CHAPTER 4
STUSS
THE BUILDING AT 33 West Thirty-third Street, close to the Waldorf-Astoria hotel on the fringes of the vice district, did not attract attention from most passersby. The premises themselves were well built and substantial, as befitted such an elegant address, but then so were many similarly solid properties in the heart of fashionable Manhattan. The casual observer, noting muted signs of wealth and taste in the exterior, might suppose the place was home to a banker from some Wall Street institution.
Upon close inspection, nonetheless, the house seemed definitely odd. It attracted, for one thing, far too many callers to be a simple private dwelling, and many of these visitors appeared at the unsocial hour of midnight, sometimes later. It was more than a little queer that all of them were male and sumptuously attired, and that many were decidedly familiar to even casual readers of the New York press. And it was stranger still that a uniformed policeman stood on guard outside the front door every evening, tipping his hat to the best-dressed callers as they swept past him up the steps.
It was only when an observer’s gaze fell upon the door itself that the purpose of the building was revealed. The entrance to number 33 looked nothing like those that adorned everyday Manhattan homes, with their knockers, bells, and polished wood. It was, for one thing, made entirely out of metal several inches thick—wrought iron so heavy that it took a husky doorman all his strength to push it to and fro—and it hung within a massive iron frame, so stoutly built and strong that it reminded people passing of the entrance to a bank vault. This impression was amply reinforced by the numerous bolts and locks that studded the door—far more than ordinary security could possibly require. And when the iron barrier swung open, affording glimpses of the entrance hall, an even stranger sight appeared: A second doorway, still more strongly armored than the first, barred the way into the interior. It, too, was of metal, this time a lavishly decorated bronze; once, long ago, it had hung across a portal in the Doge’s Palace at Venice. The purpose of this second door was not entirely decorative. Whenever it was shut and barred, unwanted visitors gaining entry to the property would find themselves trapped within its narrow vestibule. At the very least, the time required to force an entry would give the building’s occupants a head start to make good their escape—via a rear exit, over the roofs, or through one of two tunnels leading to adjacent properties with which the building was supplied. Seeing the bronze door hanging, tightly closed and defiant, within the entrance hall of number 33, any knowledgeable New Yorker would have instantly identified the building as a gambling “hell”—a private and illegal business whose prime purpose, after making money, was to ensure complete discretion to its well-heeled clientele.
The House with the Bronze Door was indeed a famous gaming club: perhaps the richest and most opulent in all Manhattan, an island rich in such amenities. The property had first opened back in 1891 and proceeded to run largely unmolested for a dozen years, a phenomenal achievement. When called upon at last, however, the metal doors did prove their worth, resisting the attentions of policemen armed with blowtorches for the better part of half an hour while the house’s staff took their equipment and their customers to safety through their secret passages.
The sums that had been invested to turn the House with the Bronze Door into one of the finest establishments in New York were colossal. The syndicate that owned the club had hired Stanford White—then perhaps the best-known architect in the United States*19 —to gut and remodel the interior, then spent a further half a million on furnishings. White had toured through Europe and Asia purchasing antiques, spending $20,000 on the bronze door alone. While still in Venice, he had hired a team of ten master carvers and packed them off to Manhattan, where they spent two years working on a single ornamental banister.
Nor was the rest of the interior neglected. According to the New York Sun,
The large reception room at the back of the street floor is of gold, and the floor is covered with red velvet carpet…. On the walls are oil paintings which cost a fortune. On the floors were the finest examples of the art of the great rug-makers of the East. The floors were of hard wood, the work of experts. The ceilings were frescoed as only the homes of the rich could be. On the second floor is the large roulette wheel room. It is arched, with the ceiling covered with paintings. On this floor is a bath with a marble reclining slab and other apparatus which is said to have cost the owners $2,000.
Fair play and courtesy were the keynotes of the place. The house had the reputation of integrity and honesty. The word of the player was always accepted without question. With admission to the house went the privilege of indulging in all the good things which the place afforded. A visitor was the guest of the house and was treated accordingly. At midnight a buffet lunch was served for guests. Between times wines, brandies, and cigars which cost a dollar apiece were there for those who wanted them. It has been estimated that at least $25,000 a year was spent in providing refreshments and food for visitors of the house.
The expenditure of the best part of a million dollars would have alarmed most ordinary investors. But Frank Farrell, the master gambler who was the House’s principal backer, had a solid grasp of economics. The sums wagered, and lost, within his club’s gorgeous interior were consistently enormous; around 1900, it was estimated that as much as $50,000 changed hands there every night, thanks at least in part to limits that were high and also elastic. The sheer variety of attractions on the premises helped; in addition to roulette, baccarat, pinochle, and poker, there was a dice game known as Klondike, too, and sundry other forms of betting. The biggest single sum ever won in the House was said to be a staggering $165,000, which must imply that larger sums by far were lost. Certainly the player who carried off $210,000 after two consecutive winning nights at the House gambled away all of that money over the ensuing weeks and lost a further $80,000 into the bargain.
It was the sheer profitability of the House with the Bronze Door that gave the place its true importance. The House was not—could not have been—in the least way typical of the ordinary gaming establishments of the city, and it had, in fact, no more than a handful of true competitors anywhere in the world. But neither was it a mere curiosity. Frank Farrell may not have been the only gambler to realize that his gentlemanly clientele made up a negligible proportion of the betting men of New York, nor even that when hundreds of thousands of clerks, laborers, and other sporting types made penny wagers on the horses or on cards, their bets—contemptible in isolation—totaled a sum in excess of the largest staked within the House. He was, however, the only man to draw the logical conclusion that money won from genteel customers could be profitably reinvested in a much rougher class of premises. Farrell’s rivals—men such as Richard Canfield, owner of the elegant Saratoga Club and perhaps the best-known gambler of the nineteenth century—had parlayed their precarious respectability into grudging acceptance by high society. Farrell, less bothered by the social whirl, cared less what his clients thought of him. He took the vast profits earned by the House with the Bronze Door and used them to open up a chain of seedy betting shops, called poolrooms, throughout the city and its suburbs. Within a few years, he controlled 250 such establishments, taking millions of small bets on racing, fights, and baseball games and swelling his profits to an almost inconceivable extent. So rich, indeed, did Farrell become that by 1903 he was able to throw away $18,000 in what many thought to be a suicidal wager: the purchase of a franchise to play in baseball’s American League and the establishment of a brand-new New York ball club to rival not merely the celebrated Giants but Brooklyn’s Robins, too. Farrell should perhaps have listened to his critics; he and his partner, Bill Devery (whose close association with the gambler in this venture no doubt explained how the House with the Bronze Door ran so freely for so long), lost money on their team in all but one of the years that they controlled the franchise. But the fact that Farrell had cash to lavish on so quixotic a gamble as the useless, struggling New York Yankees showed just how much could be made from low-class gambling in the city.
During the wide-open years that followed Tammany’s return to power in 1897, hundreds of minor entrepreneurs followed Frank Farrell’s lead. By 1900 there were well over a thousand poolrooms and card rooms in Manhattan, far outnumbering the two dozen or so substantial gambling palaces and the two hundred lesser gaming clubs scattered through the borough. Many of these places—particularly the poolrooms, which, handling racing and sports betting, required telegraph equipment and other expensive fittings—were fortified nearly as strongly as the House with the Bronze Door, a fact William McAdoo, the new police commissioner, discovered after taking office. The typical poolroom, McAdoo wrote, was a considerable enterprise, employing ten men and playing host to as many as two hundred or three hundred gamblers at a time. Such places were often concealed in lofts where,
once rented, a partition is put up, dividing the room into two unequal parts. Often there is no door whatsoever in the partition, only a small hole that would trouble a fat pigeon to go through. Behind the partition are the human spiders themselves, principals or agents of the big octopus. About one o’clock in the day…the wretched army of unfortunate and desperate gamblers, after having passed through several outer guards and two or three doors stronger and thicker than those of some safes, gather in this dingy, ill ventilated, smoke-poisoned room; for in order not to make things too public the windows are generally blinded, and the average gambler pays little attention to what he is breathing, fevered as he is by the devil of chance…. In many pool rooms, to make sure the victim cannot escape by any possible means with his money, there are various games played in the large outer room before opening time and after the races are over. The main thing that the victims want to know is the names of the horses, the jockeys and the betting odds as established at the race track. An attendant pastes lightly on the wall a sheet called the “dope-sheet” which gives this news. The poor, foolish crowd casts their eyes on this and the jabber and chatter about horses goes up.
Those who preferred to gamble on something more immediate were also well catered for in Manhattan. Numerous poker rooms flourished in the slums. Blackjack was gaining in stature, too, and roulette was—thought McAdoo—more popular than any other game of chance. Neither of these games, nonetheless, came close to being the favorite pastime of New York’s gamblers. That honor went to the now-forgotten game of faro, originally a French invention, which had first appeared in Louisiana sometime before 1800. Faro had grown in stature throughout the nineteenth century, eventually spawning a faster, simpler variant known as stuss. The game was easy enough to grasp: Players gathered around an elaborately printed table, known as a layout, and wagered against the house by betting on the order of cards drawn from a dealing case. But, as in roulette, the variety and complexity of the wagers allowed could be bewildering, and even experienced players found it difficult to master the ever-shifting odds.*20 Faro’s real attraction lay in its reputation for offering gamblers a better chance of winning than any other game of cards; the margin in the house’s favor, while difficult to calculate, was generally reckoned to be little more than 1.5 percent. “An almost conclusive argument,” one player observed in 1900, “for the theory that the percentage at honest faro is virtually non-existent is the fact that the canny management of Monte Carlo has never permitted the game to be played at that celebrated resort.”
“Honest faro” was, however, seldom found in the United States. Crooked layouts were especially common in Satan’s Circus, where the game became—in the words of one early historian of gambling—“the medium of the first extensive cheating at cards ever seen in the United States, and the rock upon which was reared the wolf-traps of the nineteenth century.” Trimmed and sanded cards and rigged dealing boxes were readily available and openly advertised as “advantage tools” in the trade press of the day. By manipulating concealed springs and sliding plates, skilled dealers, known as “mechanics,” could make cards appear as and when they wanted them, and they were paid accordingly. The potential for cheating was even greater in stuss, a game in which the cards were shuffled only after bets were made.
There were indeed almost endless opportunities for canny hucksters to rook the city’s gamblers. Crooked play was ubiquitous throughout the New York of the day, and if a scant few low establishments were honest, the vast majority were bent in varying degrees. Manhattan supported so many card sharps and con men that by 1910 the fraternity had acquired its own unofficial meeting place: a hangout known as the Stag Café, run by a gambler named Louis Harris who (under the alias of “Dan the Dude”) became another friend of Becker’s. Horse races were rigged, either in the traditional way (involving the bribing of jockeys or the doping of their mounts) or via increasingly elaborate scams involving manipulation of the posting of results. Roulette wheels were often weighted to give the house an extra edge, and lottery draws were fixed. But the most common fraud by far involved the marking of playing cards. It was not hard to obtain specially printed packs that enabled a skilled sharp to know exactly what was being dealt or to doctor a deck with a custom-made “poker ring,” worn as normal on the finger of one hand and equipped with a tiny concealed needle with which to prick the surface of a card. In these ways thousands of poor men (and a few women) were relieved of their wages every week.
It was largely thanks to endemic cheating that gambling ranked ahead of every other form of vice in terms of the profits it produced. Some notion of the sums taken by gaming clubs and poolrooms in Manhattan was given by the New York Times, which in 1900 trumpeted the results of an investigation of the city’s vice. According to the Times’ calculations, the owners of the city’s largest clubs paid as much as $12,000 a year for protection; their lesser competitors were required to part with nearly $2,000; poolrooms stayed open in exchange for $300 a month and crap games for $150. The total handed over to the police amounted to some $3 million a year, the paper added: taxes that were “as fixed as the laws of the Medes and Persians” and which could easily amount to 20 or 30 percent of a house’s turnover.*21 Yet men such as Frank Farrell prospered in the face of such demands. Gambling—more profitable than the liquor trade, more respectable than pimping, better protected, certainly, than both—was the safest way to make a fortune in Satan’s Circus. Several thousand men earned their livings from it at the turn of the century. Among them were some of the rawest characters in the city—and a handful of the richest.
The man who made more from gambling than anyone else was almost certainly Big Tim Sullivan. By 1907, when he was forty-four years old, Sullivan had emerged as Tammany’s most important conduit to New York vice, with interests that had expanded from the mere handful of saloons he had owned in the 1880s to encompass a nationwide circuit of vaudeville theaters, several dozen nickelodeons, a variety of clubs and bars, numerous gambling establishments, and—practically certainly—income from a good number of brothels.
Tim had always been careful not to say exactly how he made his money, although he vehemently denied involvement in the “white slave trade,” as prostitution was generally known. “Nobody who knows me well,” the Tammany man had declared in 1901,
will believe that I would take a penny from any woman, much less from the poor creatures who are more to be pitied than any other human beings on earth. I’d be afraid to take a cent from a poor woman of the streets for fear my mother would see it. I’d a good deal rather break into a bank and rob the safe. That would be a more manly and decent way of getting money.
Sullivan’s denials were probably true insofar as they went; no conclusive evidence ever did emerge to prove that the Tammany leader profited directly from prostitution. But it was commonly accepted that Tim’s agents and subordinates on the Lower East Side did arrange protection for brothels and more or less certain that Sullivan himself contracted syphilis, probably from a liaison with a prostitute, during the first decade of the new century. Nevertheless, the Sullivan clan’s sensitivity to the least hint of involvement with white slavery was so acute that a cousin, the diminutive and saturnine “Little Tim” Sullivan, was sent to lead an ostentatious drive against downtown bordellos in the winter of 1901, throwing furniture out into the streets and roughing up the local pimps. All this made it altogether simpler for Sullivan himself to focus his energies on gambling, and he began investing heavily in such ventures.
Big Tim was himself a committed gambler, who wagered, mostly unsuccessfully, on fights and horses and, during a brief spell in Congress, from 1902 to 1904, became the poker and pinochle champion of the House of Representatives. But the Tammany man’s own businesses catered resolutely to the working class. Though Sullivan was influential enough to be gifted memberships to many of the city’s plushest gaming clubs, he was seldom seen in any of them, preferring to devote his time to more working-class pursuits. In the late 1890s, Tim took a hand in horse racing, helping to organize the Metropolitan Jockey Club and supplying most of the funds needed to open a new racetrack on Long Island. Closer to home, he also arranged protection for dozens of small poolrooms, stuss houses, and lotteries in Manhattan and became a patron of several “private social clubs,” where gamblers and politicians mixed to make book and raise funds for the Wigwam.
The most lucrative of Sullivan’s interests were operated in partnership with the Considine family, represented in New York by the brothers Jim and George, who shared Big Tim’s interest in boxing (George was for a while the manager of the famous heavyweight Jim Corbett). But Tim also operated on his own behalf, for example by helping to found the Hesper Club, an influential Second Avenue clubhouse, popular with gambling types, where frequent poker parties were held and a small casino operated. Sullivan played little active part in the running of the club, which was founded in 1899. But his influence was obvious to anyone who glanced inside the entrance, where a letter from the big Irishman hung in an honored spot within a golden frame. “Should it be possible,” Tim’s note assured its readers, “for me at any time to serve any of the members I will gladly do so. A simple word from you will command me.”
The Hesper flourished for a dozen years, becoming a meeting place for a generation of New York fixers and aspiring politicians, and Sullivan’s prominent interest in the place was widely remarked upon. Very few of the Irishman’s casual acquaintances, on the other hand, understood the central role that Big Tim played in regulating gaming through all five boroughs of the city. According to the Times, Sullivan devoted a good deal of his energies to heading a secret “gambling commission,” consisting of four members, which not only collected and shared out the millions raised in protection money, but in effect licensed all the betting premises that operated in the city. Tim’s committee, the paper charged, met weekly in an apartment just off Broadway and consisted of “a commissioner, who is at the head of one of the city departments, two state senators, and the dictator of the pool room syndicate of this city.” It required little knowledge of local politics to identify three of these men as Sullivan, Frank Farrell, and State Senator McLaughlan, the last representing the interests of the Democrats of Brooklyn. As for the mysterious “head of one of the city departments,” only the most naïve of the Times’ readers could have failed to recognize a reference to Bill Devery, then still chief of police. The brilliance of Tim’s system would have been immediately apparent to any reader who guessed the men’s identities. Between them the four members of Sullivan’s committee controlled the police, Manhattan politics, and the State Gambling Commission. The scheme was airtight.
Sullivan never formally admitted that this secret “commission” existed. But the indications are that it did, and that it was not a recent innovation. As early as 1880, New York’s gamblers had organized an informal association to channel the payment of protection money, a wise move that had resulted in a boom in gaming in the city. By 1900, apparently, the commission had reached a high state of efficiency. According to the Times’ evidence,
the money is not only apportioned at these conferences, but licenses to run gambling houses are virtually issued there…. Not a gambling house is running in this city to-day that is not known to this board, and not a place is running that does not pay a tax to this board. Its system is as complete as any branch of city government. There are no leaks, and no unauthorized places can run for twenty-four hours without “putting up” or shutting up.
Licenses to operate, the paper added, cost $300, a sum paid to the local precinct captain, who retained it in exchange for collecting monthly payments. Thereafter, however, the vast majority of the protection money gathered from across the city—at least 80 percent—was passed up to the members of the commission itself.
Sullivan and his gambling commission were thus hugely influential in New York. They in effect regulated the livelihoods of every gambler in the city: something that the owners of gaming clubs and petty card sharps more or less openly acknowledged in their periodic complaints that the syndicate was licensing far too many premises and thus diluting the profits available to those already in business. The commission also operated as a sort of professional association, hearing complaints from aggrieved parties, issuing judgments, and above all ensuring the continuing smooth running of the industry—notably by ensuring that the premises it licensed maintained reasonable discretion. Gamblers who ran afoul of the authorities or of their fellows might be issued with warnings or paid to get out of town for a few weeks or months while things cooled down.
The appearance of Sullivan’s group—whether or not it was quite as all-powerful as the Times asked its readers to believe—made it possible for wealthy gamblers to flourish more or less free from the attentions of the police. By 1907 there were more than a dozen eminent gaming lords active in the city, every one of them—like Frank Farrell and Sullivan’s business partners, the Considine brothers—well connected politically. Not all were partisans of Tammany; Sam Paul, whose main business was running cheap stuss houses south of Fourteenth Street, was a noted Republican fixer connected to Boss Platt and the Custom House brigade. Some of these men (Paul was a good example) had once been minor gangsters; they had obtained a concession to run a club as reward for some service rendered and so clawed their way into a rough respectability. Others—generally the most successful of their breed—were lifelong gamblers themselves who had turned their knowledge of betting into a business. Men of this sort took good care to assure themselves of firm political support and often ran a wide variety of businesses, from bookmaking through gaming clubs and loansharking.
In New York in the first years of the new century, the most eminent gambler of the latter type was Arnold Rothstein. A gifted young East Sider with a marked ability to hustle pool, Rothstein—like Charles Becker—was a third-generation American gone bad. He had been born into a virtuous, hardworking family: His grandparents had fled the anti-Jewish pogroms convulsing Russia in the 1850s; his father was a respected businessman so renowned for Solomonic judgments that he was known as “Abe the Just” his brother had trained to be a rabbi. But Rothstein rebelled, shocking his devout parents by leaving school to lounge around in bars and poolrooms. The boy had talent nonetheless, and the mathematical brain of the instinctive oddsmaker; by 1900, when he was eighteen, he was already running his own card games. In a few years, he had made sufficient money to branch out by lending some to other gamblers, at rates that rose as high as 48 percent. Rothstein advanced these loans from a large wad of cash that he always carried on his person; after a run of luck, his funds might total well over $10,000. Fellow gamblers began calling him “The Big Bankroll.”
In person Rothstein struck most observers as average and unremarkable, possessing the useful ability to fade unnoticed into the background of any scene. He was of no more than average height and had an expressionless round face, dark hair, and the ghostly pallor of a man who worked mostly by night. Perhaps thanks to this avoidance of sun, he retained his boyish aspect into adulthood, always seeming, one acquaintance noted, “as if he never had to worry about razors.” Rothstein was not without vanity, at one point paying to have all his teeth removed and replaced by a set of dentures so dazzling that “they made many professional beauties jealous.” But twitting the Bankroll on his ordinary looks was hardly sensible. Rothstein could be steely and unyielding, and so obdurate that he would hang around in cold doorways for hours, waiting for the chance to waylay those who owed him cash. He had few friends and apparently no interests outside his work. “He lived only for money,” one New York journalist recalled years later. “He even liked the feel of it. He wasn’t right even with himself. For every friend, he had a thousand enemies.”
An obsession with dollars and cents was not, of course, unusual in the sort of circles that the Bankroll moved in. But Rothstein was no ordinary gambler. He was more ambitious than most of his contemporaries and made it his business to be politically connected. His principal acquaintance, unsurprisingly, was Big Tim Sullivan, with whom he had engineered a meeting, in the 1890s, by hanging around Tim’s cousin Florrie’s pool hall. The young Rothstein had made himself useful, running errands, doing favors; a decade later, thanks in part to Sullivan’s patronage, he emerged as a leading figure in Satan’s Circus. Even this, though, was not sufficient for him. He continued to intrigue, sitting for long hours in a booth at a local restaurant, receiving supplicants and doing deals. Before long he was firmly established as a kingpin, a court of appeal, and a lender of last resort. “Arnold Rothstein was chiefly a busybody,” one man who knew the gambler summarized things just after Rothstein’s death,
with a passion for dabbling in the affairs of others. He was also a fixer, a go-between, not merely between law-breakers and politicians, but between one type of racketeer and another. Because he measured his success in these roles by only one yardstick, money, he was always on the make. It follows that I may have placed his penchant for making money first, but this was a trait he shared with many. As a fixer, as a go-between, he stood alone.
The Big Bankroll took his new position as a gambling lord seriously. His aim was to avoid disruptions to the smooth running of his many business interests, and he worked hard to keep the peace in Satan’s Circus, arranging payoffs and soothing ruffled feathers; most of all he stamped out trouble and suppressed dissent. Rothstein’s most distinctive characteristic, in short, was that he thought of other people’s business as his own, insofar as the success of his own wide-ranging schemes required political calm and a minimum of unwelcome publicity.
It was in this capacity that Rothstein would stumble into Becker’s story. And the man who would drag him there was yet another gambler—one a good deal less able than Rothstein and much less savvy than Big Tim. His name was Herman Rosenthal, and in the summer of 1900 he was in trouble.
The problem, Herman sniffed, lay with his wife.
In the early months of the new century, Rosenthal was twenty-five years old and still anonymous: yet another ambitious East Sider making his way in an overcrowded city. Unlike both Becker and Rothstein, he was a first-generation immigrant, having stepped ashore in New York at the age of five. Herman’s family had come from Estonia, though there were also relatives in Germany. He had enjoyed an unremarkable childhood in the densely populated tenements of the Lower East Side, joined a modest street gang, and left school and home on the same day, aged fourteen. In his youth Rosenthal was a decent fighter, fast on his feet, and he knew his way around the streets. Having already earned a little money working as a newsboy, selling papers at one end of Brooklyn Bridge, he found work as a runner for a poolroom, carrying messages and recording bets for the place’s clients.
Work as a runner brought in little money—barely enough for a boy without a home to live on. But Herman’s prospects improved considerably when he met and married Dora Gilbert in 1897. He was by then in his early twenties; his wife was a few years older and pretty, if scarcely beautiful: a small, dark-haired woman who had been brought up in the tenements like her husband and whose morals were sufficiently elastic to make her useful to her spouse in unusual ways. Dora provided Herman with the comforts of home, of course—cooked meals, clean clothes, if not yet children. But, more than that, she was for the next two years the couple’s principal source of income. At a time when Rosenthal’s own earnings remained uncertain, his wife sold favors to provide for them. She worked as a prostitute after her marriage, and her husband was her pimp.
The Rosenthals had first gone into business around 1898, at a time when—for all the efforts of the Reverend Parkhurst—“sporting men” (the contemporary euphemism for sexually active middle- and upper-class males) could take their pick from more than 250 brothels in Satan’s Circus alone.*22 Many of these establishments advertised widely to attract customers; it was common for gentlemen arriving at the best hotels to find elegantly engraved invitations awaiting them, requesting the pleasure of their company at some high-class house. Less wealthy clients hunted through coded advertisements in newspapers in search of places touting “magnetic treatments,” “manicures,” or the ubiquitous “French lessons.” Herman, who lacked the resources to advertise, adopted a less sophisticated and more direct approach: He took to loitering in the lobby of the Metropolitan Opera House, waiting for a performance to finish, and then touted for business among the opera’s well-heeled patrons. Potential clients would follow him around the corner to an apartment on West Fortieth Street, where they were greeted by Mrs. Rosenthal and the two girls she employed. Herman stood guard and collected payment.
As Rosenthal and his wife discovered, there was plenty of business, even in the lowest brothels. It was widely accepted at this time that men of all classes were prey to a morbid degree of lust that no genteel, well-brought-up wife could be expected to satisfy. It was, in consequence, thought understandable—even acceptable—for men to frequent brothels, and there were even those who regarded the habit as admirable, since it spared girlfriends and fiancées from the perils of seduction and decent wives from submitting to practices they found objectionable. There were a million unmarried men in Manhattan, and tens of thousands of others who were dissatisfied, for whatever reason, with the sexual possibilities available at home. In these circumstances bordellos of all kinds thrived.
For a couple such as the Rosenthals, located in the heart of Manhattan, the heavy costs of working in Satan’s Circus were offset by the advantages. There was, for instance, business to be done with tourists. Sporting men were known to travel to New York from all over the country in order to sample the fleshy delights of Manhattan, where a sexual smorgasbord of possibilities scarcely dreamed of in their hometowns lay waiting to be sampled. According to Nell Kimball, a renowned madam from sinful New Orleans, even the working girls of the Deep South
sat around in their underwear or wrappers, drank beer, joshed a lot in country talk, felt at home with the simple horny guests that came to them with dusty shoes and derbys. There was a morality about those places that mirrored the words of the whores and their guests. They were…doing it mostly the straight and traditional American way, as they had been raised. Frenching was talked and joked about, but rarely asked for or offered. The Italian Way, entry through the rear, was kind of a joke carried over from farm boys experimenting on themselves and with each other, considered a sign of depraved city sinning. Memories of Bible lessons and hellfire from their country churches was still there in the middle class whorehouse…The idea of flogging for fun, or being stomped on by high heels…was like spitting on the flag.
Kimball’s views were evidently shared by the more sophisticated of her clients. As one indignant American traveler, with experience of brothels all around the world, complained, “I consider the quality of sex [generally available in the United States] to constitute an indictment against the American man’s taste and degree of civilization…. Foreign whores somehow manage to feign an attitude that leads you to believe, at least for the moment of intercourse, that you have their attention and that they are interested in seeing you and having a pleasant time…they always seem just a little surprised when you give them money.”
There were no such problems in Satan’s Circus, and it is likely that Dora Rosenthal and her girls offered the broad menu of services demanded by well-traveled clients. But that was not in itself enough to guarantee the success of an establishment bled white by demands for graft from the police and Tammany. Pimps and madams had to consider carefully the productivity of the women working for them, and it was here that Herman—with his complicated relations with the staff—apparently experienced difficulty.
Some New York whores worked at an amazing pace; according to the accounts book of one fifty-cent bordello, its most productive girl copulated with forty-nine men in one day, a total made possible by the fact that she kept the sort of hours that would have shamed a sweatshop worker. Others labored in short, intense bursts at the rate of a dollar or two for between ten and fifteen minutes of their time. The record for the fastest turnover of clients seems to have belonged to the whore who contrived to have intercourse with fifty-eight men in one three-hour period, and the houses fortunate enough to employ girls of this type could turn profits of $1,500 a month or more. But Herman, procuring for only a few hours every evening, and quite possibly unable to demand such selflessness from his spouse, never made this sort of money. The couple managed no more than a modest living—and as Rosenthal’s wife grew older and plumper, the price that she commanded fell. Business difficulties, and perhaps the strange, skewed character of the relationship, took their toll, and soon the couple separated. Shortly thereafter, Dora divorced her husband and went off to open a boardinghouse, leaving Herman in effect without a job.
By 1900, then, Rosenthal was busy casting about for other ways to make money. He promoted a few fights, but with such moderate success that a return to the world of gambling began to seem a safer option. The former pimp was, however, now too old and too grand to work as a runner, and in any case he had grown accustomed to living in a certain style. Herman knew he would be better off as the owner of some gambling concession, but he also recognized that he could not operate without protection. He turned, as if by instinct, to Tim Sullivan.
Big Tim, as things turned out, liked the idea. Rosenthal’s antecedents must have helped; the Irishman was known to have a soft spot for former newsboys, and over the years he helped many old friends from the streets to set themselves up in business. If the stories that went around New York a few years later are to be relied on, Sullivan may have gotten to know Herman as early as the mid-1890s, when the young would-be gambler—like his near contemporary Arnold Rothstein—hung out at his saloons, earning nickels running errands. But there were other, better, reasons for Sullivan’s interest in Rosenthal as well. Like many Tammany politicians, Tim had great respect for the abilities and intellect of the young Jewish men who frequented his saloons and clubhouses. He liked to keep some “smart Jew boys” around him, and—perhaps because their generally superior education made them numerate—often set them up as bookmakers or as the managers of stuss houses. “Gambling,” he always pointed out, “takes brains.”
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.
The consequences were predictable. Williams’s letter was passed on to police headquarters, where no fewer than three special anti-gambling squads stood by to act on such pseudonymous tips. There it found its way onto the desk of the man commanding the most active of all these units: a cop just then making a name for himself by cracking heads and raiding clubs throughout Satan’s Circus. Manhattan’s papers had been awash for several months with news of this man’s exploits, and by the winter of 1911, he had probably put more gamblers out of business than any other officer. He was the most admired policeman in the city. His name was Charley Becker.