Bill Simmons got himself into some trouble a few weeks ago, when he admitted on his podcast that he had engaged in proxy betting. Simmons, who lives in California, where online sports gambling is still illegal, told his listeners that he had instructed his daughter's boyfriend, who lives in gambling-friendly Massachusetts, to log into his FanDuel account and place bets on his behalf. Because this practice is strictly prohibited by FanDuel's policies, his bets were voided. But a question remained: How much action was Simmons denied?
Now, thanks to the Massachusetts Gaming Commission, we have an answer to that question. Sports betting reporter Geoff Zochodne pointed out that the commission's Investigation and Enforcement Bureau made a presentation to commissioners Thursday about Simmons's infraction. A memo announcing the presentation provided some details about how much Simmons was trying to bet:
The incident involved an admission made by media personality Bill Simmons on his August 30, 2026, podcast pertaining to his placement of proxy wagers on his FanDuel account in Massachusetts through an acquaintance who was physically present in Massachusetts. FanDuel reported that the matter involved 22 wagers with a total handle of $21,800 placed over three (3) dates: August 5, 2026, August 7, 2026, and August 19, 2026.
I have two reactions to this revelation. The first is that Simmons must be a real pain in his daughter's boyfriend's ass. The second: Wow, Simmons sure does have a lot of disposable income.
Of course, I have known for a long time that Simmons is obscenely wealthy—he was well compensated at ESPN, he owns a lot of real estate in Los Angeles, and he sold The Ringer for $250 million—but there is something about that $21,800 that really underlines just how much money this guy has. It's a clarifying number because I have never gotten the impression that Simmons, despite how much he likes to talk about gambling, is a particularly reckless or compulsive gambler. This would mean that in his world, $21,800 is an amount he can spend on idle entertainment without a second thought. Whereas a regular Joe might occasionally splurge on an expensive concert ticket or a nice dinner, Simmons can just call up his daughter's boyfriend and sprinkle 20 large on some parlays.
It's going to be hard not to think about this every time Simmons talks about his bets on the podcast. The next time he says something like, "I really like Seattle on the road this week. I'm thinking about putting them into a teaser with Denver," to Cousin Sal, I'll immediately be aware of the fact that he's casually talking about throwing away $1,000. Must be nice!
