Inside the stunning rise of Barstool Sports founder Dave Portnoy: How an admitted 'degenerate gambler' created a sports media behemoth amid accusations of misogyny, sexual misconduct and union busting

A divorced 47-year-old who describes himself as a 'degenerate gambler' isn't everyone's picture of success, but Barstool Sports founder Dave Portnoy is exactly that to his loyal army of supporters.

Thanks to nearly 5 million followers across social media as well as his wildly popular website, Portnoy is reportedly worth more than $100 million and boasts luxury properties in exclusive locales like Nantucket and the Hamptons.

Along the way, Portnoy has faced constant criticism over accusations of misogyny and unfair labor practices. He's crashed Super Bowl media day, protested NFL commissioner Roger Goodell, and as a result, has been banned from attending league events. More recently, Portnoy raised eyebrows last month by eagerly greeting Presidential nominee Donald Trump at UFC 299 after recently supporting  his Republican primary rival, Nikki Haley. 

Despite the controversies, Portnoy has become a quasi 'every man,' representing sports fans everywhere, albeit while traveling to games aboard a private jet. Just this week, he flew to tiny Albany, New York to see Caitlin Clark and Iowa upset LSU because, as he put it: 'I hunt greatness.'

So how did a directionless Massachusetts kid find himself at the center of the sports media world? The following is DailyMail.com's look at Portnoy's rise from an obscure publisher to one of the most influential people in the sports universe:

Barstool founder and CEO Dave Portnoy is seen before the Florida Atlantic Loyola (Il) game

The son of a lawyer and a high school teacher, Portnoy hails from Swampscott, Massachusetts – the same affluent North Shore enclave that produced 60 Minutes' Lesley Stahl and Orange Is The New Black author, Piper Kerman. 

Portnoy attended Swampscott High School with future NFL draft analyst Todd McShay, but didn't really immerse himself in sports media until he began attending the University of Michigan, where he published his betting picks on a long-forgotten website.

Initially, that appeared to be his final foray into sports media. Portnoy moved back to the Boston area to work for an IT market research firm, but soon grew board of the 9-to-5 life.

The solution: Publishing a four-page sports newspaper in 2003.

Considered the first iteration of Barstool Sports, the newspaper gave a good preview of what the future website would look like. There were women in bikinis and articles disparaging any perceived attempt at political correctness.

David Portnoy attends a 2023 NBA Playoff game with his then-girlfriend, Silvana Mojica

But for all of its similarities with the current website, the newspaper was far from successful.

Portnoy would file for bankruptcy protection in 2004 amid $90,000 debt -- $30,000 of which came in the form of gambling losses, according to a New York Times profile in 2022.

It's a problem that continues to face Portnoy, who regularly bets six-figure sums on sports. In fact, he recently vowed he was done with gambling, only to place a $1 million winning bet on Michigan to beat Alabama in the College Football Playoff.

But for every seven-figure success, there's been just as many pitfalls for Portnoy, whose very own father has expressed concern for his gambling addiction.

'Anyone who says my son is exaggerating his gambling issues, I wish he was,' Mike Portnoy told Barstool Radio in 2019. 'He isn't.'

Dave Portnoy seen before his success in 2011

While Portnoy never kicked his gambling demons, he did transform Barstool into a popular blog, beginning in 2007.

Regular features such as one-bite pizza reviews and 'Local Smokeshow of the Day' offered readers content on food and attractive women. Another recurring topic, 'Guess That Ass,' was more or less what you'd expect.

The blog's rising acceptance was paced by a sharp uptick in controversies, although it's hard to say which trend begat the other.

In a since-deleted post from 2010, Portnoy appeared to make light of sexual assault, writing: '[E]ven 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?'

Inside Edition's Lisa Guerrero addressed the topic with Portnoy only for the millionaire media mogul to double down.

'I stand by that,' he said. 'I think it's a funny joke.'

Guerrero countered by asking 'Do you know how offensive that is?'

Portnoy's responded: 'No. I obviously don't.'

Both Portnoy and staff members have been caught using the n-word while repeating rap lyrics. In one case, Barstooler Ben Mintz was dismissed for using the racial epithet, not by Portnoy, but by Penn Entertainment, the online betting website that briefly owned the website before selling it back to the founder. 

When Portnoy bought the site back for $1 – just six months after selling it for $551 million – the first thing El Presidente did was to re-hire Mintz.

'You're coming back?' Portnoy asked Mintz over the phone as seen in a Barstool video. 

'F***ing-A I'm coming back!' an exuberated Mintz exclaimed.  

Portnoy and his blogger Jenna Mourey were photographed at his office on February 25, 2011

Portnoy, who did not reply to DailyMail.com's request for an interview, takes particular pleasure in attacking Goodell over the league's 'Deflategate' scandal.

The issue centers on the NFL penalizing Tom Brady for allegedly deflating footballs in violation of NFL rules. Conversely, academics have insisted that the NFL failed to prove its case against Brady, who may have actually been exonerated by the league's data.

Portnoy has never forgiven Goodell for Brady's four-game ban.

As a result, Portnoy and three other Barstool employees staged a protest at the NFL's Manhattan headquarters in 2015, handcuffing themselves to each other in the lobby. Four years later, Portnoy was briefly arrested after creating fake press credentials to gain access to Super Bowl LIII in Atlanta.

It was around this time that Portnoy became increasingly political.

He had always been outspoken about his stock tips and gambling predictions, but with the emergence of Trump as a viable presidential candidate, Portnoy started to ingratiate himself to conservatives.

Barstool Sports founder Dave Portnoy is seen in attendance during the UFC 299 on March 9

'I am voting for Donald Trump,' Portnoy wrote on his blog in 2015. '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 don't care about any of it. I hope he stays in the race and I hope he wins. Why? Because I love the fact that he is making other politicians squirm. I love the fact he says s*** nobody else will say, regardless of how ridiculous it is.'

In the coming years, Portnoy would become a regular guest on Tucker Carlson's Fox News program, where he often defended himself against a growing number of attacks.

Portnoy was subject to a 2019 National Labor Relations Board investigation over Twitter posts claiming that he threatened to fire workers if they unionized. He ultimately reached an informal settlement with the Board, but suffered no significant financial penalty.

Then, after his decision to sell Barstool Sports to Penn in 2020, Portnoy was accused of sexual misconduct in a 2021 Business Insider expose, alleging that he had violent and aggressive sexual encounters with women, some of whom he filmed without their consent.

Portnoy denied the claims, insisting the article was a 'hit piece.'

Portnoy later sued Insider, claiming its reporting was 'false and defamatory,' but the lawsuit was ultimately dismissed and he dropped his appeal in 2023.

The incident foreshadowed Portnoy and Barstool's growing issues with Penn, which was concerned how the news would impact its share price and standing with regulators. Ultimately Penn thought it was easier to effectively return the website to Portnoy and strike a new 10-year, $1.5 billion deal with ESPN. Penn later reported an $850 million write-off on its balance sheet, according to Sportico. 

On its surface, Penn's decision looked like a major win for El Presidente. He got his company back and didn't really have to pay for the privilege.

But the deal did come with some strings attached.

The sale of all of Barstool's stock to Portnoy for $1 came 'in exchange for certain non-compete and other restrictive covenants,' which prevented the website from signing another deal with a sports book until the end of the 2023 NFL season.

Furthermore, if Portnoy ever tries to sell Barstool again, Penn has rights to half the gross proceeds.

Portnoy is seen years earlier with his now-ex-wife, Renee Satterthwaite (pictured right)

Portnoy reportedly dated Jordyn Hamilton (pictured) after splitting up with his wife in 2017

Barstool Sports Founder Dave Portnoy and his girlfriend Silvana Mojica at a 2022 Celtics game

Somewhere along his timeline, Portnoy met equestrian Renee Satterthwaite, who is, herself, a social media celebrity. Later dubbed The First Lady of Barstool Nation, Satterthwaite reportedly accepted Portnoy's marriage proposal in 2008 before they wed a year later.

The two later split in 2017 amid unconfirmed allegations that Portnoy had an affair with a woman named Jordyn Hamilton. Hamilton and Portnoy reportedly dated but soon ended their relationship amid rumors she cheated on him with a Soul Cycle instructor, according to the US Sun.

Since then, Portnoy was in a long-term relationship with model Silvana Mojica, although the couple has recently split.

'I guess you get to a point where you think maybe there's a difference in what somebody wants versus what the other person wants and without going into too much detail, I just didn't think I could give Silvana kind of what she deserves,' Portnoy said in November.

Throughout his own corporate and personal dramas, Portnoy has taken extraordinary pleasure in the failures of his rivals.

Portnoy typically toasts his rivals' failures by popping some champagne in his pool 

In November, when Business Insider CEO Henry Blodget stepped down as CEO, Portnoy posted a celebratory video while accusing the website of trying to ruin his reputation with allegations of sexual misconduct.

'They changed the name of the company from Insider back to Business Insider 'cause your little game of trying to ruin people, and being the crook and the scumbag and the piece of s*** that you've been you're entire f***ing life you tiny little scrawny dork,' Portnoy said in a social media video.

'The guy who tried to run me out of town with a hit piece because that's what he did at Business Insider. They try to get cheap clicks, fake stories.'

More recently he was seen toasting Deadspin's demise after the rival website announced that it was being sold to a European startup company and was dismissing its entire staff. Years earlier, Portnoy similarly popped some bubbly when a previous incarnation of the website went under.

'Listen, even I'm getting confused,' Portnoy said in a social media video while floating around in a pool. 'How many times can I pop a bottle for the same goddamn company? How many times can I kill Deadspin?'

But while Portnoy has deliberately antagonized rivals, he's also run afoul of his readers and his staff.

Most notably, Portnoy is fervently anti-union and has even threated to fire anyone caught organizing Barstool staff only to delete the social media posts amid threats from the National Labor Relations Board.

'If you're a boss tweeting firing threats to employees trying to unionize, you are likely breaking the law & can be sued, in your words, ''on the spot,''' New York Representative Alexandria Ocasio Cortez tweeted in 2019. 'ALL workers in the US have the protected freedom to organize for better conditions.'

Subsequent battles with his staff have seen Portnoy threaten to fire all of his employees, and in one instance, he removed podcast host Kelly Keegs while publicly referring to her as 'tone deaf, brain dead and idiotic.'

Fans, meanwhile, have objected to Barstool content being put behind paywalls. And Portnoy only exacerbated the situation by ridiculing customers who were upset over the $9.99 fee.

'I would never complain about nine bucks, you f***ing poor people,' Portnoy said in a self-shot video.

Portnoy's path forward isn't quite clear, but he appears to have more freedom without the presence of any corporate overlords. 

And at least from a creative standpoint, that's a good thing.  

'For us, for Barstool, for the first time in forever, we don't have to watch what we say, how we talk, what we do,' he said after repurchasing his website. 'It's back to the pirate ship.'

Dave Portnoy, host of Barstool Sports, talks with host Seth Meyers during a 2017 interview 

Portnoy has continued to bolster his reputation as a philanthropist this year by raising money for the family of a slain New York cop after donating $277,000 to an Atlanta animal shelter. And those aren't his only charitable efforts.  

Previously, in the wake of the COVID-19 pandemic, Barstool started a fund to offer relief for small business who were impacted by the work stoppage. That effort has resulted in $41 million for 443 businesses, according to the website. 

More recently, he donated proceeds from Barstool's Pride Month merchandise collection to the LGBT Center of New York, only to be attacked by homophobic critics.

'Get woke go broke,' wrote one.

Another, described as a Tea Party conservative, accused Barstool of pedophilia: '#OKGroomer.'

Amid criticism of Portnoy, he's also received support from both inside and outside of Barstool, including outgoing CEO Erika Ayers.

Although she didn't fully explain the reasons behind her departure, Ayers did offer a vote of support for Portnoy, whom she credited with the website's success.

'I feel so good about Dave,' Ayers said in a self-shot video after announcing her resignation earlier this year. 'I'm so grateful to Dave for giving me a chance in the first place. I trusted him and still trust him and he's the right person to make this a pirate ship and I think we went around the sun a bunch and now it's back exactly where it should be.'

David Portnoy hosts The Pool After Dark at Harrah's Resort on Saturday May 11, 2019

As for Barstool's future, not much is written.

Without corporate America guiding his pirate ship, Portnoy is free to move Barstool in any direction he chooses. 

Barstool recently announced a new partnership with DraftKings, indicating that the website's non-compete clause with Penn Entertainment is no longer an issue.

It also proved another important point: Despite Barstool's alleged sexism and anti-labor practices, the corporate world is still very much in Portnoy's corner.

As DraftKings CMO Stephanie Sherman said in a statement, the website is 'another valuable, high-reach addition to our marketing mix,' and there's little confusion over why that is.

According to Barstool, the website has grown its audience by 194 percent over the last three years as 1.6 billion podcast episodes were downloaded worldwide.

Perhaps most importantly, Barstool says it reaches 200 million readers on social media, making it one of the biggest brands in sports.

And whether that's in spite of Barstool's penchant for controversy, or because of it, that kind of success is hard to dispute.