by Mike Dash
Sullivan and Rosenthal, one New York journalist recalled, “hit it off at once” when Herman renewed their acquaintance in 1900 or so, and before long, Big Tim had “made a special pet” of the aspiring gambler. In the course of the next decade, the Irishman would repeatedly advance Rosenthal funds, investing in various business ventures. No doubt that money was reclaimed with interest most of the time. But Herman’s career never ran entirely smoothly, and Tim was to lose several thousand dollars backing him. Few Tammany politicians would have tolerated failure on that scale. But the friendship that had grown up between Sullivan and Rosenthal never appeared strained.
Herman’s first job as one of Big Tim’s gambling lieutenants was as the proprietor of a small-time crap game on the East Side. He did well enough at this to set up as an off-track bookmaker in Far Rockaway, at the farthest extreme of New York’s public-transportation network, and for several years commuted daily from his home in Manhattan to Long Island. By now touching thirty, Rosenthal had grown into a garrulous and rather bumptious character, clean-shaven, with the remnants of good looks, but running increasingly to fat and more and more convinced of his own importance. Herman, his friends would recall, was always full of grand ideas for getting rich, a man whose vaulting ambitions were invariably beyond his reach.
Nonetheless, oddsmaking was one of the few occupations for which Rosenthal had ever shown real talent, and after a year or two under Tim’s protection he did begin to make a better living. By 1907 his little empire had expanded to include a string of poolrooms on Second Avenue, where the stretch of road between Houston Street and Fourteenth was known as “the Great White Way of the Jewish East Side.” He also moved onto the racetracks themselves, setting up betting stalls at Belmont and at Jerome Park. At about the same time, he took over the concession to run gambling at the Hesper Club.
Within a year or two, Herman became extremely rich. The gambler himself was heard to boast that he was worth $200,000, and it could scarcely be denied that he now maintained himself in style, with a suite of rooms in a Broadway hotel costing some $25,000 a year—a sum in itself fifty times the salary of the average New Yorker—and an amply indulged taste for fine food and expensive clothes. Viña Delmar, the observant nine-year-old daughter of one of Rosenthal’s oldest friends, remembered the gambler as “quite chubby…but dressed beautifully in a gray suit, a silk striped shirt, and a collar even stiffer and snowier than Papa’s.” Others, less tolerant and no doubt more jealous, spoke of Rosenthal as “a flashy, greedy, loudmouthed braggart.”
Unfortunately for Herman, his flush years did not last long. The flow of profits from the racetracks came to an abrupt end in 1909 with the decision of the state assembly in Albany to ban gambling on horse racing throughout New York—a new law that coincided disastrously with a sharp increase in competition among East Side gaming houses. First New York’s racing fraternity led an exodus to Canada and Kentucky, and the local racetracks all closed down; then Herman found the revenues from his downtown stuss joints badly squeezed. A younger, tougher generation of East Siders had begun to press for a slice of the action on Second Avenue. Their appearance resulted in a series of violent disputes, and soon the peace that had long been maintained by Big Tim’s gambling commission began to erode. Profits slumped, and the danger of doing business downtown rose.
Turning, as he always did, to Sullivan, Herman borrowed heavily to open up a new concession miles away, in Far Rockaway, Long Island—the place where he had begun his career years earlier. This time, however, the local gamblers had better connections with the police; Rosenthal’s new club was swiftly raided and closed down. He tried again, on the Upper West Side of Manhattan, this time going into business with a fellow member of the Hesper Club named Beansey Rosenfeld. The two men opened a stuss house in the district known as “Little Russia” and ran it profitably for a while. But the partners soon fell out, and their place was raided and closed down.
Big losses on new premises and lost profits on old ones soon stretched Rosenthal’s hitherto-ample resources to the limit, and, to make matters worse, Tim Sullivan himself was also having problems. Tim’s difficulties were caused by the declining influence of Tammany Hall—which after 1905 found itself increasingly marginalized by the continuing influx of Jewish, Italian, and Eastern European immigrants with their own political affiliations and even social-welfare programs. As Tammany’s power waned, and it concentrated its dwindling powers of patronage in the hands of a few old favorites, men such as Herman Rosenthal found themselves marginalized and harder-pressed to obtain both protection and funds. The police, ever alert to subtle shifts in power, reacted by putting pressure on businesses that had once been sacrosanct, and Rosenthal’s gambling houses were among them.
Slowly but surely, then, Herman’s money ran out. True, Rosenthal could (his friends related) still be touchingly generous. One boyhood companion, who had grown up to become a poverty-stricken vaudeville artist, recalled that—desperate for money—he tracked his old friend down to his stand at a racetrack and wagered his last few dollars on a sure thing. When the horse won but was disqualified, Rosenthal took up a collection among the other gamblers at the track and, despite having been wiped out financially himself in the same race, forced several hundred dollars on his friend. But things were definitely getting tougher, and the police and East Side rivals were no longer the only enemies that the gambler had to worry about. By the first months of 1909, Herman was also receiving the unwanted attention of New York’s brash district attorney: a tough, driven lawman by the name of William Travers Jerome.
Jerome had been a power in the city for a decade. A cousin of Winston Churchill, described by one legal historian as “the most unusual jurist Manhattan had ever seen,” he had made his name as a junior counsel working with John Goff during the Lexow inquiry. Jerome’s reward for his work on that commission had been a position as a judge and a deserved reputation as one of Tammany’s most implacable foes.
Jerome had been a revelation during his first years in office, displaying all the push and pugnacity of his famous relative. Prior to his election as DA in 1901, New York’s district attorney had been hardly more than a cipher and his office a dumping ground for minor machine politicians who could be relied upon to do as they were told. Little work was done by any of the staff, and gamblers who enjoyed Tammany’s protection had no reason to fear investigation. Jerome changed all that, turning the DA’s office into a vigorous force for reform.
It was far from easy work, and the legacy of years of official neglect was palpable. When Arthur Train—one of the young lawyers brought in to replace the Tammany placemen who had run the department—first cleaned out his office, he found his desk stuffed full of ancient indictments that had never been acted on and piles of forgotten legal proceedings stored “in wastebaskets, pigeonholes, in the backs of drawers and on the floor.” There was no system, and important papers continued to turn up in odd places for months. But the new district attorney began to work his way through the backlog, issuing a blizzard of indictments and keeping his own name in the papers by pursuing high-profile cases against prominent men. Jerome’s reward for creating a template that thousands of other DAs would follow in the coming century was a personal popularity so great that he clung onto office for nearly a decade.
As Herman Rosenthal knew from bitter personal experience, Jerome’s initial impact was considerable. So great were New York gamblers’ fears of what the reformers might do that all the city’s gaming clubs, stuss houses, and poolrooms shut down the moment the new DA and his boss, the reformist Mayor Seth Low, took office, and for almost three months not a wheel was spun or a card turned throughout the five boroughs. Most places did eventually reopen as it became apparent that even the district attorney still had to obtain evidence and build a case before he could actually prosecute. But even when Tammany regained control of the city—with, in effect, a mandate from voters to leave gambling alone—Jerome continued to make high-profile raids for years. He
still courted the press as well, raiding clubs armed with a Bible in one hand and a revolver in the other, waving the pistol over his head and theatrically threatening to “shoot the next man who moves” while his men blew open safes in search of incriminating documents.
After the Tammany election victory of 1904, naturally, the DA’s effectiveness was not what it had been while the reformers were in power; there can be no doubt that Jerome himself was gradually worn down by the Democrats’ obstructiveness and the near impossibility of securing convictions from judges who were all too often part of the Hall’s corrupt system. But even with Tammany in office, gamblers could never rest entirely easy. Some raids, some arrests, and some convictions were a desirable thing to have on the Democrats’ record come election time, and since the city’s richest vice lords remained on the whole inviolate, it was men of Herman’s lesser clout who had the most to fear.
True enough, Rosenthal experienced little trouble while Big Tim reigned supreme. But by the last months of 1908, undermined by the arrival of a fresh influx of Eastern European immigrants in his East Side strongholds, Sullivan’s power was wavering, and in January 1909, Jerome—by then entering his last few weeks in office—subjected Herman to some inconclusive questioning and extracted a promise that the gambler’s various premises would be opened for inspection. Rosenthal foolishly ignored these warning signs and continued to run his houses wide open in defiance of the law. The raids that ensued were savage: Jerome, backed by a squad of fourteen brawny policemen, descended on both addresses simultaneously and pretty much destroyed them. “Axes,” the New York Times reported the next day, “were plied, doors broken down, and walls torn open.” Seven men were arrested on the spot, and Herman himself was detained a few days later. The damage to the clubs was such that they could not reopen, and, to make matters worse, Rosenthal himself was indicted for attempted bribery. He had, it seems, made clumsy efforts to buy off the DA’s process server.
Herman was in trouble, and matters were scarcely improved by mounting difficulties with the illegal off-track-betting service that was still his principal source of income. Rosenthal had been able to retain some of his old high-rolling clients for as long as they were losing. But he now lacked the funds to pay out to major winners. He reneged on a $5,000 loss to Charles Kohler, the piano magnate, and when his old friends at the Hesper Club—where he now ran the gambling concession—loaned him the funds to settle the debt, he defaulted on their repayments, too. Many of the Hesper’s members were so disgusted by his actions that they took themselves and their business around the corner to a new gaming club just opened by the Sam Paul Association.
The declining fortunes of the club and the rowdy behavior of the younger Hespers—many of whom were little more than gangsters—drove away more respectable members, and by 1909, Tim Sullivan and his henchman cousin Little Tim had both resigned their memberships. The pretense that the place was a social club was abandoned soon thereafter, and—under Rosenthal’s stewardship—the once-proud East Side institution became just another tawdry gaming joint, less wealthy, less influential, and much less remunerative than it had used to be. The Hesper limped along for a few more months, eventually closing in April 1911 when fifty policemen burst through its armored door with axes and destroyed its fixtures and equipment so utterly that the interior was beyond repair; even Big Tim’s precious letter, in its golden frame, was damaged in the fracas.
By then Rosenthal’s plight was desperate. Drained of resources, assailed on all sides by the police and rival gamblers, and increasingly unsure of protection, he had long ago been forced out of his hotel suite and into paper collars and cheap clothes. His income from gambling had all but dried up; his savings were gone; indeed he owed money, and not merely to Tim Sullivan. Nor did there seem to be much prospect that matters would improve.
Less than two years after boasting of a wealth exceeding most New Yorkers’ dreams of avarice, Herman Rosenthal was broke, and the gambler could not be blamed for wondering why his luck had changed so drastically. But the answer, he realized, was obvious: The police and the district attorney always seemed to have plenty of information regarding his activities; each new effort he made to reestablish himself soon became known to the authorities. That had to mean that somebody, somewhere, was informing on him, and the only people with a motive to take Rosenthal down were his fellow gamblers. In his own mind, Herman had little doubt who was responsible. He suspected “Bridgey” Webber.
Once, twenty years earlier, Herman and Bridgey*23 had been friends.
The two men had shared a childhood on the Lower East Side, and if they were not by all accounts particularly close—Webber’s family was more religious and much better off; Rosenthal was older by two years—they had certainly known each other fairly well, an acquaintanceship that deepened as they drifted into the half-light world of politics and gambling. Like Rosenthal, Webber had gotten his start while still of school age, though his specialty, at age fourteen, was the ominously advanced crime of kidnapping pet dogs. By the time he was twenty, Bridgey was running what was said to be the largest opium den in Chinatown. His premises down on Pell Street seem to have catered to a predominantly Chinese clientele, which would have made Bridgey unusual at a time when many of the Westerners who dabbled in opium did so with an eye not to New York’s addicts but to wide-eyed tourists: parties of slummers, their heads filled with wild stories of Tong gang wars and white slavery, who thronged the district looking for thrills and who—for a suitable fee—could be shown around a dingy apartment decked out with drug paraphernalia and peopled by louche men and women pretending to be opium fiends. Whatever the truth, however, Webber did not remain in the dangerous and insecure drugs business for long. By about 1900 he had moved into the altogether safer world of gambling, opening a number of stuss houses in the Jewish districts along Second Avenue. Having married into money—his wife’s collection of jewelry alone was reputed to be worth some $10,000—Bridgey had sufficient cash to do up his premises in style. The rewards were considerable, and before long his gambling clubs were generating an enviable income. They also placed him in competition with his old friend Rosenthal.
It was, those who knew both men agreed, an unequal contest. Webber—a slight, fastidiously dressed man with a long nose, sharp chin, bow lips, and bulging eyes—had always been the sharper, more aggressive of the two, and he was willing to go just as far as Herman, and probably further, in order to protect his interests. “He does not look like a gangster nor a gambler,” a crime reporter at the Evening Post observed in 1912. “His manner is rather that of a quiet young clerk—one even of studious and sedentary habits. Yet his record shows him to have been a factor in East Side gambling and feuds since he was old enough to be recognized as somebody.”
The first shots in the war between the friends were fired not by Herman but by Webber. Around 1908 he opened up a stuss house just along the road from Rosenthal’s most profitable club and proceeded to drain much of its business. At about the same time, the former dognapper accepted a commission from the local precinct captain and began collecting graft payments from his fellow gamblers on the Lower East Side. The police chief must have been a canny man; certainly Webber had every reason to ensure that Herman and other rival gamblers made their payments on time, in full, and without exception.
In any event, appeals to reason failed and tempers flared. When Rosenthal’s stuss house closed in the face of Bridgey’s competition, Herman was so desperate and so furious that he hired a street tough by the name of Spanish Louis to take care of his rival. Louis came cheap because he was no more than an ambitious pimp, seduced by the romance of crime, and handy with his fists.*24 Melodramatically attired all in black and—as one contemporary recalled—affecting a broad-brimmed sombrero, “a brace of heavy Colt’s revolvers, the most massive artillery in gangland, and a pair of eight-inch dirks, which he thrust into special scabbards built into his trousers,” the would-be gangster waylaid Webber late one night toward the end of 1909
and beat him almost to death. While the hired thug worked Bridgey over, Herman lurked in the shadows and watched.
Rosenthal’s message to his rival had no apparent effect; Webber’s stuss houses remained open while the injured gambler recovered. Few East Side gamblers were surprised when, soon afterward, a bomb detonated outside the busiest among them, blowing off much of its facade. Then, when Bridgey emerged at last from the hospital, Rosenthal paid for him to be attacked once again. This time the assailant was an established enforcer known as “Tough Tony” Ferraci, who caught up with Webber on voter-registration day, blackjacked him, and broke his jaw. When Tough Tony was picked up by the police and charged with carrying a concealed weapon, it was Herman Rosenthal who turned up at the station house to bail him out. Webber and his partisans drew the obvious conclusion.
Bridgey was too clever to respond to Herman’s flailing attempts to resolve their rivalry in kind, but neither did he forgive them, and he went to work surreptitiously to undermine Rosenthal’s businesses in whatever way he could. First Spanish Louis—who received an invitation to call on Herman one night, only to find his patron’s door mysteriously barred—met his end at the hands of several assailants who hailed him as he was waiting on the doorstep and cut him down as he fled onto a side street. Next Sam Paul, one of Bridgey’s oldest business associates, stepped up the pressure by luring many of Rosenthal’s remaining customers into his own East Side stuss houses. Webber proceeded to plunge Herman into further trouble by calling on his connections with Tammany. It helped that Bridgey was not part of Big Tim Sullivan’s faction at the Hall (he was a partisan of the Irishman’s clever cousin Little Tim instead) and that he had a first-rate understanding of the mechanics of city politics; in any event, such protection as Rosenthal might have enjoyed from the police was quietly removed, and shortly thereafter the first in a long series of well-informed, pseudonymous letters, signed by a certain “Henry Williams,” arrived at City Hall. The missive denounced Herman as a leading gambler and thoughtfully provided precise details as to the whereabouts of his remaining premises.