The Dave Portnoy Playbook

Staring down the sports-gambling gold rush — and sexual-misconduct allegations — Barstool’s founder bets on the culture war.

Portnoy onstage at a Barstool party in 2017. Photo: John Parra / Getty Images/2017 Getty Images
Portnoy onstage at a Barstool party in 2017. Photo: John Parra / Getty Images/2017 Getty Images
Portnoy onstage at a Barstool party in 2017. Photo: John Parra / Getty Images/2017 Getty Images

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It’s been a long 48 hours for your boy,” Dave Portnoy, the founder of Barstool Sports, said in an address to his 2.7 million Twitter followers late on a Friday night earlier this month. Portnoy was filming a response to an article published by Business Insider the day before, in which three women described distressing sexual encounters with him. One of the women, who was 20 at the time, said that in the summer of 2020, Portnoy, who was 43, filmed her performing oral sex and choked her without her permission. “It was so rough I felt like I was being raped,” the woman wrote to a friend in a text message two days later, according to Business Insider. “I was literally screaming in pain.”

A second woman, who was 19, said Portnoy had choked her and spit in her mouth. She didn’t describe the encounter as sexual assault but said she “felt very preyed on.” Another woman said Portnoy also choked and filmed her without permission. All three women were given anonymity, fearing retaliation from Portnoy and his followers, both of whom have a reputation for tormenting those who cross him.

For most public figures, this would be a moment to step back. But not for Portnoy. A few hours after the article came out, and apparently against the advice of legal counsel, Portnoy took to social media to deliver his own vigorous defense. He said that the women had approached him and everything had been consensual. He shared screenshots of what he said were Instagram DMs from the second woman in which she apparently reached out and expressed no immediate regret after their encounter.

“Miss my dick yet?” Portnoy wrote back to her.

“Hahahaha of course,” she replied.

In tweets, livestream videos, and on his eponymous weekly podcast, Portnoy claimed that the Business Insider article was a “hit piece” that was part of a “witch hunt” led by the forces that had been coming after him for a decade. He said it was hard for a guy like him — wealthy, big on Instagram, spends a lot of time in Miami — to turn away the droves of young women DM’ing him. “I don’t go after them,” he said. “They go after me.” Portnoy has made a habit of being brashly unapologetic, and watching his response to the article felt both bizarre and somewhat inevitable. Over the years, Portnoy has joked about rape while insisting he doesn’t condone it; called female sports reporters “sluts” and “cunts” in the name of comedy; and had several sex tapes that became public, one of which showed him choking another college-age woman. (The woman said the act was consensual.)

Portnoy founded Barstool Sports in 2003 as a free newspaper for lowbrow content aimed at men. Today, he is at the center of Barstool’s sprawling network of podcasts, livestreams, and YouTube shows, including one devoted to talking about what it’s like to be Dave Portnoy. The company expects to make $200 million in annual revenue next year. He is most famous for his regular Instagram reviews of pizza shops around the country, which are so popular that Walmart began selling a Barstool-branded frozen pie this fall. After the Business Insider story was published, Portnoy encouraged his followers “to beat cancel culture” by showing their support for him and buying as many pizzas as they could.

Then there is El Presidente, Portnoy’s asshole alter ego, whom Tucker Carlson has referred to as “not the president of a country but instead of a mind-set.” Since the pandemic began, he has morphed from being America’s bro-fluencer-in-chief into an icon among the Robinhood day-trading crowd and anti-wokeness crusaders. At the same time, Portnoy sold Barstool at a $450 million valuation last year and was refashioning the company and himself into aspiring players in the business of America’s next big legalized vice: sports gambling.

There was a time — call it four years ago — when allegations like the ones Portnoy was now facing would have been enough to derail a career or at least force a retreat from the limelight. But recent history has revealed that while some famous men and women have followers and fans who subject them to strict tests of virtue, others are revered for playing the heel. Portnoy spent the days after the allegations tweeting obsessively and laying out a conspiracy he believed was working against him. The article had been published on the same day that Penn National Gaming, the casino company that had acquired Barstool, reported disappointing quarterly earnings. The company’s stock took a nosedive before tanking even more after the allegations were published, ending the day down more than 20 percent. Portnoy retweeted screenshots that claimed to show heavy trading against Penn’s stock the day before, and he suggested that someone had tipped off investors. His prime suspect: Henry Blodget, the CEO of Insider, who had been permanently banned from the securities industry after settling a case over securities fraud. Portnoy suspected that some of Blodget’s powerful friends might be out to get him — perhaps one of Portnoy’s perceived enemies from his role in the GameStop meme-stock saga. “I feel like I’m in a movie,” Portnoy said. “I don’t know what to believe.”

A week after the story came out, Portnoy announced he would be livestreaming an “Emergency Press Conference,” promoted with an image that suggested he was preparing for a UFC title fight. During the hour-long video presentation, Portnoy went through slides of Instagram screenshots and text messages suggesting the reporter and her sources were biased against him. He thought his best piece of evidence was a “finsta,” or fake Instagram account, that Portnoy said belonged to one of the women, on which he said that shortly after their encounter, she posted a picture from Portnoy’s visit to the White House last year to interview then-President Trump. (The caption read: “OK. Not my proudest fuck.”) He wondered out loud if this would be his most-watched livestream ever.

Portnoy had managed to turn his defense against serious accusations of sexual misconduct into viral content. More than a million people have watched Portnoy’s press conference, and a day later, Barstool released behind-the-scenes footage of him preparing for the presentation and receiving a round of applause from his employees. “I am at the height of my powers,” he said on an episode of Davey Day Trader Global, his stock-trading show, while Bob Dylan’s “Hurricane” played in the background. Portnoy claimed his social-media following had received its biggest boost in months and that people were shouting their support as he walked around Manhattan. He said the incident had only increased “the level of loyalty, stickiness, all of that,” and that his backers were still behind him, namely Penn, which had always known it was taking the risk that Portnoy’s influence would be worth any trouble he caused the company as it tried to license and launch the Barstool Sportsbook app in states across the country. Portnoy said multiple times on air that he was nervous about what other stories might surface, while insisting there was nothing he was truly worried about. He had launched a campaign to #Cancel BusinessInsider, and his online followers went on the attack. He engraved three Champagne bottles with the names of his new enemies there, which he planned to pop whenever he felt he could declare victory. To mark Portnoy’s latest campaign for revenge, the Barstool merch store started selling a commemorative hoodie.

Bringing his defense to Tucker Carlson in November 2021. Photo: Fox News Broadcast

When I reached out to Barstool PR with fact-checking questions for this article, Portnoy himself replied a few hours later, upset that we planned to relay his recent declaration on Davey Day Trader Global that he was going to “threaten” an unnamed advertiser who was considering backing out of a deal after the Business Insider article. “Pulling quotes from my Ddtg stream is the equivalent of pulling quotes from a professional wrestler on a microphone during the middle of a telecast,” he said via email. “It is dishonest and intentionally deceptive journalism which seems to be the flavor of the day.” Portnoy was accusing me of committing the sin he has ascribed to many of his enemies over the years: taking him seriously.

I originally contacted Barstool months ago, hoping to talk to Portnoy about how a guy known for eating pizza had become a political hero and the face of a growing multibillion-dollar industry. Barstool declined multiple requests until after the Business Insider allegations were made public, at which point Portnoy agreed to sit for an interview — but only if he could record audio and video to use as he saw fit. Portnoy wanted me to step into the ring and do battle. I said he was welcome to record audio but that I wasn’t comfortable interviewing him on a serious topic while being filmed for a piece of Barstool content. Portnoy declined the offer, then posted our entire email exchange on Twitter, claiming this story was yet another extension of the conspiracy against him — “a coordinated one two punch designed to ruin my life and KO Barstool once and for all.” I quickly received hundreds of messages from his followers on Twitter, Instagram, and even LinkedIn, where one Stoolie, as Barstool fans self-identify, called me a “fuckin tool.” My agent, whose email address Portnoy retweeted a screenshot of, got a message signed by “Adolf Hitler, CEO of Bofa Deez Nuts.” Another Stoolie left a comment on Portnoy’s Instagram with the home address of one of my family members.

It was easier after all this to understand why it had been so difficult to get anyone to talk about Portnoy or Barstool at all. Some employees had signed nondisclosure agreements, and many more were just uninterested in the online harassment leveled against pretty much anyone who upsets Portnoy. Even people who liked Barstool and had admiring things to say told me they wouldn’t do so in public; Portnoy’s blustering internet presence had created such a toxic swirl around him that they were worried saying the wrong thing could make them the victim of a scary pile-on. “There’s nobody you want to be in a mess with less than Dave and Barstool,” one former employee told me.

One place where Portnoy’s fans were happy to talk was in the crowd at a live taping of the Barstool College Football Show, which Portnoy was hosting in Chicago on the last Saturday in September. “I need Portnoy,” a young man holding a sign that read I PUKED LAST NIGHT yelled at a tour bus with Portnoy’s face pasted on the side. The bus was in a parking lot just north of Soldier Field, where the Notre Dame Fighting Irish and Wisconsin Badgers were about to play. “Saturdays Are for the Boys,” as the Barstool catchphrase goes, and on this morning, the boys were carrying plastic bags filled with beer cans and ice and downing nips of premade Barstool-branded cocktails consisting of vodka and pink lemonade. During the show, Barstool was planning to raffle off $15,000 in unidentified crypto-currency to someone in the crowd — a sign of the company’s grip on a particular Zeitgeist. The kid who puked last night was wearing a shirt that read PORTNOY MUSK 2024.

When Portnoy emerged from the bus, he was wearing white Common Projects sneakers and a Hawaiian shirt and was accompanied by his 26-year-old model girlfriend. For such an incendiary personality, Portnoy, who is now 44, is a relatively unassuming presence. He stands “five-ten and a half when I’m feeling good,” and while stopping for an endless string of selfies with undergrads on his way to the Barstool stage, he looked like the much older brother of your college roommate, back on campus and down to bring the beer. Portnoy’s goal, he has said, is to become rich enough “to stuff hundred-dollar bills down people’s throats Million Dollar Man style.” At last count, his net worth was around $100 million.

While Barstool has a number of popular shows and personalities that have little to do with Portnoy, he is the company’s unquestionable star. “You’re fucking amazing, man,” Nicholas Braun, who plays Cousin Greg on Succession, told Portnoy last fall when he happened upon the Barstool founder reviewing a slice on Houston Street. “Wow, this is crazy. I’m nervous to talk to you.”

Reviewing local pizza joints in Brooklyn in September 2021. Photo: Barstool Sports / Youtube

Portnoy comes by his Everybro bona fides honestly. He grew up in Swampscott, Massachusetts, a suburb of Boston. His family is Jewish, and his father worked as a lawyer while Portnoy hung out with a crew of high-achieving athletes. (The group included Todd McShay, who is a prominent ESPN personality, as well as executives at Major League Baseball and Tottenham Hotspur, every Brooklynite’s favorite soccer team.) His friends remember him as funny and loyal, while other classmates told me he didn’t particularly stand out in Swampscott. “There are a LOT of Dave Portnoys there,” one classmate told me over email. “It’s sort of surprising that out of all of them he became the King of the Dipshits.”

After graduating from the University of Michigan and spending a few years in sales, Portnoy launched Barstool in 2003 as a free subway newspaper kick-started by $25,000 from his parents. As the origin story goes, Portnoy took a trip to Las Vegas and met a few people from online casinos that needed places to advertise. Portnoy’s plan was to create a newspaper that catered to the casinos by catering to guys like him. “The people at Barstool Sports are a bunch of average Joes, who like most guys love sports, gambling, golfing and chasing short skirts,” he wrote in Barstool’s first issue.

The Boston sports scene had recently given rise to Bill Simmons, who emerged as the voice of the common fan in contrast to the stuffy authority emanating from the Boston Globe. Portnoy knew his writing couldn’t match Simmons’s, but he also knew the common fan wasn’t really interested in glittering prose or X’s and O’s. Barstool filled its pages with irreverent columns about the local teams (“Hungover Thoughts From Titletown”) and the everyday problems of being a man in Boston (“Getting Married: A Stoolie’s Survival Guide”). The paper only started to take off, in Portnoy’s telling, when he began printing a photo on each cover of a hot Boston girl — a “smokeshow” in Barstool parlance.

The newspaper naturally evolved into a website, designed for free by a Stoolie who was moving to New York and wanted to keep reading. (He went on to become the first head of engineering at, of all places, Business Insider.) The site was devoted to any content that might be mildly diverting to a guy stuck at a boring desk job: the same kind of snarky news riffs that built the blogosphere of the aughts along with features such as “Guess That Ass,” with a photo cropped around a female celebrity’s buttocks, and “Guess That Rack,” which — well, you get the idea. Portnoy recently described early Barstool to Tucker Carlson as “a localized Maxim” for “young middle-class white guys who like sports.”

Serving sports fans something other than sports wasn’t a new idea. Sports Illustrated had been publishing its “Swimsuit Issue” since 1964. But building a modern media business on “sports-slash-smut,” as Portnoy defined Barstool at the time, required a certain amount of shamelessness and risk. In 2011, he published a paparazzi photo of Tom Brady’s naked toddler under the headline “Check Out the Howitzer on Brady’s Kid.” Howard Stern invited Portnoy on his show to chastise him, and some of Barstool’s existing advertisers got nervous. According to episode five of a 15-part Barstool-produced documentary series that covers many of the company’s controversies — it’s six hours and 21 minutes long — Coors Light asked Portnoy not to talk about children under 12. Portnoy says he only agreed not to talk about the penises of kids under 12.

By this point, Portnoy and his writers were no longer cracking jokes exclusively for people who would pick up a newspaper with a college girl in a bikini on the cover. They were getting into spats on Twitter, filming themselves busting one another’s balls for YouTube, and discovering the peril and potential profit that could accrue to anyone willing to push boundaries online. In 2012, a group of students at Northeastern University in Boston started a campaign called “Knockout Barstool” that accused the company of various sins: perpetuating rape culture, embracing misogyny, and throwing wildly successful and debaucherous parties for college students at which people were getting drunk and bad things seemed liable to happen. The protesters cited blogs Portnoy had written, most infamously one that referenced a trial in Australia in which a judge had acquitted a man on the belief that it was impossible to remove a woman’s tight jeans without her consent. “Even though I never condone rape, if you’re a size 6 and you’re wearing skinny jeans you kind of deserve to be raped right?” Portnoy wrote in 2010. “It’s almost like this guy had no choice but to teach her a lesson.” When the protests picked up, Portnoy leaned in. “Just to make friends with the feminists I’d like to reiterate that we don’t condone rape of any kind at our Blackout Parties,” he wrote, referencing a party tour Barstool was hosting. “However if a chick passes out that’s a gray area though.” There was plenty of chuckling in the comments section. “Rape??” one Stoolie asked. “I have always called it surprise sex.”

On the night of a Blackout Party at Northeastern, the Knockout Barstool group held a protest. Portnoy decided to show up. “We’re driving over to a mass protest about me,” he told a Barstool camera that was trailing him. “I’m changing the world.” Portnoy stood in front of the crowd and repeated his position: His rape jokes were just jokes. At one point, a female student got into Portnoy’s face while he stood in a North Face jacket and a beanie and responded to her accusations with something between a shrug and a smirk — an expression captured by a photographer that became a Stoolie avatar of Portnoy’s indifference to giving a shit about anyone else’s feelings. “Our fans liked that we didn’t back down,” Portnoy said later. “They realized that I was on their side.” When the protesters arrived at the party venue that night, they were shouted down by Barstool fans chanting the company war cry: “Viva la Stool!”

By this point, Portnoy had already adopted his El Presidente alter ego: a hypermasculine big boss ruling over his mini-empire with a comically iron fist. El Presidente was a little bit Vince McMahon, a little bit Tucker Max, and a little bit Apprentice-era Donald Trump. His blogging was often vitriolic, and he didn’t hesitate to yell at employees on-camera. According to many people who know Portnoy, El Presidente is an authentic expression of his personality, only heightened. “It’s his personality times a thousand,” said someone who has known Portnoy since the early days of Barstool. “He was always picking fights.”

More than anything else, Portnoy seemed to thrive off accumulating enemies: worthless interns, feminists, the entire staff of Deadspin. Sports fandom has always been fueled by the fact that hating a rival team gives people something silly to get worked up about, and Portnoy recognized early on that there was no territory to be gained online by playing it neutral. In whatever online battle emerged, the Stoolies backed up Portnoy as if he were their home team’s quarterback; after an article accused Barstool of using “social media as a weapon,” Barstool printed shirts that read, “WE WEAPONIZE SOCIAL MEDIA.” In 2015, Portnoy waged an unceasing war against the National Football League over its ongoing Deflategate investigation into Brady and the New England Patriots, at one point handcuffing himself and three Barstool employees together in the lobby of the NFL headquarters. It was an absurd stunt that matched an absurd situation far better than more self-serious commentary from sports broadcasters about the integrity of the game. When Portnoy was arrested, he used his one phone call from jail to make sure Barstool had FREE BRADY shirts in stock and ready to sell.

Interviewing President Trump in the Rose Garden in July 2020. Photo: Barstool Sports / Youtube

By the mid-2010s, Barstool was profitable, but the company’s revenue had plateaued at a few million dollars a year. Portnoy had canceled the parties, which he said were more of a headache and a potential liability than they were worth. Some advertisers remained wary. Portnoy seemed to have found his ceiling: the King of the Massholes selling T-shirts to other Massholes.

Then, in 2016, Barstool got a boost from an unlikely source. The Chernin Group, an investment firm run by Peter Chernin, the former president and COO of News Corp., was on the hunt for small media companies that were good at building an audience and bad at making money. Mike Kerns, one of Chernin’s partners, happened to be a Stoolie, and he persuaded Portnoy to sell a majority stake in Barstool at a $12.5 million valuation. Chernin is a Democrat megadonor, and a spokesperson said he was unaware of Portnoy’s politics prior to the deal. (Portnoy endorsed Trump’s presidential candidacy in 2015 by saying, “I don’t care if he’s a joke. I don’t care if he’s racist. I don’t care if he’s sexist … I love the fact he says shit nobody else will say.”) Chernin seemed to find Portnoy’s eagerness for controversy to be a welcome shift, or at least a potentially profitable one. “Not only were we comfortable with edgy content,” Chernin said in the Barstool documentary, “I viewed it as being really important and something to encourage and protect.”

With the Chernin money in hand, Portnoy moved Barstool to New York in 2016. The hope was to take Barstool mainstream, much like Vice had taken on investors while attempting to soften its crass edges just enough to achieve broad appeal without alienating fans. In 2017, Kerns admitted that Barstool was a risk but said “younger folks within agencies and brands get Barstool and recognize the world is increasingly taking itself less seriously.”

The early results were fitful. A short run on Comedy Central netted the same ratings as reruns of Futurama. A college-football show on Facebook lasted just six episodes. Advertisers would agree to a deal only to get cold feet when a fresh controversy emerged: Portnoy defending Harvey Weinstein — he didn’t see anything wrong in offering a job in exchange for sex — or telling a female employee during a podcast taping that her on-camera career would be over at the age of 25.

The biggest blowup came at the end of 2017, when ESPN agreed to air a televised version of Pardon My Take, Barstool’s wildly popular football podcast. The show is hosted by Dan Katz and Eric Sollenberger, who go by Big Cat and PFT Commenter, respectively. They are the most popular Barstool personalities beyond Portnoy and the ones that even people who object to Portnoy or Barstool will admit to liking. For ESPN, the show was a chance to hit demographics the network was struggling to reach: young people cutting the cord and anyone turned off by a perceived activist tilt as Colin Kaepernick’s national-anthem protest took over the sports world.

But as the show premiered, multiple ESPN personalities publicly and privately objected to the network’s association with Barstool. Sam Ponder, a female ESPN reporter, tweeted screenshots of a blog post from 2014 in which Portnoy had written that Ponder’s primary job requirement was to “make men hard.” Others resurfaced a clip in which Portnoy had called Ponder a “fucking slut” who should stop talking about being a working mom and instead “sex it up and be slutty.” Portnoy had also called another ESPN reporter a “cunt.” The show was canceled after a single episode.

Outside of Barstool, the incident seemed like a major blow for the company. But the internal concern was relatively muted, multiple people told me. The controversy was good for traffic, and Barstool was unchastened: A week later, an employee tweeted that a female ESPN reporter had “cankles.” Pretty much everyone at Barstool came to agree that the company was better off going it alone rather than trying to partner with mainstream outlets. Barstool would find out what might have happened if Vice had never traded in punk rock and cocaine for a nightly slot on HBO.

The give-no-shits ethos wasn’t for everyone. The most common explanation I heard from people who had left the company was that they had simply grown up. But the cultural winds were blowing in Barstool’s favor. It was an uncomfortable reality for many in sports media that even if they believed that, say, Kaepernick’s protest was righteous, many fans didn’t and had little interest in being convinced otherwise. Barstool appeared to be a welcome harbor for sports fans, who suddenly felt poorly served. “I prefer Dave Portnoy to ESPN,” Lindsay Wallace, a 53-year-old contractor wearing a hat with the logo of Barstool’s golf podcast, Fore Play, told me at the Barstool event in Chicago. “He laughs in the face of everything woke.” In The New York Times Magazine in 2017, Jay Caspian Kang noted that, for a certain kind of sports fan, “Barstool is their safe space.” The safe-space business was a good one: By 2019, Barstool was bringing in almost $100 million in revenue.

Multiple political commentators have suggested recently that we are witnessing the rise of the “Barstool conservative” — a largely male and white demographic that feels put-upon by the progressive strictures of modern society and enlivened by a rich, successful guy thumbing his nose at all that. Last year, in the wake of George Floyd’s murder, Portnoy was criticized for rapping the N-word in a Barstool video from several years before — even after his employees told him it might be a bad idea — and for joking that he thought Kaepernick looked “like a bin Laden.” Portnoy initially refused to back down yet again and declared himself “uncancelable.” (He eventually apologized only after some of his employees told him his comments were offensive; Portnoy said he wouldn’t make comments like that again.) A few weeks later, President Trump granted Portnoy an exclusive interview at the White House that the Trump campaign aired as an ad.

Portnoy insists he and Barstool are apolitical. Critical race theory is not regularly discussed on Barstool podcasts, and plenty of progressives both consume and produce the company’s content. (One of Barstool’s earliest writers went on to become Ayanna Pressley’s chief of staff when she was a Boston city-council member.) If Barstool and Portnoy can be said to have a cohesive political ideology, it is probably some kind of libertarianism mixed heavily with indifference, an appetite for casual cruelty, and a desire to dunk on the libs not for political points but for the LOLs and the clicks. Erika Nardini, a former AOL executive who has served as Barstool’s CEO since the Chernin investment — she also sits on the board of World Wrestling Entertainment — has willingly acted as a heat shield for the accusations of misogyny leveled against Barstool. She hosts a podcast called Token CEO.

Jumping into day-trading in May 2020. Photo: Screenshot from Dave Portnoy’s Twitter from CNBC broadcast

When I spoke to other executives in the media about Barstool, many of them didn’t care for Portnoy or for most of the company’s content. But they all admired the business and the remarkably devoted, if volatile, audience he had developed. They were most envious of Barstool’s ability to seemingly pivot on a dime, which came in handy when the world changed overnight. “Don’t care about the people dying, don’t care about a lot of things,” Portnoy said in March 2020. “I care about my wallet.” With lockdown setting in and no sports to bet on, Portnoy put $3 million into an E*trade account and announced he would be livestreaming himself doing the next best thing: day-trading stocks. Portnoy admitted to having no idea what he was doing. He bought John Deere because he saw a deer. He bought some bitcoin and some shitcoins. Hundreds of thousands of similarly bored people started watching Davey Day Trader Global, having realized that the stock market bore little relationship to the economic situation around them. Portnoy’s entertaining ignorance, alongside some impressive returns, seemed just as worth watching as any of the experts on CNBC, who didn’t seem capable of explaining what was going on either.

Barstool was wounded by the pandemic like every media company, but Portnoy has had a way of turning failures into victories. In 2018, the company acquired Call Her Daddy, a raunchy sex podcast co-hosted by Alex Cooper and Sofia Franklyn that became one of the most popular shows in the world until going inexplicably dark shortly after the pandemic hit. A few weeks later, Portnoy commandeered the Call Her Daddy podcast feed and delivered a 30-minute solo address in which he accused the show’s hosts of treachery while renegotiating their contracts. Franklyn never came back to Barstool, while Cooper returned for a year before taking Call Her Daddy to Spotify, where she is being paid $60 million over three years. Portnoy later claimed the departure didn’t upset him: He said Barstool got to keep a cut of the show’s merch sales.

The pandemic also introduced new opportunities to stoke controversy. In May 2020, Portnoy delivered a pair of speeches in which he called Anthony Fauci “one of the great criminals of our civilization.” (On a whiteboard behind his Davey Day Trader Global desk, he wrote FUCK THAT MIDGET ANTHONY FAUCHI.) Portnoy was speaking out in defense of small-business owners who were losing their livelihoods in the face of government lockdowns; Turning Points, the conservative PAC, put Portnoy’s face on a flyer. A few months later, Portnoy launched the Barstool Fund, which has raised more than $40 million for small businesses — another move that few other media companies had the agility or the fan base to pull off. (The Times’ Neediest Cases Fund, for example, raised $9 million last year.) His rant brought in a fresh burst of attention and newfound praise. “Well said!” Elon Musk tweeted at Portnoy. The Barstool merch store immediately started selling the PORTNOY MUSK 2024 shirts.

The most significant pivot Barstool and Portnoy had made took place just before the pandemic arrived. In January 2020, Penn National Gaming acquired roughly a third of Barstool at a valuation of $450 million — a 36-fold increase over the Chernin valuation four years earlier. In 2018, the -Supreme Court had overturned a federal ban on sports gambling, which launched a gold rush. The adoption of legalized sports gambling was left to each state. In New Jersey, which was among the first to open up, gamblers bet more than a billion dollars in October, almost all of it through their smartphones.

For Penn, the Barstool acquisition offered instant name recognition for its app — Barstool Sportsbook — as it faced off with big brands like DraftKings, FanDuel, and MGM, which were spending lavishly to take over the market: One estimate projected that sports-betting companies will spend as much as a billion dollars on ads this NFL season. (Vox Media, which owns New York Magazine, has a content-and-advertising partnership with DraftKings.) Penn’s plan was to avoid burning cash on ads by using Portnoy and the company’s other personalities as a street team in each state where the Barstool Sportsbook launched. “We are the marketing,” Portnoy has said.

Penn knew about Portnoy’s history of controversy, but the risk of making him the very loud mouthpiece of a $9 billion publicly traded company — he constantly pushed Penn stock during his Davey Day Trader Global broadcasts — was apparently deemed worth the potential reward. The terms of Penn’s investment in Barstool require Portnoy “to go balls-to-the-wall,” as he has put it, for the next five years, and he has spent much of this fall visiting the ten states where the Barstool Sportsbook is live, reviewing local pizza shops and throwing parties to drum up potential gambling customers.

A day after the college-football show at Soldier Field in September, Barstool was holding an event at a Penn casino in Aurora, a suburb west of downtown Chicago. Illinois requires residents to sign up for betting apps at a physical casino, and getting Chicagoans to make the 45-minute drive to Aurora had been difficult, so Penn had asked Portnoy, Big Cat, and several other Barstool personalities to spend an afternoon watching a Bears game in the parking lot with fans. When I arrived, an extremely long line that I assumed led to a beer vendor was actually a queue for selfies with Portnoy. He wore a shirt that read GUARANTEED NUMBIES, in reference to the fact that in Portnoy’s world — page views, stock-market returns, gambling winnings — everything was always going up.

The crowd was mostly male, decked out in a mixture of Bears and Barstool gear, and generally psyched to be there. Plenty of people there were Barstool loyalists. “If I’m gonna lose money, I’ll lose it to them,” said Troy Baebler, a sales rep from Chicago, who was wearing a T-shirt with the infamous photo of Portnoy from the Boston protest. But others told me their Stoolie affiliation didn’t necessarily mean they were going to gamble exclusively with the company. One 25-year-old from Skokie who identifies as a Stoolie told me he gambles as his full-time job — he said he bets $100,000 on football every weekend — but that he uses pretty much all of the new mobile sportsbooks, depending on whoever is offering the best deal. FanDuel, DraftKings, and MGM have collectively gobbled up more than two-thirds of the mobile-betting business, leaving Barstool and Penn among a second tier of competitors with a single-digit percentage share of the market. Shortly after the sexual-misconduct allegations against Portnoy were published, Penn suffered another blow when the company was denied a license to operate in New York, which is expected to launch sports gambling in time for the Super Bowl. “They’re coming from all angles,” Portnoy said on Davey Day Trader Global, describing what he called another “hit piece” published by the New York Post, with anonymous sources claiming Barstool had been kept out of one of the winning bids because Portnoy’s reputation was seen as a “risk.”

Hosting one of his sports-betting shows on YouTube in November 2021. Photo: Barstool Sports / Youtube

The day after Portnoy’s “Emergency Press Conference,” Jay Snowden, the CEO of Penn, hosted a conference call with non-Barstool employees at Penn. More than 300 people were on the Microsoft Teams call at 4 p.m. on Friday, November 12. According to multiple people on the call, Snowden more or less defended Portnoy, dismissing the Business Insider story as sensational and suggesting that other media companies like to take shots at Portnoy because they are jealous of his success. The furthest he went to acknowledge the severity of the allegations was to say that the story had been “emotional” to read, and he encouraged his employees to watch Portnoy’s press-conference response. Penn’s head of HR asked Snowden a few questions, and the meeting ended. During the call, Snowden wore a Barstool quarter-zip sweatshirt. (Penn did not respond to a request for comment.)

So far, Portnoy’s supporters have continued to stick by him. Walmart was still selling Portnoy’s pizza, and a college-football bowl game in Arizona that signed Barstool as its title sponsor this past summer would only say it was “closely monitoring” the situation. (The local county government objected to the partnership when it was announced and cut $40,000 of funding to the game.) If more unseemly stories about him come out, as Portnoy himself suggested on his podcast might happen, Penn might have to reassess. But for now, the company doesn’t seem to see much business choice beyond sticking by Portnoy. Penn has no brand in the sports-gambling race without Barstool, and Barstool isn’t Barstool without Portnoy.

Portnoy, meanwhile, has been working to keep his coalition together. Donald Trump Jr. and J. D. Vance tweeted their support, and Portnoy took his grievances to Fox News multiple times. But that only builds the brand in one direction, and he seems to know that his revenge campaign wasn’t necessarily going to land with everyone he was trying to reach. Like the audience of BFFs, the weekly podcast he started co-hosting last year with 19-year-old TikTok star Josh Richards, in which Portnoy largely plays the befuddled old man trying to decipher who’s who in various TikTok dramas. The show released no episode the week after the sexual-misconduct allegations, and when it returned the following week, Portnoy would only say they had skipped the episode because his co-hosts were traveling and he had been “going through shit.” Portnoy didn’t say what the shit had been, but later in the episode, he couldn’t resist noting his pleasure at the fact that his fans had started to defend him by sending pizza emoji to his enemies, “like the Swifties will leave snakes and Beyoncé people leave bees.”

He also got back to the gambling. Ten days after the Business Insider story, Portnoy spent a Sunday afternoon hanging out at the Barstool Sportsbook house in Hoboken, where he and other Barstool personalities regularly livestream themselves sitting in recliners for hours on end while they gamble on sports. Barstool would only hit its projection of $200 million in revenue this year if Portnoy kept up his appearances, and the central concern on the stream today wasn’t the controversy swirling around him but a $500,000 bet Portnoy had placed on the Green Bay Packers. There wasn’t much sense from Portnoy that he was going to dramatically change his approach to work or life anytime soon. As for the Packers, they started off slow, leaving Portnoy’s bet in doubt well into the fourth quarter. But Green Bay eventually took control and won in a blowout. Portnoy walked away with half a million dollars.

*This story has been updated to reflect that Aurora is west of downtown Chicago.

The Dave Portnoy Playbook