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.
NBC NEWS
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.
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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.
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The Sussexes judgement is 💯 correct . Duchess Meghan and Prince Harry bullshit detector is on point.
Hyprocrital moron, who should have the full force of law enforced on his scandalous criminal behaviour.
Hypocrisy warning: People in glass houses should not throw stones, in other words do not judge other people when you are a degenerate low life, existing without a moral compass.
Watch Elizabeth Solaru Podcast on YouTube
3 Sept 2026
Description
“Bill Simmons, yes THAT Spotify executive is under investigation for illegal conduct”
“When Spotify and Harry and Meghan parted ways, reports at the time indicated the couple were exercising a legitimate contractual option to end the arrangement, not breaching an agreement or failing to deliver on obligations. Simmons, in characteristically blunt fashion, called them grifters anyway, a serious accusation implying deliberate deception or fraud, for what was, by all accounts, an entirely lawful business decision within the terms both parties had already agreed to. That’s worth sitting with on its own before even getting to what’s happened to him since. Calling someone a grifter for exercising a contract right they were legally entitled to exercise was never an accurate characterization in the first place”.
“Now the actual, documented irony. Simmons is reportedly under review by the Massachusetts Gaming Commission after openly admitting, on his own podcast, to proxy betting, having his daughter’s boyfriend log into his FanDuel account and place wagers on his behalf while Simmons was apparently in a state where sports betting remains illegal. That’s not an accusation. That’s Simmons’s own words, recorded and published, describing exactly how the arrangement worked, down to the detail of sending a verification code to make sure the account access was legitimate”.
“Proxy betting isn’t a grey area here. It’s explicitly against Massachusetts law, which requires sportsbooks to prevent exactly this kind of arrangement, and it’s explicitly against FanDuel’s own terms of service, which state proxy betting can result in permanent suspension and forfeiture of winnings. FanDuel has already reported the matter to the Gaming Commission, voided the relevant bets, and taken action on the account. The Commission itself has confirmed it’s actively reviewing the matter”.
“Here’s the actual point worth drawing out plainly. A man who threw around a serious, inaccurate accusation of fraud against two people who did nothing more than use a contractual right available to them is now facing genuine regulatory scrutiny for something he openly admits doing, an actual violation of both law and the terms of service governing his own betting activity. That’s not a minor rhetorical gotcha. That’s a real, substantive contrast between manufactured outrage aimed at legitimate conduct, and actual documented misconduct casually confessed to on air by the person who threw the original insult”.
“The broader point worth naming is one that’s shown up repeatedly throughout this entire conversation. Public figures who reach for harsh, moralizing language to describe other people’s entirely legal decisions rarely hold themselves to anything resembling that same standard. Simmons didn’t need to be caught doing anything to make his original comment inaccurate, it was inaccurate the moment he said it, since acting within a contract isn’t grifting by any reasonable definition. But watching him now face actual regulatory consequences for genuinely admitted rule breaking does add a certain clarifying symmetry to the whole situation, the kind that tends to arrive right when it’s least convenient for the person who threw the first insult”.