Dave Portnoy’s improbable middle class-to-riches saga is the subject of a new biography. By David McKee
You don’t sell the dream of a lifetime.” – The Man with the Harmonica (Charles Bronson), in Sergio Leone’s “Once Upon a Time in the West.” But Barstool Sports founder Dave Portnoy did, twice, and bought it back once for a mere dollar. So maybe there are lessons to be gleaned from Charlie Stanton’s new Portnoy biography, How the Jester Became King (Post Hill Press).
Forty chapters and 374 pages later, the foremost lesson learned is an old one, courtesy of P.T. Barnum: “Nobody ever lost a dollar underestimating the taste of the American public.” Portnoy aimed low and consequently soared high, the object of adulation by millions of that species of American known as douchebags, unshaven louts like Portnoy himself, but far less intelligent.
Portnoy’s Horatio Alger saga starts in Massachusetts in 2003 with $25,000 borrowed from his lawyer father to start a sports-talk newspaper. A literally tireless hustler, Portnoy pushed papers around the clock, year after year. Gradually his unkempt empire spread to the Internet, where it metastasized into blogging, podcasting and talk radio. (TV is the one frontier that steadily defies Portnoy.) Fueled by undeniable business savvy, a bottomless sense of grievance and no small amount of pure luck, Portnoy turned the massive chip on his Bostonian shoulder into a fungible asset worth hundreds of millions of dollars. His Barstool brand eventually encompassed sports bars, apparel and even a Walmart-peddled line of pizzas. Nothing Succeeds like Excess Practically born bearing a grudge, in 1977, Portnoy
would later say, “I’ve been a degenerate gambler my whole life.” In a manner that would do credit to the Mafia, he used his media assets like a protection racket, declaring, “If you won’t play ball, prepare to get bashed.” And he made good on the threat, as NFL Commissioner Roger Goodell can attest.
From the start, Barstool Sports was openly sexist in its appeal, prominently featuring photos of scantily clad women – not infrequently without their permission. Portnoy’s own credo can be found on p. 59, where he says, “Bottom line is that chicks that aren’t prepared to be sexually assaulted just a little bit shouldn’t go on pub crawls to begin with.”
Similar comments would eventually help undo Portnoy’s Penn Entertainment bid for respectability … but we’re getting ahead of ourselves.
Like someone who compulsively yells “Fire!” in crowded rooms, Portnoy reveled in the role of irresponsible provocateur. We find him, in September 2010, inciting a riot on a University of Massachusetts campus.
Of course, such events wouldn’t be possible without Portnoy’s growing and uncouth army of followers. As Stanton puts it aptly, “He cornered the market on white privileged male humor.” That “privileged” is a key distinction: Like the country club wannabe he was (but is no longer), Portnoy specialized in punching down, taking merciless aim at the unfortunate, the handicapped and the underrepresented.
True, Portnoy could be a leading fundraiser for charitable causes, especially during the Covid pandemic. But such excursions into philanthropy were largely out of character.
Fortune smiled on his misbehavior, even when Portnoy threatened – as was so often the case – to be his own worst enemy. Such as the case with the Barstool Blackout Tour, which began as a disastrous series of Portnoy-sponsored drinking parties but which became an important branding exercise.
Portnoy’s dismissive attitude extended to his hardscrabble business, which evolved from a series of warrens in the greater Boston area where Barstool employees worked without air conditioning – and not infrequently without pay. If you think this would spark resentment, you would be wrong.
Although Portnoy was incredibly insensitive to the needs of his underpaid underlings, it perversely worked to his benefit. His abusive managerial style and slavery-like working conditions created a Stockholm Syndrome-like sense of loyalty among the inner core of “Stoolies.”
Every Man for Himself
It couldn’t have worked out better for Portnoy if he had designed it that way. “Alpha males take what they want,” was one of his mottos and it became the lodestar for a wholly unfortunate twist in the American psyche, with selfishness to the fore. Portnoy didn’t create this problem but he certainly continues to exploit it to the maximum.
By the way, that’s “selfishness” spelled with many an $. For instance, Hulu founder Peter Chernin saw value and online sports betting potential in Barstool (whose hosts babbled incessantly about their gambling habits). He would buy it in 2016 for $12.5 million.
Teaming with a former Fox Network boss (Chernin) suited Portnoy’s grandiose ambitions. He aimed to make Barstool “this generation’s SNL.” However, his generation already had Saturday Night Live (still does) and Portnoy’s complaints would never become mainstream consumption.
Which is not that Barstool didn’t flourish under the aegis of The Chernin Group. It would eventually realize a valuation of $100 million, somewhat in spite of itself. Portnoy and his bumbling cast of sidekicks could never manage to produce polished content, which Stoolies brandished as a shibboleth of authenticity. Paradoxically, the perpetual ineptitude of Barstool’s content would be intrinsic to its business success.
That reclamé would be heightened when Portnoy found a female kindred spirit in CEO-to-be Erika Nardini. She would come up with new and lucrative ways of monetizing the Barstool brand. After Nardini came onboard, Barstool went from eight million online visits per month (in 2017) to 66 million per month in 2020.
Nardini was almost as hard-edged a character as Portnoy himself, which was a useful attribute. The latter comes across in Stanton’s pages as a vile sexist, as witnessed by his unprintable attacks on then-ESPN anchor Sam Ponder.
Ironically, ESPN would try to co-opt the Barstool brand and a watered-down version of its psyche, to provide overnight programming. It was a move that backfired, partly due to the anodyne content and partly due to Portnoy’s big, foul mouth, which he tended to shoot off at the most inopportune junctures.
Despite such missteps, Barstool continued to burgeon, picking up even more steam in 2008 when the U.S. Supreme Court nixed the Professional & Amateur Sports Protection Act. This opened the floodgates to sports betting outside of Nevada, a Portnoy godsend.
Betting content moved front and center on Barstool. Portnoy’s endgame became to sell out to FanDuel or DraftKings for a massive payday. However, nobody wanted to touch Barstool … until Penn Entertainment came along.
A Fool and his Money
Penn was – and is – steered by Jay Snowden, a CEO that Stanton describes as “a chiseled former Harvard quarterback.” The ex-footballer and the jockstrap-sniffing Portnoy were a marriage made in Hell. For his part, Snowden saw in Barstool a potential marketing arm and mouthpiece for Penn. He would get more than that for which he bargained. And a strange bargain it was, as Snowden paid $450 million for Barstool, 4.5 times its Chernin Group valuation.
Portnoy’s racism immediately created public relations headaches for Penn. Not coincidentally, Portnoy began to be pulled into the orbit of President Donald Trump and his clan. He also became a fixture on right-wing broadcast outlets like Fox News.
It was at this time that Portnoy also began an on-again/off-again dalliance with cryptocurrency. He was wise to the fraudulence of Sam Bankman-Fried but wasn’t above some questionable cryptocurrency dabbling of his own.
The bloom started to come off the Penn rose in April 2021, when a Portnoy sex tape surfaced, becoming a drag on PENN shares. Seven months later, Portnoy’s sexually abusive past went viral, sending Penn stock into a 21 percent tailspin.
And yet no Portnoy misadventure was too seamy for Snowden, who liked to sport Barstool apparel around the office. His misguided ‘bromance’ with Portnoy will be fodder for amateur psychologists for years to come, as the CEO seemed to crave the shock jock’s approval. Sticking to his new pal like glue, Snowden even had Penn underwrite a Chicago office for Barstool to the tune of $20 million.
Image: Charlie Stanton, author
It was an asymmetrical relationship, one that was very good for Barstool (whose monetization exploded) but not so much for Penn. The latter’s sports book applications couldn’t make it out of seventh place in the market, with a three percent share – half of what had been desired.
In addition to not moving the Penn needle, Portnoy was a regulatory liability, costing the company hefty fines in the Midwest with Barstool’s indiscreet pronouncements on sports betting. Snowden may have wanted to push the sports book envelope but Portnoy and his gaggle of podcasters tended to tear it instead.
The final straw was broken in May 2023. That’s when Portnoy ripped Penn on air, causing the company to lose $633 million in market capitalization in one day, in a sudden sell-off of stock. Contrary to what Snowden may have thought, the Barstool rabble could not be controlled and could even be his company’s worst enemy.
By August it was all over. Snowden cut a secret deal with Barstool’s old nemesis, ESPN, and Portnoy was suddenly out in the cold. But not poor. That $450 million deal with Penn (which would ultimately cost the casino company at least $551 million – some estimates place it closer to $800 million) made him a very rich and respectable man.
***This exclusive interview was originally published in Casino Life Magazines March 2025 Edition Issue 175 ***
