Amid a bit of internal turmoil, the last thing The Ringer needed was a regulatory inquiry into founder and prominent sports media personality Bill Simmons. But that’s exactly where he has found himself after admitting on his podcast that he engaged in illegal proxy betting.
The controversy began when Simmons revealed on an episode of The Bill Simmons Podcast that while at his primary residence in California, where sports gambling remains illegal, he repeatedly instructed his daughter’s 21-year-old boyfriend to place wagers on his behalf in Massachusetts.
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While online sports betting is legal in Massachusetts, proxy betting is not. And that’s put Simmons in hot water.
Fanduel, whose terms and conditions state that a user’s account is strictly for personal use, also does not allow anyone placing bets on behalf of someone else. After his admission, FanDuel confirmed it has taken action.
“We became aware of the issue and handled it consistent with our Terms and Conditions and Massachusetts Gaming Commission regulations, including reporting the matter to the MGC, voiding the bets, and actioning the account,” a FanDuel spokesperson told media.
The Massachusetts Gaming Commission (MGC) confirmed that its staff is actively reviewing the matter following Simmons’ public admission. According to Massachusetts sports wagering statutes and standard gaming regulations, proxy betting, that is, when another individual places wagers or accesses an online betting account on someone else’s behalf, is explicitly prohibited.
It’s not just on an individual level. The admission created an immediate conflict with FanDuel, the exclusive sports betting partner of The Ringer network. The sportsbook confirmed that it reported the incident to the MGC, voided the illicit wagers, and took action against Simmons’ account.
FanDuel’s official terms of service state that proxy betting can trigger account confiscation and permanent bans.
NBA Sportscaster, Bill Simmons’ podcast faux pas least of his troubles
The popular sportscaster has never been shy about discussing his bets and odds. It also made sense given that The Ringer and FanDuel have a partnership. But Simmons’ casual admission on the August 30 episode backfired.
Simmons detailed the mechanics of the arrangement with his daughter’s boyfriend on air, framing it as a lighthearted bonding experience.
“I get the code to make sure it’s me to my phone; I give him the code, he logs in. And I have all this money that I had from last year because I actually hit a bunch of futures last year. And he’s putting in bets for me,” he narrated to viewers.
On Tuesday, right after FanDuel’s action, Simmons addressed the issue.
“I talked about how I got my daughter’s boyfriend to place some bets for me in Massachusetts, because I was in L.A.,” Simmons said. “Did not know about the proxy rules. … I learned my lesson. Apparently, proxy betting, not allowed. I actually thought it was, but that’s fine.”
The consequences for proxy betting are usually limited to fines. Simmons might also be banned from online sportsbooks and casinos in Massachusetts.
The gambling investigation crowns a challenging week for Simmons, who is also confronting intense public backlash and internal dissent over his editorial choices and commercial partnerships.
Film buffs and media critics slammed Simmons over segments on his movie podcast, The Rewatchables, alleging he utilized ChatGPT to simulate reviews in the distinct voice of the late Pulitzer Prize-winning film critic Roger Ebert.
The discontent has spilled into the open among key figures within The Ringer network. Sean Fennessey, host of The Big Picture and former head of content at the company, expressed his dissatisfaction on Talk Easy about Ringer’s partnership with AI businesses and its non-exclusive licensing of Ringer content to Netflix.
As the Massachusetts Gaming Commission continues its review, the convergence of regulatory scrutiny, ethics complaints, and internal pushback presents one of the most volatile stretches for Simmons since Spotify acquired The Ringer in 2020 for over $200 million.