It was March 19, 2004. A 26-year-old ‘dead broke’ Dave Portnoy stood on the corner of Beacon Street in Brighton, Massachusetts with his girlfriend Renee. Staring up at the Cityside Tavern bar, the home of his first ever March Madness party, it was going to be the day it all changed.
Two months earlier, he had filed for bankruptcy. He was his own delivery boy for his Barstool Sports newspaper, which he self-published at a loss of $1,000 a month. But sensing a groundswell of loyal readers, he hired the bar and invited everyone through his paper, charging $100 entry for all the beer and food they could want. ‘Girls can come for free (As Always!)’ he added.
But Portnoy, decked out in his red Barstool t-shirt, was horrified as he pushed open the doors. Nobody was there.
‘I was so embarrassed. That day was one of the darkest days of my life,’ Portnoy would say in 2016, although he has since had a few to rival it. ‘It was an unmitigated disaster.’
Fast forward almost 21 years, Portnoy is worth an estimated $150 million, and has just had a bombshell new book written about the ups and downs of his life, titled ‘How the Jester Became King’.
Barstool, meanwhile, is an empire that has helped propel hugely popular media personalities such as Alex Cooper, host of the ‘Call Her Daddy’ podcast, and ESPN’s Pat McAfee.
And the king of the castle is the self-styled ‘El Presidente’ Portnoy himself, now 47, as admirably tireless and aggressively belligerent as ever. At times, he resembles a South Park character come to life as he wades in on the day’s talking points – from Donald Trump to the NFL to Taylor Swift – ranting and raving like a man summoned to settle the score. And there are millions of devout Barstool followers, or ‘Stoolies’, who wouldn’t have it any other way.
Dave Portnoy, pictured in 2011, built Barstool Sports into an empire worth hundreds of millions
A man who thrives on confrontation, Portnoy has ridden out many scandals along the way
Portnoy interviewed Donald Trump in 2020 and says the President offered him a job this year
But Portnoy’s life story took a striking turn last week after saying he rejected a role in Trump’s administration – working under Howard Lutnick, the secretary of commerce – because he’d have had to hand over control of Barstool. The chance to have a say in running the country is a revelation that underlines his life story as a resilient survivor, more than a rags-to-riches tale.
That day in Massachusetts in 2004, Portnoy had ‘Barstool Sports’ emblazoned across his t-shirt. Now, he might as well have the saying ‘never waste a good crisis’ etched into his skin. While he has air in his lungs, Portnoy will shout for the cause he believes in. At times, he has drawn so much controversy, it has taken him to the edge of the law.
In 2011, Portnoy published naked pictures of Tom Brady’s two-year-old son Benjamin on the beach, joking about the size of the baby’s genitals. Portnoy titled the Barstool post ‘Check Out the Howitzer on Brady’s Kid’.
Portnoy was utterly defiant in the face of an unsurprisingly huge backlash which cost him a spot on a weekly Boston radio show at a pivotal time in Barstool’s rise.
‘I said he had a big howitzer. So that’s not sexual. If you’re making a connection to that being sexual then I would look into the mirror is what I would say, because it’s not sexual at all,’ Portnoy said on WBZ NewsRadio. ‘I don’t know how anyone with a rational brain could say, ‘Oh, that’s because I said that, that’s sexual.’ It’s a ‘Curb Your Enthusiasm’ joke.’
He kept the pictures on Barstool for a week, until a visit from police officers convinced him to finally take them down.
Explaining the knock on the door from the cops, Portnoy wrote on Barstool: ‘They were friendly, non threatening and basically just said they were getting lots of complaints from the lunatic fringe (my words, not theirs, on lunatic fringe) and it would be in the best interest of everybody involved if I’d just take them down.
‘I obviously still stand by the fact I had every right to do everything I did, but I’m not looking to make cops’ jobs more difficult than it already is so I complied. Granted it seems ridiculous to me that they had to waste time paying me a visit over this, but they did.
Two early front covers of the Barstool Sports newspaper Portnoy would deliver by hand
After Portnoy split with his wife Renee (pictured) his private life would become news
‘And yes a part of me still feels like I sold out but what are you gonna do? I guess I could have dug my heels and seen what would have happened next, but it didn’t seem like the right move. I went with my gut and my gut said just make it easy on everybody at this point.’
Portnoy was never charged with any crime. Brady remained silent on the issue but in the years that have followed, appears to be friendly with Portnoy. He notably donated to Portnoy’s fundraiser during the height of the Covid-19 pandemic, saying his work to help small businesses stay afloat was ‘awesome’.
By 2017, the man who marketed himself as ‘a degenerate gambler’ had married and then split from Renee and began dating Jordyn Hamilton – there were rumors of an overlap. But however it started, it ended badly with Portnoy announcing Hamilton had allegedly cheated on him with an instructor at a Soul Cycle in New York.
Hamilton never responded to Portnoy’s claims but according to the ‘How the Jester Became King’ book about Portnoy’s life, she reached out with a message of support for Portnoy when he was embroiled by sexual misconduct allegations.
With there being no such thing as bad press for Barstool, Portnoy relayed the story in full detail from his side on Barstool radio. The Stoolies went to work, hounding Soul Cycle’s social media to the extent that the organization sent a message to its trainers telling them to call the police if anyone appeared at any of their studios and made them feel threatened.
That message made its way back to a merciless Portnoy, who shared it on X and wrote: ‘Best way to avoid calling 911? Don’t have your instructors f*** the girlfriend of head of major media company.’
He cashed in on his heartbreak, too, selling t-shirts with the word ‘CuckCycle’ emblazoned across it. But for many, the way that Portnoy, a powerful man touching 40, publicly took shots at his younger ex and weaponized his fanbase left a bad taste.
In July 2020, Portnoy was invited to the White House to interview Donald Trump in the run-up to that year’s election. Trump’s political emergence shattered what had been a firm Barstool rule of avoiding political talk. Portnoy backed Trump to win in 2016 and again four years later. He has only become more political in the years that have followed.
Portnoy’s wild social media rants have formed a key part of his online presence
In 2017, Portnoy said ex-girlfriend Jordyn Hamilton cheated with a Soul Cycle instructor
That day in DC, Trump praised Portnoy for offering to shake his hand in the era of social distancing. And while Portnoy’s questions were soft, Trump did at one stage rail against other countries taxing American imports in remarks that now appear to form the basis of his plans for tariffs in 2025.
But the timing was remarkable. Just a month earlier Portnoy had branded himself ‘uncancellable’ when footage of him using the N-word years earlier resurfaced at the height of the Black Lives Matter movement.
‘I’m big. You’re little. I cancel you,’ Portnoy wrote in response to the outrage. ‘I knew this was coming before you did. And I’m ready. You don’t cancel me. I cancel you.’
It was an ethos that was going to be tested again a year later when he was fighting to keep his private life out of the news. And after finding himself center of a huge dispute amid BLM, he was about to be at the heart of a ‘MeToo’ scandal.
First, in April 2021, a graphic sex tape leaked of Portnoy with 22-year-old Sydney Raines. Portnoy was holding a leash attached to a collar around her neck. Neither knew how it leaked but Raines said she had no regrets over what happened, the incident was consensual and that Portnoy had repeatedly checked that she was ok after the footage surfaced.
Portnoy, meanwhile, responded on social media with a profane video mocking the fact that stock in Penn National Gaming, which owned 36 percent of Barstool, was dropping as a result of the clip going viral.
‘Wait $penn is dropping cause I have a sex tape? Are you kidding me,’ Portnoy said, urging his followers to buy it up at a low price. ‘Ps – It’s a federal crime to watch or post it. Double Ps – I f***. Who cares.’
In April 2021, a sex tape leaked of Portnoy with Sydney Raines, who was 22 at the time
Portnoy was his usual combative self in response to the video going viral online
But weeks later, things took a sinister turn. Portnoy was accused of sexual misconduct in a Business Insider expose, alleging he had violent and aggressive sexual encounters with women and that he filmed them without their consent. ‘I was literally screaming in pain,’ one woman was quoted as saying.
Portnoy vehemently denied the claims, insisting the article was a ‘hit piece’ that had been eight months in the works and went as far as to say the article insinuated he was a rapist.
He went on the rampage after it was published, highlighting a string of perceived inaccuracies that he felt undermined the reporting and even eventually sharing personal direct messages from the women he had been involved with, before and after his alleged actions. He was also represented legally by Andrew B. Brettler, the Hollywood-based ‘MeToo’ lawyer who also defended Prince Andrew, Danny Masterson and Armie Hammer.
‘I’ve built this company by being blunt, brutal and honest,’ Portnoy said in an Emergency Press Conference about the piece. ‘Along the way, I’ve created a s***-ton of enemies. The enemies crawl out of their holes and take shots. I would do the same.’
Curiously, Portnoy also addressed a claim from the distinguished stock market news account ‘@unusual_whales’, which today has over 2million followers.
They replied to a Portnoy video defending himself against the claims with a graphic of Penn stocks, saying: ‘It seems someone was frontloading it (Penn Stock), too, buying large put positions. Someone was seemingly planning the dip. Let me know if you need help explaining this!’
Portnoy asked them to explain it to him ‘like I am two’, to which another account said: ‘Someone knew about the story and leveraged up short against $PENN.’
After a second sexual misconduct piece was published, Portnoy later sued Insider, claiming its reporting was ‘false and defamatory,’ but the lawsuit was ultimately dismissed and he dropped his appeal in 2023. Portnoy was never charged with any crime, nor was anyone charged with insider trading around the allegations against Portnoy being broken by Business Insider.
But the grudge stayed strong. At the end of 2023, Portnoy celebrated Business Insider CEO Henry Blodget stepping down to become chairman by saying he was ‘fired’, telling his followers: ‘I’ll get the bottle and I’ll pop it. Henry, you piece of s***, kicked upstairs.’
As he wrote in 2021, when he was fighting for his reputation after the first Insider piece: ‘Here is what people have to know about me. If you wrong me I will burn you to the ground. If I burn with it that’s the cost of doing business. I’ve always been that way.’
Today, even without a job in the White House, Portnoy’s position and influence appears greater than ever. He ended up buying the entirety of Barstool back for $1 from Penn in 2023, in order to forge a partnership with ESPN instead.
He appears to be increasingly confident discussing politics, despite first carving out Barstool as a place where sports would not overlap with the White House. He is, unquestionably, more eloquent on the subject as well – his video the day after Trump’s 2024 election win calling out the Democrats for alienating and insulting the middle-ground rang true on both sides of the debate.
Portnoy’s most recent public relationship was with the model Silvana Mojica, ending in 2023
Despite sexual misconduct allegations in 2021, Portnoy now appears more influential than ever
His ‘One Bite’ pizza reviews of establishments across the United States are watched by millions around the world and regularly spark wild surges in sales for local businesses.
He owns lavish properties in Miami and Nantucket. He fights the good fight a little more often – not just against Kanye West and his Nazi sympathizing. As well as raising millions for small businesses in the pandemic, he also fundraises for animal shelters and in 2024, donated $750,000 of his own money to support the family of slain NYPD officer Jonathan Diller.
Portnoy remains publicly single. He split from Renee but they didn’t divorce, with Portnoy saying a judge denied their petition because ‘I have too much money’. He added: ‘we have a great relationship’ and said she has access to his bank account.
His most recent public relationship was with model Silvana Mojica for three years, which ended in November 2023.
But at the core of it, Portnoy remains the same provocative figure fiercely committed to his own opinions. Toxic in the eyes of many, a man of the people to many others. As those early Barstool newspapers had as a slogan; ‘By the common man, for the common man’.
Love him or loathe him, he just doesn’t want you to ignore him.
