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FanDuel Faces Massachusetts Probe After Bill Simmons Admits Proxy Bets

By jili tutorial · September 3, 2026

FanDuel Faces Massachusetts Probe After Bill Simmons Admits Proxy Bets

Massachusetts gaming regulators are investigating FanDuel after sports media figure Bill Simmons publicly admitted that an associate placed bets through his account — a violation of the state’s proxy betting laws.

Bill Simmons speaks at a Grammy Museum event on Dec. 2, 2025, in Los Angeles. Simmons made headlines this week after revealing on his podcast that he used a proxy to place bets from California, where sports gambling remains illegal, through his daughter’s boyfriend in Massachusetts. (Image: Getty)

Bill Simmons Admits Proxy Betting on Podcast

On The Bill Simmons Podcast this week, joined by fellow Ringer personalities Joe House and Cousin Sal, Simmons — a California resident — disclosed that he had recently placed several 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 shared.

There will be no more bonding over sports betting, however. The Massachusetts Gaming Commission (MGC) has since informed Simmons that his actions violated the state’s ban on proxy betting. FanDuel, which accepted the wagers, subsequently voided them.

Massachusetts Gaming Commission Investigates

The MGC explicitly prohibits proxy betting — when one person places a bet on behalf of another. Regulatory responsibility falls on the operator under Regulation 205 CMR 238.32(4), which states that “the Sports Wagering Operator shall prevent persons from placing Sports Wagers as agents or proxies for others.”

Additionally, Regulation 205 CMR 238.33 requires that “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.” The state’s definition of a “prohibited person” includes “agents or proxies for others.”

Although the MGC has a long history of penalizing sportsbooks for accepting prohibited bets — such as wagers on college games involving in-state schools — it has not yet fined a licensee specifically for failing to block proxy activity. The MGC confirmed its staff is actively reviewing the Simmons situation.

Potential Penalties for Proxy Wagering

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 collaborated with a friend in New Jersey to place high-volume bets, including a $50,000 wager on an NFL game.

Simmons Responds and Apologizes

Simmons acknowledged the sports betting incident on his Tuesday (Sept. 1) podcast, admitting he had believed his conduct was allowed.

“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 also mentioned he plans to be in Boston “at some point” and will “make more wagers down the road.”

With proxy betting strictly banned across legal U.S. markets, the outcome of the MGC inquiry will signal how aggressively regulators intend to penalize major operators when high-profile account sharing becomes public.

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