The Massachusetts Gaming Commission opened a review of sports media figure Bill Simmons after he described on his podcast how he had his daughter's boyfriend log into his FanDuel account and place wagers on his behalf, an arrangement that violates state law.
Simmons, 56, a Massachusetts native now living in California, laid out the scheme himself during a recent episode of the Bill Simmons Podcast. He explained that he wanted to bet on UCLA overs and a Houston line he believed the market had mispriced, but could not place the wagers from California, where sports gambling remains largely illegal. So he turned to "Hank," his daughter's 21-year-old boyfriend, who lives in Massachusetts, one of the states where FanDuel operates legally.
Simmons walked listeners through the mechanics. He had Hank log into his FanDuel account using his credentials, then forwarded a two-factor verification code sent to his own phone. Hank used the existing account balance, money Simmons said he had built up after hitting "a bunch of futures" the previous year, and placed the bets Simmons wanted. About a week later, Simmons called Hank and they did it again.
The whole thing might have stayed a colorful podcast anecdote. But Massachusetts strictly prohibits proxy betting, and FanDuel's own terms of service bar anyone from wagering on another person's behalf. Simmons broadcast his admission on a show that FanDuel sponsors.
On the episode, Simmons explained why he picked Hank for the job. As the Daily Mail reported, Simmons told listeners he considered and rejected other family members before landing on his daughter's boyfriend:
"I can't have my daughter do it. My dad would have no idea how to do it. But [my daughter's boyfriend] Hank, I really trust Hank."
He then described the process in detail:
"I let Hank log into my FanDuel as me. 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, and honestly, it was the closest I've ever felt to Hank. It's a real bonding moment for us."
Simmons added that the arrangement did not stop there. "A week later, called him up, ran it back. We did some more," he said on the podcast.
The specific dollar amounts wagered and the outcomes of the bets have not been disclosed. Simmons referenced wanting UCLA overs and a Houston wager where he believed the line had not yet adjusted, but provided no further detail on air.
FanDuel moved quickly once the comments surfaced. The sportsbook voided the proxy wagers and sanctioned Simmons' account, as Front Office Sports first reported. The exact nature of the sanction, whether it amounts to a temporary suspension, a permanent ban, or a forfeiture of funds, has not been made public.
The irony is hard to miss. FanDuel sponsors the very podcast on which Simmons described circumventing the platform's own rules. Simmons used his sponsor's product, broke his sponsor's terms of service, and then told the story to the audience his sponsor pays to reach.
Thomas Mills, a spokesman for the Massachusetts Gaming Commission, confirmed the state regulator is now involved. Mills told the Daily Mail:
"The Commission is aware of the comments made on the Bill Simmons Podcast and staff are currently reviewing the matter."
Mills did not say whether the review constitutes a preliminary inquiry or a formal investigation, and he did not outline potential penalties. Massachusetts law prohibits proxy betting, but the specific statutes and their penalty ranges were not detailed in the commission's statement.
Simmons' initial public reaction suggested he did not grasp the seriousness of the situation, or chose not to show it. He posted on X promoting his next podcast episode with the line: "New BS Podcast! (hosted by me and not a proxy)."
But he later struck a different tone. Simmons acknowledged he had been unaware that proxy betting was prohibited:
"Did not know about the proxy rules. Yeah, there's some real rules with this stuff... and I learned my lesson. Proxy betting, not allowed. I actually thought it was, but that's fine... but I did learn, not allowed to do that."
That defense, ignorance of the rules, may not carry much weight with regulators. Simmons is not a casual bettor stumbling into a new hobby. He is a former ESPN star, the founder of The Ringer, and one of the most prominent media voices in the sports-gambling space. His podcast carries a sportsbook sponsorship. The idea that he did not know the basic legal guardrails around the product he promotes for a living raises its own questions.
One dimension of the story that has drawn less attention is Hank's position. He is 21, old enough to bet legally in Massachusetts, but he did not place wagers under his own name on his own account. He logged into someone else's account, used someone else's money, and followed someone else's instructions. Whether Hank faces any regulatory exposure of his own remains unclear. The commission's statement referenced only Simmons' comments, not any action directed at the boyfriend.
The Daily Mail sought comment from spokespeople at The Ringer. Whether the outlet received a response has not been reported.
Simmons' California residency adds another layer. He lives in a state where sports gambling is predominantly illegal, and he used a proxy in Massachusetts specifically to get around that restriction. Whether California authorities have any interest in the matter, or whether the arrangement creates additional legal exposure beyond the Massachusetts review, remains an open question.
What makes the Simmons case unusual is not the alleged conduct itself, proxy betting is a known problem in legalized gambling states, but the fact that every piece of evidence came from Simmons' own mouth. He was not caught by an algorithm, flagged by a tipster, or exposed by an investigation. He sat behind a microphone, described the scheme step by step, and published it to a national audience on a show bankrolled by the very sportsbook whose rules he broke.
Regulators, sportsbooks, and state legislatures spent years building the legal framework for sports wagering, complete with identity verification, geolocation requirements, and terms of service designed to prevent exactly this kind of arrangement. Simmons treated those safeguards like a minor inconvenience and bragged about sidestepping them.
Rules exist for everyone, even the people with the microphones. Especially the people with the microphones.
