The following is excerpted from a chapter of Everybody Loses: The Tumultuous Rise of American Sports Gambling, by Danny Funt. The book is available for purchase now.
Bill Simmons never seemed like the type to bite his tongue. In many ways, he earned the nickname he gave himself, “the Sports Guy,” by sharing beliefs—in his ESPN column, on the pregame show NBA Countdown, on his podcast, on the long-form sports-writing site Grantland that he launched under ESPN—without a filter, as someone might while watching a game with buddies at a bar. He was also fluent in what boorish men call “locker-room talk” (like when he told a reader that his friends “lost the ability to call themselves guys the moment they allowed a female in their football fantasy league”), but his brazenness about sports usually came off as bravery, and for that he became one of ESPN’s most valuable stars.
He could also be their biggest liability, most famously during the Ray Rice scandal. After the Baltimore Ravens’ starting running back was arrested in February 2014 for assaulting his then fiancée in a hotel elevator, NFL commissioner Roger Goodell handed Rice a two-game suspension. (The assault took place at a casino, coincidentally, though there’s no evidence that Rice or his fiancée had been gambling that night.) This seemed absurdly lenient, especially come September, when TMZ published surveillance footage showing Rice delivering a brutal left hook to the woman’s head, then dragging her limp body out of the elevator. Goodell said Rice hadn’t been forthcoming about what happened and this time suspended him indefinitely. (He would never play in the NFL again.) For ESPN’s Outside the Lines, Don Van Natta Jr. and Kevin Van Valkenburg published a remarkably detailed investigation of what unfolded from February to September, reporting that the Ravens’ owner and other team executives had urged Goodell to go easy on Rice and documenting why it seemed highly unlikely that Goodell hadn’t seen the disturbing footage before the rest of the world did, as he claimed.
Simmons’s mind was made up. “I just think not enough is being made out of the fact that they knew about the tape and they knew what was on it,” he said on his ESPN podcast. “Goodell, if he didn’t know what was on that tape, he’s a liar. I’m just saying it. He is lying. I think that dude is lying. If you put him up on a lie detector test, that guy would fail. For all these people to pretend they didn’t know is such fucking bullshit. It really is. It’s such fucking bullshit. And for him to go in that press conference and pretend otherwise, I was so insulted.”
Simmons had a hunch this wouldn’t go over well at ESPN and made it clear he didn’t care. “I really hope somebody calls me or emails me and says I’m in trouble for anything I say about Roger Goodell. Because if one person says that to me, I’m going public. You leave me alone. The commissioner’s a liar and I get to talk about that on my podcast. . . . Please, call me and say I’m in trouble. I dare you.”
In response, ESPN said Simmons had violated the company’s “journalistic standards” and suspended him for three weeks, burnishing his reputation as someone willing to speak truth to power. Of course, it’s not like ESPN was trying to bury the story: they were the ones who reported it. Simmons was suspended because he took his colleagues’ painstaking reporting and misrepresented their findings while publicly taunting his employer in the process.
For the most part, ESPN really did leave Simmons alone, especially when he expressed his love of gambling. Once, ESPN had him write about a six-day trip to Sin City—or, as he called it in a column, “VEHHHHHHH-GASSSSSSSSSSSSSSSSSS!!!!!!!!!!!!!!”
Beginning in 2002, he would publish an annual “manifesto” on how to bet on the NFL playoffs, and in 2007 he introduced a popular podcast segment with a friend, “Cousin Sal” Iacono, in which they guessed the opening lines of NFL games each week (a conceit they may have ripped off from two guys playing the same game on their Las Vegas radio show). Simmons also let it be known that he thought the leagues, and many prominent media companies, were dumb for thinking it was irresponsible to encourage gambling. “Fans are brainwashed to believe gambling is dangerous, that it’s a potential gateway to self-destruction, that it can destroy your life if you aren’t careful,” he wrote in 2006. “Gambling is a part of sports; we may as well accept it.”
In his memoir, You Can’t Lose Them All: Tales of a Degenerate Gambler and His Ridiculous Friends, Iacono (a cousin of ABC late-night host Jimmy Kimmel) describes playing blackjack with Simmons. “He will play all night at the same table and refuse to leave until they implode the casino and turn it into a Wet’n’Wild,” Iacono wrote. “I’ve been with him until 5:00 a.m. where he’s literally being asked to lift his feet so they can vacuum.”
In 2015, ESPN decided not to renew Simmons’s contract after he got into another spat with them, this time for questioning Goodell’s “testicular fortitude.” His next stop was at HBO to host a talk show, Any Given Wednesday with Bill Simmons, which was canceled after four and a half months, its final episode drawing just 82,000 viewers. In the unsparing sports blog Deadspin, Kevin Draper apologized to readers who were expecting a savaging postmortem. “There isn’t anything unkind to write about AGW that hasn’t already been written,” he noted, adding that it was fair to begin wondering if Simmons would be a “failure” without ESPN’s backing.
In 2016, Simmons launched a media organization, the Ringer. It embraced the staff’s interest in other areas—one popular podcast debriefed Game of Thrones episodes; another reevaluated old movies—but sports was central. Simmons’s style of discussing it from a gambler’s perspective rubbed off, not only on many of his employees, but across much of the industry: what was once risqué became, at many outlets, the de facto approach to sports talk. If you’re analyzing a new crop of rookies, for example, referencing the odds to win rookie of the year is now as basic as citing any other stat. “It’s a storytelling technique,” explained Kevin Clark, a football reporter who left the Ringer in 2024 to host a show for ESPN2 that’s sponsored by Caesars.
“Bill Simmons is my hero,” he said. “I’ve probably read every word he’s ever written. To me, the gambling part was just entertainment.”
Clark doesn’t bet on football. Simmons, meanwhile, boasts and moans about gambling on basically everything. This can pose a conflict, like the time he said he’d bet on LeBron James to win MVP, only to let slip that, of course, he’d also voted for James as one of the hundred media figures who decides NBA end-of-season awards. The league discounted his ballot and reiterated that journalists shouldn’t be wagering on outcomes that they help decide.
Simmons, who declined to be interviewed for this book, never addresses how he places his wagers. He lives in Los Angeles, where bookmaking is illegal.
The Ringer didn’t just talk about gambling for entertainment; it became a primary source of revenue. In 2020, the company signed an advertising partnership with FanDuel (in the low eight figures annually, I’m told) and was acquired by Spotify for $196 million, all while staff and management battled over a proposed collective bargaining agreement.
During the unionization fight, a former employee said colleagues discussed, “Should we be in bed with a big gambling company?” The benefits of that deal weren’t trickling down. “We’re barely getting paid to work,” the ex-employee said, “and Bill continues to buy new houses that we’re reading about on the internet.”
For some, conflicting feelings about gambling never went away. A handful of Ringer podcasts were “presented” by FanDuel, which often meant hosts had to suggest bets to their listeners, especially same-game parlays, FanDuel’s most profitable product. “Same-game parlays are not designed for the player,” another former employee said. “Everyone knows that. By that I mean everyone on our side, not the gamblers.”
“Not to sound like a weirdo old person,” the ex-staffer added, now addressing sports media’s relationship with gambling more broadly, “but this is kind of a slippery slope. It’s actively bankrupting some people on a regular basis, so that makes me feel a little gross. But also it pays all our paychecks.”
On its app, FanDuel promotes the Ringer’s recommended bets, often alongside Simmons’s headshot. After he suggested a same-game parlay for the 2024 Super Bowl, Pat McAfee mocked him for only getting about 8,000 customers to follow his bet, McAfee claimed, while his own suggested Super Bowl SGP was copied by a quarter-million bettors. McAfee didn’t mention if the parlay he’d endorsed was successful. (He might have been pissed about Simmons doing an impersonation that made McAfee sound like a dufus.) “Keep running your mouth, Bill,” McAfee jeered. What a sign of the times: two of the wealthiest men in sports media bickering about who gets more of their listeners and viewers to place foolish bets.
Everyone knows that. By that I mean everyone on our side, not the gamblers.”
Sophisticated bettors, or “sharps,” have a saying: “You’re not betting the team; you’re betting the number.” Any team facing any opponent might be worth taking if the price is right; to a sharp, “I just can’t bet against so and so” is nonsense. Simmons, meanwhile, exemplifies why sports fans often make for lousy gamblers: they fixate on which teams and players are good and bad or hot and cold. Take his annual tradition of predicting whether NBA teams will go over or under their projected win totals. Evaluating whether the Los Angeles Clippers would win at least 37.5 games during the 2024–25 season, Simmons, a Clippers season-ticket holder, dwelled on whether the team would be fun to watch, especially without Paul George, an aging all-star who had just left in free agency. “It sounds horrible!” he concluded. “Under, and it’s a lock for me.” The Clippers went on to eclipse their projected win total handily.
Once, Simmons and Cousin Sal let on that they’re not so naïve. Toward the end of an episode during the football season, Simmons went on a tangent about how sportsbooks had taken to skewing the odds so that betting on underdogs or parlays would have skimpier payouts. “I feel like there’s less value than there’s ever been,” he said, comparing it to when casinos started paying 6 to 5 instead of 3 to 2 when a player was dealt twenty-one in blackjack.
The two started giggling, realizing the naughtiness of implicating their sponsor. “Let’s make a promise,” Sal said, “that as longtime gamblers . . . let’s try to never get in business with these odds providers. Oh, wait.”
For much of his career, Simmons was primarily a writer, known for going to phenomenal lengths to make a point. In 2014, for example, he devoted 5,300 words at Grantland to the question of whether the NBA all-star Kevin Love was “overrated, underrated, or properly rated.” (His verdict: underrated.) His beloved bestseller from 2009, The Book of Basketball: The NBA According to the Sports Guy, is 736 pages. But at the Ringer, Simmons gave up writing, joking that “my fingers stopped working.” There are plenty of rigorous thinkers who express themselves exclusively through a microphone, but that shift for Simmons seemed to coincide with shallower analysis and a growing reliance on shtick over substance. When I asked around, many sports journalists, including some former Ringer employees, said they think that in recent years Simmons has been mailing it in.
I don’t think it’s a coincidence that these days, promoting simplistic sports bets for FanDuel comes so naturally to him. Nor do I think it’s a coincidence that Simmons, who used to take such pride in being a defiant truth teller, is now conspicuously silent—or, at best, tongue-tied—when it comes to the potential drawbacks of the leagues embracing sports betting.
He did address the Jontay Porter scandal, if reluctantly. In March 2024, ESPN reported that the NBA was investigating Porter, a 24-year-old bench player on the Toronto Raptors earning $410,000 that season. (His older brother, Michael Porter of the Denver Nuggets, made about $31 million.) After DraftKings grew suspicious about the huge amounts of money being wagered on this obscure player, the NBA and FBI eventually investigated, finding that Jontay owed “significant gambling debts” and had encouraged a group of bettors to take the “under” on his props for two games in which he went on to remove himself mid-game, once for an eye injury, the other time because he said he felt sick. NBA commissioner Adam Silver imposed a lifetime ban on Porter, who later pleaded guilty to conspiracy to commit wire fraud.
“It’s crazy. It’s just part of our sports now,” his teammate Ochai Agbaji said. “I feel like sports betting has always been around, but . . . it’s becoming more popular and obviously you’re gonna have stuff like this.”
On his first podcast after the Porter news broke, Simmons waited an hour and forty-three minutes to address it. “There’s going to be an overreaction about, well, this is what happens. We gamble on everything,” he said.
He stopped to let his guest, the Ringer’s Van Lathan, weigh in. Many people learned of Lathan when, while working as a TMZ host in 2018, he admonished Kanye West face-to-face for calling slavery a “choice.” He’s at ease speaking expansively about pop culture and sports as a Ringer host—and politics, too, as a frequent guest on CNN—but in this moment Lathan let out a burst of nervous laughter before asking Simmons to go first.
Simmons recounted decades of gambling scandals, from Green Bay’s Paul Hornung in 1963 to more than a dozen Italian soccer players caught gambling in the past year. “I think what strikes me about the Jontay Porter thing specifically is how good the sportsbooks and casinos are at sniffing shit out, right?”
He interrupted himself to ask Lathan, “Why are you making a sly smile?”
“Let me ask you something,” Lathan said. “Are you uncomfortable with the idea . . . that the access and the popularity of gambling throughout these different gambling sites, how intertwined the gambling sites are into sports culture now . . . that this is going to lead to a disintegration of the competitive integrity of the game because it’s all in everybody’s phones?”
“I just don’t see that at all,” Simmons replied. He acknowledged that his show was sponsored by FanDuel, rambled a bit, then said, “Just because Jontay Porter, if he did that, is an idiot doesn’t mean we’re headed toward, like, the 1919 Black Sox Scandal. One of the things is these guys are making a shitload of money.”
Lathan posed another question: “Is there any chance to you that this fractures or slows down the relationship between the different gambling sites and entities and the professional sports leagues?”
Simmons exhaled, pausing to choose his words. “I could see them being reevaluated in some ways, but I don’t see it slowing down because for the leagues it’s too much money and for the culture it’s more intertwined.”
A few things should be clarified.
It didn’t take any sort of sophisticated oversight to “sniff out” the Porter scandal. The bettors who exploited his props were shockingly reckless, showing off their bets to fellow gamblers, one of whom sent me a screenshot of a six-leg, $80,000 DraftKings parlay on Porter’s props that stood to win $1,120,000. These guys were actively seeking attention. Porter wasn’t very discreet, either: he texted an accomplice while he was at the Raptors’ arena about their scheme, hours before one of the games he manipulated.
That type of bet hadn’t been going on under the table for years. In fact, until recently, most bookmakers would never dream of accepting a five-figure same-game parlay revolving around an irrelevant bench player in the middle of the season. A bet of that kind, and that size, is decidedly a modern phenomenon. Robert Walker, an industry veteran who ran the MGM Mirage when it was the largest sportsbook in Vegas, said he and his peers in Nevada would have never let someone bet that type of six-leg player prop for more than a few hundred dollars.
Today’s athletes aren’t immune from getting caught up in gambling just because they make “a shitload of money,” either. Calvin Ridley, a rising star wide receiver on the Atlanta Falcons, forfeited his 2022 base salary of $11.1 million as a result of wagering $5,200 on NBA and NFL games, including a parlay involving picking the Falcons to win. This, he said, wasn’t a calculated attempt to leverage inside information for profit but rather an impulsive attempt to relieve boredom while he was away from the Falcons to receive treatment for depression. “One day, I saw a TV commercial for a betting app, and for whatever reason, I downloaded it on my phone . . . literally just for something to do,” he wrote on the Players’ Tribune. “When you’re depressed, you’re not thinking about anything in the future. You’re just trying to get through the day,” he continued. “I made the worst mistake of my life.”
Finally, to brush Jontay Porter off as an “idiot” misses the point. Though he was making significantly less money in the NBA than Ridley was in the NFL, Porter was addicted to gambling, according to his attorneys. With that disease, any player, regardless of their income or intelligence, could make the same regrettable choices.
As for all the money that operators spend to intertwine gambling with the culture of sports, on that topic, Simmons certainly knows what he’s talking about.
