Bill Simmons Faces Gambling Scrutiny After Proxy Betting Admission

Bill Simmons, the sports media executive who once branded Prince Harry and Meghan Sussex “f—ing grifters,” is now facing scrutiny of his own after admitting that he used his daughter’s boyfriend to place sports bets for him in Massachusetts while Simmons was in California. The Massachusetts Gaming Commission says it is reviewing the matter after Simmons described the arrangement on his podcast. FanDuel, which has a commercial partnership with The Ringer, has already voided the wagers and taken action on the account.  

The commission announced the review Tuesday, two days after Simmons said on an episode of his podcast that he’d used a proxy on multiple occasions to log in to his account and make wagers in Massachusetts.

Simmons, founder of The Ringer, is based in California, where sports betting is not legal. In Massachusetts, mobile and online betting is allowed.

But proxy betting — having someone place bets on behalf of someone else — is illegal in Massachusetts and is not allowed by FanDuel, the sportsbook with which the wagers were issued.

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The irony is difficult to miss. In 2023, Simmons publicly attacked Harry and Meghan after their Spotify deal ended, calling them “grifters” and saying “f— them” on his podcast. Now the man who was so comfortable questioning someone else’s professionalism is explaining that he did not know the rules after using another person to access his betting account and place wagers on his behalf.  

Simmons said he trusted his daughter’s boyfriend, gave him the authentication code and treated the betting as a “bonding moment.” He later acknowledged that proxy betting was not allowed and called the episode a “lesson learned.” Massachusetts permits mobile sports betting, but its rules prohibit people from placing wagers as agents or proxies for someone else.  

That makes the story more than an embarrassing betting mistake. Simmons has spent years helping normalise sports gambling through one of the most influential sports podcasts in America, while The Ringer maintains a commercial relationship with FanDuel. For someone who has made a career out of judging other people’s decisions, the spectacle of regulators now reviewing his own is an unusually sharp reversal.  

Bill Simmons is only the latest outspoken Sussex critic to experience an awkward reversal. Journalist Andrew Pierce spent years making intensely personal attacks on Meghan before ending his run at the Daily Mail this summer.  

Then there is Variety executive editor Matt Donnelly, whose reporting painted the Sussexes’ Hollywood operation as dysfunctional. He is now at the centre of his own ugly industry dispute, with UTA CEO David Kramer accusing him of threatening the agency and behaving unprofessionally toward female employees. Variety disputes UTA’s characterisation, so those claims remain allegations.  

Eamonn Holmes once suggested Harry should leave Meghan and return to his family without her. Holmes subsequently separated from Ruth Langsford after 27 years together.  Sarah Vine spent years dissecting the Sussex marriage in print, only to go through a very public divorce from Michael Gove herself.

Add Martha Stewart’s silent Netflix reception after questioning Meghan’s lifestyle credentials, Tina Brown’s confident predictions failing to match Netflix’s public position, and other prominent critics facing their own professional or personal setbacks, and the irony starts writing itself.

At this point, we are willing to believe the cosmic scoreboard might be real. Again and again, people who spoke with extraordinary certainty about Harry and Meghan’s supposed failures have found themselves facing their own scandals, reversals and uncomfortable headlines. The irony is becoming difficult to ignore.