Bill Simmons Admits to Illegal Proxy Betting, Now Under Review by Massachusetts Gaming Commission

Bill Simmons built a media empire telling other people how sports work. Turns out he didn't know the rules of his own biggest advertiser.

On the September 1 episode of his podcast, released Sunday, the Ringer founder told cohost Sal Iacono that he'd wanted to place futures bets on UCLA and Houston but was stuck in Los Angeles, where sports betting is illegal. So he called his daughter's boyfriend, Hank, who lives in Massachusetts, where it's legal, and had him log into Simmons' FanDuel account.

"I get the code to make sure it's me to my phone, I give him the code, he logs in," Simmons said, according to NBC News. "And he's putting in bets for me, and honestly it's the closest I've ever felt to Hank. Real bonding moment for us." Simmons said he did it more than once. "A week later, I called him up, ran it back. We did some more," he said.

Proxy betting is illegal in Massachusetts.

Massachusetts requires bettors to be physically present in the state when they place a wager online. State regulations also bar sportsbooks from letting one person bet on behalf of another, and classify anyone who does so as a "prohibited person," according to Front Office Sports. Operators are required to block that person and confiscate any winnings tied to the bet.

FanDuel's terms of service say the same thing in plain English: "Customers are prohibited from wagering on behalf of a third party and/or allowing other individuals to access their account." Violators can face permanent suspension and forfeited winnings.

Simmons is not just some random FanDuel customer. FanDuel is the exclusive sports betting sponsor of The Ringer, the network he founded and sold to Spotify in 2020. Simmons also now runs Spotify's podcast strategy. He confessed, on his own show, to breaking the rules of a company that pays to be on that show.

Two days after the episode aired, the Massachusetts Gaming Commission confirmed it's looking into it. "The Commission is aware of the comments made on the Bill Simmons Podcast and staff are currently reviewing the matter," a spokesperson told NBC News, Front Office Sports and other outlets.

MGC chair Jordan Maynard gave more detail to the Boston Globe's Michael Silverman, according to Boston.com. "We are aware of that activity, it is sitting with the proper staff members in this building," Maynard said. "I don't ever want to prejudge a matter that hasn't come before me. I'm not trying to be cagey. It's here at the commission. We're aware of it, and we'll take whatever actions we have to take."

FanDuel says it acted first. A spokesperson told Front Office Sports the company "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." FanDuel wouldn't clarify what "actioning" means, telling Boston.com it doesn't comment on individual account decisions.

Simmons addressed it again on Tuesday's episode. "I talked about how I got my daughter's boyfriend to place some bets for me in Massachusetts because I was in L.A.," he said. "Did not know about the proxy rules. Yeah, there are some real rules with this stuff, and they've ruled that not only are the bets going to be voided, and I learned my lesson. I actually thought it was [allowed], but that's fine."

Simmons claims he genuinely didn't know proxy betting was against the rules, and there's reason to think that's plausible. Northeastern law professor Mark Gottlieb told Business Insider that proxy betting is "so common" that Simmons may not have realized he was breaking the law. Not knowing the law isn't a legal defense, but it does undercut any claim that Simmons was deliberately gaming the system for an edge.

Legal experts told Business Insider this likely ends quietly. Gottlieb called Simmons "an unlikely candidate" for aggressive civil penalties, even though he appears to have violated the law. Boston College gambling researcher Richard McGowan said he'd "really be surprised" if Simmons got anything worse than a one-month suspension from FanDuel.

Massachusetts regulations do allow leniency. Sportsbooks can avoid terminating an account if they determine in "good faith" that the proxy betting wasn't done to gain a competitive edge, which fits Simmons' story about simply being out of state.

Awful Announcing raised a more cynical read: FanDuel is unlikely to nuke one of its most valuable spokesmen, but the Gaming Commission has no such conflict. The Commission can void wagers and confiscate funds tied to proxy bets if it finds a violation, and unlike FanDuel, it answers to state law, not a sponsorship contract.

No hearing has been scheduled, and the Commission has not announced findings or a timeline. Whether Simmons faces anything beyond voided bets and an "actioned" FanDuel account remains unclear.