Massachusetts Sportsbook That Took Bill Simmons Proxy Bets Faces Regulatory Repercussion

The Massachusetts sportsbook that accepted sports bets through a proxy acting on behalf of sports writer Bill Simmons could face regulatory repercussions. Bill Simmons speaks at a Grammy Museum event on Dec. 2, 2025, in Los Angeles. Simmons made headlines this week for admitting on his podcast that he has made proxy bets from Los Angeles through his daughter’s boyfriend in Massachusetts. (Image: Getty) On The Bill Simmons Podcast this week with fellow The Ringer personalities Joe House and Cousin Sal, Simmons, a California resident where sports gambling is illegal, revealed that he recently made some NFL futures bets through his daughter’s boyfriend, Hank. I can’t have my daughter do it. My dad would have no idea how to do it. But Hank, I really trust Hank. I let Hank log into my FanDuel as me. I get the code to make sure it’s me on my phone. I give him the code, he logs in, and he’s putting in bets for me, and honestly, it was the closest I’ve ever felt to Hank. It’s a real bonding moment for us,” Simmons revealed. There will be no more bonding over sports betting, as the Massachusetts Gaming Commission (MGC) has since informed Simmons that his conduct violated the state’s ban on proxy betting. FanDuel, which accepted the bets, subsequently voided the wagers. Possible Disciplinary Action The MGC bans proxy betting, or a person placing a bet on behalf of someone else. The regulatory responsibility relies on the operator, with Regulation 205 CMR 238.32(4) stating that “the Sports Wagering Operator shall prevent persons from placing Sports Wagers as agents or proxies for others.” A system of Internal Controls submitted by a Sports Wagering Operator… shall include commercially reasonable methods to prevent a prohibited person from placing a Sports Wager,” reads Massachusetts Gaming Commission Regulation 205 CMR 238.33. The state’s definition of a “prohibited person” includes “agents or proxies for others.” While the MGC has a lengthy history of penalizing sportsbooks for taking prohibited bets, such as wagers on college sports involving in-state schools, the commission has not yet fined a licensee for failing to block proxy activity. The MGC said its staff is actively reviewing the Simmons situation. In 2022, the New Jersey Division of Gaming Enforcement fined DraftKings $150,000 for “negligently allowing a patron to engage in proxy wagering.” In that case, a Florida man worked with a friend in New Jersey to facilitate high-volume wagering, including a $50,000 bet on an NFL game. Simmons Apologizes Simmons acknowledged the sports betting situation on his Tuesday (Sept. 1) podcast. Simmons said he thought the conduct he engaged in was permissible. There’s some real rules with this stuff,” Simmons said. “And now my daughter has to break up with her boyfriend. That was the other thing they ruled. No, I’m kidding. They’re going to stay together, but I did learn.” Simmons said he plans to be in Boston “at some point” and will “make more wagers down the road.” The post Massachusetts Sportsbook That Took Bill Simmons Proxy Bets Faces Regulatory Repercussion appeared first on Casino.org.