In August, Bill Simmons had a stretch of making bizarre, unprompted admissions on The Ringer's The Bill Simmons Podcast that he absolutely should have kept to himself.
Simmons offered up that he doesn't wear a seatbelt while driving, which bewildered Kevin Wildes and drew a hilarious reaction from Nick Wright . Otherwise, that one didn't really break containment beyond sports media.
But then, Simmons admitted that his daughter's boyfriend, Hank, placed proxy bets for him on FanDuel, a longstanding partner of The Ringer.
"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," Simmons said , in part. "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."
And that time, airing out his own dirty laundry had consequences, as proxy betting is illegal on FanDuel and in Massachusetts.
The Massachusetts Gaming Commission reviewed Simmons' claims, as Front Office Sports reported in early September, and the results of that review are in.
On Thursday, Geoff Zochodne of Covers relayed a memo to the Massachusetts Gaming Commission Investigations and Enforcement Bureau stating the total amount of bets and sums in Simmons's sports wagering noncompliance matter.
"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," the memo reads, in part. "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."
As of this writing, Simmons hasn't acknowledged the memo. But back on Sept. 1, Simmons said on his eponymous podcast that he " did not know about the proxy rules ," and all bets were voided.
But I did learn," Simmons said. "Not allowed to do that. So all those bets went out the window. All that special time I had with Hank out the window as well. The good news is I'm going to be in Boston, and maybe at some point I'll make some more wagers down the road. There you go. Lesson learned."
The post Massachusetts Gaming Commission presented with findings from Bill Simmons proxy betting controversy appeared first on Awful Announcing .
