TLDR
- A Massachusetts Gaming Commission memo puts Bill Simmons’ proxy betting at 22 wagers.
- The bets had a total handle of $21,800.
- The wagers were placed on August 5, 7 and 19, 2026.
- Simmons said his daughter’s boyfriend logged into his FanDuel account to place them.
- FanDuel voided all the bets, and Simmons said he did not know the rules.
A memo from Massachusetts gaming regulators has put numbers on the proxy betting case involving podcast host Bill Simmons. FanDuel reported that the matter involved 22 wagers with a total handle of $21,800.
The memo was sent to the Massachusetts Gaming Commission’s Investigations and Enforcement Bureau. Geoff Zochodne of Covers shared it publicly on Thursday. It outlines the bets and sums tied to what regulators called a sports wagering noncompliance matter.
The case began with comments Simmons made on his own show, The Bill Simmons Podcast. He said a family acquaintance had been placing bets on his FanDuel account.
The comments came during a stretch in August when Simmons made several unprompted admissions on air. In another episode, he said he does not wear a seatbelt while driving.
How the Bets Were Placed
Simmons said his daughter’s boyfriend, Hank, logged into his FanDuel account as him. A security code was sent to Simmons’ phone, and he passed it along so Hank could sign in.
“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. He added that he had money in the account from futures bets that won the year before.
Simmons described the arrangement in friendly terms. “Honestly it’s the closest I’ve ever felt to Hank,” he said. “Real bonding moment for us.”
Proxy betting means placing a wager on behalf of another person. It is against FanDuel’s rules and is illegal in Massachusetts.
FanDuel is owned by Flutter Entertainment. The sportsbook has been a longtime partner of The Ringer, which produces Simmons’ podcast.
What the Memo Says
The memo states that the admission came on Simmons’ August 30, 2026, podcast. It says the bets were placed through an acquaintance who was physically present in Massachusetts.
According to FanDuel’s report, the 22 wagers were spread over three dates. Those dates were August 5, August 7 and August 19, 2026.
That works out to an average of just under $1,000 per bet. Handle refers to the total amount of money wagered, not whether the bets won or lost.
The Massachusetts Gaming Commission began reviewing the claims in early September. Front Office Sports first reported the review at that time.
On September 1, Simmons addressed the matter on his podcast. He said he “did not know about the proxy rules” and that all of the bets had been voided.
“But I did learn,” Simmons said. “Not allowed to do that. So all those bets went out the window.”
He joked that the bonding time with Hank was gone too. Simmons said he would be in Boston and might place more wagers “down the road,” adding, “Lesson learned.”
The memo detailing the 22 wagers was presented to the commission’s investigators this week. As of this writing, Simmons has not publicly responded to it.
