Next week caps an eventful three weeks for Barstool Sports, the highly-popular sports and entertainment multi-media site known for its locker-room humour, eccentric personalities like Big Cat, Frank the Tank, and Mintzy, and hugely-loyal audience.
It started on Wednesday, August 9 with the surprise announcement that Penn National, the gambling company that acquired Barstool for $500 million in a two-staged transaction between 2020 and early 2023, was selling it back to its founder, Dave Portnoy, for $1.
It culminates on Wednesday, August 23 with Barstool’s twentieth-anniversary party in Boston where Portnoy started the company as a low-budget gambling newsletter that he distributed himself at subway stops across the city’s metropolitan area.
The frenetic period reflects Barstool’s inherent energy and intrepidity that remains core to its appeal two decades after its genesis. It’s spontaneous and purposeful, scrappy and endearing, successful and ordinary. Its massive popularity relies in large part on these seemingly dichotomous characteristics. Barstool has successfully figured out how to deliver content and a broader image that appears simple and straightforward but that actually conveys deeper ideas and impulses about culture, society, and politics.
This Straussian dimension has to led growing commentary about the rise of so-called “Barstool conservatism” and its consequences for public policy and current affairs in the United States. Yet even though its content is highly popular in Canada—including owning three of the country’s top 50 podcasts—there hasn’t been similar discussion about what Barstool’s popularity might tell us about the state of Canadian politics in general and Canadian conservatism in particular.
My own anecdotal experience tells me that Barstool’s “folk libertarianism” resonates with a lot of Canadians—particularly young men. It’s important therefore to better understand its appeal, reach, and possible influence over a key part of the country’s body politic.
Barstool’s origins: The rise of the ‘Stoolies’
Barstool Sports will be familiar to younger readers. It’s difficult to explain to older ones. It describes itself as a “sports and pop culture blog covering the latest news and viral highlights of each and everyday with blogs, videos and podcasts.” But that doesn’t begin to fully capture what it is or the size of its influence and reach.
Barstool Sports was started in 2003 by Portnoy as a free print publication on sports gambling. He began with about $25,000 from his parents and personally oversaw the production and distribution of the low-budget newspaper mostly at subway stops in the Boston area. My brother, a so-called “Stoolie”, characterizes Barstool’s early business model as a “glorified paper route.” Portnoy’s bet was that he uniquely understood what “guys want to do.”
The subsequent two decades have proven that he was right. Barstool has since evolved into a digital media company with a massive online audience and annual revenues of more than US$100 million per year. As its current CEO, Erika Ayers Badan, put it an interview last year:
Barstool is the most influential digital media brand in the country. Our audience are true fans of Barstool and the franchises we build. The deep engagement and connection we have to our audience base moves products for our brand partners that no other media company can match.
Its sagacious mix of sports, culture, and lifestyle is a potent content offering for its target demographic of university-aged men. Its content and traffic numbers are staggering. According to a recent Vanity Fair profile, Barstool has “more than 100 podcasts, YouTube shows, and social media series; 95 personalities; 65 advertisers; 17 content verticals; countless merchandise sold; and more than 230 million followers across social media.” Ayers Badan has described it as “an IP company.”
I asked one of my closest friends—another “Stoolie”—to define Barstool and its success in simple terms. He described it as “sports entertainment by the common man, for the common man.”
He’s not wrong. Barstool users are generally under the age of 30 and one-third engage its content multiple times each day. That level of sustained loyalty is basically unmatched on the internet. Barstool’s most avid audience—its “Stoolies”—is doubtless a key source of its success.
Another is Portnoy himself who is known to his fans as “El Presidente” or “El Pres.” Although he’s no longer the company’s CEO, he has full control over its content and remains the face of the organization. He’s 46 years old but he seems much more youthful than his age. A big part of that is his own lifestyle. He lives, acts, and even dresses like someone in his twenties or thirties.
One profile described him as “Mark Zuckerberg after five years of hard drinking and even harder tanning.” He certainly drinks, gambles, parties, watches sports, and generally seems to have a lot of fun. Portnoy is someone that his audience would naturally hang out with to watch a game or drink a beer.
Perhaps as a result, he seems to have an instinctive understanding of the Stoolie’s habits and tastes. His decisions on content and personalities (many of whom he discovered before they had a public profile) reflect his powerful intuition about who and what will resonate with the audience. There are plenty of examples including for instance the Spittin’ Chiclets podcast with former NHL players Paul Bissonette and Ryan Whitney and their co-host, Brian “Rear Admiral” McGonagle, which is the most popular sports podcasts and among the top twenty of any genre in Canada.
Portnoy’s own personality is shot through the company. He has something of a populist appeal. He once described his audience as “a bunch of average Joes, who like most guys love sports, gambling, golfing and chasing short skirts.” It’s a classic Portnoyian line that reflects the two-sided coin of his personality. He’s funny, irreverent, and a great communicator. He’s also crass, confrontational, and a bit raw. The same Vanity Fair article referred to him as “God to cancel-culture-bemoaning, pizza-loving, red-blooded Robinhood traders.” He has even been characterized as “Donald Trump without the politics.”
Although the comparison is mostly unfair, it must be said that Portnoy and Barstool have crossed the line at various times. Criticism that they can be “chauvinistic,” “misogynistic,” and “toxic” isn’t without merit. You probably wouldn’t want your mom or daughter to spend too much time on the site.
It’s definitely a place for guys who still make up more than two-thirds of the audience. One of its most popular tag lines is “Saturdays are for the boys” for a reason. In an era in which gender norms and roles are being redefined, Barstool’s masculinity still resonates with a large and motivated audience.
Barstool’s month of milestones: ‘It’s a big victory’
As mentioned, Portnoy and Barstool have been in the media in recent weeks because of his acquisition of the company after fully selling it mere months ago. The transaction reverses the previous deal with Penn National which had been based on ambitions about leveraging Barstool’s audience for its new sports gambling business, including theScore mobile gaming app in Canada.
The marriage never quite produced the outcomes that were hoped for in part because Barstool’s edginess was poorly received by gambling regulators and in turn caused some hassle for Penn National. When the company recently signed a major gambling partnership with ESPN, whose parent company is Disney, one of the conditions was apparently that Penn spin off its ownership of Barstool. That’s how Portnoy was able to purchase his old company at such an extraordinary discount.
The deal between Penn and Portnoy reportedly comes with some additional conditions including restrictions on Barstool competing in the sports gambling business and a claim on future sales profits—though Portnoy has said that he never intends to sell it again.
The upshot is that the company is back in Portnoy’s hands and returning to its original mission as a source of irreverent news and information about sports and entertainment free from the reach of bureaucrats and regulators. As Penn’s president and CEO Jay Snowden put it in a statement:
The divestiture allows Barstool to return to its roots of providing unique and authentic content to its loyal audience without the restrictions associated with a publicly traded, licensed gaming company.
The timing is rather fitting because of the forthcoming anniversary. It’s like the company is rediscovering its original start-up identity after a brief yet somewhat disappointing experiment as a mainstream media player. There’s good reason to think that Barstool will be as edgy and irreverent as ever as a result. As Portnoy recently explained: “It’s a big victory when you get your company back. Not being part of a publicly traded company is probably a relief for everyone.”
The basic business model is unlikely to change. Portnoy’s instincts have generally led him in the right direction up until now. The Penn deal is bound to cause him to essentially double down. Barstool’s ongoing success or failure will depend on his ability to continue betting right on content, personalities, and his audience.
Next week’s anniversary party is bound to be a spectacle. Portnoy is a modern P.T. Barnum who has come to leverage the Barstool platform to sell alcohol, t-shirts, watches, and more. That hustler instinct will undoubtedly be on display at the much-touted party and in the coming years as the company’s once-again unrestrained commanding head.
The politics of Barstool: ‘folk libertarianism’
One of the sources of Barstool’s success is that Portnoy has intentionally avoided politics. As a 2017 New York Times profile explained:
There exists a swarm of angry sports fans who maintain that they do not want to talk about Colin Kaepernick or the national anthem, and Barstool has cleared a space for them to gather and talk, mostly, about just how much they don’t want to talk about politics.
There have nevertheless been growing efforts to analyse the cultural and political influence of Barstool Sports. One of the most prominent was a 2021 article for This Week about the rise of so-called “Barstool conservatives.” As the author explained, this distinct political constituency combines a mix of socially liberal views on pornography, homosexuality, drug use, and gambling, with an instinctive libertarianism on taxes and regulations and a pseudo-populism in terms of its self-image and place in the broader society.
The Hub’s Stuart Thomson has described this political tendency as “middlebrow populist libertarianism that has roots in the American frontier more than the writings of the Austrian economist Friedrich Hayek.” New York Times columnist Ross Douthat summed it up as “folk libertarianism.”
It’s a good description of Portnoy’s own inchoate politics which don’t neatly graft onto the conventional Left-Right paradigm. He certainly supports more business-friendly policies with respect to taxes and regulations and was strongly opposed to COVID lockdowns of businesses and sports. He also clearly stands in tension with the Left’s tendency towards political correctness. If there’s one overarching ethos at Barstool, it’s anti-political correctness. Yet he’s pro-choice and doesn’t particularly live a conservative lifestyle or project ideas of morality and virtue.
Conservative writer Ben Domenech sought to define Barstool conservatism on a recent New York Times podcast:
We want to be able to gamble. Porn is good; it’s not bad…We want people to have fun, drink High Noon, gamble more. We want them to be entertained by the people who we have on our programs, who are both big winners and big losers, buy cheap T-shirts, and just keep the ethos rolling… it overlaps with the Gadsden flag just leave us alone coalition, whether that be going after menthol cigarettes or vaping or any of these things that are kind of nanny state government stuff that they rebel against.
Although these various definitions are broadly correct, they probably underestimate the role of gender in Barstool’s appeal and the experiences and worldviews of its audience. As we discussed on a recent episode of The Hub Roundtable podcast, young men are facing a series of new pressures in school, the economy, and the broader society including increasingly being outperformed by female students, new norms about gender roles and male-female relationships, and growing hostility to certain forms of masculinity. It can be a destabilizing context for young men who themselves are struggling to find meaning and purpose, build adult relationships, and define their own manhood.
Barstool offers an imperfect (though far better than some alternatives) source of community and even identity. As I wrote in a 2021 column about the company’s appeal:
Barstool Sports’ significant popularity is a sign that young people—particularly young men—are in search of a source of community and kinship in our secular age. It will necessarily take different forms than in the past. And there are no doubt limits to virtual communities compared to the traditional, face-to-face ones that they’re replacing. But our natural desire to belong to a little platoon hasn’t gone away.
The political implications of Barstool conservatism can probably be overstated. My sense is that many of its audience members would be counted among the ranks of eligible non-voters. If however a politician or political party could speak to their “leave-us-alone” mentality and legitimate anxieties about the place of masculinity and manhood in modern society, they could be a sizeable constituency.
Pierre Poilievre seems to be tapping into it. His early success with younger voters is at least in part a reflection of his own youthfulness and vitality. Although he may not be someone young men would necessarily watch the game or have a beer with, he has found issues and messages that resonate with them. His overarching message of personal freedom clearly has an audience among parts of the Barstool crowd.
The key will be to respond to their concerns with policy substance rather than online memes and pop culture references. They already have Barstool for the latter. And no politician is going to compete with Portnoy for the Stoolies’ attention or affection. He is El Presidente after all.
