All In

Gamblers would give anything to peek at Ian Rapoport’s notes. In late April, Rapoport—a reporter at the NFL Network, known on air as an “insider”—was sitting on a scoop about the draft’s most intriguing story line. Until then, it had been considered a done deal that the San Francisco 49ers would select an Alabama quarterback named Mac Jones with the third overall pick; bettors, expected to risk tens of millions of dollars on the draft, were counting on it. But Rapoport’s sources told him that the 49ers were seriously considering Trey Lance, a quarterback from North Dakota State otherwise thought to be a long shot for the top five. Landing the story placed Rapoport in a devilish dilemma, one that sports journalists now confront often: publish the news and send sportsbooks scrambling to update their odds, or wait a few seconds, place a bet first, and give himself a good shot at winning a small fortune. “It’s kind of like insider trading,” he said.

Rapoport listened to the angel on his shoulder. He went straight to Twitter. “My tweet went crazy,” Rapoport told me. Someone who’d bet a hundred dollars on San Francisco to take Lance a few weeks earlier stood to profit fifteen hundred dollars; after Rapoport’s report, the odds swung dramatically. (In sports betting, odds are fixed the moment a bet is placed, no matter what news comes to light after the fact.) Four days later, when Roger Goodell, the commissioner of the NFL, took the stage to announce that San Francisco had drafted Lance, anyone who had just bet a hundred dollars on that outcome walked away up a mere fifty-five bucks.

For years, the NFL draft has provided endless fodder for proposition bets, or “props”; this year, they ranged from how many wide receivers would be selected in the first round (five) to the color of the dress worn by Marissa Mowry, the wife of No. 1 pick Trevor Lawrence (black). Annually, the illegal market for sports gambling in the United States has been known to draw an estimated $150 billion. But ever since 2018, when the Supreme Court struck down a federal ban on most sports gambling outside Nevada, more than two dozen states have legalized it, and there’s been a mad dash to build upon the fanaticism: Last summer, DraftKings, an online sportsbook, paid $100 million for the right to open a gambling parlor at Chicago’s Wrigley Field—an idea that NBA owners, too, have endorsed for basketball arenas. The PGA Tour agreed recently to open a sportsbook at one of its tournament courses. In April, the NFL partnered with three sportsbooks in a deal worth nearly a billion dollars. By 2025, legal sports gambling nationwide is projected to be worth $10 billion.

Media companies have also entered the business—sports bettors watch about twice as many games as non-bettors do, and Bleacher Report found that gamblers are five times more engaged with its app than other spectators. In the past year, NBC Sports negotiated a partnership with a sportsbook called PointsBet worth nearly $500 million. ESPN, Fox, and CBS signed deals with other gambling companies, including old-school casinos like Caesars. DraftKings agreed to pay $50 million to distribute podcasts by Dan Le Batard, formerly of ESPN. In May, the Associated Press announced that it would exclusively reference betting odds from FanDuel, DraftKings’ archrival. And still, the integration of sports media and gambling is probably in just the top of the first inning.

With thousands of props available every day, updating online in real time during games, the opportunity for journalists to capitalize on behind-the-scenes access would seem irresistible. Not everyone plays it like Rapoport. Reporters covering Wall Street would, in theory, find themselves in the same ethical mud, except that mainstream outlets strictly prohibit their employees from investing in the companies they cover. (The Securities and Exchange Commission wouldn’t approve, either.) By contrast, some two dozen prominent sports journalists told me, gambling in the press box is common, especially in football, and few sports outlets bar reporters from betting within their beats.

Perhaps no one is as open on the subject as Bill Simmons—the CEO of The Ringer, the media company he sold to Spotify last year for $196 million, and a proud gambling obsessive. On his podcast, Simmons provides sports analysis interspersed with boasts and moans about his recent bets. Occasionally, his disclosures have gotten him in trouble: Simmons, one of a hundred media figures who votes on NBA end-of-season awards, said that he’d bet on LeBron James to win Most Valuable Player, only to let slip that, of course, he’d also voted for James; the league didn’t like that, and discounted his ballot. But by and large, Simmons, and The Ringer, have benefited enormously from going all-in on gambling. In May, The Ringer reached a partnership agreement with FanDuel for an undisclosed sum.

So it goes for many media companies, at a loss for revenue and drooling over the profit potential in sports betting. As gambling swallows up sports media, anyone pausing to consider editorial conflicts (or, in the case of bets based on nonpublic information, possible law-breaking) might feel left out. Michael Lombardi, a former NFL team executive who later became a sports reporter, now gives gambling advice at VSiN, known as “the CNBC of sports betting.” Recently, he told me, “If you don’t like change, you’re going to like irrelevance even less.”

 

The DraftKings vision for a betting venue at Wrigley is, in a sense, baseball come full circle. In the 1870s, gambling lured fans to the first professional ballgames, where bookmakers stood in the stands, accepting fistfuls of cash as they shouted odds on everything from the next at-bat to whether the wind would change direction. Newspapers began publishing box scores—an unintended aid to bookies, who traffic in statistics. Once it became clear that baseball attracted more gamblers than idle spectators, some papers became openly disdainful in their coverage of games. In 1872, the New York Times claimed that, despite baseball’s popularity, “it is simply ridiculous to style it a national pastime,” adding, “Base-ball, so far as it can claim to be a typical American institution at all, is simply a contrivance for gambling that most honest men would cheerfully see suppressed.” Four years later, when the National League was founded, its officials vowed to rid the sport of gambling.

On that front, baseball failed spectacularly. After years of rumored fixed games, gamblers bribed eight players on the Chicago White Sox to throw the 1919 World Series—a scandal that, for the next century, would be cited as evidence of betting’s corruptive influence, and inspired many states to outlaw sports gambling. In 1947, Jake LaMotta paid Mafia members twenty thousand dollars and took a dive in a fight in exchange for a shot at a title bout, a shameful boxing moment memorialized in Raging Bull. Las Vegas began collecting bets in 1949, but Congress did all it could to undermine bookmakers, from imposing a 10 percent tax on sports gambling revenue to criminalizing the use of wires and mail to place bets or share gambling information across state lines. Journalists often helped expose gambling scandals, as in 1951, when Max Kase, the sports editor of the New York Journal-American, tipped off prosecutors that college basketball players were taking bribes to shave points—including at the City College of New York, the reigning NCAA champion. Kase won a Pulitzer Prize.

By the seventies, sports gambling had been linked to seedy mobsters, demonized by the Christian right, and fiercely opposed by owners of teams. Nevertheless, it flourished underground as a multibillion-dollar industry. Jimmy “The Greek” Snyder, a Vegas oddsmaker and syndicated columnist, was hired in 1976 to join The NFL Today, a CBS pregame show, at a time when it was still verboten for sports broadcasts even to acknowledge gambling’s existence. On air, the Greek would predict winners and final scores—a compromise with polite society that surely fooled no one, like drinking on the street from a bottle wrapped in a paper bag. (He had a popular run until he was thrown off air for making racist comments about Black athletes.)

Across the country, sports pages increasingly featured gambling advice. In Las Vegas, full-time bettors, or “sharps,” would huddle outside McCarran Airport, waiting for deliveries of out-of-town newspapers with updates on injuries, lineups, and any other scraps of information. John Clayton, a top football reporter, started out as a teenager covering the Pittsburgh Steelers for a local paper in Pennsylvania. “It was a steelworker town,” he said. “Other than going out to drink, what you did was gamble.” Some bettors tried to bribe him for information before it was published. (He declined.) The market for gambling news was undeniable. “No medium has been quicker to adapt to that phenomenon than newspaper sports sections,” Sports Illustrated observed in 1979. “It’s now an open question whether their most avid readers are fans or bettors.” That year brought the founding of ESPN, which soon aired a gambling show from Caesars Palace during the NFL playoffs.

By the mid-eighties, roughly three-quarters of newspapers published NFL betting lines. There remained gambling dissenters: Bob Knight, the volatile Indiana University basketball coach, said that papers “might just as well run the telephone numbers of prostitutes”; the Times refused to publish lines and picks on the grounds that most of them would be used illegally, though its sports editor told SI that moral protest might seem like “sticking your head in the sand.” In 1985, the Cincinnati Enquirer announced that it would cease printing point spreads, only to relent after getting bombarded with furious calls from readers.

Gambling on certain sports was more palatable than others—namely horse racing, because of a carveout that made it legal (and taxed): horse gambling is conducted in a pool, through “pari-mutuel betting,” with odds that fluctuate based on who bets what, as opposed to everyone competing against a house oddsmaker. For a while, the Times and Washington Post each had a Harvard alum covering the horse racing scene: Steven Crist, at the Times, and Andrew Beyer, who in the Post offered such advice as “Mortgage the house. Hock the family jewels. Crack open the kids’ piggy bank. Badger Land is a mortal lock to win at the Preakness.” They were credible, as an SI profile reported: “Beyer and Crist both bet as well as they write.” At tracks with clerks ready to take bets from inside the press box, Beyer claimed to make upwards of $50,000 a year picking horses. Crist, prohibited by the Times from betting on races he was covering, still once managed to win $90,000 on other horses.

But when journalists placed illegal bets, they had to be discreet. Bud Geracie, a longtime sports editor of San Jose’s Mercury News, got his start in journalism—and gambling—working nights at United Press International in Madison, Wisconsin. “I was mostly the only person in the office except for the security guy, Jack, a small-time bookie who had moved from Las Vegas,” Geracie said. Jack took Geracie’s bet on the 1982 Super Bowl: San Francisco versus the Cincinnati Bengals. “I’m still a college student,” Geracie remembered. “I took four hundred dollars out of my savings account and handed Jack an envelope”—not realizing that illegal bets were accepted on credit. He picked the 49ers, who won 26–21. “I got eight hundred dollars back from Jack,” he said. “I was off and running.”

 

More than a decade before Congress declared sports gambling “a national problem” and prohibited states from legalizing it if they hadn’t already, a writer named Daniel Okrent cooked up an alternative market. Called the “Rotisserie League,” it provided a means by which baseball fans could invest in a lineup of real players, as the theoretical managers of their own teams, over the course of a season. On a trip to Austin, he pitched the idea to editors at Texas Monthly; they passed. But in 1980 he went ahead, charging friends an entry fee of $250. The winner would collect half the pot. In time, “Rotisserie” was formalized as a trademarked company; eventually, more contests sprang up, across more sports. Crucially, “fantasy leagues,” as they became known, were considered a “game of skill,” rather than a “game of chance,” making them legal even after 1992, when Congress laid down its broad ban. Mostly, prize money was modest, which helped coworkers and college buddies justify what seemed a dubious loophole. Because fantasy leagues started in an analog era, early participants sometimes attempted to collect data through extraordinary means. (As Okrent told Ben McGrath in The New Yorker, there were “people calling the P.R. department and pretending to be journalists, asking whether the pitcher’s arm was still hurt.”)

Even in the internet age, managing one’s fantasy roster for an entire season can be labor intensive. FanDuel, in 2009, and DraftKings, in 2012, began promoting daily contests—a shrewd way of attracting interest while draining customers’ accounts drip by drip. (My dad bets about a buck seventy-five on daily fantasy baseball, a seemingly modest wager that adds up to roughly three hundred dollars over the course of a season.) When these companies emerged, sports-journalism outlets recognized them quickly as gambling in disguise. Nigel Eccles, FanDuel’s founding CEO, told me, “I remember one senior ESPN executive telling us we were going to jail.”

But there were some boosters. One was Simmons, who in 2002 issued his first “manifesto” for ESPN about how to bet on the NFL playoffs. “Fans are brainwashed to believe gambling is dangerous,” he wrote a few years later. “Gambling is a part of sports; we may as well accept it.” Another early advocate was Chad Millman, the editor in chief of ESPN The Magazine, where he established a gambling beat, devoted an issue to the subject, and launched ESPN.com’s “Chalk” section for betting news. He was drawn to the lingo—“It’s a very clubby, insidery, 1950s Rat Pack cool,” he told me—and aimed to fill a massive reporting void. “Why do point spreads move the way they do? Why are professional bettors making certain decisions? At the time this was still a vein that was only remotely tapped by deep journalism.”

Today, as states legalize sports gambling, roughly 60 percent of daily fantasy players are converting to betting. At The Ringer, Simmons and his team are eager to serve that audience, with a hybrid dialect of gambling analysis and conventional sports talk. “It’s a storytelling technique,” Kevin Clark, a football reporter, told me. “In 2021, when you’re saying who’s going to be rookie of the year, it would be weird not to discuss the odds. That’s now just part of the conversation.” In Detroit, where the Pistons have had an awful few years, Rod Beard, a Detroit News basketball beat writer, took a stab at writing a fantasy advice column. “Within a day or two,” he said, “I got four thousand additional Twitter followers.” Lately, he’s covered Pistons games with an explicit daily fantasy “slant.” Doing so could be the saving grace for struggling newspapers, he said: “Just like people pay for stock tips, they’ll pay for paywalled content on betting.”

ESPN’s gambling-coverage offerings have expanded to include a Daily Wager talk show hosted by Doug Kezirian, who, in April, became part of the story: A pro bettor reportedly tipped him off that Tyson Campbell, a cornerback at the University of Georgia, was likely to be drafted much sooner than expected. Kezirian discovered that BetMGM had labeled Campbell as a safety by mistake, making his odds (100-to-1) to be the first safety off the board seem absurdly low. “We all have different strengths as bettors, and mine are instincts,” Kezirian later told the Las Vegas Review-Journal. He drove to the Bellagio, saddled up to a self-serve kiosk, and placed about a dozen $200 bets on Campbell. When the Jacksonville Jaguars selected Campbell at the top of the second round, Kezirian and his pro-bettor partner won nearly $300,000. (Kezirian never touted his bet on air.)

Increasingly, sports betting news comes directly from sportsbooks—often by way of former journalists who have decamped for higher-paying posts. Millman decided to raze the wall separating sports reporting from the action when, in 2017, he left ESPN to help found a sports betting media startup called the Action Network. Like VSiN, the Action Network offers articles, podcasts, and data-crunching tools for gamblers. The site publishes betting-minded sports coverage (e.g., a recent assessment of “swirling winds” that were forecast ahead of the MLB All-Star Game) and provides a Consumer Reports–style ranking of the best sportsbooks (DraftKings earns the top spot, with a 9.9 out of 10). “We’re digging into information; we’re providing a service,” Millman said. They’re also doing extensive business with companies they cover, such as charging a referral fee on placed bets. It’s a blatant conflict of interest—though not so different from that of conventional newsrooms striking deals with gambling companies. “Are you going to allow sponsors to dictate coverage?” J.A. Adande, Northwestern University’s director of sports journalism, wondered recently. “You can’t tell me that it’s impartial now.”

This spring, after receiving bids from DraftKings and FanDuel, the Action Network was sold to a Danish betting company called Better Collective for $240 million. “It’s pretty insane,” Millman said. Around the same time, DraftKings bought VSiN for nearly $70 million. Lombardi, who has spent his career on all sides of the sports-media-betting playing field, waved off any concern about crossing over into gambling—the only difference between covering sports for a news outlet and a gambling site, he told me, is who signs his paycheck. A number of sports journalists have, apparently, accepted those terms, as sportsbooks morph into media operations, poaching more talent from traditional outlets: Ryan Spoon, ESPN’s former senior vice president of digital content; Len Mead, recently of NBC Sports; Joe Lago, of The Athletic.

It’s slippery turf, though: gamblers are competing, in a sense, against the company taking their bets; sports reporters at DraftKings, FanDuel, and casinos could face pressure to tip off their coworkers before breaking news; analysts might be asked to promote betting strategies that favor their employers’ interests. Teddy Greenstein, a longtime Chicago Tribune writer, assured me that he hasn’t encountered any of those conflicts in his new gig, providing gambling advice at PointsBet. “My buddy said, ‘In ten years, we’re all going to be working for teams, leagues, or online sportsbooks,’ ” he said. “People in the industry know who’s got the money.”

 

A decade ago, Jim Armstrong, a twenty-seven-year veteran of the Denver Post, was covering the Colorado Rockies. He was also, apparently, betting on games. He probably could have carried on doing both, but in 2011 he was named in an indictment that revealed an illegal, high-stakes gambling ring operating out of bars and restaurants. Some of the bettors involved wagered fifty thousand dollars a week. Armstrong wasn’t personally charged, but the Post fired him.

These days, you can place a bet from a smartphone in seconds, which makes it far more difficult to monitor journalists’ gambling—or, for that matter, bets they ask neighbors or cousins to place for them. In theory, sportsbooks can flag a bettor who has been enjoying an improbable winning streak, but companies lack the resources or incentive to investigate individuals. (Even if a four- or five-figure payday would thrill someone on a reporter’s salary, it wouldn’t draw much attention inside FanDuel.) It’s impossible to know exactly how many sports journalists are also sports gamblers, though lately more of them have become more open about placing bets. When Kezirian cashed in, he faced no penalty from ESPN.

“I think sportswriters are betting on games they’re covering,” Vic Tafur, The Athletic’s Las Vegas Raiders beat reporter, told me. He knew of a basketball writer who acted on word from a coach: his team planned to slow down its pace on offense—meaning the next game’s final score would likely be lower than oddsmakers expected. The writer “unloaded on the under and made a killing,” Tafur said. “It’s not a rare story.” The opportunities for insider betting are even greater in college sports—which, unlike the pros, don’t require teams to disclose injuries before games. Peter King, a football columnist at NBC Sports, told me that he knows “a lot of sportswriters who gamble.” He also has a friend who quit gambling when it almost ruined his life. “I have a lot of empathy for people who say maybe we shouldn’t be in bed with these gambling companies,” King said. (There’s never such thing as a sure bet, regardless of what you think you know; even successful pro gamblers get just over half their bets right.)

The increasingly comfortable relationship between sports journalism and gambling has, not coincidentally, developed alongside a decline in sports media—and a collapsing market for the press at large. In recent years, Sports Illustrated laid off nearly half its staff; employees of Deadspin, beleaguered by the desperation of their corporate bosses, resigned en masse; even The Athletic, a once cash-flush upstart, let go of forty-six people. The Athletic went on to debut a sports betting section, walled off from the rest of the newsroom, with new hires including James Holzhauer, a pro gambler who won nearly three million dollars on Jeopardy! On television, leagues and networks are panicked over declining sports viewership; they can only hope that spectators will tune in to otherwise dull matchups if they have skin in the game. To lure fans, broadcasts air ceaseless gambling promotions: NBA playoff games are interrupted so that TNT studio hosts can offer tips on FanDuel props; MLB and NHL games run live betting odds onscreen. The Sinclair Broadcast Group renamed nineteen regional sports networks after Bally’s casino; ESPN has experimented with airing gambling-focused alternate broadcasts of football and basketball games.

Displaced sports journalists may hope that gambling operators can provide them a home. But don’t bet on the heroic rescue of a struggling outlet by a benevolent sportsbook. “At the end of the day, all they want is to become the biggest gambling company in America,” Albert Chen, the author of Billion Dollar Fantasy, told me. He cited DraftKings’ reported interest in acquiring Bleacher Report. “Swallowing up Bleacher Report would certainly help acquire customers,” he said. “But that’s the bottom line. That’s it. It’s not a vision of FanDuel or DraftKings to become a repository of good sports content.” Eccles, of FanDuel, agreed. From a gambling company’s perspective, he said, if a sports site “is totally independent and really run from an editorial angle, if it’s not benefiting you, why the hell own it?”

For sportsbooks, reporters merely provide a means to an end: credibility by association. “I still follow journalism rules,” Greenstein said of his job at PointsBet. “But I joke with people, ‘It’s not journalism—it’s much more fun.’ ”

Danny Funt is a senior editor at The Week and a former CJR Delacorte Fellow. Follow him on Twitter at @dannyfunt