Some major names in the world of professional sports are allegedly embroiled in an illegal gambling racket organized by the Mafia — but Jay Leno wouldn’t know anything about that, so don’t ask him about it unless you want to “fall down a hill” too.
Last week, an explosive scandal overshadowed the beginning of the 2025-2026 National Basketball Association season as federal law enforcement officers arrested both Portland Trailblazers coach Chauncey Billups and Miami Heat point guard Terry Rozier. The high-profile arrests followed a years-long investigation into illegal sports betting and rigged poker games allegedly perpetrated by some of the most powerful Mafia families in the country, and the news rocked the NBA while further inflaming the greater discussion about the growing influence of gambling in sports.
But, more than that, the revelation of Mafia ties to popular sports figures shocked the community of basketball fans who forgot that the mob isn’t just a thing from the movies.
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To the surprise of these room-temperature-IQ basketball fans, yes, the world of organized crime is alive and well, even if it is, by design, out of sight from the layman. Comedy fans, however, aren’t surprised by the Mafia’s NBA racket, having kept a good eye on the mob since a certain suspicious incident — and, if they’re smart, they’ll learn to keep their mouths shut, too.
As comedy fans and the terminally online will recall, last year, the long-time Tonight Show host suffered a nasty shiner while touring in Greensburg, Pennsylvania, an injury that he attributed to falling down a hill when trying to take a short cut from his hotel to a lunch spot nearby. Immediately, the internet agreed that the likelihood of Leno getting himself hospitalized in an incident that involved zero vehicles is much less likely than the logical alternative: Someone made Leno an offer that he couldn’t refuse, even though he tried.
When the Leno-Mafia connection got too much attention on social media, the comic attempted to dissuade the public from looking any deeper into his possible connection (and debt) to the Cosa Nostra, arguing that, if he really owed the mob money, they would steal one of his hundreds of classic cars rather than jump him outside a Hampton Inn in small-town Pennsylvania.
But, of course, that’s what anyone who feared retribution from their old poker buddies over at the Gambino high-rollers’ game would say, and the public isn’t as easy to fool as the marks from the NBA gamblers’ alleged fixed tables. We know that Leno is afraid to speak the truth, and we suspect that he might know a little something about the biggest scandal in professional sports — after what he did to Conan O’Brien, I wouldn’t be surprised if Leno is behind the Celtics’ three-game skid.
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