Boardwalk Empire Season 5: The Real Arnold Rothstein

We take a look at the real story of Arnold Rothstein, who inspired stories in Boardwalk Empire season 5.

On the “All In” episode of Boardwalk Empire, Arnold Rothstein requests the company of Enoch Thompson at a card game he’s staked for 100 large because you only really know a man when you play cards with him. This is true. I grew up in a card-playing house and between the patter (“Ace of Spades, no help,” “straightening out”) and the way people act when they’re losing or winning money says a lot about them. What Nucky learned about Arnold Rothstein on that felt was that “The Brain” was a degenerate gambler who didn’t know how to lose.

Considering what we know about A.R. from Boardwalk Empire, this could look like it’s out of character, but A.R.’s been winning. Winners keep a good poker face. Arnold Rothstein himself, the real A.R., not the character, was whacked because he welched on a bet. No one takes your markers when you don’t pay out. A.R. was a great man, as Meyer Lansky says, but that business with Nucky is gonna be the death of him. On Boardwalk Empire, Arnold Rothstein is played by Michael Stuhlbarg.

Arnold Rothstein was known on the streets as “the Brain” because he had a head for figures and hedged his bets. People say Rothstein was the Moses of the Jewish gangsters. Rothstein was also called “Mr. Big,” “The Fixer,” “The Man Uptown” and “The Big Bankroll.” Rothstein is best known for fixing the World Series in the “Black Sox Scandal” of 1919, the year that the Volstead Act was passed. He also put the fix in at the 1921 Travers Stakes horse race. The Brain was convicted of neither. F. Scott Fitzgerald based the character Meyer Wolfsheim on Arnold Rothstein in The Great Gatsby. He was also the basis for Nathan Detroit in the original Damon Runyon story “The Idyll of Miss Sarah Brown,” before they taught the gamblers to sing and made Guys and Dolls out of it. Because of the first name, most people assume it was based on Meyer Lansky. Arnold Rothstein went in his father’s business. Abraham Rothstein was also a gangster-businessman.

Arnold Rothstein started casinos in Manhattan, distributed drugs and was a bootlegger who also ran speakeasies. Rothstein was a New York crime boss who did his dealings at the restaurant Lindy’s on 49th Street. He saw the early potential in Lucky Luciano, Meyer Lansky, Jack “Legs” Diamond and Dutch Schultz. Luciano said Rothstein “taught me how to dress. He showed me how to act like a gentleman.” The Brain was the CEO of New York’s mob business, but ultimately he lost to a stacked deck.

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Arnold Rothstein was born in New York City. His father, Abraham Rothstein, made his early money in the rackets but later did a turnaround and reinvented himself as a philanthropist who gave to Beth Israel Hospital. Arnold Rothstein was supposed to take over his old man’s legit businesses, but liked the shady ones better. He dropped out of school and lent his head for figures to his father’s old associates.

Arnold Rothstein opened a casino on West 46th Street in Manhattan’s red light district, the Tenderloin section, which ran from 23rd Street up to the low sixties between Fifth and Eighth Avenues, sometime around 1910. Rothstein put some money in a horse racing track at Havre de Grace, Maryland, where he could put the fix in at his leisure. Rothstein masterminded huge bond robberies, once turning over $25 million in bonds for a 10% cut. Rothstein was also a fence who specialized in jewelry and other high-end swag. Rothstein had eyes and ears all over the city and he was a millionaire by the time he was 30. Rothstein stopped carrying a gun after he was indicted on a charge of felonious assault for wounding two cops who raided his gambling den in 1919.


Some people say that some guys who worked for Rothstein paid off the heavily favored Chicago White Sox to throw the best-of-nine 1919 World Series. Most World Series had seven games, but you could better roll a bet over nine games. Rothstein bet on the underdog, the National League’s Cincinnati Reds. The series went to eight games on Redland Field and Comiskey Park and Rothstein made a small fortune. The next year it exploded in what was called the “Black Sox Scandal.” The White Sox players confessed, but were acquitted. The Baseball League commissioner Kenesaw Mountain Landis, didn’t buy that and he didn’t want people to think that the league itself was bought, and ruled “Regardless of the verdict of juries, no player that throws a ball game, no player that entertains proposals or promises to throw a game, no player that sits in a conference with a bunch of crooked players and gamblers where the ways and means of throwing games are discussed, and does not promptly tell his club about it, will ever play professional baseball.”  The players for banned for life.

Rothstein had to appear in front of a grand jury in Chicago but testified that he was an innocent businessman who just wanted to clear his name and his reputation. Prosecutors could find no evidence linking Rothstein to the affair, and he was never indicted. Rothstein testified that “The whole thing started when (Abe) Attell and some other cheap gamblers decided to frame the Series and make a killing. The world knows I was asked in on the deal and my friends know how I turned it down flat. I don’t doubt that Attell used my name to put it over. That’s been done by smarter men than Abe. But I was not in on it, would not have gone into it under any circumstances and did not bet a cent on the Series after I found out what was under way.” Rothstein probably actually hedged his bets.

The Volstead Act was passed in 1919 and Rothstein was the first to get into the action, smuggling booze up the Hudson and from Canada. He also gave people a place to drink, opening speakeasies all over New York. Rothstein did his business on the street outside Lindy’s Restaurant on Broadway and 49th Street and did it better than Tammany Hall. He negotiated peace and settled turf wars among gangs and finally, Tammany Hall had to go to him too. Rothstein won $500,000 on the first Dempsey-Tunney heavyweight championship bout. He raked in $800,000 when Sidereal came in at good odds at Aqueduct on July 4, 1921. Later that year, Arnold Rothstein’s horse, Sporting Blood, won Travers Stakes after a scheme with horse trainer Sam Hildreth drove the odds up to 3-1 by entering heavy favorite Grey Lag. Rothstein bet $150,000. Grey Lag was scratched from the race just before post time and Rothstein won more than $500,000.

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In October 1928, Rothstein played in a marathon poker game in Apartment 32 of the Congress Apartments at 54th Street and Seventh Avenue. The game was fixed by Titanic Thompson and Nate Raymond and after three days Rothstein owed $319,000: $100,000 to Nate Raymond, $30,000 to Thompson and about $200,000 to the other players. Rothstein said he was good for it, he was waiting on the November elections where he had heavy action on Hoover for President and Roosevelt for Governor. Rothstein was ambushed at a meeting at the Park Central Hotel on 55th Street and Seventh Avenue on November 4, 1928. He had $6,500 in his wallet. When the cops tried to get Rothstein to drop dime on his killers he said “My mother did it.” His mother, Edith, had an alibi.

Arnold Rothstein died on Election Day, Nov. 24, 1928, at the Stuyvesant Polyclinic Hospital in Manhattan. If he lived he would have won the $500,000 he laid on Herbert Hoover. Gambler George “Hump” McManus was arrested, but the charges didn’t stick. In the book Kill the Dutchman!, crime reporter Paul Sann says Rothstein was killed by Dutch Schultz as payback for the hit on Joey Noel, by Legs Diamond. Rothstein died in police custody and his corporation was busted out and spread among the other mobs. When Rothstein died he took Tammany Hall with him. Fiorello La Guardia got himself elected mayor on a promise to clean up New York City. Ten years later, Rothstein’s brother, a rabbi, said that The Brain’s money was all gone and that his estate was bankrupt.

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