Bill Simmons has learned quite a few lessons over the past few weeks.
Early in August, Simmons made headlines for his anti-seatbelt stance (he just doesn’t like them), earning jeers from fans and the media alike.
But that was nothing compared to what Simmons got into this past week, when he admitted to using his daughter’s boyfriend as a proxy to place bets despite not being in a state where sports betting was legal.
Simmons shared the story in the tone of an amusing anecdote, calling it a bonding experience between himself and his daughter’s boyfriend.
“I let Hank log into my FanDuel as me, [sent] the code to make sure it’s me to my phone, I give him the code, he logs in,” Simmons said. “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’s the closest I’ve ever felt to Hank. Real bonding moment for us.”
Obviously, this was not a smart admission, as proxy betting is illegal on FanDuel and in Massachusetts, where Hank resides.
The Massachusetts Gaming Commission got involved, and by Tuesday night, Simmons said on his podcast that the bets had been voided and he had learned his lesson.
“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 began, speaking alone before the proper start of his podcast. “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,” he said.
Simmons noted that the bets in question had been ruled void and added jokingly, “And now my daughter has to break up with her boyfriend.”
“But I did learn,” Simmons concluded. “Not allowed to do that. So all those bets went out the window. All that special time I had with Hank out the window as well. The good news is I’m going to be in Boston, and maybe at some point I’ll make some more wagers down the road. There you go. Lesson learned.”
Bill Simmons addresses ProxyGate:
“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.” https://t.co/ivHqxYpaQt pic.twitter.com/S4nBgxJCDk— Ben Axelrod (@BenAxelrod) September 2, 2026
The brazenness with which Simmons shared the initial anecdote is pretty clear evidence that he didn’t think he was doing anything wrong, which makes the entire scenario all the more baffling.
Simmons was talking publicly about sports betting long before it was an everyday part of the sports media discourse, with his Guess the Lines podcast segments dating back decades. He’s also an extremely public partner with FanDuel. If anyone should be familiar with the rules regarding sports betting sites, it’s him.
Anyways, it seems that Simmons’s bets on the upcoming NFL season will have to wait until he makes his way back to Boston. As for the daughter’s boyfriend, well, he has quite a story to share on his own podcast someday.
About Tyler Lauletta
Tyler is a editorial contributor at Awful Announcing, with previous stops at Sports Illustrated and Business Insider during his career covering sports in digital media. He is, begrudgingly, a Truster of the Process and general Philly sports sicko.