Bill Simmons’ ignorance on the rules regarding proxy betting almost cost him dearly, and the longtime media personality realizes he may have dodged a bullet.
During Monday’s episode of “The Bill Simmons Podcast,” Simmons admitted to using his daughter’s 21-year-old boyfriend to enter bets on his behalf in Massachusetts, since Simmons lives in California, where sports betting remains illegal.
“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. And I have all this money that I had from last year because I actually hit a bunch of futures last year,” Simmons said.
“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. A week later, I called him up, ran it back. We did some more.”
Betting booboo
The problem with Simmons’ humorous admission is that proxy betting is illegal. The Massachusetts Gaming Commission wound up having to get involved, as Simmons and his “partner” were investigated.
Nothing major ultimately happened, but Simmons admitted on his podcast Tuesday that all bets had been voided, and he “learned his lesson.”
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/ivHqxYpaQtpic.twitter.com/S4nBgxJCDk— Ben Axelrod (@BenAxelrod) September 2, 2026
Mea culpa for Simmons
“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. “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 added.
Despite all of his bets being thrown “out the window,” Simmons says he will be in Boston soon and plans on making a few wagers of his own while there.
“Lesson learned,” he concluded.
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