Eighteen hundred dollars, gone in a single night of basketball betting, is the kind of loss a reasonable person might expect a sportsbook to notice, and perhaps to mention. DraftKings noticed. The next morning, according to a first-person investigation by ProPublica reporter Jake Pearson, the platform sent him an invitation to its VIP program.
Pearson was not betting carelessly by accident. Over ten weeks he deliberately reproduced the behaviors that addiction specialists catalogue as warning signs: chasing losses, escalating wager sizes, switching sports late at night, leaning hard on parlays and microbets. After roughly three weeks and $5,800 in deposits, DraftKings formally enrolled him as a VIP, a status that carried a personal representative, deposit matches, and bonus bets. By the experiment’s end he had deposited $21,600 and finished $10,702 down, net.
Gone in sixty seconds
The loyalty mechanics rewarded the riskiest play. Long-odds wagers accumulated loyalty credits fastest, meaning the structure paid out, in perks exactly the behavior most likely to produce large, rapid losses. ProPublica also reports that DraftKings had built a data-science tool designed to flag customers nearing dangerous loss thresholds — and chose not to deploy it, defending its existing methodology instead. The company’s 51-person account-review team never flagged Pearson’s account for a manual look, despite the deposits, the escalation, the chasing, the marathon sessions.
Lori Kalani, DraftKings’ chief responsible-gaming officer, told ProPublica the company’s system worked as intended throughout the experiment.
Every guardrail is opt-in
The safety apparatus existed, but each piece of it waited for the customer to act first. Responsible-gaming prompts surfaced after big deposits and long sessions; activating a limit was the bettor’s chore. When Pearson set a two-hour daily session cap and a $100 daily deposit limit, promotional alerts arrived roughly thirty minutes later — the marketing engine and the protection engine running side by side, in opposite directions.
From sports, Pearson moved into DraftKings’ online casino, which cross-promoted sports-themed products under a ‘Suggested For You’ banner after he placed sports wagers. Over one New Jersey weekend he played about 500 hands of blackjack and lost nearly $3,000. Natasha Schüll, an anthropologist who studies gambling behavior, told ProPublica that rapid microbetting — resolutions arriving on single pitches or possessions within seconds — is structurally similar to slot-machine play.
Pearson ran a week-long comparison on FanDuel. There, he reports, ‘Reality Check’ reminders appeared six times during one extended session, reporting his time in the app and amount wagered, and no VIP invitation followed under comparable conditions.
It’s like an entire system that’s just built to appear to be doing something good while giving them basically like a free pass to do everything bad by saying, ‘Hey, we told you, you know, you have a responsibility, it’s your fault.’
That is Rob Minnick, a recovering gambling addict and co-founder of a gambling-industry watchdog nonprofit, quoted by ProPublica.
The arithmetic of the minority
The context is a market built since the Supreme Court’s 2018 decision letting states legalize sports betting; Americans have since wagered more than $600 billion on sports, according to ProPublica. Gambling-disorder diagnoses rose from 3.0 to 4.8 per 100,000 people in legalizing states between 2018 and March 2026, according to Epic Research data reported by NBC News; diagnoses declined in states that did not legalize.
Then there is the concentration problem. A 2024 Connecticut study cited by ProPublica found that 1.8 percent of problem gamblers generated 51 percent of sports-betting revenue. Massachusetts data in the report showed only 0.64 percent of gamblers had their betting limits reduced as of December 2024 — and winning bettors were more likely than losing ones to have their maximum wagers cut. At a June investor conference, CEO Jason Robins looked ahead to the online casino market: ‘I do think it’s a when, not if, that a lot of these states are going to legalize iGaming.’
Pearson’s ledger closed at $21,600 in, $10,702 out, and one VIP membership, earned the morning after his worst night. The question the investigation leaves for regulators is structural rather than personal: whether protection should remain something a bettor must find, activate, and maintain while the promotions keep arriving, or whether the platform itself should carry the default obligation before the losses define the relationship.