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Home » What Will Happen to Bill Simmons After Proxy Betting Mistake: Lawyers
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What Will Happen to Bill Simmons After Proxy Betting Mistake: Lawyers

EditorBy EditorSeptember 2, 2026No Comments3 Mins Read
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Bill Simmons has said he authorized another person to place sports bets on his behalf, but don’t expect the podcasting star to get more than a slap on the wrist.

Simmons, who runs Spotify’s podcast strategy, said on his show on Sunday that he’d enlisted his daughter’s boyfriend to log into his account and place NFL futures bets for him.

The issue is that Simmons lives in California, where online sports betting is illegal, and his daughter’s boyfriend lives in Massachusetts, where it’s legal. So-called “proxy betting” is illegal under Massachusetts state law.

Simmons’ bets have caused a stir, especially since he said they were placed on the online sportsbook FanDuel, which has major sponsorship deals with Spotify and The Ringer, the sports-and-culture site Simmons started.

However, legal experts say that the Spotify executive likely won’t be in too much trouble.

Simmons is “an unlikely candidate” for aggressive civil penalties, though he appears to have violated online gaming laws in Massachusetts, said Mark Gottlieb, a law professor at Northeastern University in Boston.

Simmons may get a ‘good-faith determination’

Under Massachusetts law, sportsbooks can only accept bets from people who are 21 or older and are physically present in the state. Sportsbooks can’t allow customers to have more than one account or to place bets on behalf of someone else.

If sportsbooks find that users have multiple accounts, including through a proxy, the law says they “shall implement procedures to terminate all accounts” associated with them.

Sportsbooks can make exceptions if they investigate the account and make a “good-faith determination” that the violator’s behavior “was not intended to obtain a competitive advantage,” according to the Massachusetts Gaming Commission’s rules.

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Richard McGowan, an associate professor at Boston College who studies gambling, said he’d “really be surprised” if Simmons received a penalty, other something like than a one-month suspension from FanDuel.

A FanDuel spokesperson said the company “became aware of the issue” and handled it according to its terms, which meant reporting it to the Massachusetts Gaming Commission and voiding the bets.

Sportsbooks like FanDuel can also suspend or close an account at their discretion for severe or repeated violations of their terms.

A spokesperson for the Massachusetts Gaming Commission said they’re “aware of the comments made on the Bill Simmons Podcast” and that “staff are currently reviewing the matter” but declined to share specifics.

Simmons put himself in ‘a very awkward place’

Gottlieb said proxy betting is so common that Simmons may not have realized he could be breaking the law. Simmons said on his Tuesday show that he “did not know about the proxy rules” but that he “did learn.”

Not knowing isn’t a bulletproof defense, though.

“The law presumes that people know the law — even if they do not,” said Jeffrey Eilender, a civil litigation partner at New York-based Schlam Stone & Dolan LLP.

While FanDuel might decline to drop the hammer on Simmons, who regularly promotes the sportsbook to his audience, this incident could be a wake-up call in the fast-shifting world of sports betting.

“It puts FanDuel and Bill Simmons in a very awkward place,” Gottlieb said. “He shouldn’t have been doing this in the first place, and he shouldn’t have announced it.”



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