Gambling has been a reliable cash cow for organized crime for more than a century. Larger than life figures including Meyer Lansky, Bugsy Siegel, and Frank Rosenthal (portrayed by Robert De Niro in the 1995 film “Casino”) have shaped  the public’s understanding of gambling’s role within the broader mafia ecosystem. 

But for every mythical figure of the gambling underworld, there are countless neighborhood bookmakers, or “bookies,” hustling the streets simply to make ends meet. In the second bonus episode of the new season of Up Against the Mob, we’re introduced to the self-described “best bookmaker” in town, Lou “The Shoe” Santos. While Lou never became a “made man” because he wasn’t Italian, he was admired by the Springfield mafia for both his ability to earn money and inflict violence.

Because betting on sports was illegal in Massachusetts, Lou's success as a bookie was due in large part to his mob ties. But the laws around sports betting have since changed: In 2018, the Supreme Court struck down a 1992 federal law banning sports gambling, effectively making the practice legal nationwide. 

This begs the question: would any of Lou’s old-school bookmaking skills be viable today given the sudden ubiquity of legal sports betting?