Mere hours after coaching the Portland Trail Blazers to a 118-114 loss against the Minnesota Timberwolves, Chauncey Billups was arrested and charged with wire-fraud conspiracy and money-laundering conspiracy. The probe has alleged that Billups was involved in an illegal gambling ring with members and associates of the La Cosa Nostra organized crime families.’
Now, former Trail Blazer Anfernee Simons has expressed his shock at the arrest.
“It hit me pretty tough for sure. Just in shock. And obviously I’ve got a great relationship with Chauncey. Even after the trade, he’s checking in on me and I’m checking in on him,” he said, per The Athletic’s Jay King.
Anfernee Simons on the Chauncey Billups news: "It hit me pretty tough for sure. Just in shock. And obviously I’ve got a great relationship with Chauncey. Even after the trade, he’s checking in on me and I’m checking in on him. So we had a great relationship and I think like I…
— Jay King (@ByJayKing) October 24, 2025
Billups arrived in Portland back in June 2021 and immediately helped Simons become a high-scoring guard.
“So we had a great relationship and I think like I said before it’s an unfortunate situation for him to be in, especially for him and his family, all the media attention that’s coming in, the scrutiny. It’s just an unfortunate situation,” he continued.
Prosecutors allege the poker ring used Billups as a recognizable “face card” to lure victims with the promise of playing against celebrities.The poker scheme is separate from, but related to, a broader federal probe that also includes an insider sports-betting case involving other defendants.
Authorities say the poker games were run in multiple hubs since 2019, including Manhattan, the Hamptons, Las Vegas, and Miami, per Reuters. Investigators describe sophisticated cheating technology at those games, including altered shuffling machines that read decks, an X-ray poker table to reveal face-down cards, and marked-card systems visible through special contact lenses or glasses.
Officials said the poker conspiracy defrauded victims of at least $7 million, with some individual losses reaching seven figures. Billups appeared in federal court in Portland after his arrest and is expected to post a substantial bond as the case proceeds.


















