Barstool Sports Is Betting Big on Philly. But Are We the City They Think We Are?

Crude, lewd Barstool founder Dave Portnoy thought this was the perfect city from which to launch his new sports gambling app. Maybe once upon a time, it was.

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Barstool Sports founder Dave Portnoy. Photograph by Tom Briglia/Getty Images

It’s a rainy Friday afternoon in Havertown, and a guy from Boston is about to try a slice of pizza.

Dave Portnoy, founder, president and face of Barstool Sports, emerges from Sam’s Boardwalk Style Pizza with a large pie in hand, wearing a Barstool cap and a black hoodie bearing what looks like the Eagles logo but upon closer inspection actually says “Scumbags.” Portnoy delivers his catchphrase — “One bite, everyone knows the rules” — and stuffs a piece in his yapper. He did the same thing a half hour ago at Pica’s Restaurant in Upper Darby. No one paid much attention to him there, probably because most folks in its queue appeared to be north of 40 years old.

Sam’s is a different scene completely. “They’re very excited to see me,” Portnoy says into a camera, and seconds later, the Sam’s crew emerges to watch his critique, which is part food review and part Friars Club roast. One teen staffer seems so starstruck that he won’t look directly at El Presidente, as the 43-year-old is known to his fans. Portnoy sarcastically notes the “super-romantic outdoor seating” along the curb in front of Sam’s and glances at the bar next door. “I bet people get fucked up at the Jug’s Inn,” he says in what’s still a remarkably thick Boston accent. After noting that Delco is only the second locality that’s threatened him with physical harm if his ratings aren’t high enough (never change, Delco), Portnoy gives Sam’s a fine-but-don’t-go-out-of-your-way-to-try-this 7.3.

After he leaves for the next pizza shop, a young redheaded woman who works the counter at Sam’s remains breathless. “Oh my God,” she says. “I’m still shaking. I can’t believe that just happened. He walked in and I was like, That’s Dave Portnoy.”

If you’re wondering what pizza-tasting has to do with Barstool Sports, it’s a fair question that deserves an answer. Barstool, born in Boston and now based in New York, began as a four-page newspaper; since then, it’s grown from a one-man blog to a full-blown media empire. Today, the Barstool universe includes more than 100 million total followers across its social media platforms (among them “I Can’t Even,” an Instagram for cute pet videos), 40 podcasts (including a business-themed show co-hosted by Alex Rodriguez, with a J-Lo cameo), Barstool coverage individually tailored to nearly every major college, a SiriusXM channel, merchandise, a vodka brand, and, along with Portnoy’s day-trading channel, his “One Bite” pizza reviews, which have a dedicated app and more than 330,000 YouTube subscribers. Similar to Vice in its scope and outside-the-mainstream attitude, Barstool is also a lifestyle brand — one that’s squarely aimed at the advertising grail of 18-to-34-year-old men. With revenue in 2019 just south of $100 million, it’s an undeniable success. “We make charismatic content,” Barstool’s CEO, Erika Nardini, says with typical Barstool swagger. “We’re the fastest-growing on the fastest-growing, not on dying platforms like cable.”

Now, in the realization of Portnoy’s longtime business fantasy, Barstool Sports has entered the gambling arena with help from an unusual partner: Wyomissing-based casino and racetrack operator Penn National Gaming, Inc. Barstool and Penn National launched their gambling app, Barstool Sportsbook, in Pennsylvania in September. Since by law you can only use the app if you’re physically in the state, Portnoy and a cast of Barstool characters moved into an Old City townhouse to livestream games, place wagers and bust balls. At first glance, it was an ironic moment for Portnoy: Die-hard Bah-ston fan and Patriots lover needs Philly to get even richer and make his dream of running a sports gambling empire come true.

But the full story isn’t so neat and tidy. There’s Portnoy the businessman, who’s built a company valued at $450 million from nothing and was once named by the Forward as one of the “Internet’s Biggest Jewish Stars.” And there’s El Presidente, who’s like a poor man’s Howard Stern in the ’90s, which is not a great fit for 2020. He is, though, a man for our time. There’s something eerily Trumpian about Portnoy and, in turn, about what Barstool Sports represents. If you’re familiar with the brand at all, it’s probably for its aggregation of chuckle-­worthy videos like the PornHub logo appearing on CNN’s election coverage or a FedEx guy’s flatulence caught on a Nest cam. The flip side of that content coin, however, has drawn the ire of everyone from ESPN to Alexandria Ocasio-Cortez. Barstool goes far beyond funny-dumb in appealing to the male id. It traffics in everything from misogyny to racism to outright violent, abusive language directed at women. It also speaks to a growing divide among Philly sports fans — one that, in turn, reflects the greater chasm in America right now.

Barstool goes far beyond funny-dumb in appealing to the male id. It also speaks to a growing divide among Philly sports fans — one that, in turn, reflects the greater chasm in America right now.

As Portnoy tells me, “Philadelphia is a very Barstool city.” Seeing as Barstool is a lot more than sports, that statement suggests that we as a city accept, even embrace, Barstool’s ugly side — that we’re cool with an N-word here and a rape joke there and a history of online attacks aimed at women. But Philadelphia got rid of Donald Trump. We trashed the Frank Rizzo statue. Wing Bowl is long gone. Are we really a Barstool town? And if so, do we want to be anymore?

Are you a Stoolie?” That’s the first question I was asked by a PR person when I took my initial peek into the deep rabbit hole of everything Barstool encompasses. I’d only casually followed it on social media and knew of Portnoy’s more notorious stunts — making t-shirts featuring NFL commissioner Roger Goodell’s face adorned with a clown nose, getting physically removed from Super Bowl LIII in 2019 for using a fake media credential, being denied his prize after casting a winning $250,000 bid for a charity evening with Goodell. (He really hates Goodell.)

I started to get a better sense of what Stoolie life means at the Barstool Sportsbook house on Arch Street. Before I joined Portnoy for his pizza reviews in Delco, he gave me a tour of the three-story pad. While no one actually lives here — Portnoy himself bounces from a hotel near Rittenhouse Square to his home in New York — in the fall it came alive on weekends for football. The ­second-floor den is the focal point, with three black couches accented by a Hooters pillow beneath Barstool signs with slogans like “It’s Only Money” and a wall of six huge flat-screen TVs.

This Dave Portnoy isn’t the high-­volume guy in the videos and on the podcasts. As he sinks into the center of a couch, he vaguely resembles a bearded Mark Zuckerberg if you dialed the Facebook founder’s coding ability down to zero and amped the bro factor way up — that “Scumbags” hoodie, skinny-ish jeans, lime green socks, white kicks. (No mask, of course.) Portnoy explains that the sweatshirt and his Pats-loving grudge against Philadelphia is shtick, which his Stoolies understand. “Our fans, they get that it’s a give-and-take,” he says, acknowledging his status as a “Masshole.” “I like the city a lot … it’s an East Coast vibe, sarcastic, cutting. I think people are excited that we’re here. If we walk outside, every time, I get, ‘Welcome to Philly.’”

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Dave Portnoy at a Barstool pizza-tasting. Photograph by Tom Briglia/Getty Images

Portnoy’s aim wasn’t to become a celebrity when he launched Barstool in Boston back in 2003. He liked sports, gambling, and the idea of working for himself, so he started printing a broadsheet paper and taking ads from offshore betting sites. After a couple years of handing out copies at T stations every morning, Portnoy saw Barstool take off when he leaned into low-hanging humor and put photos of scantily clad models on his covers. Much as the 700 Level at the Vet was shorthand for rabid Philly fandom, Barstool became Boston’s insiders’ sports club.

Credit Portnoy for two qualities that led to Barstool’s wild growth — a willingness to try anything, and an appetite for risk. Barstool expanded to regional coverage in New York and Philly and stretched beyond sports, with features like “Smokeshow of the Day” babe pics, a “Barstool Blackout Tour” that barnstormed college towns with all-night EDM dance bacchanals, and catchphrases like “Saturdays are for the boys,” which became so ubiquitous that the official Flyers Twitter and athletes from Rob Gronkowski to Michael Phelps used it on social media.

Barstool saw its majority stake purchased in 2016 for a reported $10 million by a venture capital firm and moved its offices to New York’s Flatiron district. With an accomplished CEO in Nardini to handle the business side — and provide a respectable female face for the company — Portnoy kept cranking out content. Today, Barstool has some 250 employees, and among the many pro athletes who are fans is Phillies star Bryce Harper, who’s on the official “Team Portnoy” roster of El Presidente’s celebrity pals.

Portnoy saw his next big play in 2018, when the Supreme Court paved the way for legalized sports gambling outside Nevada. Rather than team up with an established online leader like FanDuel or DraftKings, Portnoy found the perfect foam-party dance partner in Penn National Gaming. Penn CEO Jay Snowden says of his first sit-down with Portnoy and Nardini, “We knew what we needed to go after with this app, and they had it — the brand and the audience. What they needed was a partner who understood the gaming industry.”

Most importantly for Portnoy, Penn wanted to let Barstool take the lead; the gambling company operates the app, but the user experience is all Barstool branding. Portnoy pushed to launch in Pennsylvania to capitalize on the state’s $463 million-and-growing online wager market and Barstool’s robust following in Philadelphia. In a win-win for Sportsbook and Portnoy’s temporary adopted town, he initiated a promo to raise money for the struggling Reading Terminal Market that ultimately scored $250,000 in donations for the market and roughly 1,500 new customers for the app.

The other highlight of Sportsbook’s brief history is a video of Portnoy watching as the Chicago Bears bench their starting quarterback in favor of Nick Foles. “Everything I’ve got on fuckin’ Big Dick Nick,” he says as he drops $20,000 on the Bears. To date, that video has been viewed more than 277,000 times; it was followed by one of Portnoy rejoicing in the face of a very dejected dude when Chicago took the lead. Like a certain president, El Pres loves nothing more than winning and values the time-honored American tradition of reveling in someone else’s defeat. “People like watching people die on the couch,” Portnoy tells me. “They like heartbreak. If your team loses in the end, people like watching the fans of those teams die in real time.”

Barstool counts a few born-and-bred Philly guys among the personalities who frequent the Sportsbook house. “Dave has created this environment where the college living room is a viable workspace,” says Adam Ferrone, a.k.a. Rone, who appears in the first Bears video. The 32-year-old Penn State grad and Delco native is one of Barstool’s creative fire hoses, generating a seemingly endless stream of material like man-on-the-street interviews conducted with an exaggerated Philly accent under the nom de mic of “Angelo Paolantonio.” He describes working for Barstool as the best job he’s ever had, thanks to the freedom Portnoy gives him: “I just want to keep churning out content. It’s sensory overload, a 24-hour-a-day job.” As for why Barstool feels so at home in Philly, Ferrone says, “There’s some grit about Barstool. Someone from Philly doesn’t necessarily give a fuck about what you think. And there’s a lot of that in Dave as well.”

In Barstool circles, the joke is that articles like this one always mention the controversies. Most of those controversies involve Dave Portnoy, who used to be a blogger and now is a multi-channel content creator and internet personality. He’s always seen himself as a comedian, and the site, and specifically Portnoy, has long trafficked in the kind of humor that was once called “locker room” and more recently “presidential.” In a nod to Ben Roethlisberger, who’d been accused of rape, a Barstool t-shirt in the late aughts featured the QB’s jersey number and the motto “Throwing picks, assaulting chicks.” (Roethlisberger was never criminally charged.) When asked about an article from 2010 suggesting size-six women “kind of deserve to be raped” for wearing skinny jeans, Portnoy told the Huffington Post his intent was to mock skinny jeans, and that rape jokes are “such a small fraction of what we do.” (Portnoy also defended posting a naked pic of Tom Brady’s then-two-year-old son by saying critics who feared it would become fodder for pedophiles “have never been on the internet.”)

The man has a history of turning his Sauron-like gaze on critics of Barstool. A long-standing beef with ESPN Sunday NFL Countdown host Sam Ponder began when she took offense to a Barstool blog opining that her primary job was to “make men hard.” He doubled down in a podcast, saying no one wanted to see Ponder’s child on camera and calling her a “fucking slut.” Like the jeans comment, he later said it was all sarcastic — Of course a mom isn’t a slut, people! Ponder didn’t buy it. She complained publicly when ESPN signed Barstool for a TV show, and other ESPN staffers did so in private, according to reports. The show was canceled after one episode because the network couldn’t separate the program from “the Barstool site and its content,” ESPN’s then-president said.

What always follows any criticism of Portnoy’s misbehavior is the wrath of a passionate band of Stoolies who defend him and their beloved brand via social media and online comments. As detailed in an HBO Real Sports with Bryant Gumbel piece by Soledad O’Brien, former Deadspin writer Laura Wagner — a frequent target of ­Barstool — was subjected to vicious tweets from Stoolies that included one calling her a “miserable cunt.” Portnoy penned a mock article under her byline for Barstool, and sexual comments aimed at Wagner are still visible on Barstool’s site.

Just before the Daily Beast posted a detailed inventory of the controversies, Portnoy posted the cell number of the reporter, Robert Silverman, on Twitter — accidentally, he claims, but the damage was done, and the Barstool troll army mobilized. “That was a bad four days of getting text messages and FaceTime requests from the Stoolies,” says Silverman. “But it pales in comparison to what a woman on the internet who says something critical about Barstool Sports has to deal with.” HBO’s O’Brien reached out to 15 women who’d been targeted by Barstool and its fans, and none were willing to speak on camera for fear of enraging the Stoolies again.

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Dave Portnoy yukking it up with President Trump last year. Photograph by Mallory Blount

Portnoy — who considers himself apolitical and says he’s not registered to vote — earned national buzz by interviewing Donald Trump at the White House in July. It was a natural pairing, since both men follow an identical playbook: Court controversy, never apologize, and play victim to a politically correct culture run amok. Ponder confronted Portnoy recently in a New York restaurant, a meeting he gleefully recounted in a podcast. (“She came out swinging,” he said. “I respect that.”) Asked about Wagner, Portnoy says she started it by writing about his marriage — he’s separated from his wife — and calling him “sociopathic.” He’s certain the number of women Real Sports claimed wouldn’t discuss him is a lie and says he believes O’Brien actually liked him but was pushed by host Bryant Gumbel to call him “vile.” (In response to a request for comment from O’Brien, an HBO spokesperson said, “We stand by our reporter and our reporting.”) Asked to comment for this story, Wagner, who now writes for Vice, gave her stock reply: “I can’t believe this guy is still talking about me.”

Portnoy’s offensive discourse isn’t solely aimed at women. In tweets and a since-deleted piece, he said protesters against police brutality who blocked a Boston highway in 2015 should be killed. Old Barstool videos surfaced last year of him using the N-word while reciting rap lyrics and musing that Colin Kaepernick looks like “an ISIS guy.” Such was the reckoning within Barstool over Portnoy’s comments that one personality quit, and its 2Biggs podcast devoted an 80-minute episode to giving seven minority Barstool talents time to explore their conflicted feelings about the company and Portnoy. (In true Barstool fashion, the episode’s title included both the phrase “Now It’s Going to Get Extremely Real” and its acronym, which set off more social media outrage.)

Hoping to make sense of all of this with local people close to Portnoy, I reached out to a popular former employee, Maurice “Tall Mo” Peebles, who as the first Barstool Philly beat editor was one of its few Black staffers and is now the new editor in chief of Complex. He declined an interview. Through the Phillies, “Team Portnoy” member Bryce Harper also said no thanks. Barstool PR connected me with two hugely successful Philly natives with a podcast on the Barstool network, cousins Wallace “Wallo” Peeples and Nasir “Gillie Da King” Fard, of the Million Dollaz Worth of Game show. Both said Portnoy reached out and “spoke his piece” about the racially charged videos, but they wouldn’t go into details. “We dealt with things personally,” Wallo said. “We’re not perfect — I served time. But we wouldn’t deal with him if he wasn’t a solid person.”

One unlikely critic of Portnoy is Will Leitch, founder of the trailblazing sports blog Deadspin, which in its heyday was an uncomfortable thorn in the side of establishment sports journalism. In a 2018 piece for New York titled “What Fresh Hell is Barstool Sports?,” Leitch took Portnoy to task for Barstool’s treatment of women and for allowing the Stoolies to act out. Leitch also drew a comparison between Portnoy and a co-founder of Vice who was eventually driven out of that company, in part for his “virulently intolerant” views. That founder, Gavin McInnes, has become better known for a group he started — the Proud Boys.

Calling me from Georgia two days after the November election, Leitch pauses from vote-count-watching to put Barstool into context. “It’s not like everything they do is diseased,” he says. “And not all of their readers are raging misogynist shitheads. But whenever you get in the Barstool crosshairs, it is real. And they’ve never said stop it or taken responsibility for it.”

Now that Barstool, via Sportsbook, has entered an industry that’s highly regulated, some observers wonder if we might be on the verge of a kinder, gentler Dave Portnoy era. Penn National CEO Snowden talks about certain “guardrails” they’ve established so Portnoy doesn’t break any laws while mouthing off. He may have come close to hitting one of those guardrails in October, when he made comments that appeared to suggest he runs the same Sportsbook he’s also betting on, saying of Penn National, “They answer to [Snowden], and they answer to me.”

Another off-limits topic is union-­busting. When Portnoy threatened to fire any Barstool employee interested in organizing in a series of tweets in August 2019, New York Congresswoman Alexandria Ocasio-Cortez replied to inform him he was “likely breaking the law & can be sued.” (She didn’t respond to his invitation to a debate and celebrated on Twitter when Barstool settled with the National Labor Relations Board over the incident.) “Dave has a mic and a camera in front of him 24/7,” says Snowden. “Sometimes he’s in a good mood. Sometimes he’s not. He’s learning. We’re all learning together. There are going to be some bumps in the road.” While ESPN couldn’t take the heat stoked by Barstool’s ugly side, Penn National seems confident there’s just enough separation to make the partnership work.

Portnoy describes Barstool, sans irony, as “a comedic website — in, like, a Seinfeld-esque way. Like, you know, cutting observations of society.” The closest he comes to a mea culpa in our conversations is in regard to the N-word. “Would I have sang that lyric now? No,” he tells me. “Times are very different. … I wouldn’t do it again. [But] I can’t go back and apologize for that because in that moment, it was like, what I thought a harmless — like, I was never trying to cause harm. So is it a gray area? Is it semantics? A little bit. If enough people are truly incensed, whose opinion I respect … ”

The bad-boy governor in Portnoy’s head kicks in before he says he’d ever atone for past behavior. Causing harm, he claims, “is never the goal. We’re trying to make people laugh and entertain.” But like the president he once interviewed, Portnoy knows controversy is essential to his identity; as recently as June, he declared himself “uncancellable.”

Leave it to the Sixers to turn a marketing layup opportunity into a culture-wars misfire that clangs off the rim. Upon unveiling new alternative jerseys featuring Boathouse Row, team president and Villanova alum Chris Heck coined the term “New Philadelphia” to define what the Sixers see as a city rich with “culture … education … diversity.” Which is great, except that in doing so, Heck simultaneously took swipes at “blue-collar” identity, the Flyers, and the use of the word “Philly” itself, deeming it “lazy.” After well-deserved mocking online, Heck issued the requisite apology.

There’s a kernel of truth in what he tried to express, however. Our fandom contains multitudes, and we’re seeing a fracturing in the fan base that runs deeper than the economics of who sits in which seats — ­corporate fat cats in the lower bowl, salt of the earth in the nosebleeds — at the games. With analytics seeping into every aspect of all sports, and eggheads like current Eagles general manager Howie Roseman and former Sixer GM Sam “Trust the Process” Hinkie, not the jocks, making franchise-altering decisions, a growing number of fans — largely the craft-beer-drinking hipster types — would rather take deep dives into data and debate player contracts than get shit-faced in the Jetro tailgate lot and start fights with rival fans.

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Dave Portnoy at a Buffalo Bills tailgate in 2019. Photograph by Brett Carlsen/Getty Images

But those fans don’t make up Barstool’s core audience, which is essentially young white males who think like old-timers: I want my sports free of crap like math, women without pompoms, and athletes with agendas. (It’s fitting that Portnoy has embraced the old Michael Jordan anti-activist quote that’s long haunted the Hall of Famer: “Republicans buy sneakers, too.”) Even the Sportsbook is an extension of a throwback mentality. You used to need to know a guy if you wanted some action on the Birds to beat Dallas. Now, Dave Portnoy is the guy, and he’s in your pocket. You, too, can be a degenerate gambler, kid. Like Barstool says, it’s only money, right?

When it comes to Barstool’s future, Penn National may eventually have more to say about it than Portnoy. It purchased 36 percent of the company this year and will own 51 percent in year three, with an option for full control by 2025. Early returns on the Sportsbook are trending up but mixed: At its launching in September, it was fourth in market share in Pennsylvania, but it stayed in the red that month with minus $2.8 million in net gaming revenue (perhaps not surprising, given the $2.2 million in promotional credits used to lure new users to sign up. By late October, revenues were up to $3.1 million.). It planned to launch in Michigan in late December, and Snowden aims to add at least 12 states in 2021, including New Jersey. Penn National has said its “guardrails” include “harassment or discrimination of women or minorities,” but Portnoy insists the only content restrictions he’s been given relate to gambling regulations and “tiffs with elected officials.”

Asked what’s ahead, Portnoy embodies one of his alter egos, Davey Pageviews — a man sustained by the instant gratification of modern media. “I don’t think that far in advance,” he says. “I’m not going anywhere anytime soon. At least for five years.” Which is a lifetime, considering that TikTok — the hottest platform for Barstool’s video content, with 12.3 million followers and ­counting — is barely four years old. “The world changes so fast,” he adds, “and we’ve been very good at adapting to change, but I — we’re not good at predicting it. But we’re mobile, agile, and as long as we remain that way, I think we will have a good future.”

It’s likely the Sportsbook house will shut down after the Super Bowl and Portnoy will return to New York, where he’ll watch as the app creeps into new markets across the country and think back fondly on his brief time eating pizza here. Still, there’s something uncomfortable in the realization that Philly, vis-à-vis the Sportsbook, could help catapult Barstool into another decade of success. Being a sports fan here means acknowledging both the sublime and the despicable of our history. Maybe you’re fine with booing the home team and climbing greased light poles on Broad Street. But the racism once aimed at the late Dick Allen; the thuggery that necessitated a jail at the Vet and resurfaced as recently as the Eagles/Baltimore game in October; the leering legacy of Wing Bowl; and the feeling that you still need to keep your head on a swivel and maybe think twice about bringing your wife or daughter or mom to certain games — that’s not for the boys. It’s for actual scumbags. Like the majority of Philly fans, most Barstool followers are harmless. The difference is that their leader tacitly engages in and condones behavior that has a very tangible, damaging impact. Imagine Jeff Lurie allowing morons to start brawls or shout rape jokes at the cheerleaders.

The truth is that we are both New Philadelphia and a Barstool city. We stanned hard for Joe Biden even as large swaths of Northeast and South Philly and the River Wards stayed solidly Trump. So memo to everyone hailing Portnoy as a hero on the streets of Old City: Remember what you’re also supporting when you log on to Barstool for guy-takes-Wiffle-Ball-to-the-nuts videos or to lay a few bucks on the Birds. And lest you kid yourself about whether Portnoy, chastened by justified criticism or raised stakes in a new arena, can evolve, remember when people thought Trump could become presidential once he was actually the president.

Meantime, in this moment, just as the country needs healing, let’s imagine a future of our fandom in which the analytics crowd isn’t so elitist and the 700 Level throwbacks are a bit more open-minded. Let’s, you know, reach across the aisle at the Linc and share an overpriced beer despite our differences. Sure, some people are incapable of growth. But let’s also remember one of the lessons of the 2018 Eagles championship — that sometimes this city can exceed even our wildest imaginations.

Published as “Can’t Anybody in Philly Take a *&%&%@&%$ Joke Anymore?” in the January/February 2021 issue of Philadelphia magazine.