While today's Bill Simmons is something of a media mogul, he’s historically played the everyman. He was, after all, “The Sports Guy.”
So Bill’s admission of proxy betting on his podcast, to me anyway, was a bit of a throwback.
- Bill Simmons’ proxy-betting mistake could serve as a lesson in how modern “sports betting” rules have become murky for everyday bettors.
- With sportsbooks, state laws, and prediction markets offering different rules, it may be becoming increasingly unclear what betting is actually legal.
- Remember: all bets are action.
I’m choosing to take Simmons at his word here. And in doing so, I see the seeming gaffe of the everyman.
Bill Simmons also (intentionally or not) raised a decent point about the rules of modern “sports betting,” in that they may have become increasingly difficult to grasp for the average person.
Again, if you take him at his word, Simmons was operating under an assumption that maybe other people operate under: That letting someone else log into your online sportsbook account in a completely different state and make a bet for you with your own money is totally fine. As FanDuel’s response showed, it’s actually against the rules.
“We became aware of the issue and handled it consistent with our Terms and Conditions and Massachusetts Gaming Commission regulations, including reporting the matter to the MGC, voiding the bets, and actioning the account,” a FanDuel spokesperson told Covers on Tuesday.
Bets are being voided, reports filed, and a million tweets have been launched (seemingly) over Simmons’ talk of letting his daughter’s grown-man boyfriend log into his FanDuel account and make some bets.
New BS Podcast! (hosted by me and not a proxy)
— Bill Simmons (@BillSimmons) September 2, 2026
—Make or break NFL QBs, Stafford’s HOF ceiling and a stacked CFB season w/ @McShay13
—@DianaTaurasi on a spirited WNBA season, Kobe lessons and Geno is so polarizing.
Watch/listen on Spotify or Netflixhttps://t.co/I9wXOjTiKL
Yet let he who has never unknowingly violated a term or condition of their sportsbook cast the first stone. It’s a mistake you could forgive most people for making. Simmons just talked about it on “the most downloaded sports podcast of all time,” wherein he discusses sports betting and is sponsored by an online sportsbook operator. He’s held to a higher standard.
Now, you SHOULD always read the terms and conditions. You SHOULD read the house rules. Bill Simmons SHOULD know that proxy betting wasn’t allowed. Especially as a pitchman for a book that forbids it.
But Bill says he was just trying to get some bets in. And I’m going to go out on what is probably a rather thick limb and say that many other people just want to bet. They’re not looking under the hood of the betting machine.
Don't do what Donny Don't does
Is every single sports bettor going line by line through the Ts & Cs of their book? Are they reading the house rules for every wager they make? Are they even caring if the site they use is authorized by the jurisdiction in which they live? Do they even know what “preemption” means, or what a “swap” is???
Many people don’t read the fine print of stuff they sign. The same probably goes for the fine print of their sportsbook or prediction market.
There’s even an argument to be made for proxy betting in certain circumstances. Allowing it could keep more handle within a state-regulated framework for that betting. Isn’t it preferable to have people betting with a regulated sportsbook than an unregulated one?
We can argue that another day, though, because there are arguments against it as well, and I’m not trying to just wave all of this away. I just think there’s a broader point to be made here, which is that there are probably people who have no idea exactly what legal sports betting even is anymore.
Bill Simmons, the popular sports podcaster who has championed sports betting, is under review by the Massachusetts Gaming Commission after he admitted on a recent episode to using his daughter’s boyfriend to place bets for him. https://t.co/r5Y9Nrp4SH
— NBC News (@NBCNews) September 2, 2026
Technically, what Simmons said he did was not a proper bet, hence FanDuel’s voiding of said bets. But Simmons said he thought it was fine until he realized that it was not.
I’ll give you another example. FanDuel’s terms and conditions for opening an account include you representing that you’ve actually read the terms and conditions. If you didn’t read them, you have misrepresented yourself.
Look at the house rules for any given betting market. Is everybody reading those? Check the replies to any sportsbook on Twitter. ALL YOUR BETS COULD BE ACTION.
Bill Simmons also apparently knew that sports betting isn’t legal in California, which is why he wanted someone else to make a bet in Massachusetts. But does everyone else in California know that sports betting is illegal there?
Stop whatever you're doing, it's happening!!!! @FanDuel is NOW available everywhere! #fdpartner pic.twitter.com/zxqksnpFVR
— The Ringer (@ringer) September 1, 2026
I mean, how could they at this point?
On the same day that Simmons noted his proxy error, FanDuel trumpeted that it is “now available everywhere.” DraftKings has engaged in similar marketing.
“This is our first football season with DraftKings Sports available to fans nationwide,” an exec said in a press release.
So if “sports” are available everywhere, why did Bill even need Hank?
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Because prediction markets
Because that’s the world we’re living in right now, which includes, of course, prediction markets. The federally regulated exchanges are offering sports event contracts for trading all over the U.S., including in states where officials believe it’s sports betting they didn’t authorize. This includes California.
There is intense argument over the legality of sports-related event contracts. But, at present, they are indeed almost everywhere. They also allow people as young as 18 to trade, whereas state-regulated sportsbooks may require 21 or older.
Someone placing a prediction market trade in California could even conceivably have a counterparty in Massachusetts these days. There are also people who still prefer the state-regulated sportsbook style.
Is that forgiving everything and everyone for not knowing the rules of state-regulated sports betting? No. But it’s just throwing some context around it all. Because the rules may not be very well-known by your average bettor, and there are now other rules.
That could mean increased difficulty in trying to communicate what’s permitted because some of what’s permitted these days (namely, sports-focused prediction markets) wasn’t around a few years ago. Has every Kalshi trader studied their member agreement and the exchange’s rulebook?
If you’re an operator or regulator trying to communicate the rules, you need to find your bettors or traders and make them listen. They also need to understand. And, now more than ever, if your bettors don’t like the rules, they could just take their business somewhere else, and that somewhere else could be technically legal. Which rules are the real rules?
It’s all gotten a bit wacky, even as it’s still quite serious. And if FanDuel-sponsored Bill Simmons says he didn't know what’s allowed, what are the odds for anyone else?
