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Mass. regulators investigating Bill Simmons after claims of proxy betting on his podcast

By Bryan Lambert, Boston 25 News Staff
Reel To Reel: It's Never Over, Jeff Buckley LOS ANGELES, CALIFORNIA - DECEMBER 02: Bill Simmons speaks onstage at Reel To Reel: It's Never Over, Jeff Buckley at GRAMMY Museum L.A. Live on December 02, 2025 in Los Angeles, California. (Photo by Rebecca Sapp/Getty Images for The Recording Academy) (Rebecca Sapp/Getty Images for The Recording A)
By Bryan Lambert, Boston 25 News Staff

Massachusetts gambling regulators say they are looking into Bill Simmons after The Ringer founder recently said he has been having his daughters’ boyfriend place wagers for him using the Boston sports superfan’s FanDuel account.

During Monday’s episode of The Bill Simmons Podcast, Simmons, who lives in California where sports betting is illegal, said he has been having his daughter’s boyfriend log in to his FanDuel account in sports gambling-friendly Massachusetts.

“I can’t have my daughter do it. My dad would have no idea how to do it. But Hank, I really trust Hank. I let Hank log into my FanDuel as me,” Simmons tells Cousin Sal. “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.”

Proxy betting, having someone else use your account to place bets, is illegal in Massachusetts and prohibited by FanDuel.

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“The Commission is aware of the comments made on the Bill Simmons Podcast and staff are currently reviewing the matter,” Massachusetts Gaming Commission spokesman Thomas Mills told Boston 25 News.

A FanDuel spokesperson told Boston 25 News that Simmons’ bets were voided and his account was actioned.

Simmons, a Marlborough native and Holy Cross graduate, first grew to national sports media prominence through his blog “The Boston Sports Guy.” Simmons joined ESPN in 2001 and eventually established the website Grantland before splitting from the station and founding the sports and pop culture website and podcast network, The Ringer, in 2016.

The Ringer did not immediately respond to Boston 25’s request for comment.

This is a developing story. Check back for updates as more information becomes available.

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