Bill Simmons on Ryan Clark and Peter Schrager Credit: The Bill Simmons Podcast

Bill Simmons finally said the quiet part out loud.

Simmons, one of FanDuel’s biggest promoters as part of a long-running and seemingly lucrative partnership between the online sportsbook and The Ringer, has long built gambling into his content. But nearly a decade after the Supreme Court struck down a federal law prohibiting sports betting, California has still not legalized it, leaving Simmons unable to use the FanDuel app he so often references on his show.

From time to time, Simmons will reference loading up on bets while visiting family in the Boston area, or while traveling for business. Mostly, the audience is left to connect the dots on how Simmons bets New England Patriots futures or Steph Curry props from his Los Angeles home.

Until this past weekend.

In an NFL preview edition of The Bill Simmons Podcast picking win total over/unders for the AFC, Simmons admitted to using a process that is in clear violation of FanDuel’s rules, known as “proxy betting.”

In short, Simmons sent his login credentials to his daughter’s Massachusetts-based boyfriend, who placed a few season-long over bets in the FanDuel app for Simmons.

“My daughter’s boyfriend, Hank, who’s a great kid, turned 21 this summer, as did my daughter,” he explained. “And there was a couple bets that I really wanted to get in, the 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 Hank, I trust Hank.

“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. 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.”

As the sports betting outlet InGame laid out earlier Monday, FanDuel’s terms and conditions state that a user could have their account permanently suspended and their winnings taken back if they are found guilty of proxy betting. Massachusetts law suggests Simmons’ accomplice should be banned from using FanDuel.

Previously, others in the industry have been critical of Simmons for keeping quiet about the risks associated with gambling (and the many scandals across sports) while pitching FanDuel. The story of these Houston Texans and UCLA overs is as vocal as Simmons ever really gets about his sports betting habits, and the legal questions his story raised probably explain why.

It would be hard to imagine FanDuel banning Simmons, but the operator probably didn’t love the light Simmons’ story shed on the workarounds he and other partners used in states where sports betting is not yet legal.

About Brendon Kleen

Brendon is an Editorial Lead at Awful Announcing overseeing digital content and special projects. He lives in Phoenix and has covered sports media for Awful Announcing since 2023.