Podcaster Bill Simmons is under review by the Massachusetts Gaming Commission after admitting on air that he used his daughter’s 21-year-old boyfriend as a proxy to place bets for him via FanDuel while Simmons was in California, prompting the sportsbook to void the wagers and action the account.
Sports media personality Bill Simmons found himself at the center of a regulatory review on September 1, 2026, after casually detailing a proxy betting arrangement on his podcast. Simmons, the founder of The Ringer, discussed win-total bets involving the Houston Texans and UCLA during an episode featuring Cousin
Sal Iacono. Because online sports wagering remains illegal in California, where Simmons lives, the commentator enlisted a local resident to handle the transactions in Massachusetts.
The arrangement relied on his daughter’s 21-year-old boyfriend, a college-age resident named Hank. My daughter’s boyfriend, Hank, who’s a great kid, turned 21 this summer, as did my daughter,
Simmons explained on the podcast, according to USA Today.
How the Proxy Wagers Exceeded State Rules on FanDuel
The mechanics of the bet bypassed geographic restrictions through digital authentication. Simmons detailed that he initiated access by having the sportsbook’s verification code sent directly to his own mobile phone in Los Angeles. He then relayed the code to Hank in Massachusetts, who logged into Simmons’ pre-funded account using winnings from previous successful futures bets.
I let Hank log into my FanDuel as me,
Simmons said on the podcast, as reported by Front Office Sports. 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.
The podcast host noted that the pair repeated the arrangement a week later
to place additional wagers. However, state regulations and sportsbook terms prohibit anyone from placing wagers as an agent for another party. Massachusetts law designates individuals who place bets on someone else’s behalf as prohibited persons, which mandates that operators cancel the wagers and confiscate the funds. FanDuel’s terms specify that accounts are strictly for personal use, warning that proxy betting can result in permanent suspension and forfeiture of winnings.
Massachusetts Gaming Commission Launches Official Inquiry
State regulators moved quickly after the podcast episode aired. The Massachusetts Gaming Commission confirmed that it launched an inquiry into the podcast comments, putting the media executive under formal regulatory scrutiny.
We 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,
a FanDuel spokesperson told Covers.com.
Simmons Addresses Regulatory Fallout on Follow-Up Episode
Appearing on his podcast on September 1, 2026, Simmons acknowledged that he was entirely unaware of the regulatory restrictions governing proxy accounts when he asked his family member for assistance.
Did not know about the proxy rules,
Simmons said on the program, as documented by New York Post. Yeah, there’s some real rules with this stuff, and I learned my lesson. Apparently proxy betting not allowed. I actually thought it was, but that’s fine. I did learn, not allowed to do that.
The inquiry arrives as state regulators maintain strict oversight on mobile wagering compliance. While the MGC continues its review following its agenda-setting schedule, Simmons confirmed that his wagers are out the window
alongside the bonding experience with his daughter’s boyfriend.
Related reading
