Arnold Rothstein – A Poker Game Gone Wrong

While he may not be as well-known as may other 20th
Century gangsters, Arnold Rothstein may very well be the father of organized
crime in America. Rothstein was one of the original gangsters who took crude,
street level rackets and elevated them into big business, becoming wealthy
himself in the process. Rothstein was instrumental in turning prohibition into
a lucrative money-making opportunity for gangsters across the United States; he
also may have been involved with some of the most infamous sports fixing
scandals of all time. While he died rather ignominiously in the wake of a 3-day
poker game gone wrong, and may be forgotten to everyone but historians, Arnold
Rothstein undoubtedly left a controversial mark on American history.

The Early Years: A Love of Gambling

Unlike many of his contemporary gangster counterparts, Arnold Rothstein was born in the 1880s in Manhattan, the younger son of a successful Jewish businessman. Rothstein’s family was well-regarded in the community, and his elder brother Harry even studied to become a rabbi. While both brothers did well in school, the younger Rothstein was alleged to harbor resentment of his parents’ doting on the elder Harry; this may have led him to become somewhat of a rebel from an early age.

Rothstein’s rebellion against his straitlaced family often
manifested itself in gambling. Even as a young boy, Rothstein loved to gamble.
He would often play dice or poker wherever a high stakes game could be found,
much to his parents’ chagrin. However, while it may have started as an outlet
to strike back at his parents, gambling grew to become Rothstein’s life
passion; it likely even played a role in his death years later. 

Betting Big

While it remains open to debate, Rothstein may have been involved in two of the biggest sports fixing scandals of all time. First, he is alleged to have played a key role in the infamous 1919 Black Sox scandal. Rothstein, along with several other associates is alleged to have bribed eight members of the 1919 Chicago White Sox to intentionally lose the World Series, so that Rothstein could make a fortune betting against them. Rothstein was implicated by witnesses at the players’ trial (which ended in acquittals) but was never tried himself for the alleged crime.

In 1921, two years after allegedly fixing the World Series, Rothstein was involved in yet another major sport fixing scandal, this time in horse racing. Rothstein entered a colt he owned, named Sporting Blood, to race in the 1921 Travers Stakes. A horse named Prudery was the odds-on favorite to win, until a late entry named Grey Lag became part of the race and became the new favorite. In the end, Grey Lag dropped out of the race as rapidly as he’d entered, Prudery performed poorly, and Sporting Blood won the race. Rothstein, whom many believed was behind Grey Lag’s entry and exit and was at least knowledgeable of Prudery’s condition on race day, pocketed a windfall of  over $500,000 on his initial $150,000 bet. In doing so, he created a controversy in American horseracing that is still debated to this day.

Prohibition: A Gangster’s Windfall

By the time of prohibition, Arnold Rothstein was already a wealthy man of questionable morals, and saw the ban on alcohol sales in America as yet another business opportunity to exploit. He soon built an impressive smuggling network that brought in alcohol from Canada, both from New York State as well as the Great Lakes Region in Chicago and the Midwest. Rothstein even used his fleet of merchant freighters to purchase scotch whiskey from overseas and smuggle it into the states as well.

With his lucrative control over a massive liquor distribution network, Rothstein rose to become the most powerful member of American organized crime. Nicknamed “the Brain,” or “the Big Fixer,” Rothstein mentored and inspired several younger gangster contemporaries, notably Charles “Lucky Luciano and Meyer Lansky, among others. His level head and business acumen often enabled him to play the role of mediator among various organized crime factions, enabling the Mafia and other syndicates to spread further and wider across America’s cities and states.  However, despite his clear involvement in the rackets and other criminal activity, Rothstein never spent a day in jail.

The End: A Poker Game Gone Wrong?

In October 1928, Rothstein was allegedly involved in a high
stakes poker game. Over the course of three days of poker, Rothstein was
reportedly in the red for over $320,000. Claiming the game was rigged,
Rothstein allegedly refused to pay his gambling debt and left the game. Several
weeks later on November 4, Rothstein was shot in the middle of a meeting at New
York’s Park Central Hotel. He died from his wounds on November 6th
but refused to implicate the shooter; no one was ever convicted of the
shooting, but Rothstein’s gambling debt remains the most likely motive for his

Parting Thoughts

Arnold Rothstein, the high stakes gambler and ruthless
opportunist, helped elevate organized crime into a corrupt but lucrative
business in every large city across America. He turned Prohibition into a major
money-making endeavor for the Mob and mentored young gangsters who led the
Mafia and other rackets well into the final decades of the 20th
Century. However, despite his fierce intellect and shrewd business sense, Rothstein’s
 passion for gambling proved to be his
undoing. While he narrowly avoided an indictment for fixing the World Series in
1919, his cold streak at a high stakes poker game in 1928 led to his untimely
death. Today, Rothstein is known more for mentoring or inspiring the more
violent and infamous New York and Chicago mobsters who succeeded him.

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