A dream book is an anatomy of dreams, with numbers trailing after. For more than a century, dream books served as the bibles of New York gambling. Their mystic authors—often women, often claiming a Caribbean origin—would pair dreams with numbers, and those numbers would be used to play the locally run lotteries:
A dream book uses the irrational to rationalize the irrational. Something uncontrollable, a dream, gets translated into something controllable, a set of numbers, which can then supply the winning digits. Gambling proceeds out of such cycles of hope and superstition.
There’s an unchanging principle to gambling: people like to lose money guessing at the outcomes of unpredictable events. We convince ourselves that the next thing about to happen—the outcome of a horse race, the turn of a card—can be known before it does, and that believing in our prescience will allow us to take money from those who believe in their own. Of course, gamblers think they don’t like to lose money; the gamblers’ conviction, naturally, is that they will not lose but win. Yet this happens so rarely that even the greatest overseer of gambling in New York history died because of his gambling debts.
Indeed, a point made repeatedly during the public hearings on whether to bring a casino to Times Square—a competition likely to be settled before long, likely in favor of the inside-track runner, Caesars Entertainment—is that casinos are a unique kind of business. It’s not just a matter of paying for a service; it’s a service designed, at its core, to drain you of your money. As one person remarked at the hearings, “There’s no Theatre Anonymous. There’s no Restaurant Anonymous! No one has to protect working people from losing their money seeing Broadway shows.”
Though gambling, in the long run, leads to ruin, it offers, in the short run, moments of illusory triumph. The mystic’s goal, to live wholly in the present, is available to the fervid, sweating gambler in a way that it is not to the rest of us. The inside move of a Thoroughbred on the homestretch, the last roll of the dice—such moments pulse with urgency and splendor. Guessing crazily at the future, the gambler is granted, briefly, the gift of now.
Given our civic predilection for the now, it’s no surprise that New York City has, throughout its history, been the national center of illegal gambling. As Gay Talese once observed in conversation, “Life in New York is in its nature a gamble. It’s the city where you come to be lucky—so it’s the place to come and be unlucky.”
As plans are being made for a new casino in the city, one can trace, over the past century, four chief eras of gambling in New York. Call them, in order, high-stakes gambling, high-hopes gambling, back-room gambling, and big-room gambling. Each has its own protagonist, its own art form, and, this being New York, its own tangle of ethnic and racial coalitions and rivalries.
Nineteenth-century gambling in New York was a rich, if essentially provincial, affair, centered on the now forgotten card game of faro. Only in the nineteen-tens and twenties did high-stakes gambling take this universal human urge, spike it with bootleg hooch, and transform it into a lucrative, criminal, and increasingly national enterprise.
In the middle of this transformation was Arnold Rothstein. Rothstein is to gambling what Houdini is to magic—the one name from that world which people with little interest in the pastime may recall. The reason for the parallel resonance of gambler and magician lies partly in timing: both are icons of the twenties, the dawn of an era when local legends became national celebrities. Rothstein’s persona endures, too, in his guise as F. Scott Fitzgerald’s Meyer Wolfsheim, in “The Great Gatsby”—though Wolfsheim’s human-molar cufflinks seem outlandish for such an Anglophile dresser.
Rothstein was a major figure long before Prohibition. His later myth—of a wise man thrust into crime by circumstance—owes more to Hollywood than to history. In reality, Rothstein was a louse, forever at odds with his Orthodox father, Abraham, and upright brother Harry. He was the image of the “wicked son” of the Passover Haggadah: contemptuous of his heritage and dismissive of its demands, marrying outside the faith and, more flamboyantly, mistressing outside it as well. He kept a roster of Ziegfeld Follies girlfriends scattered across town, but, like his racehorses or his English suits, they were little more than trophies, accessories for a man in his position. His wife, Carolyn, recalled that even after he’d become wealthy—owning a couple of hotels, including the Fairfield on West Seventy-second Street—he would go out late at night to collect the smallest of debts. In photographs, he strained for geniality, but what lingers is a peculiar rictus: his nearly invisible upper lip clamped over a row of sharp false teeth. In every portrait, he appears more raptor than rabbi.
Nick Pileggi, a longtime chronicler of New York’s underworld, calls Rothstein “the key figure in the history of organized crime, the godfather to both Meyer Lansky and Lucky Luciano, the man who taught the untutored Italians.” One way to understand Rothstein is as a player in the city’s endlessly evolving wars of ethnic succession. He began by courting—and then manipulating—the fading Irish bosses of Tammany Hall, who ruled New York through their intricate collusion of politicians, police, and clergy. Tim Sullivan, once the city’s dominant boss, was first Rothstein’s patron, then his dependent, ultimately borrowing money from him to pay off his gambling debts.
But Rothstein’s true significance lies elsewhere. Just as Houdini understood that his real audience wasn’t in the theatre but in the national press, Rothstein knew that New York gambling could be scaled up. He became the master of the “layoff.” The bookmaker’s challenge, from the beginning, was simple: if too much money poured in on the favorite, the bookie risked ruin. The solution was to balance the action by “changing the line,” adjusting the odds in order to encourage wagers on the underdog. If that failed and the favorite was still too heavily backed, the bookie would “lay off” the excess bets with another bookmaker, essentially betting on the favorite himself, to hedge.
Starting in the nineteen-tens, with his acquisition of a string of Long Island casinos, and continuing into the twenties, Rothstein was the first to regionalize—and then nationalize—the layoff. He grasped the essential truth: everyone loses in the end, so the real art isn’t to pick winners but to have enough money to lend to those who imagine that they can. His two most famous nicknames—the Brain and the Big Bankroll—were interchangeable, since the bankroll proved the brain. The bankroll also let him hunt for tiny arbitrage opportunities by shifting odds across different books, squeezing profit from the ceaseless churn of other people’s hopes.
As Rothstein’s operation expanded, independent bookmakers became nodes in his network. He put the “organized” in organized crime. The next generation of gangsters—those who carved New York into families and divided the country into regions under a single Commission—inherited the scope and the national infrastructure of his layoff system.
Yet the reason Rothstein’s legend endures is mainly because of two much debated mysteries: the fixing of the 1919 World Series and his murder, on November 6, 1928. Both have inspired a literature far out of proportion to the sordid events, perhaps because each holds a certain moral voltage: evidence that even the invulnerable can be undone, that anything can be fixed, and that anyone can be killed.
Did Rothstein fix the World Series, as Fitzgerald’s Wolfsheim, and most early histories, would have it? More recent, careful scholarship by the lawyer William Lamb suggests that it was the ballplayers themselves, not the gamblers, who were behind the scheme. The favored Chicago White Sox were divided by class—well-educated, Ivy League types looking down on rougher, less literate teammates such as Joe Jackson and Chick Gandil, who ultimately arranged the fix. It now seems likely that there were actually two separate schemes for throwing the Series, and that confusion between them helped expose the whole affair. Whatever the truth, Rothstein profited immensely from people thinking that he had fixed the Series.
The second great enigma of his life was the manner of its end, what the crime writer Nick Tosches has called “the bullet from nowhere, the theody in the gloam, the silent stones.” Rothstein had lost a substantial sum—by the standards of the day, a fortune—in a poker game run by George (Hump) McManus, an Irish political fixer and a gambler whose brothers were, fittingly, a priest and a policeman. On the night of November 4th, after a tense hour-long conversation with the newspaperman and short-story writer Damon Runyon at Lindy’s restaurant, Rothstein received a call from the Park Central Hotel. He told Lindy’s nighttime cashier Abe Scher, “I’m going over to see McManus.” (The Park Central, on Seventh Avenue in midtown, is weirdly unaltered over the years: the barbershop where Albert Anastasia was later murdered is still there—though now, of course, it’s a Starbucks.) An hour later, he was found in the service entrance of the Park Central, shot in the groin and bleeding out.
What happened? The most probable scenario is that McManus’s gun went off by accident—either when McManus threatened Rothstein or when McManus, feeling threatened himself, pulled it. A 1929 account by a newspaperman who’d known Rothstein noted his habit of keeping his right hand in his jacket pocket, finger pointed, which may have contributed to the panic. Only one shot was fired, and the gun was flung, in haste, out a window and onto the roof of a passing taxi—details that seem to rule out any elaborate plot.
The real mystery is why Rothstein, a seasoned pro, was so sure he’d been cheated—a suspicion his friends found hard to credit—and so enraged by the idea that he wouldn’t simply shrug and settle, as a pro should. Recently, though, the magician Allan Zola Kronzek, in a little-known book on poker cheats, described what may actually have happened: a “diabolical” scheme called “papering the neighborhood,” in which sealed packs of marked cards are planted in likely retail spots. The target, thinking himself clever, buys and introduces the cards into the game, unwittingly outfoxed. In small Midwestern towns, entire blocks of shops might be papered; in New York, a single block—or, in this case, a hotel gift shop—was enough. The story is corroborated in the magician John Scarne’s privately printed notes from the nineteen-fifties. In the end, Rothstein—a master spider—was ensnared in a web even more ingenious than his own, woven, maddeningly, by lesser spiders.
His final hours, shadowed as they were, took on a comic turn—thanks, in part, to that conversation with Runyon, who recast Rothstein’s last night as a spirited yarn, transforming the sinister, ambitious figure into an appealing Runyonesque character, the Brain, in the evergreen story “The Brain Goes Home,” which became a radio drama. There is a peculiar New York tendency—it endures into the Trump years—to entwine comedy and corruption so closely that one obscures the other. Once Runyon’s story had circulated, it became difficult to see Rothstein as anything but the amiable Big Brain, despite his sidelines in cocaine and heroin trafficking. Today, he is often lazily identified in biographies with Nathan Detroit, from Runyon’s “Guys and Dolls,” though in truth Nathan, a sweaty, small-time hustler and a lovable loser with a showgirl fiancée, bears no resemblance to Rothstein. Such collisions of caricature and crime are still the stuff of New York lives, and scandals.
The rise of Rothstein’s network marked a turning point in New York’s underworld, as entrenched Irish bosses clashed with rising Jewish and Italian syndicates. The next chapter saw a newly confident Black gambling establishment in Harlem confronting Rothstein’s downtown system. The policy and numbers rackets of the twenties and thirties became, by all accounts, something like a cult—or even a substitute religion—in Harlem. On the whole, these games were honest, and sometimes yielded life-changing results: Colin Powell’s father, for instance, bought the family home in Queens with his winnings.
For much of their history, policy and numbers were not only under local control but, frequently, run by Black women. Policy—the precursor of the numbers racket—involved drawing a winning number from a rotating drum, usually in a gym or a church basement. The numbers game proper used a three-digit number published in a public source, such as a newspaper, which kept things more or less on the level. “Basically, policy was played in Chicago, and New York was the place for numbers,” says the historian LaShawn Harris, the author of “Sex Workers, Psychics, and Numbers Runners.” By December, 1930, numbers bankers were using the pari-mutuel total—the sum wagered on a particular horse—to determine the day’s number. Among the era’s ironies is that the winning number in one gambling racket was, for a time, produced honestly by the results of another.
Numbers in Harlem was the subject of anxious debate—caught between the demands of Black “respectability” politics and the temptations of ordinary American greed. Many Harlem pastors denounced the racket; others participated as contentedly as their Roman Catholic counterparts downtown did with bingo night. As Harris explains, “There were some churches that got people to come if the pastor was known for giving out lucky numbers. If you were religious and still played the numbers, you could go to church and get a religious number—Matthew 5 or John 8.”
Outside the Black church, a whole industry sprang up—populated by Orientalized, often vaguely Muslim, numbers gurus and fakirs, who, free from ecclesiastical constraints, could go fully mystic. From this world emerged the great era of the dream books, a remarkable chapter of entrepreneurial Black publishing. Dream books offered augury, poetry, and purpose—a kind of secular scripture for the numbers game.
It was this world which the racketeer Stephanie St. Clair came to dominate in the early nineteen-twenties, when she became known citywide as the Queen of Numbers. Though she always insisted on her French nationality, she seems to have come from Guadeloupe by way of Quebec. She understood the value of conspicuousness. She lived in one of Sugar Hill’s most fashionable buildings, 409 Edgecombe Avenue, and was often photographed in furs and pearls.
Exactly how she ran her book—and kept it safe from rivals—remains mysterious. But by the nineteen-thirties she had forty or fifty numbers runners collecting bets for her and ten comptrollers, along with bodyguards and maids. Her reputation as Harlem’s most stylish woman was legendary; her neighbor, the playwright Katherine Butler Jones, remembered St. Clair “breezing through the lobby” of their apartment building in exotic dresses and brightly colored turbans. In 1930, in an act of extraordinary audacity, St. Clair even testified against the N.Y.P.D. for corruption. Her testimony led to the suspension of thirteen officers.
Unlucky number! On a fateful November day in 1931—just three years after Rothstein’s murder, and still known in Harlem as Black Wednesday—a large, loosely coördinated group of bettors all played the same number: 527. The choice represented the date of the upcoming Thanksgiving holiday (November 25th) and the sum of that date (two and five). Disastrously, 527 was the official number produced by the pari-mutuel the next day. St. Clair and the other Harlem numbers bankers, unable to lay off the bets, were instantly insolvent—a possibility that Rothstein’s Jewish and Italian networks downtown had long anticipated. The Harlem bankers simply didn’t have enough pooled resources to absorb the blow.
And so one of Rothstein’s protégés, Dutch Schultz—who, thanks to the layoff networks, had access to ready cash—began lending to the Harlem numbers bankers, at ruinous rates. St. Clair’s empire began to crumble overnight. The mythology, which has already inspired at least one film, casts St. Clair as boldly resisting Schultz’s incursion: a lone queen defending a thriving Black business against a predatory assault by white gangsters. In reality, what felled her was not just one gangster’s greed but an entire organization’s—the inheritors of Rothstein’s operation—zeroing in on a mom-and-pop, or at least a mom, business, as big enterprises always do. (Schultz’s heavy-handed foreclosure on the Harlem numbers was, no doubt, one among many reasons that his colleagues had him gunned down soon afterward. St. Clair was rumored to have sent a telegram to his hospital bedside: “As you sow, so shall you reap.”)
It was during these years that St. Clair, in another public flourish, married Sufi Abdul Hamid, the leader of a Harlem cult. Said to be ferociously antisemitic, Hamid was something of an early Louis Farrakhan—newspapers called him Harlem’s Hitler. When she discovered him having an affair, she shot him, Frankie-and-Johnny style. He survived; she went to prison. The other woman turned out to be a dream-book entrepreneur who styled herself as Fu Futtam. The irony was that Harlem’s numbers queen, a model of rational risk-taking, found herself in a love triangle with a dream-book mystic—then took to the newspapers to denounce Futtam’s obvious impostures.
Historians tend to approach the era’s mysticism and invented names with understandable tact—after all, Harlemites had as much right to adopt Islamic personas as their Jewish Zionist contemporaries did when assuming new Hebrew names. Still, the pure rascality in these extravagant self-inventions shouldn’t be overlooked. Nor should the contradictions surrounding St. Clair’s undoing. A woman running something like a private bank, she was felled by a classic structural trap: her business had been effectively redlined by the larger Mob banks downtown, leaving her with no reserves to draw on when crisis struck, only predatory loans. Then, too, just as Rothstein was undone by his blind faith in his cleverness—a cheat out-cheated—St. Clair lost her balance on a tightrope she’d stretched between mysticism and materialism. The pseudo-mystics soon invaded her private life, pushing her toward violence and, ultimately, ruin. Hamid and Futtam, for their part, reinvented themselves as Buddhists, opened an “Enlightenment Temple,” and, in Hamid’s case, met an untimely end in a plane crash—leaving Futtam, the supposed clairvoyant, to explain why she hadn’t seen it coming.
Rothstein and St. Clair represent two great nodes of organized crime as it wrapped itself around New York gambling—each a cultural figure who controlled the games. But the steady, thrumming heartbeat of New York gambling wasn’t the big games run by Rothstein or the neighborhood numbers of St. Clair but the countless unrecorded card games and bridge sessions unfolding compulsively in apartments and back rooms.
Jack Richardson, for instance, was a playwright of enormous promise who gave up playwriting for card games in the back room of Elaine’s, the storied restaurant on Second Avenue. From his years at the table, Richardson took—or perhaps gave—a single embittered, poetic confession: a book now almost forgotten, but shimmeringly alive on the page.
That book, “Memoir of a Gambler” (1979), may be the most distinguished literary work to emerge from the world of New York gambling. It’s the story of a boy who was born in 1934, grew up in Queens, and, in the spirit of those ascending times, made his way to Columbia, then into Army intelligence in Europe, picking up Anglophile manners along the way. He stares out from the dust jacket, horse-faced and glowering in tweeds—the plaid just a bit too loud, well over the Rothstein speed limit. He was one of those people friends and lovers forgave—at least up to the last breach of faith or the last bad loan. (Richardson’s first wife, the novelist Anne Roiphe, wrote in the nineteen-seventies an alarming roman à clef about their marriage, “Torch Song,” ascribing to him various erotic exoticisms that were possibly more shocking then than now, but are still pretty shocking.)
Richardson’s first play, “The Prodigal,” was a sensation when it premièred, in 1960. A retelling of the saga of the House of Atreus, it reimagined Orestes as a kind of Zooey Glass figure: fluent, funny, defiant, and at odds with both the militarism of his father, Agamemnon, and the counterfeit piety of his stepfather, Aegisthus. For a moment, Richardson seemed poised to become a major theatrical presence, photographed alongside the likes of Edward Albee and Arthur Kopit.
But his later plays flopped, and, by then, the gambling bug had already entered his soul. Strange as it may sound in today’s New York, his one professional ace was his friendship with a Village restaurateur named Elaine Kaufman. In the early nineteen-sixties, when Kaufman moved uptown to what was then the no man’s land of the upper Upper East Side, also known as Yorkville, Richardson became her very first literary regular. (As Nick Pileggi put it when discussing the era, “You have no idea now what a desert East Eighty-eighth Street was then. Chicken Delight itself wouldn’t deliver north of Eighty-sixth Street.”) Richardson was a favored child at Elaine’s, and for years she presided over his nightly back-room poker game. The table attracted a shifting cast: the director Robert Altman, the occasional Hollywood star, and, most often, his fellow-writer Bruce Jay Friedman. It was, so to speak, an expense of shame in a waste of spirits.
David Black—the novelist, biographer, and showrunner who shared the high Elaine’s years with Richardson, and who gave him a chance to write his final drama, an arresting episode of “Miami Vice” inspired by Fritz Lang’s “M”—spoke about him not long ago over lunch at the mediocre French bistro that now occupies the old Elaine’s space. Though the Park Central remains eerily intact, no trace of the legendary writers’ restaurant survives, and the staff tending tables today seems unaware of what the place once was. As so often in New York now, physical erasure meets generational amnesia.
Looking around warily, as if half expecting phantoms—perhaps seventies novelists still chained to their advances, like Marley’s ghost to his moneybags—Black recalled Richardson’s high, imperious style: “He would lift one eyebrow, and then lift his chin, and that was Jack, dancing.” He laughed. Black and Richardson had shared books and talk—and, as Black ruefully admitted, cocaine—in the back room at Elaine’s. “His fate was ultimately tragic,” he added, “because he knew everything, spoke every language you can think of, and he was always talking about the Enlightenment. Voltaire, Rousseau, and Diderot—he’d say, ‘They made the worst bet in the world. If there is a God, I’m damned. If there is no God, I’m facing the void.’ ”
In his memoir, Richardson attributes his turn toward gambling to a glimpse of that void, in the form of his exposure to Gödel’s proof. As a philosophy student in Munich, Richardson was shaken by the Austrian logician’s demonstration that even mathematics is “incomplete,” lacking secure foundations and harboring truths it cannot prove. On a memorable summer day, he wrote, “As I stared into paradox, I vowed never again to think formally about anything that mattered or worry that I hadn’t earned the right to express anger about, and snatch relative pleasure from, a universe that tolerates no sincere predicates.” In such an absurd universe, the sordid becomes the sublime. If life is a meaningless roll of the dice, the only meaning lies in the rolling itself—however little comfort that offers those waiting at home for the grocery money from the roll.
Many have read Gödel and come away chastened by the limits of certainty—without concluding, as Richardson did, that the logical next step was to spend your life playing cards and paying prostitutes. (Richardson, a man of his era, did not call them sex workers.) Yet his memoir—a book very much in the spirit of William Hazlitt or Thomas De Quincey, and worthy of standing beside them—probes his descent into compulsion. Stripped of glamour, his dissolution produces a kind of glamour of its own: that of pure addiction, the allure of never saying no. He careers from New York to Vegas to Hong Kong to Macao, trying to win, trying not to care about winning, making love to anonymous women.
In Macao, Richardson claims to have met the Devil—and, according to Black, however cocaine-fuelled the episode, Richardson truly believed it. The Devil, in Richardson’s telling, says that he is as dead as God, and that the old Baudelairean quest for the ecstasy of sin through chance is now as doomed as the mystic’s search for the ecstasy of God. “The excitation, the energy, the joy, despair, manias and mopings—in short, the high-fevering of life that gambling gave you may once have been the devil’s element, but I assure you it is no longer,” the Devil explains. “I’ve no desire now to take the measure of those whose souls would add heat to hell itself, because I discovered long ago that it’s all one whether I trip a Caesar or a fool. . . . You’re so desperate to believe in something you would even believe in me.”
When the Devil himself yawns at your private abyss and refuses the sale of your soul with a weary shrug, what’s left to do? In the book, to end the story; in life, to return to Elaine’s and play more poker. “If the soul finds no true action for itself, it must make do with agitation,” Richardson’s memoir concludes. In that coke-fuelled era, he was a standout performer—the long tail of Arnold Rothstein’s shadowy business of drug trafficking coming back to haunt his ostensible business of gambling.
Black recalled that, after drying out himself, he’d eventually persuaded Richardson to do the same. “It was the worst thing I ever did,” Black reflected. “A body that depended on cocaine could not long survive its absence.” Richardson had a heart attack soon after sobering up, then, depressed, another in the taxi coming from the hospital, and was gone by 2012. He no longer haunts even his haunt, but “The Prodigal” deserves a revival, and his book deserves to be reread.
Richardson’s game was perhaps among the last in the city to retain a trace of cloistered sophistication. By the nineteen-nineties, what had formerly been private damnation was becoming public spectacle. A once obscure poker variant—Texas hold ’em—had soared in popularity, owing in part to the invention of the “hole” camera by the poker player (and Holocaust survivor) Henry Orenstein, which let television audiences see the players’ hidden cards. Into this new scene parachuted Molly Bloom, who eventually ran a high-stakes game in Manhattan—an episode later recounted in her memoir, “Molly’s Game,” and in the Aaron Sorkin film based on it.
Bloom arrived in the city in 2009, fleeing the fallout of a celebrity-studded poker game in Los Angeles that she had first managed for a dubious boss, then taken control of, and finally lost. Raised in Colorado, with a salubrious background in Olympic skiing, she found New York’s poker scene to be the realm of “billionaire boys’ club” types, Wall Street titans, and old-school gamblers, where the buy-in alone could hit a quarter of a million dollars.
Taking over a series of suites at the Plaza, Bloom set out, as Rothstein and St. Clair once had, to wrap gambling in a halo of glamour. She assembled a crew of young women to craft a carefully curated fantasy in which finance guys playing cards after hours in a rented hotel room could imagine themselves as mavericks.
“That was the plan,” Bloom said recently, laughing from her home in Colorado. Still striking, she’s become a thoughtful analyst of gambling psychology. “That was the pre-game talk: Please don’t sleep with these guys. It’s a great job until you get involved—then it all falls apart. The more you could raise the stakes in the room, without making it trashy or truly illegal, the more it felt like you’d entered a different world.” She was acutely aware of the dream she’d conjured: “Sometimes the men would think they had feelings for me, and I’d have to tell them, This is not real life! Here, I’m the anti-wife. In a real relationship, I’d make you take out the trash. Here, I’m the one who says, You never have to take out the trash.”
Within months, Bloom and her team were running Manhattan’s big game. At first, she shrewdly played the innocent impresario, subsisting only on tips from the players—a legal compensation. Temptation arrived in the form of the “rake,” that tiny cut which gradually transformed her role from hostess to outlaw. New York’s gaming laws, like its morals, permit a little vice for pleasure, but punish it for profit. “By the end, I was gambling just as much as they were,” Bloom admitted. “I was gambling on my ability to outwit criminals, competition, federal statutes, and debt sheets. I thought I had an edge—human psychology.”
The games were marked by excess and anxiety: fortunes shifted across the table, hedge-fund prodigies sat elbow to elbow with film stars and men of ambiguous reputation, all of them suspended in the Plaza’s shimmering twilight. Where once the ballplayers were the easy marks, now athletes sat at the top of the hierarchy. “Bringing in an A-Rod or a Knick gave the room real cachet,” Bloom said. “These big finance guys would become starstruck twelve-year-olds again.”
As the pots grew, so did the dangers. The curtain fell, as always, with a predawn knock, handcuffs, and a federal indictment. What remains, in Bloom’s telling, is less the memory of cards or cash than the spectacle itself—the interplay of aspiration and appetite. Never especially interested in gambling as such, she now describes the period with detachment. “Poker was simply having a moment,” she said. “Nothing to do with me. It could have been Go Fish.”
Bloom suspected, from a distance, that the era of glamour games was already ending. Even casual card games, she noted, have been transformed by the arrival of the “quants”—math-minded players who know all the odds and play accordingly. “Now it’s men in sunglasses, playing the algorithms,” she said. “ They would never have been allowed in my game. Mine was still the Wild West—people trying to read each other. You look at the final table at the World Series of Poker, and it’s not guys in cowboy hats anymore. It’s not Doyle Brunson. It’s people who study ‘perfect poker’ all day long.”
No doubt the proliferation of probability brokers—who can break down every hand, every proposition, into its likeliest outcomes—has leached some of the mystery and excitement from gambling. Today, earnest twentysomething Ph.D. candidates dive into their phones, use their training in statistics to play perfect poker, and hunt for the fine arbitrage advantages that Rothstein once had to enforce at gunpoint.
If there’s anything startling about games today, it’s that the more thoroughly they’re “solved,” the less compelling they become. Baseball, famously, grew dull as it became more perfectly understood, reduced to its three true outcomes—strikeouts, walks, home runs—while the color and chaos of the bunt, the stolen base, the suicide squeeze, and the pickoff became little more than decorative frosting.
Gambling, too, now divides the world between those who know enough to make it boring and those who—bored—prefer not to know. They play and lose anyway. Thrilling games, like thrilling cities, thrive on enigmatic imperfections: the small market anomalies that quants scour for an edge, the tells and giveaways that reward the observant and elude the rest. Once all is understood, all is dull. Gambling may once have belonged to the Devil, but I assure you it does no longer.
The arrival of organized gambling in its casino form has stripped away even the faded glamour of old miscreants like Rothstein and St. Clair. When, at last, detailed renderings of the proposed Caesars Palace emerged, they were hilariously decorous, showing not crowds of modern Harry the Horses and Nathan Detroits but elegantly dressed men and women in dignified black, playing in poker rooms that looked ready to host a seminar on, well, Gödel. (The only certainty is that Caesars Palace will persist without its possessive apostrophe—a Las Vegas tradition meant to Everyman the Roman-imperial ideal.)
Yet, however the thing is finally realized, Times Square will no doubt be diminished by the arrival of a casino, with its endless rows of slots, tables, and mechanical, emotionless losing. Casinos have a chancy reputation for a reason: they promise economic growth but tend to end up as factories of bad faith, processing steady columns of disappointed players.
Gambling is guessing, and guessing at future events is a way of hoping they might turn out better. Once gambling becomes just a set of algorithms to be parsed, it becomes severed from even its debased romantic aspiration, from its original wellspring of unreasonable expectations—for a sudden shower of fortune. In gambling, as in history, we have to work our way back from the book to the dream. Otherwise, it’s nothing but numbers. ♦
