Two high-profile betting controversies — one involving former congressman George Santos and another tied to sports media personality Bill Simmons — are drawing renewed attention to how deeply online wagering has entered the mainstream.
Taken together, the episodes reflect a shift in the United States. Gambling that was once treated as taboo or fringe is now increasingly packaged as finance, fandom, or entertainment — and delivered directly to people's phones.
Here's what to know
In a commentary for The Guardian, Los Angeles-based writer and humorist Dave Schilling argued that the rapid spread of prediction markets and sports betting has made gambling feel increasingly ordinary in the U.S., even as the same legal and ethical problems persist.
Kalshi's lifetime ban of Santos was one of Schilling's examples. The former congressman made more than $17,000 by betting that he would skip the State of the Union and then not showing up, but he has to return those winnings. His combined penalties from Kalshi and the Commodity Futures Trading Commission exceed $80,000.
Another case Schilling highlighted involved Simmons, the sports media commentator and founder of The Ringer. On his podcast, Simmons admitted that his daughter's boyfriend used Simmons' FanDuel account to place bets for him from Massachusetts, even though Simmons lives in California, where FanDuel Sportsbook is illegal.
After that remark, listeners quickly raised the possibility of proxy betting, which Schilling wrote can violate platform rules and may also conflict with state gaming regulations. On the show, according to The Guardian, Simmons said, "I get the code to make sure it's me to my phone; I give him the code, he logs in. 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."
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More background
Online gambling has expanded quickly, often under different labels.
That growth has come through several related products. Prediction markets such as Kalshi and Polymarket are usually classified as financial exchanges rather than gambling products, while fantasy sports companies originally built support by presenting their contests as games of skill. Schilling noted that a 2018 Supreme Court decision let states determine whether sports betting would be legal, and 39 states plus Washington, D.C., now permit some form of it.
Schilling said critics' concerns go well beyond the industry's presentation of these apps as harmless fun. They have pointed to predatory design, constant advertising, financial danger, and the simplicity of placing live bets from a couch or in the middle of a game. He also wrote that the World Health Organization has linked gambling harms to stress, lack of self-control, and financial insecurity.
He also pointed to the money pouring into the sector. Schilling wrote that Polymarket is valued at more than $20 billion after investments from Donald Trump Jr., the president's son, underscoring how much capital and political influence now surround a business reaching further into daily life.
What's being done?
The Santos case ended with a lifetime Kalshi ban and added financial penalties from federal regulators. Simmons' podcast comments, meanwhile, raised separate questions about how proxy betting operates in practice and how hard it may be to police when wagers can be placed remotely.
Some companies have also tried to set boundaries around the most extreme wagers. Schilling noted that Polymarket moved away from allowing bets on the likelihood of nuclear strikes, suggesting that even inside the industry, certain markets are viewed as too ethically fraught or dangerous.
Schilling's broader warning is that new branding does not change the underlying business model. As he put it, "No rule or regulation or law will make these services clean, because they are inherently built on a messy, morally compromised activity."
Where can I learn more?
Schilling's warning applies to more than celebrity scandals and prediction markets. Gambling culture also shows up in ads aimed at young men, in investor fights over gambling company priorities, and in game mechanics that critics say can get children used to betting.
• Across sports media and betting apps, nonstop gambling ads increasingly target young men.
• At Penn Entertainment, shareholder pressure over executive perks highlighted deeper tensions inside the gambling business.
• On Animal Jam, loot boxes and TikTok trends fueled accusations of grooming kids for gambling.
These examples show why the industry's polished, mainstream image matters. As betting gets folded into media, investing, and everyday digital life, its risks become harder to separate from ordinary entertainment.
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