Amid speculation about Gilbert Arenas’ involvement with Portland Trail Blazers’ Chauncey Billups’ arrest, he isn’t exactly denying it.
The NBA was rattled by a gambling scandal Thursday morning, with Billups, Miami Heat guard Terry Rozier, and former Cleveland Cavaliers player Damon Jones being arrested in separate sports betting probes. Hours after coaching the Trail Blazers to a season-opening loss, Billups was arrested in Oregon and charged in an illegal poker operation tied to the Mafia.
Ironically, the charges against Billups come less than three months after Arenas was arrested on a federal indictment and accused of running an illegal gambling business with five others, including a suspected Israeli crime figure. Arenas was alleged to have rented out his Encino, CA, mansion to host high-end, illegal poker games.
Facing up to five years in prison, Arenas posted a video after being released on bail in July, implying he would be willing to cut a deal by using the hashtag #SnitchingGilComingSOON.
Gilbert Arenas says “snitching Gil coming soon” after being indicted on three federal charges accusing him of renting out his house for, and helping arrange, an illegal poker gaming racket. Gil is facing up to five years in prison but seems, um, willing to cut a deal. pic.twitter.com/cJLCoiUO3D
— Rachel Nichols (@Rachel__Nichols) July 31, 2025
Three months later, Billups was arrested on charges that sound, ironically, similar to those Arenas is facing. And as people began to speculate about Arenas’ potential involvement, he only fueled those thoughts and theories by showing up to his Gil’s Arena show with a bag labeled “Informant Lunch.”
Agent 0 Days in jail 💀😭 pic.twitter.com/YU6jpQ00Zc
— Gil’s Arena (@GilsArenaShow) October 23, 2025
“This is my lunch, man, I didn’t get to eat it over there, I was talking too much,” Arenas said at the start of the show. “The Blazers wasn’t gonna win anyway, the last thing they needed was their coach.”
Further, an old video surfaced of Arenas claiming he, Larry Hughes, and Damon Jones were “at LeBron’s place gambling” during a 2006 NBA playoff series between the Washington Wizards and Cleveland Cavaliers. In the video, Arenas noted James wasn’t gambling. But Jones has now been arrested for allegedly trading inside information on a LeBron James injury in 2023.
This Gilbert Arenas story about Damon Jones is INSANE 👀
This NBA gambling story keeps getting crazier and crazier pic.twitter.com/239pHvopTr
— New York Post Sports (@nypostsports) October 23, 2025
Maybe Arenas is just leaning into everything for show and attention, and this is just one giant coincidence. But we know Arenas was arrested for ties to an illegal gambling business. We know he implied he was willing to cut a deal to stay out of prison. We know Billups was arrested for alleged involvement with an illegal poker operation three months later. And we know Arenas is now leaning into being an informant.
Beyond that, we’ll avoid any speculation and wait for more details.
About Brandon Contes
Brandon Contes is a staff writer for Awful Announcing and The Comeback. He previously helped carve the sports vertical for Mediaite and spent more than three years with Barrett Sports Media. Send tips/comments/complaints to bcontes@thecomeback.com