- The Cautionary
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- Learning AI #40
Daniel Vest of West Virginia says that in the month before September 26, 2026, DraftKings sent him about 70 emails, texts, and app notifications urging him to bet more. He lost thousands of dollars.
On October 1, he filed a proposed class action against DraftKings in federal court in Boston.
The suit says the company used AI to find customers likely to gamble and lose, then aimed promotions at them.
The suit claims there was a DraftKings employee who worked on a system to pull back users who were trying to leave. Another built a program that boosted promotions for people gambling "more aggressively than usual." One former employee called the practice "as predatory as it sounds."
The money is huge. DraftKings took in about $8.7 billion in gross gambling revenue in 2025. The lawsuit says DraftKings’ AI personalized hundreds of millions of promotional dollars aimed squarely a Daniel West and other prolific losers.
AI just makes it easier for the house to always win.
DraftKings denies it. A spokesperson said the company does not use AI to target customers based on their losses or signs of problem gambling. CEO Jason Robins called a New York Times report "slanderous" and said DraftKings uses its tools to find problem gamblers, warn them, and close accounts when needed. Yeah, right.
A court will sort out who is right. Massachusetts law says operators must disclose their AI use to the Gaming Commission and can't use personal customer information in AI-driven promotions.
The same kind of customer data that finds losers also finds winners.
Massachusetts regulators released the first public numbers on how sportsbooks treat good bettors. Less than 1% of sportsbook accounts limit the amounts someone can bet. An account gets limited when it is too successful. More than half of the limited accounts could only bet up to 25% of the maximum bets.
The people most likely to get limited were the ones who consistently beat the house, which is widely seen as the best sign a bettor knows what they're doing. People whose limits went up were far more likely to be VIPs. Very few limited players had VIP status.
So the system works in both directions. If you lose a lot, you get VIP status and 70 messages a month. If you win steadily, the $500 bet you want to place gets limited to $50.
People ask me whether AI can help them win at sports betting. Maybe a little, at the margins. If it works, the sportsbook's AI will probably notice what you are doing before your bank account does. There is plenty of truth to the saying, “heads I win, tails you lose.”
Things I think about
Sea level isn't level. At the Panama Canal, the Pacific sits about 8 inches higher than the Atlantic on average. Pacific water is warmer and less salty, so it's less dense and takes up more room, and winds and currents add to the difference. Ships never notice, because the canal's locks lift them 80 feet at a time.