Bill Simmons & FanDuel Could Still Face Penalties After Proxy-Betting Controversy in Massachusetts

The Massachusetts Gaming Commission (MGC) and its Investigations and Enforcement Bureau (IEB) are still considering taking action against FanDuel and Bill Simmons in the wake of his betting-by-proxy controversy.
SportsBettingDime regulatory writer Robert Linnehan broke the story.
“The IEB hasn’t foreclosed any kind of condition here going forward. Obviously, we’ll be digging in on all facets of this and making determinations as the facts guide us. We’ve conducted a preliminary review and understand the facts as we have them at this point,” said Zachary Mercer, senior enforcement counsel for the IEB.
The MGC also released a memo on the proxy-betting controversy on Thursday. Simmons, founder of The Ringer, had his daughter’s boyfriend, Hank, place 22 bets for him, totaling $21,800 in August. FanDuel is slated to meet with MGC officials for an adjudicatory hearing on the incident.
Simmons was in California, where sports betting is not legal, when the bets were placed. Hank was in Massachusetts. Simmons publicly admitted to giving Hank his FanDuel login information on his podcast in August.
“I let Hank log into my FanDuel as me,” Simmons said at the time. “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 Unaware Of Proxy-Betting Rules
The problem is that placing proxy bets is not allowed by the MGC or FanDuel. Simmons noted that FanDuel voided all of the bets and “actioned” his account.
“I talked about how I got my daughter’s boyfriend to place some bets for me in Massachusetts, because I was in L.A.,” Simmons said on his podcast in September. “Did not know about the proxy rules. Yeah, there’s some real rules with this stuff. … I learned my lesson. Apparently, proxy betting, not allowed. I actually thought it was, but that’s fine.”
FanDuel’s connection to Simmons also includes a “multi-million-dollar advertising and content partnership” that began in 2021. FanDuel is the exclusive sportsbook and fantasy partner across all of The Ringer’s platforms.
It remains to be seen whether Simmons or FanDuel will face penalties from the IEB and/or MGC, but all options remain under consideration some three months after the incident.
Kris Johnson is a graduate of Middlebury College. He has spent most of his life working in sports, primarily writing about them. Before starting his most recent position as Deputy Editor in the summer of 2025, Johnson spent nearly four years with Catena Media as...
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