7 hours ago
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If only George Santos and Bill Simmons had my parents, they wouldn’t be facing down a hailstorm of condemnation for circumventing the basic rules and regulations of dubious “prediction markets” and online gambling. Kalshi just banned the former congressman George Santos from its service and he was forced to pay back his winnings after he was accused of the dumb person’s version of insider trading. He bet on himself to not attend the State of the Union address, then conveniently didn’t go. For his trouble, he won (and will be forced to relinquish) more than $17,000; he’ll also have to pay more than $80,000 in total fines from Kalshi and the Commodity Futures Trading Commission.
Bill Simmons, the sports commentator, podcast host, and founder of The Ringer, had a different story.
While prediction markets are federally legal because they’re considered financial exchange services and not gambling, FanDuel’s gambling application, called Sportsbook, and other sports-adjacent services are legal in some states and not others. Sportsbook is illegal in California, which is inconvenient for anyone who spends most of their time worried about such intellectual pursuits as “the spread”, “the line”, and “the juice”. Contrary to what you might be thinking, those are real gambling terms, not nicknames for pro wrestlers.
Anyway, ol’ Billy Boy, who lives in California, couldn’t contain the action burbling up inside of himself, so he had his daughter’s boyfriend bet for him from Massachusetts, a state where FanDuel sports betting is legal. All the boyfriend had to do was log in to Bill’s FanDuel account from Massachusetts and make the most epic parlay known to man. Or something like that.
Folks, he got away with it! This audacious scheme, on par with the 1978 Lufthansa Heist, was a rip-roaring success. Until Simmons decided to admit to the wrongdoing on his podcast, cooing romantically about how clever he was, like a Bond villain aiming a laser at 007’s crotch.
“I get the code to make sure it’s me to my phone; I give him the code, he logs in,” Simmons said in a podcast episode last Sunday. “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.” Almost immediately, listeners took to social media to announce that the Sports Guy had admitted, on a live microphone, to violating not only FanDuel’s terms and conditions, but potentially also Massachusetts Gaming Commission regulations. Although Simmons claims he didn’t realize proxy betting was illegal in the state, these infractions come with penalties ranging from a small fine to the loss of gambling privileges in Massachusetts. The latter sounds especially grim for Simmons, as the last thing anyone wants is for him to have to develop a hobby.
If only someone had explained to these two famous individuals that gambling is a sordid, dirty activity, they could have avoided all this drama. But alas, my saintly parents only had time in their schedule to raise me. And boy, did my parents hate gambling.
When I was a callow young lad – preoccupied with sucking my thumb or trying to suss out if Sesame Street was a transit-accessible neighborhood – my parents made sure to instill real, American values into my psyche. To be honest, to be kind, to celebrate 39-cent burrito day at Taco Bell like it was the holiest holiday on the calendar. Most importantly, they told me not to gamble. Gambling can be deeply addictive, can lead to obsessive behavior, and can bankrupt a person. The World Health Organization lists some of the deleterious effects of gambling – stress, lack of self-control, and financial insecurity. I’d hear about this stuff all the time as a kid, coloring my perspective on gambling for years.
Card games, roulette, sports betting, and the like were just not allowed in my household. At most, my mother – lost in a reverie about her own mom’s gambling habits – would nostalgically purchase a Lotto Scratcher from the 7-11 down the street as a most illicit treat. She never won, which was just a reminder to me to keep my money away from such frivolous activities. I was told to save my earnings, be smart with my spending, and not to waste time on what amounts to jumping out a plane, DB Cooper-style, with a bag of cash and no parachute.
My parents weren’t alone in their disdain for the business of gambling. It was an activity relegated to dirty, sinful places such as Las Vegas, Atlantic City, and the alley behind the liquor store. But in other countries, like the UK, gambling has long been a legitimate big business – worth billions in revenue, with high street betting and online casinos advertised everywhere. America’s puritanical legacy meant gambling had to be sequestered and treated like a filthy habit to satisfy our moral outrage.
Those days are done. Through innovations in mobile phone technology, insidious branding (“prediction markets”, “daily fantasy” and other mouthfuls of marketing nonsense), and our collective exhaustion from all the other things to be mad about, America collectively shrugged its shoulders as gambling became our true national pastime. Polymarket, which allows users to bet on mundane yes-or-no questions regarding the color of a celebrity’s tie or the eventual outcome of the bloody conflicts in the Middle East, is considered to be worth more than $20bn in the wake of investments from Donald Trump’s son Don Jr.
How is this all legal? Well, as I mentioned, prediction markets are not considered gambling. FanDuel and its main rival, DraftKings, gained an initial foothold in the US thanks to a legal loophole. You see, fantasy sports games are considered a game of “skill” rather than the blind guessing of sportsbook betting. In 2018, in the wake of the explosion of the fantasy sports industry, the supreme court cleared the way for states to decide for the legality of sports betting for themselves. (Kalshi and Polymarket, on the other hand, are not considered gambling. They’re financial markets in a legal sense.) Sports betting in some form or another is legal in 39 states and Washington DC. I’m fairly certain Bill Simmons is not the first person to think about using a proxy to do his gambling for him. He’s just the only one to admit to it on a podcast listened to by hundreds of thousands of people.
I doubt America will ever put an end to the experiment of government-sanctioned gambling, but it will try to punish a few notable bad apples here and there. Regulations will pop up to make it all seem slightly more palatable, such as when someone inside Polymarket realized you probably shouldn’t let anyone wager on the likelihood of nuclear strikes. Especially when these prediction markets are used by political figures like George Santos or invested in by scions to power like Donald Trump Jr.
While it was easy to catch George Santos in his alleged misdeeds and even easier to accept Bill Simmons’s titillating on-air admission, we can’t rely on people being that sloppy forever. Polymarket lets people monetize anything. Proxy betting isn’t that hard to pull off, provided you don’t have a podcast network worth millions of dollars and a thirst for self-embarrassment. No rule or regulation or law will make these services clean, because they are inherently built on a messy, morally compromised activity.
Now, I’m no Mister Rogers, and I’m certainly not my parents. No one will catch me handing out morality police citations. I have been to Vegas sports books. I’ve used FanDuel’s daily fantasy app, which is still legal in California. But when money, especially the so-called “easy” variety, comes into play, you can bet (pun intended) someone will try to make the easy even easier. The illicit nature of gambling, the thrill of the score, and the idea of making money for nothing is the core of its appeal. At least my parents’ generation saw it for what it was – a risky activity that could wreck your life – and not a way to break the law from the comfort of your own couch.
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Dave Schilling is a Los Angeles-based writer and humorist
