The Massachusetts Gaming Commission has confirmed it will launch a full investigation into an alleged proxy betting case involving The Ringer Founder Bill Simmons and FanDuel.
Simmons, who currently partners with FanDuel for The Bill Simmons Podcast, admitted to having his daughter’s boyfriend place wagers on college football and the NFL due to sports betting’s illegal standing in California.
On his podcast, Simmons stated: “There was a couple bets I really wanted to get in. I wanted – there was UCLA overs, but Houston, the market had not shifted appropriately yet. 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.
“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.”
Unfortunately for Simmons and “Hank,” proxy betting is prohibited by both Massachusetts gaming regulations and FanDuel. The case involves 22 wagers placed on Simmons’ FanDuel account in August – totaling $21,800.
Massachusetts Gaming Commission Senior Enforcement Counsel Zak Mercer stated regulators "will be digging in on all facets of this and making determinations as the facts guide us."
Commissioner Eileen O’Brien spoke on her concerns regarding proxy betting as well, having said, "I'd like this to come in front of us. One of the huge issues that we've had, especially with youth and college-age people betting, has to do with proxy betting. And I've been a little disturbed by the lack of full appreciation… I think in general to the fact that it's illegal.
“To me, this is not singling someone out, but this is the first one we sort of had openly referred to us as a possibility. I think it is a an opportunity to have an operator do a deeper dive as well into proxy betting."
Proxy betting includes any wagers placed by an individual who resides outside of the sportsbook’s legal jurisdiction, such as Simmons in California, typically using an acquaintance who lives in a market where sports betting is regulated – or “Hank” in Massachusetts.
Simmons later addressed the proxy betting case after the Massachusetts Gaming Commission placed him under review in August, stating he “did not know about the proxy rules” and “learned my lesson” regarding such regulations.
FanDuel expanded its partnership with The Ringer – currently owned by Spotify – during April 2023, while FanDuel Sports Network agreed to a new partnership with the media company to host two podcasts on live television beginning in November 2025.
The Massachusetts Gaming Commission reported total gaming activity for September 2026 on October 26, as operators combined to produce $153.9m of revenue, representing an increase of 4%
