In the early 20th century, one of the most integral members of the criminal underworld was Arnold Rothstein, the archetype of the old school mobster. He was intelligent, charming, well-spoken, grotesquely wealthy, and a sharp dresser, often pictured with a patterned bowtie and a flat-top fedora snugly fit over his receding hairline. And yet, he was nothing like the stereotypical mobster; Arnold was not a drinker or smoker, and he was not one to be tempted by illicit substances. He was a notorious high roller, with pockets holding wads of $100 bills, but to the casual eye, he was just another dapper, well-mannered gentleman who frequented the tracks and casinos after a long day at the office.

Today, Rothstein is remembered for his murky association with the most notorious event in the history of American sports: the fixing of the 1919 World Series by the Chicago White Sox. The White Sox were favored 5:1 to beat the Cincinnati Reds, and for the first time since 1903, the Series would be a best-of-nine format. However, at a time when players were treated as second class, some sought a payday beyond what they made in the leagues, and the White Sox players were some of the most poorly paid in the league. The owner of the team, Charles A. Comiskey, was one of the cheapest owners in the game.

Around two weeks before the World Series, Chicago first baseman Chick Gandil met with a gambler in his Boston hotel room. During that meeting, Gandil told Joseph Sullivan that for $100,000, he and other members of the White Sox were willing to take a dive and make sure that the Reds won the World Series. Gandil was able to convince the team’s top two pitchers to go along with the plan, as well as five other players. With that, the plan to throw the World Series was put in motion, and rumors began to spread around the country prior to the start of the series as gamblers wagered large sums of money on the Reds.