On a recent Saturday, at a bar in New York City’s Tribeca, a couple of hundred young sports fans in T-shirts and baseball caps ordered light beers served in tall glasses and shouted over a bellowing sound system under the confining fluorescence of 57 televisions. It was raining hard outside, but the weather didn’t lessen the excitement of the crowd, which was watching the second round of the N.C.A.A. Division 1 men’s basketball tournament, or March Madness.

As likely representatives of the 68 million Americans estimated to have bet on the tournament last year, a percentage of those who studied the flatscreens that day had inevitably lost money gambling on the games. The group of men in their mid-20s who I stood with at a counter were an illustrative party—before arriving for the 7:10 P.M. start of North Carolina State versus Oakland, our quartet had already squandered hundreds of dollars on various bets from the weekend’s preceding contests.

Around the bar, gambling phrases (“over-under,” “good odds,” “Will they cover?”) reverberated, while the familiar, number-filled dashboards of the most popular digital sportsbooks—namely DraftKings and FanDuel, which as of last year owned nearly 75 percent of their market—populated most patrons’ phone screens. (Representatives of both companies declined to comment for this story.)

Connecticut Huskies center Donovan Clingan (32) shooting the ball over San Diego State Aztecs forward Miles Heide (40) during the “Sweet 16” round of the N.C.A.A. March Madness tournament in Boston last week.

Scoring plays in an ongoing blowout game were greeted with cheers and groans from viewers who evidently had money on the line. At one point, a large, gregarious man placed $10 on the method of the next basket—he forecast a three-pointer—in order to win back losses from the four previous times that very bet had failed him. (A few seconds later, Oakland’s sharpshooting guard nailed an off-balance three-pointer, and the man won his $10 bet. He laughed. “Next time, I’m thinking layup,” he said.)

Around the bar, gambling phrases—“over-under,” “good odds,” “Will they cover?”—reverberated.

Across the U.S., this scene is getting increasingly more common. The American Gaming Association predicted that American adults would stake up to $2.72 billion on the men’s and women’s March Madness tournaments this year.

Last year, Americans wagered $119.8 billion on sports (compared to $93.2 billion in 2022 and $57.2 billion in 2021), and the nationwide revenue from sports betting increased 44.5 percent from 2022. A recent Siena College poll found that 39 percent of Americans have bet on sports, the majority of whom are men aged 18 to 34. Men’s Health conducted its own study in 2023 and found that 38 percent of surveyed men had bet on sports in the past year, and that 61 percent of them bet “either daily or weekly.” Almost one in five said that their habit was “destroying their life.”

The U.S. government doesn’t provide funding for gambling-addiction research, but studies by the National Council on Problem Gambling (N.C.P.G.) concluded that from 2018 to 2021, the overall risk of gambling addiction had risen by 30 percent. “The majority of this growth is young, male, online sports bettors,” Keith Whyte, the N.C.P.G.’s executive director, says. “That’s who’s driving the biggest change in [overall] risk … the group with the highest level of participation, and, to follow, the highest level of problems.”

In a country whose first president once called gambling “the child of avarice, the brother of iniquity, and the father of mischief,” a wicked in-law has joined the fray: the ability to bet in a casino that fits conveniently in one’s back pocket.

The Color of Money

Since as early as the colonial era, Americans have liked to gamble, and they’ve often done it irrespective of the law. By 1910 gambling had been made all but illegal in the U.S. (though Nevada legalized casinos in 1931), and large-scale crime syndicates quickly established control over underground betting, including sports betting, in states where it was a criminal offense.

The eight Chicago White Sox players charged with fixing the 1919 World Series.

A negative association formed between gambling, crime, and spectator sports, in part thanks to events such as the Black Sox scandal, wherein eight Major League Baseball players were accused of intentionally losing the 1919 World Series at the behest of Arnold Rothstein, a prominent Mob boss. Forty-two years later, John F. Kennedy signed into law the Federal Wire Act, which was specifically in opposition to the criminal groups that ran illegal sportsbooks (rumors of his alleged Mob connections notwithstanding).

Then things changed. A single law enacted by Congress in 1992, called the Professional and Amateur Sports Protection Act (P.A.S.P.A.), prevented new states from offering sports betting, but it included a clause that gave state governments a one-year period to declare their intent to allow it, and to ultimately exempt themselves from the restriction.

In 2012, New Jersey representatives—led by then governor Chris Christie—realized that they’d missed out on the lucrative immunity of the exempted states and pushed legislation to legalize the practice in their own. (Gambling was legal in Atlantic City’s casinos at the time, but they were still prevented from accepting sports bets under federal law.) In the foreground of New Jersey’s argument was the idea that P.A.S.P.A. violated the 10th Amendment and that the federal government had no right to tell states who could or could not bet on home runs.

New Jersey’s gripe led to a lawsuit, Christie v. National Collegiate Athletic Association, that eventually reached the Supreme Court in 2018. On May 14 of that year, a landmark vote in favor of New Jersey struck down P.A.S.P.A., and immediately thereafter, the floodgates opened for states to legalize sports betting at their whim. By the end of 2018, seven new states had legalized sports betting (including Pennsylvania, New Mexico, and Rhode Island), and DraftKings had launched its first online sportsbook outside of Nevada, in New Jersey.

Today, sports betting is legal in 38 states, 9 of which require that it take place offline. And the major leagues, which long shunned sports betting, have come to love their old enemy.

Before 2018, the National Football League would not so much as acknowledge the existence of sports betting, let alone allow a team to promote it. Just a few short years later, however, they permitted the Washington Commanders to install the first ever physical sportsbook inside a stadium. Today, the N.F.L. are official partners with multiple online gambling companies, and more than 25 of their teams are sponsored by gambling sites.

It’s only fitting that this year’s Super Bowl took place in Las Vegas. In Nevada alone, a record $185.6 million was bet on the game.

Today, Major League Baseball is investigating its wunderkind and highest-paid player, Japan’s Shohei Ohtani, after his interpreter was alleged to have stolen millions from the player to place bets. (Some believe the interpreter may have taken the fall for baseball’s golden boy, though Ohtani denies all involvement.) Simultaneously, the N.B.A. is looking into Toronto Raptors forward Jontay Porter, after betting sites reported a suspicious correlation between his gameplay and his betting lines.

Japan’s Shohei Ohtani, the star L.A. Dodgers pitcher, at a press conference following a sports-betting scandal on the part of his longtime friend and translator.

Betting is now so pervasive in professional athletics that N.C.A.A. president Charlie Baker released a public statement on March 27—just ahead of March Madness’s “Sweet 16” round—in opposition to “prop betting,” or betting on the performance of an individual player. “Sports betting issues are on the rise … with prop bets continuing to threaten the integrity of competition,” he said. “Issues across the country these last several days show there is more work to be done.”

In a country whose first president called gambling “the child of avarice, the brother of iniquity, and the father of mischief,” a wicked in-law has joined the fray.

Yet with the N.F.L., N.B.A., and others by and large promoting the sites, gambling has become accepted as “part of the fan experience,” Lia Nower, the director for the Center for Gambling Studies at Rutgers University, says—something “tied to people’s loyalty to their favorite teams,” which is also “tied to socializing with friends and family and entertainment.”

“The gambling landscape has totally changed since the advent of legalized online casino and sports wagering,” Nower says. Similar to the N.C.P.G.’s findings, she observed that a new demographic—young men, aged 21 to 27—was introduced to sports gambling after 2018.

“Betting can make a boring game, between teams you don’t care about, completely riveting,” says one twentysomething I spoke to. “Imagine what it does for a game you do care about.”

“In terms of excitement,” says another, “there’s a night-and-day difference between watching all these different stats with the prospect of winning money versus not betting at all.” This person revealed that over the last calendar year, he’s placed a sports bet nearly every day.

Keith Whyte, of the N.C.P.G., believes that much of the blame for gambling’s recent growth should fall on the states that legalized sports betting. As in the waves of pro-lottery legislation in the 1980s and pro-commercial-casino legislation a decade later, the end of the P.A.S.P.A. was followed by state governments being enticed by what they saw as a new, harmless revenue stream.

“Many state governments see gambling as a painless tax—a tax only paid by the willing,” Whyte says. But, he points out, they disregard the pitfalls of their profitmaking, since this tax is also “paid by people with gambling problems, and their families. Most legislators are looking at the benefits, not the costs.”

“Betting can make a boring game, between teams you don’t care about, completely riveting. Imagine what it does for a game you do care about.”

The central cost that has so far eluded legislators is addiction. Take New York governor Kathy Hochul, who earlier this year said that she looked forward to further “successful gaming policies that deliver top tier mobile sports wagering experiences,” which will “continue to generate revenue that will enrich the lives of New Yorkers.”

Her state is currently the largest market for online sports betting in the country, collecting $211.7 million in revenue just this January, a month in which residents bet almost $2 billion. But all the while, as tax revenue rises, rates of “problem gambling”—the official term for gambling addiction—also increase.

According to the N.C.P.G., around nine million Americans are problem gamblers. In 2013, the American Psychiatric Association elevated problem gambling’s addiction classification, making it the only behavioral addiction listed alongside clinical disorders.

Of those who reach out to the N.C.P.G. for help, on average, their gambling debt amounts to twice their annual income. “The more frequently you gamble, the more it becomes a habit, and the more you become ‘hooked’ on the possibility of winning at some uncertain point in the future,” Nower says.

And once the cycle begins, it’s a short road to Catch Me if You Can. “Some people resort to behaviors they would never otherwise consider,” Nower says. “Passing bad checks, stealing from family and employers, lying to borrow money or conceal their losses, stealing or robbing, and so on.”

Where gambling goes, problem gambling follows, and after sports betting’s legalization, organizations that offer services to gambling addicts saw the evidence firsthand: 325,000 people contacted the N.C.P.G.’s hotline for help with problem gambling last year, a 100 percent increase over the last three years.

Chinazo Cunningham, the commissioner of the New York State Office of Addiction Services and Supports, identified the same pattern. She told me that since New York’s legalization of online sports betting, in 2022, the most common form of problem gambling people call the N.Y.S. Hopeline about has become online betting.

Where gambling goes, problem gambling follows, and once the cycle begins, it’s a short road to Catch Me if You Can.

Standing between the problem gambler and continued sportsbook use are two barriers: the 1-800-GAMBLER, number promoted by the betting Web sites, and debt severe enough to sound alarms on the sportsbook itself. Although these guardrails may be preventative for some, many others have progressed toward addiction despite them.

An employee at one of the world’s largest sportsbooks, who preferred to remain anonymous, told me that his company has a dedicated team for addiction prevention. He said that the team will flag players who are clearly “having issues,” and that their accounts get restricted until bank statements proving financial stability are uploaded.

He added that the addiction-prevention team is “something we have to have, based on regulations,” the state-by-state laws and programs that govern sportsbooks, “but it’s not a super-comprehensive program.”

Most of the sports-betting sites’ resources seem to be aimed at attracting and keeping users. It takes approximately one minute to download the DraftKings or FanDuel apps on a cell phone, and another few minutes to input the requisite information—name, address, date of birth, e-mail, phone number, and Social Security number. At best, your identity is verified on the spot; at worst, you might have to wait a day or two before starting to place bets.

Once you’re in, the options are endless. In a quick scroll through FanDuel and DraftKings on a recent Sunday night, I found bets for darts, the Tour de France, handball, a South Korean volleyball game (in which I could attempt to predict the final score), and table tennis. There were, of course, countless betting options for the major American sports as well. Ahead of a Pacers-versus-Lakers basketball game, FanDuel allowed me to bet on different possible methods for the first scored basket, with odds reaching +25,000 (meaning a $10 wager could potentially result in a $2,500 win).

Online sports betting feels as much like an engrossing video game as it does a precarious habit once relegated to smoke-filled rooms. Combining individual bets into parlays is akin to an exercise in intelligence, testing the user’s mathematical and sports knowledge. And the number of available bets—across different sports, or within a single game—which can be placed live create an immersive, gamified experience.

Once you’re in, the options are endless.

And then there are gambling advertisements, which are as unavoidable as they are effective. DraftKings, FanDuel, BetMGM, and PrizePicks reportedly spent almost $1 billion in advertising last year (Flutter Entertainment, the company that owns FanDuel, took in $12.1 billion in revenue), and their spending went to advertisements specifically tailored to the sports fanatic. Sportsbooks’ logos are plastered around stadiums and arenas. Commercials feature well-known athletes such as Rob Gronkowski and Charles Barkley and will soon feature LeBron James, who in late January signed a blockbuster sponsorship deal with DraftKings.

The sportsbook employee told me that since he started to work at that company, less than a year ago, its marketing team had grown drastically. “The advertisements have gotten completely crazy in the last year,” he says. “If you watched the N.F.L. this season, you’re seeing an ad for DraftKings or FanDuel every commercial break. That didn’t used to be the case.”

He’s right. A study conducted by CBC’s Marketplace and researchers at the University of Bristol found that over the course of seven sports broadcasts in five days last October, 21 percent of the screen time was filled with gambling messages. The same could be said for watching an hour of ESPN or walking through Times Square.

As was true of the advertising strategy of tobacco companies in the 1950s, concerns with sportsbooks’ marketing tactics stem from the fact that they depict an addictive product as harm-free.

But with regard to the marketing of sports betting, what most frustrates clinicians who treat problem gamblers are the promotional offers. In a practice that the psychoanalyst and addiction researcher Harlan Matusow calls “insidious,” all major online sportsbooks provide certain “free bet,” “cash bonus,” “no sweat,” or “risk-free” deals for participants who sign up for their sites, or who meet certain conditions.

These offers are used by sportsbooks to attract potential customers through the promise of complimentary funds. And they are no small sums: a sampling of “promo” deals for this year’s March Madness tournament includes a $1,000 first-bet-back offer on Caesars Sportsbook and $1,500 in “bonus bets” on BetMGM. These sites “initiate you into playing by giving you money, and crediting it back to you in the form of house credit if you lose,” Matusow says, “which is unconscionable.”

Similar to the debts incurred by those tempted with the increasingly popular buy-now-pay-later financing options set forth by companies like Affirm, sportsbooks entice bettors with a crediting strategy that, as always, has a catch.

“Free money” bonuses also make it difficult for problem gamblers to quit. Sportsbooks collect extensive amounts of data on their player base, and sites such as DraftKings use artificial-intelligence and machine-learning models to target ads at specific users. (They also use A.I. to price their odds.) Like sites that promote advertisements based on an individual’s interests, sportsbooks can encourage odds and promotions of particular intrigue to a particular gambler.

Whyte presents the hypothetical of a problem gambler who hopes to quit but is sent marketing messages listing bets that were created expressly for him. “It would be almost impossible to resist,” he says. “Relapse is becoming more prevalent than ever.”

As was true of the advertising strategy of tobacco companies in the 1950s, concerns with sportsbooks’ marketing tactics stem from the fact that they depict an addictive product as harm-free.

For some, the reality of A.I.’s presence in the world of online sports betting is a step too far. Congressman Paul Tonko, a Democrat from New York, is the strongest voice in opposition to online sports betting in Washington.

On March 19, he announced the SAFE Bet Act, a bill that seeks to impose federal regulations on online sports-betting companies. Restrictive legislation would limit live advertising by sportsbooks, excessive depositing by players, and the use of A.I. to track gamblers and create odds, all of this with the hope of containing or reducing the consequences of sports gambling.

During a press briefing for his new proposal, Congressman Tonko called sports betting a “growing public-health crisis” and referred to the current state of online sports gambling as the “Wild West,” wherein sportsbooks are free to operate however they please. He stressed that his legislation deals with “a known addictive product” that is being marketed and advertised without any federal regulation.

Despite his efforts, Tonko has failed to pick up any real steam on Capitol Hill. As the online-betting industry continues to generate cash, it’s unlikely that any majority of representatives—none of whom have shown public support for Congressman Tonko’s initiatives—will get behind this bill anytime soon.

The sportsbook employee told me that at his company, no one has actually brought up the potential negative aspects of their industry. “For us, we’re just doing our job,” he said. “You’re trying to make as much money as you can. It’s like someone who works in banking in New York City.” A more fitting comparison might be to that of a lender who pushes subprime mortgages without regard to the risks faced by unsuspecting investors and homeowners, who are sold unstable products wrapped in bows.

The betting numbers on this year’s March Madness tournament, which ends on Monday, are still unknown, though if there were one safe bet to make, it would probably be that any 21-to-27-year-old American with a vague interest in sports will have money on the line for it.

Some money will be won, ending up in the pocket of a grateful fan. A lot will be lost and will go to DraftKings or FanDuel, and to the state governments. Some gamblers will win or lose and will continue on with their lives, unaffected by what is, to them, a casual hobby. And many others will win or lose—and not be able to stop.

Jack Sullivan is an Associate Editor at AIR MAIL