Bill Simmons allegedly made more than $20,000 in proxy bets via FanDuel, and Massachusetts regulators are now digging deeper into the situation.
- Bill Simmons allegedly placed 22 proxy bets totaling $21,800 through FanDuel using an acquaintance in Massachusetts, prompting the sportsbook to void the wagers and report the incident to regulators.
- The Massachusetts Gaming Commission is investigating potential violations and will hold an adjudicatory hearing to examine the incident and FanDuel’s handling of it.
- Regulators highlighted ongoing concerns about illegal proxy betting, particularly among younger bettors, and see the case as an opportunity to scrutinize sportsbook safeguards.
The California-based Simmons discussed making proxy bets using his daughter’s boyfriend in Massachusetts during an Aug. 30 podcast episode.
That admission attracted attention from media outlets (such as Covers). It also prompted FanDuel to report the issue to the Massachusetts Gaming Commission (MGC), void the bets, and “action” the account in question.
MGC commissioners received a presentation during their meeting on Thursday about the “potential violations."
A related memo detailed the amount of money allegedly wagered through a proxy.
“The incident involved an admission made by media personality Bill Simmons on his August 30, 2026, podcast pertaining to his placement of proxy wagers on his FanDuel account in Massachusetts through an acquaintance who was physically present in Massachusetts,” the memo said. “FanDuel reported that the matter involved 22 wagers with a total handle of $21,800 placed over three (3) dates: August 5, 2026, August 7, 2026, and August 19, 2026.”
The Simmons situation is a novel one for Massachusetts sports betting regulators. It is a higher-profile matter, too.
However, proxy betting has long been an issue that state sports betting regulators have had to confront.
Bill Simmons shared an in-depth story with his audience about how he used his daughter's boyfriend to engage in "proxy betting" on FanDuel. https://t.co/LcVDaKWfHb
— Awful Announcing (@awfulannouncing) September 1, 2026
Given the state-by-state legalization and regulation of sports betting, the risk of someone in a state without legal sports betting (like California) trying to get someone to make a bet for them in a state where there are legal sportsbooks (like Massachusetts) is always there.
Although prediction markets have offered a way for people to make a de facto wager almost anywhere in the U.S., Simmons said he used his FanDuel Sportsbook account, triggering state-level concerns.
The MGC commissioners ultimately decided on Thursday to hold an adjudicatory hearing on the issue at a later date. What the ultimate result of the proceeding will be remains to be seen.
Get the shovels
Zachary Mercer, senior enforcement counsel for the MGC, said its Investigations and Enforcement Bureau (IEB) “hasn’t foreclosed any kind of condition” for the matter.
“Obviously, we'll be digging in on all facets of this and making determinations as the facts guide us,” Mercer told the commissioners. “We've conducted a preliminary review and understand the facts as we have them at this point. But certainly, [we] wouldn't be beholden to any certain chapters, sections, etc. If anything arises through our further investigation, we will be certain to chase that down.”
Bill Simmons addresses the proxy betting thing in his podcast that dropped today. In short: -did not know about the proxy rules -says bets are going to be voided -"lesson learned" https://t.co/vOmOm3zRC6
— Geoff Zochodne (@GeoffZochodne) September 2, 2026
While the facts of what Simmons did do not sound like they are in dispute, because he disclosed them himself on his podcast, the commissioners wanted more information about how FanDuel handled the situation.
“I'm more interested in how the operator let something like this happen and the actions they took after it was public,” MGC Chair Jordan Maynard said.
Commissioner Eileen O’Brien said she wanted the matter to come back before the commission because it would be a first for the regulator and because of the problems the MGC believes it is having with proxy betting, particularly with younger people.
“And I've been a little disturbed by the lack of full appreciation, I think, in general to the fact that it's illegal,” O’Brien said.
She added later that this could be “an opportunity to have an operator do a deeper dive as well into proxy betting.”
