Now We Know How Much Money Bill Simmons Had His Daughter’s Boyfriend Bet For Him

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 today 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.