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The Real American Gangster: Arnold Rothstein


Herald Square, 34th and Broadway (1936). Photo courtesy of the New York Public Library.

And the CLERK’s mind is now suddenly impervious to the threat of Night and Silence as it pursues an ideal of fame and glory within itself called Arnold Rothstein…

In Hughie, one word pierces the fog of the Night Clerk’s boredom: gambling. “I beg your pardon, Mr. Erie,” he says, “do you, by any chance, know the Big Shot, Arnold Rothstein?” Suddenly another world opens up before him, a world beyond the gritty, sordid hotel lobby. The real Times Square, just a few blocks away, was the realm of gangsters and showgirls, of high stakes and large bankrolls: the irresistible underworld of New York City in the 1920s. Here, men mastered their destiny and no obstacle—police, law, or rival—stood in their way. It may have been the moral underbelly of the city, but to these men, it was the top of the world. And Arnold Rothstein was at the center of it all.

By the time Prohibition became law, Arnold Rothstein was already notorious as a gambler in New York. He had entered the realm of legend when he was rumored to have fixed the 1919 World Series and grossed a huge sum off insider bets. In typical Rothstein fashion, he ducked the blame in the scandal and still had the nerve to act insulted when he was accused of being involved. Having built his empire on fixed horse races, card games and a Manhattan gambling house, he set his sights on the illegal liquor trade as well. Bootlegging and bribery, rum-running and racketeering, narcotics, loan-sharking, fencing stolen property and cheating on everything from boxing to cards—not to mention of course, murder—Rothstein had a hand in every crime and cash pot in New York. Nicknamed “The Brain” for his incredible intellect and well-heeled demeanor, he built a web of contacts from the top to the bottom, bridging ethnic gangs, politicians and legitimate businessmen.

Rothstein famously used Lindy’s Restaurant in Times Square as an office, taking calls and messages and holding business meetings at his customary table, just a few blocks from Erie’s seedy hotel. Abe Scher, Lindy’s nighttime cashier, described Rothstein’s routine. For the full effect, it’s best to read this aloud:

Every night he comes here. Regular as clockwork he comes here. Sunday night, Monday night, any night. Everybody knows that. Like always, there are some people waiting for him. They are waiting near his table, the same one where he is always sitting…All day and night, they are telephoning for him here. It ain’t that Mr. Lindy likes the idea, but what can he do? An important man like Mr. Rothstein, you do not offend. So like I am saying, he comes in and goes to his table. He is saying ‘hello’ to people and they are saying ‘hello’ to him. Some fellows, they go to his table and they are talking confidential to him. You know, they are talking into his ear…Did he give anyone money? Who knows? Mr. Rothstein you see, but you do not watch…

Sounds like a gangster movie, doesn’t it? In fact, Mr. Scher’s statement is from an actual police report. Arnold Rothstein lived in a real world populated by legends, any of whom might be seen at a nearby table on any given night: Nick the Greek, the famous gambler; Jack Dempsey, heavyweight champion; “Legs” Diamond, a bootlegger and bodyguard; “Titanic” Thompson, so named for the rumor that he survived the sinking of the famous ship; Broadway’s Fanny Brice, of Funny Girl, and her husband Nicky Arnstein, Rothstein’s protégé; and Charles “Lucky” Luciano, who would father the modern mafia, reorganizing New York into five crime families. Luciano says it was Rothstein who dragged him to a department store and taught him the importance of an impeccable suit, the trademark of mafia bosses for generations afterward. These faces blended with countless more thugs, gamblers and showgirls, creating a social landscape whose truth was more incredible than anything the Night Clerk could dream up.

In August 1928, when Hughie takes place, New York City stood unwittingly at a precipice. That November, the untouchable Arnold Rothstein would be shot and killed by rival gamblers for not paying his debts, inciting upheaval in his illicit society and a massive scandal in the city. Less than a year later, the great Wall Street crash upended the economy and signaled the start of the Great Depression. But even as the underworld unraveled and Americans struggled to survive, the gangster life never lost its romance. Even now, Arnold Rothstein and his supporting cast fire our imaginations. Rothstein was the basis for the character of Nathan Detroit in Guys and Dolls, while his cohort “Titanic” Thompson was the model for Sky Masterson. Rothstein also appears in Fitzgerald’s The Great Gatsby as the gangster Meyer Wolfsheim. In the more recent HBO series Boardwalk Empire, Michael Stuhlbarg’s Rothstein is a recurring character, warring with Atlantic City’s Nucky Thompson, played by Steve Buscemi.

Complete freedom and complete power. In the blazing chaos of the Jazz Age, these men created a new world order, where thugs were as influential as judges, and criminals had a code of conduct and respect more sacrosanct than the clergy. Erie describes how Hughie thirsted for stories about the mobsters, imagining Erie among the bosses. The stories keep both of them going. The Big Shots, as Erie calls them, had the guts to change their circumstances—while O’Neill’s characters can only yearn and pretend.


Laura Henry Buda started as STC’s Education Coordinator in April and was STC’s 2011–2012 Artistic Fellow. She holds an MFA in dramaturgy from the A.R.T./M.X.A.T. Institute at Harvard University.

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