It was late May, the French Open was on and DraftKings was pushing me into the action.

A promotion pinged on my phone. “BET & GET,” it boomed, offering to boost my profits if I threw down on tennis, punctuating the point with a cartoon stack of cash. I was already in the middle of a two-hour betting spree, ripping 64 wagers on the clay courts of Paris from my 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? Wrong. How about an easy $300 on Francisco Comesana to win the first game of the second set against Luciano Darderi? Negativo.

I’ll be the first to admit that my backhand needs some work. But this wasn’t about sports. It was about scratching an itch.

For the past six weeks, I’d been gambling like a man out of control, testing the guardrails of one of America’s most popular — and controversial — products: online sports betting. I’d morphed from a prudent, just-for-fun $40 bettor into a “degen” (sports betting slang for a degenerate gambler) who casually yeets $1,500 on a game. I’d feverishly jumped from sport to sport, following playoff basketball bets with live Czech table tennis. And I’d gone hog wild at the online casino, doubling down at the blackjack table. Most of the time, I’d lost — then chased those losses with more bets. Now, I was in the grips of yet another binge.

And as I approached $4,500 in losses in 24 hours, transferring money from my bank directly into my DraftKings account, the company seemed to clock the problem, sending me an in-app notification.

“Take a loss? Now take a beat,” it read. This felt right after the tear I’d been on. To date I’d blown about $12,500 in total on DraftKings. That’s the equivalent of six months of mortgage payments in as many weeks.

I followed the prompt to the site’s “responsible gaming” center, where I opted to limit myself to just two hours per day on the app and barred myself from depositing more than $100 in a 24-hour period. That pause is an essential part of DraftKings’ seemingly paradoxical business model — to make as much money as possible from the nation’s growing ranks of sports bettors without encouraging gambling addiction. The company says these limits are a cornerstone of that strategy.

Yet 30 minutes later, the company pushed me in the other direction. My phone buzzed with the first of four promotional alerts that day. Betting opportunities, they said, were waiting.

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This wink-and-a-nod dynamic is now at the center of a fierce public policy debate over online gambling, addiction and consumer protection.

Since 2018, when the Supreme Court allowed states to legalize sports betting, Americans have put more than $600 billion into play. Sports betting is now legal in 39 states and Washington, D.C. Add in prediction markets like Kalshi and Polymarket, and more people are betting on sports than ever before.

That explosive growth has come with consequences: About a quarter of active sportsbook account holders surveyed by the Siena Research Institute this year said that they’d lost enough on a bet that they’d have trouble meeting their financial obligations. As a result, regulators and lawmakers from Colorado to Massachusetts are starting to question whether things have gone too far — and some are now proposing stricter consumer protections.

Amid the mounting scrutiny, major operators like DraftKings have pushed back, arguing that their responsible gaming system provides adequate safeguards to protect their customers from spiraling out of control. “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,” Lori Kalani, the company’s chief responsible gaming officer, told me. If a customer waves too many red flags, she said, the company will proactively close the account. But when I asked how often this actually happens, DraftKings wouldn’t say.

So I decided to find out for myself: If I bet like a compulsive gambler, would DraftKings stop me — even if it cost the company money?

I opened an account under my own name and linked it to my debit card. ProPublica bankrolled me. When the app asked me what I did for a living, I disclosed that I was a reporter. I assembled a panel of addiction specialists, recovering gambling addicts and professional sports bettors who pointed me to the telltale wagering habits of someone who’s out of control. And then I got to work.

Over the next 10 weeks, I’d mimic those patterns and come to find out just how much DraftKings would encourage my recklessness — and just how little pushback I’d get as I spiraled downward.

I used the NBA playoffs as my launching pad, and, like much of New York, I was all in on the Knicks. After a week of moderate betting, I waved my first red flag during Game 3 of the Knicks vs. Atlanta Hawks first-round series.

I slept fitfully after my night of loss chasing and awoke at dawn to catch a train to Boston, where I attended a symposium on online gambling put on by the Public Health Advocacy Institute at the Northeastern University School of Law.

There, Matthew Gaskell, a British psychologist and expert on gambling addiction, said that the bettors that companies are most interested in are, well, losers like me. Indeed, a modest set of very active losers account for a substantial amount of sportsbooks’ revenue, he said. (A 2024 study out of Connecticut found that 1.8% of problem gamblers in the state accounted for 51% of sports betting revenue.) And the companies have created sophisticated technology products designed to squeeze maximum engagement out of them, just as social media companies like Meta did years earlier with users of Facebook and Instagram, added Darragh McGee, a researcher at the University of Bath.

In fact, as The New York Times reported, DraftKings employs machine learning and data scientists to identify losing customers and entice them with promotions to keep them going — even if those are exactly the kinds of customers at risk of becoming addicts. DraftKings told the newspaper its promotions are geared toward 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.”

To keep users loyal, the major operators offer VIP programs, not unlike what airlines or rental car companies do. As a bettor climbs the tiers, the perks get bigger and better, from free bets and swag to primo seats at games, fancy dinners and even concert tickets. A FanDuel VIP in Pennsylvania received a personalized video message from MLB slugger Bryce Harper.

I wanted to be a VIP. I wanted cool perks.

To help get that status, I’d tapped the skills of Isaac Rose-Berman, a precocious 26-year-old professional sports bettor and policy expert at the American Institute for Boys and Men, a think tank that focuses on policy issues impacting dudes. He had a hunch that by chasing losses and displaying other signs of problem gambling I’d eventually get an invite. We just didn’t know when it would come — or how much it would cost.

It happened sooner than either of us thought.

At 5:01 p.m. the day after I lost nearly $1,800 on basketball in one night, during the closing remarks of the gambling addiction symposium, an email popped into my inbox. “Welcome to the DraftKings VIP Showcase,” the subject line read. I couldn’t believe it. My night of loss chasing was being rewarded.

The VIP showcase is basically a three-week tryout. Every week I’d get a new promotion as the company sussed me out to make sure that I was worthy of the title. It wanted to know whether I was actually a big spender, aka a whale, or a wolf in sheep’s clothing — a pro bettor, like Rose-Berman, who, armed with math, can beat the house more often than most by exploiting mispriced odds. Bettors like these, known in the business as sharps, calculate savvy wagers that have as much to do with sports knowledge as with probability. The apps do not like losing money to them and so limit how much they can bet.

For long-term losers like me, though, those limits don’t apply. I’m not a sharp. I’m a square.

And when I read the fine print of the VIP loyalty program, I was floored to see the incentive structure laid out so plainly: The more I spent on long-odds wagers, the quicker I’d accumulate the credits I needed to advance from tier to tier — from bronze, to silver, to gold, to diamond, to Onyx — and thus get closer to the cool perks I so desired. The upshot? Full send every time, baby!

Before I could get started though, I encountered my first in-app responsible gaming prompt since I began betting.

In just over a week, I’d gambled away roughly what a minimum-wage worker in New York City earns in a month by chasing my losses and repeatedly tapping my bank account. But the notice wasn’t served to me because of how I’d been betting. It was sent because when New York lawmakers legalized mobile sports betting in 2023, they required the apps to notify users when they hit $2,500 in total deposits.

The law also requires sportsbooks like DraftKings to submit a “problem-gaming plan” to the state regulator but leaves the specifics of it up to the companies. The plan must include, among other things, procedures “for identifying users with suspected or known problem-gaming behavior” and for “providing information to users concerning problem-gaming identification and resources.” But the exact details are unclear because such plans are not publicly available. (A DraftKings spokesperson wouldn’t provide a copy, and my request for it under the state’s open records law with the gaming commission is under review.)

The app’s response to my $2,500 in deposits was tepid. With a click I could either set limits on my betting or avoid doing so altogether. Eager to gamble, I clicked “I Understand” and moved on. That was it, warning resolved. I got on the horn with my panel of experts to map out the next phase of my experiment. It was time to up the ante.

One of my advisers, Joshua........

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