by Mike Dash
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 runni
ng 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.”