It was late May, the French Open was underway, and a ProPublica reporter had just ripped 64 wagers on the clay courts of Paris in a single two-hour session from his office chair in New York City. A $75 bet that Claire Liu would win the fifth point of her first-set tiebreak against Maria Sakkari came back wrong. So did a $300 bet on Francisco Comesana to win the first game of the second set against Luciano Darderi.
Mid-spree, a promotion pinged his phone. “BET & GET,” it read, offering to boost his profits if he threw down more money on tennis, complete with a cartoon stack of cash.
A Deliberate Descent Into Reckless Betting
The tennis binge was one stop in a 10-week experiment by Jake Pearson, who set out to test whether DraftKings would stop him if he bet like someone spiraling out of control — even if stopping him cost the company money. He opened an account under his own name, disclosed that he worked as a reporter, and let ProPublica bankroll the wagers.
A panel of addiction specialists, recovering gambling addicts and professional sports bettors helped him identify the telltale patterns of a bettor in trouble, and he set about mimicking them. He morphed from a cautious $40-a-game bettor into someone tossing $1,500 on a single wager, jumping between sports and going “hog wild” at the online casino.
The escalation added up fast. He lost roughly $4,500 in a single 24-hour stretch and about $12,500 total over six weeks, transferring money straight from his bank into his DraftKings account along the way. The night after he blew nearly $1,800 chasing basketball losses, an email landed in his inbox: “Welcome to the DraftKings VIP Showcase.”
That showcase amounts to a three-week tryout, during which DraftKings tests whether a bettor is a genuine high-spending “whale” or a sharp using math to beat the house — the kind of player operators limit rather than reward. Bettors like Pearson climb a tier system running from bronze to silver, gold, diamond and finally Onyx, and the program’s fine print rewards spending on long-odds wagers with faster progress up the ladder. The scrutiny facing rival VIP programs at other operators has followed a similar shape, with perks reportedly including free bets, merchandise, premium seats, dinners and concert tickets for top-tier players.
This individual case sits inside a much larger shift in American gambling. Since the Supreme Court cleared the way for state-level legalization in 2018, Americans have put more than $600 billion into sports bets, and the activity is now legal in 39 states and Washington, D.C. Lawmakers have separately pushed for a federal study of gambling disorder as the industry’s footprint keeps expanding.
Warnings Followed by More Promotions
As Pearson’s losses approached $4,500 in 24 hours, DraftKings sent an in-app notification: “Take a loss? Now take a beat.” He followed the prompt to the site’s responsible-gaming center and set a two-hour daily app limit along with a $100 cap on deposits in any 24-hour period.
Thirty minutes later, the company sent the first of four promotional alerts that day, each one dangling a new betting opportunity. A similar pattern repeated on May 7, when a “responsible gaming” pop-up followed more parlay losses — only for DraftKings to send a 20% profit-boost promotion on live baseball microbets just hours afterward, encouraging Pearson to keep betting until the offer expired that same day.
Some of these interventions weren’t triggered by his betting patterns at all. New York law requires sportsbooks to notify users once they hit $2,500 in total deposits, and that threshold — not the shape of his wagering — is what generated his first in-app warning. The same state law requires operators to submit “problem-gaming plans” covering how they identify at-risk users, but those plans aren’t public, and DraftKings declined to provide a copy when asked. The push-and-pull between caution and promotion is consistent with what DraftKings’ use of loss-prediction data to shape its marketing has previously suggested about how the company targets users likely to keep losing.
Why the House Wants Its Biggest Losers
Matthew Gaskell, a British psychologist who studies gambling addiction, told Pearson that the bettors companies care most about are exactly the ones losing the most money. A 2024 study out of Connecticut, cited in the reporting, found that just 1.8% of problem gamblers in the state accounted for 51% of sports-betting revenue — a concentration that helps explain why operators build systems to keep struggling bettors engaged rather than push them away.
Darragh McGee, a researcher at the University of Bath, compared the industry’s engagement technology to what social media companies like Meta built years earlier to maximize time on Instagram and Facebook. DraftKings uses machine learning and data scientists to identify losing customers and target them with promotions, according to reporting by The New York Times cited in the ProPublica investigation.
DraftKings told the Times its promotions are aimed at users who spend a lot of time on the app and that the company “rejects any implication that its marketing practices are unfair or improperly targets customers.” Lori Kalani, DraftKings’ chief responsible gaming officer, offered a similar defense directly to Pearson: “I think as a business, as an industry, we’re doing a good job of educating people, of raising awareness, of making tools and resources available, of monitoring accounts.”
A Program Built on Contradiction
Kalani said DraftKings will proactively close an account when a customer waves too many red flags, but the company would not tell Pearson how often that actually happens. Joshua Grubbs, who studies gambling disorders at the University of New Mexico, said a bettor on Pearson’s trajectory would be expected to bet more frequently, spend longer on the app, jump between sports and start experimenting with parlays and prop bets — a progression Pearson was already moving through by the time he was accepted into the VIP program.
DraftKings frames its opt-in limits and pause prompts as a cornerstone of a business model the company describes as balancing revenue against addiction risk. Pearson’s experience suggests those tools ran on a different clock than the marketing engine sitting right next to them — one that kept firing promotions within minutes of a warning designed to slow him down.
His VIP invitation arrived less than 24 hours after a night of chasing basketball losses, a sequence he described plainly: “My night of loss chasing was being rewarded.” The reporting captured here ends as Pearson was preparing to escalate further into parlay betting, so the ultimate trajectory of his account — and whether DraftKings ever intervened more forcefully — falls outside what’s documented in this stretch of the investigation.
The post Losses, Warnings and a DraftKings VIP Invitation appeared first on ReadWrite.
This articles is written by : Nermeen Nabil Khear Abdelmalak
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