Vice Was His Business: The Notorious Life of Arnold Rothstein
From baseball to horse racing, Arnold Rothstein played a role in some of the more dubious sports moments of the early 20th century. Born with a head for numbers, Rothstein became enamored of games of chance early and turned his love for gambling into a vast criminal empire that made him not only a legendary racketeer and kingpin, but also a character in popular culture, with references to him appearing in the works of F. Scott Fitzgerald and Damon Runyon and television programs like Boardwalk Empire†
With his penchant for risk, Rothstein tried his hand at more than one role within the sport of kings, and the stories of his exploits are part of racing history.
Born the second child of Abraham Rothstein, a cotton goods dealer and devout Jew, Arnold Rothstein grew up on the Lower East Side of New York, an area rife with gangs and vice, like prostitution and gambling. He got into gambling early, eschewing schoolwork for games. After dropping out of school at sixteen, Rothstein worked briefly for his father as a traveling salesman but did not stay on the job long. Instead, he parlayed money from odd jobs and gambling into bankrolling other gamblers. The money was due the following week and those who did not pay got a visit from the muscle that Rothstein hired to collect on those debts.
Instead, he parlayed money from odd jobs and gambling into bankrolling other gamblers. The money was due the following week and those who did not pay got a visit from the muscle that Rothstein hired to collect on those debts.
Rothstein worked his way up to owning his own casino, accruing enough wealth that he was able to develop some powerful friends: police, politicians, and Broadway personalities. His wealth also allowed him to indulge his other interests, including horse racing.
In 1912, Rothstein joined August Belmont II and others in financing a new Maryland racetrack, Havre de Grace. At a time when the anti-gambling laws had shuttered racing in New York, the new track offered fans another place to wager and win and horsemen more opportunities to race.
But Belmont did not relish this connection to Rothstein: when New York allowed racing to resume in 1913, the chairman of the Jockey Club remained conscious of the sport’s image. Wary of Rothstein’s reputation, Belmont and his other partners in Havre de Grace tried to buy him out. When he refused, they had the Maryland legislature pass a law limiting the number of shares an out-of-state resident could own in any Maryland racetrack. Anyone with a connection to the unseemly side of life was not someone Belmont wanted seen at racetracks under his jurisdiction.
Also working against Rothstein was his betting coup in the 1917 Hourless-Omar Khayyam match race. When other big-time gamblers offered to take Rothstein up on his large bets on Hourless, the crime boss smelled a rat. Did these gamblers have a jockey in their pocket?
Concerned that a fix was on, Rothstein convinced Hourless’s trainer Sam Hildreth to substitute regular rider Jimmy Butwell for Frank Robinson. If Butwell did not ride Hourless, then the fix could not happen. Hourless won and the notorious gambler netted $300,000 in the race. An already dubious reputation gained a new level of suspicion. Though he had no evidence, Belmont suspected that Rothstein’s wins were often connected to his influence, as in the case of the Hourless-Omar Khayyam match race, or straight-up cheating, like race fixing.
Though he had no evidence, Belmont suspected that Rothstein’s wins were often connected to his influence, as in the case of the Hourless-Omar Khayyam match race, or straight-up cheating, like race fixing.
Without proof, all Belmont could do was ask Rothstein to reduce his visibility. Rothstein, of course, did not oblige. He made large wagers whenever he could, even betting Commander JKL Ross that Eternal would beat Ross’s Billy Kelly in the 1919 Kentucky Derby. Of course, Sir Barton would win, Billy Kelly would be second, and Ross would collect $50,000 from Rothstein.
Rothstein’s name also came up during the Black Sox Scandal, which erupted after the Chicago White Sox lost the 1919 World Series to the Cincinnati Reds. Unhappy with White Sox owner Charles Comiskey, a group of players conspired with gamblers to throw the World Series. When the conspiracy was finally revealed, Rothstein was named as one of the gamblers working with the accused players, but any connection the crime boss might have had was through intermediaries. Since he could not be directly linked to the scandal, Rothstein escaped prosecution for his role in that infamous series.
In the early 1920s, as the Black Sox Scandal was playing out, Rothstein expanded his role from gambler to owner, buying horses just as he branched out in other ways.
Sir Barton after winning the 1919 Kentucky Derby (Courtesy of the Kentucky Derby/Churchill Downs)
With Prohibition in full swing, Rothstein became a bootlegger, setting up a smuggling business that would bring liquor into the United States from Canada. The crime boss was expanding his interests beyond casinos and gambling but continued going to the races.
Under the banner of Redstone Stable, Rothstein raced a few horses, none of any serious import; nevertheless, he found a way to make money off his horses. One particular high-profile instance involved Harry Payne Whitney, a stakes-winning filly, and a horse named Sporting Blood.
One particular high-profile instance involved Harry Payne Whitney, a stakes-winning filly, and a horse named Sporting Blood.
Sporting Blood had yet to show anything special in a stakes, but trainer Willie Booth entered the colt in the Travers Stakes anyway. Whitney’s filly Prudery was the favourite, her recent stakes wins scaring off any competition – except Sporting Blood. Looking to profit, Rothstein convinced Sam Hildreth to enter his Belmont Stakes winner Gray Lag in the Travers, which would drive up the odds on Sporting Blood. Hildreth would then scratch Gray Lag – but not before the gambler had placed sizable wagers on Sporting Blood.
The strategy worked. Gray Lag scratched, leaving the Travers with just Sporting Blood and Prudery. Prudery took the lead early, but Sporting Blood kept pace with her, passing her as they straightened into the Saratoga stretch. The filly had not been herself since her win in the Alabama, sulking when jockey Laverne Fator asked her to pick up her pace in the stretch. Sporting Blood won by two lengths. Rothstein brought home the winner’s purse of $10,275 – and $450,000 in winning bets.
Within two months, Rothstein announced he was out of the racing business, selling his small stable of six horses, including Sporting Blood. the Daily Racing Form reported that Rothstein would instead focus on “his real estate and insurance business.” That was the end of his horse business, but not the end of Rothstein’s criminal empire.
In 1928, seven years after selling out of the sport of kings but not out of the gambling business, Rothstein succumbed to a bullet to the abdomen, allegedly fired by a man he owed money to after a three-day poker game. He built an empire on his penchant for gambling and vice, dabbling in some of the most infamous sport moments of his era, but ultimately that passion for games of chance became his undoing, leaving behind an infamous reputation and a