltrating others, and threatening costly strikes and sabotage against employers who refused to pay them off.
The advent of so much easy money changed the New York underworld forever. The Eastmans and the Five Pointers were the last of the large gangs. Their successors were smaller, less stable, more aggressive groups, led by ambitious minor thugs who fought endless wars among themselves. Kelly’s successors included a pair of violent saloonkeepers named Jack Sirocco and Chick Tricker; Eastman’s was one Max Zweibach, better known on the East Side by the sobriquet “Kid Twist.” Twist did not last long; he was shot down outside a Coney Island music hall in May 1908. Sirocco and Tricker survived him, but neither man commanded the loyalty of more than a handful of followers. The rest of Kelly’s men joined other gangs or set up on their own. Some up-and-coming toughs had no firm loyalties, hiring themselves out to one group or another while also working for themselves. And, at about the same time, the racial loyalties that had bound together so many nineteenth-century gangs also began to dissolve. It was no longer utterly unheard of for an Irishman to work for an Italian gang or an Italian for a Jew. By 1912 gangland was more fragmented than it had been for half a century, which made it easier than ever for a ruthless, charismatic man like Zelig to scrabble his way to a position of some power in the city.
Zelig himself was an interesting study. His real name was Selig Harry Lefkowitz, and he was born, most accounts agree, into a fairly well-off family on Broome Street, in the heart of the tenements. As a youth (an East Side police detective testified) the future gangster was “not a bad boy at all—not a tough guy, I mean,” and Jack could no doubt have pursued a respectable career had he wished to. By the time that he was twelve, however, Zelig had already succumbed to the lure of crime and was working Second Avenue as a “stall,” a boy whose task it was to jostle the chosen victim of a “tool”—that is, a pickpocket. He was good at the job and soon picked up the tool’s skills as well. Even at his apogee, in 1912, Jack was still capable of seizing a good chance to rob a victim. He was, wrote the private detective Abe Shoenfeld, an expert on East Side crime, “known as a very good tool and a very good stone-getter*38 —perhaps one of the best in the world.”
Zelig attributed his own fall from grace to a childhood love of marbles: “One of the worst things a small boy can do is play marbles for keeps,” he told one reporter. “That is the thing that started me wrong. It gives a boy his first taste of gambling and gives him an idea of getting something without working for it, which is a mighty bad thing to get a taste for.” But to many of his contemporaries, he seemed made to be a gangster. He was tall for the period, at five feet eleven inches, clean-shaven and slimly built, with a handsome oval face spoiled by a squashed and broken nose. He was also markedly intelligent, always elegantly dressed in suits, high collars, and straw boaters, and reputedly a decent conversationalist. These characteristics were, however, secondary to his prowess as a fighter. According to one police detective, Zelig was “bandy legged” and “raw boned,” had “healthful dark fearless eyes [and a] splendid disposition.” According to another, he was the toughest man on the East Side, as handy with his fists as he was with a gun. One contemporary who knew him well explained in cheerfully mixed metaphors that the Zelig of 1912 was
a fighting terrier—the man is a demon when his blood is boiling. He can fight fifty men at once if he has them in front of him and is not taken unawares. In other words he is a wild cat. When in action he plants his feet firmly, throws out his chest (he has no stomach at all but is all bone and muscle) and when he hits with his fist it descends like a lion’s paw.
It was this reputation as a brawler that first enabled Zelig to establish himself at the head of a gang. He had been little more than an anonymous sneak thief when, in 1910, he found himself surrounded by members of a rival gang while sitting down to dinner in a Chinatown restaurant. Most gangsters of the day would have beaten a hasty retreat or summoned aid. Not Zelig. Sitting alone and unprotected, the East Sider “single-handedly took on, beat up, and knocked out three of the neighborhood’s most feared Italian gangsters in front of an astonished crowd of hoodlums”—the first decisive victory ever recorded by a Jewish man over the Mafia. In the annals of East Side crime, Zelig’s achievement was notable in itself. But it was what the former pickpocket did next that set him apart from his contemporaries. Rather than simply boasting of his victory, or even attempting to exploit his rivals’ momentary weakness, Zelig formally declared a vendetta against the presence of “foreign” gangs in the Jewish areas of Manhattan. News of his announcement caused a sensation in the closed world of Second Avenue, where storekeepers and ordinary pedestrians had grown increasingly used to being harassed by Irish or Italian thieves and muggers. Word that Zelig was actually making good on his promise sent the gangster’s stock soaring even higher. Within a few months, the former pickpocket and his fast-growing gang of followers had driven so many Italian and Irish gangs out of the East Side that even honest citizens acclaimed them. Jonah Goldstein, then a lawyer, later a New York judge, wrote that the gangster had “rendered a public service,” and the balls that Zelig and his men held at the popular Arlington Hall were patronized not merely by criminals, as was usual at the time, but by respectable Jewish businessmen anxious to show support and gratitude for the man who, in Abe Shoenfeld’s encomium, “was the great emancipator of the East Side.” Zelig, the private detective added,
cleared the East Side dance halls and academies of Italian pimps,…cleared the East Side of Italians who were wont to hold up stuss houses and legitimate business places,…and prevented more hold-ups and other things of a similar nature in his career than one thousand policemen.
By 1912, when he was first approached by Rose, Zelig was at the height of his powers, and his popularity on the East Side was unrivaled. He had a well-developed sense of his responsibilities and was married, with a son (his wife, many East Siders were surprised to learn, was Christian, a former good-time girl named Henrietta Young). Even the police seemed powerless to stop him. Charles Becker, for one, had tried; during his days with the anti-gang Special Squad, the lieutenant had arranged for two of his men to concoct evidence against the gangster in an attempt to get him jailed for carrying a concealed weapon. Fortunately for Zelig, the attempt was a clumsy one. The gangster had swiftly been discharged and was pictured leaving the police court with a broad grin on his face.
Exactly what passed between Rose and Zelig is unknown. Bald Jack was well known on the East Side, and Zelig must certainly have been aware that he worked as a collector of graft for Becker. Possibly he was at least reluctant to involve himself with one of the policemen’s men. But Rose was offering a substantial sum—$1,000 or $2,000 it seems—to have Rosenthal disposed of. Even $1,000 was a lot of money to most East Side gangsters; low New York thugs would kill a man for change, and even Zelig had murdered for $100 or less.*39 It does not seem to have taken Zelig long to accept the commission.
Rose’s money was enough to buy the services of experienced assassins, and the four men Zelig supplied were certai
nly among his best. The best shot was probably Louis Rosenberg, a young, left-handed gangster known throughout the East Side as “Lefty Louie” he had killed at least two other men. Jacob Seidenschmer—better known as “Whitey Lewis”—sometimes worked as Zelig’s bodyguard; he “had been a third-rate pugilist, but under Jack’s tutelage he became a blackjack artist of rare merit.” The third man, “Dago Frank” Cirofici was—at least according to Val O’Farrell, a noted Central Office detective—“the toughest man in the world” and had, the writer Herbert Asbury recalled, “a girl called Dutch Sadie, who was also a noted fighter; she carried a huge butcher knife in her muff, and frequently employed it to good effect when her lover was hard-pressed.”
The leader of the little group was another East Side thug—a small, deceptively slight gunman known familiarly as “Gyp the Blood.” Gyp—whose real name was Harry Horowitz—was then a part-time dance-hall “enforcer” and leader of a group of burglars and pickpockets working around 125th Street. He owed his memorable nickname not so much to any act of savagery as to the combination of a swarthy, Romany complexion and a taste for fashionable clothes. But Gyp was certainly no less brutal than his three companions. “What time he was not working on commissions for Jack Zelig,” notes Asbury,
or robbing drunken men in the Bowery dives, Gyp the Blood was a sheriff and gorilla at the cheap dances of the East Side; he soon became known as the best bouncer since Monk Eastman and “Eat ’Em Up Alive” McManus, which was no light praise. He possessed extraordinary strength, and frequently boasted that he could break a man’s back by bending him over his knee. Moreover, he performed the feat several times before witnesses; once, to win a bet of $2, he seized an inoffensive stranger and cracked his spine in three places. He also became an expert revolver shot, and was extremely accurate at throwing a bomb, a task in which he delighted. “I likes to hear de noise,” he explained.
