The compliance story the sports betting industry tells is that its own responsible-gaming systems catch the customers who are in trouble, and that regulation can therefore stay light. ProPublica’s Jake Pearson spent ten weeks testing that claim from the inside, betting from a single account the way a compulsive gambler bets — loss chasing, escalating stakes, all-night sessions, parlays, prop bets, microbets — with the funding and the methods disclosed to the company. DraftKings rewarded the behaviour with a personal VIP host. After $21,600 in deposits he had lost $10,702, and the system had not once put a human in front of him.
The important finding is not that a gambling company likes heavy customers. It is the sequence. Pearson’s first bout of textbook loss chasing — close to $1,800 in a night of Knicks playoff basketball, funded by three top-up deposits — produced a VIP showcase invitation the following afternoon, a three-week audition for the programme. Formal acceptance came after three weeks and $5,800 in deposits. The signal that a customer is in trouble and the signal that a customer is worth cultivating are the same signal, and the company reads it in one direction.
What the tiers reward
The VIP programme’s fine print, as Pearson describes it, does the advertising work: the more a customer spends on long-odds wagers, the faster credits accumulate toward the next tier — bronze, silver, gold, diamond, Onyx. Long odds means high margin, and high margin on repeated losing bets is where sportsbook revenue actually comes from. A 2024 Connecticut study cited in the piece found 1.8% of problem gamblers in the state accounted for 51% of sports betting revenue.
The perks arrive as a relationship. Accepted bettors get a named concierge they can text, and Pearson used his the way the product invites: after serving a three-day “cool-off” — a period in which the app locks you out entirely, imposed at his own request after a losing run on French Open tennis — he asked his host about a deposit match, was offered $1,250 in credit against a $5,000 deposit, and took it. That is about a week after the strongest distress signal the app offers. DraftKings’ chief responsible gaming officer told him the sequence was acceptable because the customer initiated it, and because it was a perk any customer could ask for.
Where the guardrails were
Pearson counts 32 responsible-gaming notices from DraftKings over ten weeks, a figure that includes emails sent to every customer; in-app notices about his own betting reached him on 14 of the 71 days he gambled. The New York-mandated disclosure at $2,500 in deposits offered a limit-setting button beside an “I Understand” dismissal. A blackjack table “time reminder” after three hours and 45 minutes occupied a corner of the screen and could be swiped away. When he did use the tools — a two-hour daily session cap, a $100 deposit limit — four promotional push alerts arrived within the same day, the first thirty minutes after he set them.
The design worked against the prompts. As his volume grew, the quick-deposit buttons in the app grew with it, to $500, $750 and $950. The blackjack table served a “Double” button directly after the deal, one thumb-tap for the fastest way to lose more in a bad hand. Microbets — a single tennis point, a single baseball plate appearance — collapse the interval between stake and result to something close to a slot pull, which is the comparison NYU anthropologist Natasha Schull draws. And the casino travelled with the sportsbook: after betting NBA games in New Jersey, his bet-slip receipt carried a “Suggested For You” panel advertising basketball blackjack. He asked his host whether the casino could be removed from his phone. It could not.
For scale on the priority, consider what the industry does with the machinery it already has. Massachusetts regulators found that of the roughly 0.64% of gamblers whose accounts were limited as of December 2024, winning bettors were more likely than losers to have their maximums cut. Identifying and constraining an account is not an unsolved technical problem; it is pointed at customers who cost the house money. As of April, just over 8% of active DraftKings users in Massachusetts were using the responsible-gaming tools at all, a company official told state regulators.
Who bears the cost
The regulatory architecture is opt-in by design. New York requires operators to file a “problem-gaming plan” but lets the companies write it and does not publish the contents; Pearson’s records request was still pending. Advocates want the default inverted — limits on unless a customer removes them — and point out that the products at issue, VIP programmes and microbets, are also revenue lines, which is what makes statehouses reluctant to touch them while the tax receipts are in the budget.
DraftKings disputes the framing. It says all 5,000-plus employees are trained annually on responsible gaming, that the practice is “embedded across our business,” and that the sample here is one account. Its responsible gaming chief said the system “worked the way it was supposed to” in his case, because his behaviour never met the company’s internal thresholds — among them, apparently, betting between 1:30 and 5:30 a.m. — and that the company closes accounts on betting history alone “all the time,” while declining to say how often.
Two further numbers in the piece are worth keeping. Siena Research Institute found this year that about a quarter of active sportsbook account holders said they had lost enough on a bet to have trouble meeting their financial obligations. And Pearson’s experiment did not end in a hole because he lost every bet. He was up $25,350 when the Knicks won the title, and up $16,000 during the World Cup, betting as much as $7,000 a day. He kept going and returned it all, which is the outcome the business model is built on and the one that responsible-gaming systems are not built to interrupt.