In the summer of 2020, Madison sent Barstool Sports’ founder, Dave Portnoy, a direct message on Instagram complimenting his famous “one bite” pizza reviews.

“Sick pizza reviews,” she wrote. “Thanks fly bitch,” Portnoy responded. She was a 20-year-old college student at the time, Portnoy a 43-year-old multimillionaire. The conversation soon moved to Snapchat and text, where it quickly turned to the topic of sex. He sent her graphic videos of other women he’d slept with, according to Madison, and in messages reviewed by Insider, he pressed her to tell him about her sexual fantasies.

“I mean actually this ones kind of common,” she wrote. “Like a rape fantasy, where I don’t have any control of what’s going on.”

“You and I are going to get along so well,” he responded.

“But I will say, in order to do that one I have to be pretty comfortable with you,” Madison said.

“Of course,” Portnoy said, and he bought her a first-class plane ticket to visit him at his $2.2 million Nantucket home.

The trip was a “traumatic experience,” Madison told Insider.

She arrived at Portnoy’s four-bedroom home about 3 p.m., tired enough from her travels that she didn’t mind when Portnoy told her they would order in pizza instead of going out. Still, she was surprised to find him nothing like his charismatic online persona. “He was very rude. He wasn’t funny at all. He just reminded me of a boring, grumpy old man,” Madison said.

After dinner, they started kissing. Madison said she first became uncomfortable when Portnoy pulled out his phone and started filming her — without asking permission — as she performed oral sex on him. “I never said anything. I was scared. He was just so mean,” she said.

From there, things escalated until, as Madison put it, “I felt like I was just a human sex doll.”

Two days later, Madison texted a close friend. “It was so rough I felt like I was being raped he video taped me and spit in my mouth and choked me so hard I couldn’t breathe,” she wrote in messages viewed by Insider. “And it hurt and I was literally screaming in pain.”

She recalled crying and shouting, “Too much! Too much!” and “It hurts!”

“It was so painful,” Madison said. “I kept trying to get away and he was like, ‘Stop running away from me. Stop running away from me.'”

But Portnoy, she said, “just went harder.”

Madison’s flight home wasn’t until two days later, so she slept on Portnoy’s couch both nights. They did not have sex again.

Dave Portnoy makes no secret of the fact that he likes to have sex with young women, and to push the boundaries of what is considered socially acceptable. In many ways, that image is at the core of the brand that has made him one of the wealthiest and most powerful figures in digital media. There are the rape jokes, his repeated use of the N-word on camera, and his harassment of female journalists.

Last July, he released a viral TikTok video that offered women three tips for how to slide into a celebrity’s DMs: “Be very hot. Don’t be ugly. And say this, two words: I fuck.” Since 2019, he has appeared in three sex tapes that have leaked online. The stock price of Barstool’s parent company plunged after the most recent leaked video, in which he violently chokes a woman using a collar and a leash. Both Portnoy and the woman said the encounter was consensual.

“I used to sling it,” Portnoy responded at the time, “I’ve gotten better.”

For years, Portnoy has managed to escape scrutiny. His behavior and comments weren’t just accepted; they were expected. And commoditized. A 2020 Barstool documentary series produced by the media company features Portnoy forcefully digitally penetrating a sex doll while donning a tuxedo, later declaring himself “the finger king.”

Young men, who call Portnoy “El Presidente,” follow the mogul’s every move, buying up Barstool merchandise printed with logos like “Team Portnoy” and “Portnoy/Musk 2024.” Young women tag him in provocative videos and photos in an attempt to get his attention. The woman who appeared in his third leaked sex tape even went on a publicity blitz this past May to defend him. In October, when Portnoy visited the campus of the University of Tennessee at Knoxville for a college football game, Barstool’s official Instagram page posted a picture of a house whose front porch had a huge sign that said “Dave, come on in. We have pizza and pussy. 10/10”

A post shared by Barstool Sports (@barstoolsports)

For many, Dave Portnoy is a hero. But some in his orbit, particularly women, have told Insider they felt as though he abused his fame and power and put them in compromising positions.

Insider spoke with more than two dozen people with direct experience with Portnoy and Barstool, including eight current or former employees. Some women, as young as 19 who had no professional connection to Portnoy, recounted having sexually explicit online exchanges with him. Three of these women said they had sex with Portnoy, now 44, and that the encounters turned into frightening and humiliating experiences that have taken a toll on their mental health. Two, including Madison, said Portnoy both choked and filmed them without advance permission; another, who has had

depression

, said she was suicidal after the two had sex. And all three were afraid to speak out, fearing retaliation from the media mogul and his rabid fan base. This article uses pseudonyms chosen by Insider, which is aware of the women’s real identities.

“I know how he is when someone goes after him,” said the second woman, who said she was both choked and filmed without advance permission. She asked not to have the specific details of her experience publicly revealed, fearing harassment from Portnoy or his fans. Insider spoke to someone with whom the woman shared details of her rough sex with Portnoy. “I thought he would say something in public, or share videos of me.”

In an email, Barstool Sports’ attorney said many of the accusations in the article “embody half-truths, are highly misleading, lack appropriate context, and appear to have been provided to you by individuals whose motivations and trustworthiness should at least have been fully vetted.” The attorney asked for more time for further comment. Insider provided an additional two days, but Barstool’s attorney did not provide additional comment or communication.

Perpetually tan and bearded, Portnoy has built a half-a-billion-dollar digital-media empire off of sports gambling, crude humor, and barely clothed women. Barstool Sports — whose slogan is “By The Common Man, For The Common Man” — does for digital media what Donald Trump did for politics. It speaks to the masses: no pretension, no highfalutin language, and, notably, no apologies. The company says it reaches an estimated 54 million monthly unique visitors. In 2020, Barstool was valued at $450 million; Portnoy has an estimated net worth of $100 million.

Portnoy founded Barstool in 2003 in his hometown of Swampscott, Massachusetts. The free four-page newspaper offered betting tips alongside rambling sports rants. Portnoy hit the streets every day to distribute the paper to Boston-area commuters, writing all the articles under various pseudonyms. To drum up more interest, Portnoy started hiring young local models to hand out the paper in skimpy outfits (one of whom, Renee Satterthwaite, became his wife; they separated in 2017).

By 2007, Barstool had taken its operations online. In the heyday of stream-of-consciousness blogging, Barstool featured early columns like “Smokeshow of the day,” in which employees scoured Facebook for photos of attractive local women, and “Guess that Ass,” which invited readers to guess which female celebrity was pictured in each meticulously cropped image.

A 2013 profile in Entrepreneur magazine described Barstool’s original Milton, Massachusetts, offices as “the unholy union of a fraternity house and a crime scene: Beer advertisements featuring half-naked women adorn the walls, towers of junk wobble in every corner, and the carpet is soiled with a panoply of dark dribbles and stains.”

The environment reflected their company’s irreverent attitude. Portnoy didn’t just court controversy; he relished in it. As he became increasingly known for going against the grain, fans who felt alienated by modern-day “woke” culture turned to him as the antidote.

Take a 2017 episode of the podcast “Barstool Radio,” during which Portnoy seemed to defend a hypothetical casting-couch scenario in which Harvey Weinstein says to a struggling actress, “Hey, if you sleep with me, I’m going to put you in a starring role.”

“No force, just a question,” the Barstool founder said. “Do you have a problem with that trade?”

He’s ignited feuds with female journalists, like the ESPN sportscaster Sam Ponder, whom he told to stop posting pictures of her “ugly kid” and to “sex it up and be slutty” while she hosted the college football pregame show “College GameDay.”

In 2010, Portnoy infamously wrote a blog post defending an Australian man who had been acquitted of raping a 24-year-old woman on the so-called skinny-jeans defense.

“I never condone rape, but if you’re a size six and you’re wearing skinny jeans, you kind of deserve to be raped,” Portnoy wrote. The post has since been removed from Barstool’s site, but just this May, Portnoy told the Fox News host Tucker Carlson there was only one part of that statement that he regretted. “I thought size 6 was like size 20,” he said. “I had my, I had my measurements screwed up. I wasn’t on top of that.”

Portnoy’s brashness is exactly what fans and some colleagues say they love most about him.

“The big thing about him is he’s very truthful,” Portnoy’s longtime friend Elio Imbornone said. “You might not want to hear exactly what he wants to say, but he says what he believes and you’ve got to respect that.”

Still, not everyone at Barstool is free to broadcast their opinions. In 2018, Portnoy removed two posts that cast a sympathetic light on Brett Kavanaugh’s sexual-assault accuser Christine Blasey Ford, citing Barstool’s “no politics” policy, but left other posts on the hearings in place. Two years later, amid Black Lives Matter protests, Portnoy told his content team, in an email reviewed by Insider: “If anybody wants to write about politics or mentions white privilege or BLM on either side of the fence it must be approved by me and only me. Nobody else has the authority to publish anything.” He told them “not to bother” asking Barstool’s editor in chief, Keith Markovich. “Ask me.”

It’s even written into Barstool contracts that employees need to check their political correctness at the door.

In 2017, the sportscaster Elika Sadeghi leaked the terms of the Barstool contract she was offered after the company pursued her for an on-camera position.

“I understand and acknowledge that as part of my job I may be exposed to speech and conduct that explicitly relates to sex, sexual orientation, gender, national origin, religion, disability and age,” it said. “I expressly agree and represent that I do not object to being exposed to such speech and conduct and do not find it otherwise offensive or objectionable, and that I am willing to work in such an environment.”

Sadeghi did not accept the job.

Critics of Barstool, both within and outside the company, told Insider there’s a real risk to speaking out.

The online community of Stoolies, as Barstool’s fans call themselves, have waged harassment campaigns against detractors. These have included death threats, doxing, online harassment, and targeting of people’s families, friends, and workplaces.

Bob Murchison, a private-equity investor with no professional connection to Barstool, first began tracking Barstool’s content in 2019 after it hired a radio host with a history of transphobic comments. Murchison, who has a transgender son, has taken it upon himself to privately warn advertisers of what he perceives to be the company’s transphobic, misogynist, and racist content.

In 2019, a Barstool employee shared a tweet containing Murchison’s cellphone number and email address; his home address was posted on fan-run message boards. In response, Stoolies sent Murchison death threats and packages (including one with an object meant to look like a bomb and another containing feces), staged a “prayer vigil” in his hometown that was also attended by Barstool employees, contacted organizations with which he was affiliated to make false claims of criminal activity against him, and showed up to his house, where they filmed videos of their trespassing, which they later posted online.

“I reached out to Erika Nardini” — Barstool’s CEO — “and Barstool counsel several times asking them to address this horrific behavior,” Murchison told Insider. “Their responses left me with the impression that the harassment would only be stopped if I agreed to stop my criticism of their content. I believe the harassment was intended to intimidate and silence me.” Nardini did not respond to our request for comment.

Portnoy declined to get involved, saying on “Barstool Radio” in 2019: “This Murchison guy, he sounds like a crazy person. I’m not going to war with someone I’ve literally never said a word to.”

But Portnoy doesn’t always stay silent.

This spring, Nantucket magazine featured a glowing profile of Portnoy, including a cover shot with Portnoy lounging in the ocean atop a rosé floatie. After readers complained about being offended by Portnoy’s inclusion given his history of misogynistic and racist comments, the magazine issued an apology. Portnoy went on the attack, telling Page Six that the Nantucket magazine editors were “spineless jellyfish who are held hostage by the whims of the vocal minority.” He added that anyone who didn’t like him “can go fuck themselves.”

Since 2020, Portnoy has issued commands on Twitter for his fans to “ATTACK!!!!” people who criticize him or Barstool, tagging an employee who was hired expressly for the purpose of harassing Portnoy’s enemies.

In 2017, Portnoy publicly accused his ex-girlfriend Jordyn Hamilton of cheating on him with a SoulCycle instructor. Stoolies responded en masse, waging a harassment campaign not only against Hamilton but against SoulCycle. When Portnoy saw a message from SoulCycle’s corporate office advising studio managers on how to deal with harassment from Stoolies, he tweeted: “Best way to avoid calling 911? Don’t have your instructors fuck the girlfriend of the head of major media company.”

“It was really, really tough for me and my family, everything being put online,” Hamilton told Insider.

Despite Hamilton’s personal experience, she said she continued to be on good terms with Portnoy. “Dating him, you kind of have to go into it with a thick skin,” she said, adding: “I think that today a lot of people are kind of soft.”

Not everyone is as forgiving.

The podcaster Ali Weiss told Insider she was on the receiving end of Stoolie harassment for several months in 2016 and 2017 following an appearance on “Barstool Idol.” The commentary, she said, included calls to kill her and jabs about “my shitty sense of humor, my shitty eyebrows, the fact that I looked like a man.”

While Portnoy was not a perpetrator in her harassment, Weiss believes he has created a culture in which the Stoolies run wild and Portnoy rarely tries to stop them.

Weiss described the Stoolies as “h​ordes of basically crazed superfans of Dave who were trying from afar to impress him.”

“And Dave was hyperaware of this,” she said. “Everything that Dave Portnoy does is to incite the Stoolies to do his dirty work for him.”

Last July, a young woman, Allison, was at her family’s home on Nantucket. She had just graduated from high school. According to several people on the island, Portnoy was a celebrity on Nantucket. Recent high-school graduates from wealthy New England towns would try to land an invitation to Portnoy’s house while summering on the island.

“The reputation on the island is that he is a God and a king and kind of untouchable,” Allison said. “And everyone wants to get into his house for parties.”

Allison’s sister, Olivia, who had recently graduated from college, told Insider that some of her friends were sending Portnoy direct messages attempting to get the mogul’s attention but he “wasn’t giving them the time of day.” Then they realized that her 19-year-old sister, Allison, might be more his type.

“They said: ‘You should reach out to him, he likes younger girls.’ And he completely took the bait,” Olivia said. “He was much more interested in her than any of my 22-year-old friends.”

Allison sent Portnoy a message telling him she was on the island and would love to see him. He invited her over to his house, and she asked him whether she could come by with a couple of friends.

“While we fuck? Seems weird,” Portnoy wrote in a message viewed by Insider. Allison responded, “Nah they don’t mind.”

Portnoy told Allison he didn’t like her friends messaging him, then wrote: “I’m not cool with your friends coming. Sorry.” Allison called off the meetup, unwilling to go alone.

About a week later, though, she messaged him again. This time, the two agreed to meet up in the afternoon. “I was definitely pushed by my friends,” Allison said.

Allison recalled sitting by the pool. Portnoy offered her watermelon and water. He asked her which school she went to and which grade she was in, Allison recalled. Then, she said: “He got up to go inside and I was like, ‘OK, I’ll go in with you.’ And he was like, ‘I didn’t know it would be that easy.'”

“He leaned in and started kissing me and I didn’t know what to do at that point,” she added. “And we went upstairs and he was really aggressive and I didn’t know what to do and we had sex and that was it and he kicked me out.”

Allison said her memories were fuzzy because of her emotional distress surrounding the event, but, like Madison, she said Portnoy choked her.

“​​He kept spitting in my mouth, which was really gross,” Allison said. “I was kind of scared. I didn’t want to disappoint him.”

A little over an hour later, Allison’s friends picked her up. One of the young women who was in the car told Insider that Allison was uncharacteristically quiet. “She was clearly almost in shock,” she said.

“She basically couldn’t talk the next day,” Allison’s mother told Insider.

Allison does not describe what happened to her as sexual assault but said she was still deeply disturbed by the experience. “I just felt very preyed on,” she said.

Soon after Allison’s encounter with Portnoy, two photos — a selfie Allison had taken with Portnoy and a photo her friend took of her leaving his house — began to circulate the island. Both were posted on private Snapchats by Allison’s friends but were then screenshotted and shared widely. Before long, it felt as though the entire island knew what had transpired between Allison and Portnoy, Olivia said.

Allison, who has had depression, said she felt stressed and overwhelmed following her sexual encounter with Portnoy and the subsequent attention it got. “I guess it was kind of my breaking point,” Allison said.

Three nights after having sex with Portnoy, Allison was suicidal and was hospitalized.

While she was in the hospital, her mother began going through her phone trying to understand what had happened. After finding Portnoy’s messages, Allison’s mother called the Nantucket Police Department.

She told the police, “Go put somebody outside his door because you’re going to see every day there’s some young girl being dropped off.” Insider viewed police documents confirming this call.

Her mother wanted to pursue some sort of legal action against Portnoy, but Allison refused.

“I knew he would drag me through the mud,” Allison said.

For years, Dave Portnoy has been untouchable. In 2020, following the controversy surrounding his use of the N-word, Portnoy declared himself “uncancellable.” Throughout all the scandals and controversies, Barstool has attracted advertisers like Dunkin’ Donuts and Coors, partnered with Walmart on a line of frozen pizzas, and nabbed the rights to broadcast the Arizona Bowl from CBS Sports. 

But insiders say Barstool has been slowly distancing itself from its founder in an attempt to reshape its image.

In 2016, Erika Nardini beat out 74 men to become Barstool’s new CEO, and she brought with her an influx of high-level female executives. The company began to branch out in its content, as well, launching five female-lifestyle podcasts including “Chicks in the Office,” “Call Her Daddy,” and Nardini’s own “Token CEO.”

Then, in 2020, Penn National Gaming purchased a 36% stake in Barstool. The next year, Penn National’s stock joined the S&P 500 index. Portnoy suddenly was newly accountable as part of a publicly traded company.

Eric Schippers, Penn National’s senior vice president, told the local news site Billy Penn in an email that the company was confident Barstool “has the right guardrails in place to ensure that their comments won’t negatively reflect on PENN or the gaming industry in general.” He said this included “comments that might be deemed as harassment or discrimination of women or minorities.” (Penn National did not respond to our request for comment.)

Following the Penn National acquisition, Portnoy convened his staff for a meeting. According to numerous former employees who attended, he told them he was contractually obligated to stay at the company for five years but planned to leave afterward to pursue other ambitions like sports team ownership.

Portnoy’s celebrity status and professional success should open many doors should he choose to leave Barstool. But some who have worked with Portnoy can’t help being concerned by his past behavior, particularly his sexual exploits with young women, some recently graduated from high school.

In the popular r/barstoolsports Reddit thread, Stoolies regularly discuss Portnoy’s conquests.

“Playing a dangerous game here Davey,” is the title of one thread, referring to a since-deleted TikTok posted by a 19-year-old who said Portnoy began pursuing her on Instagram shortly after her high-school graduation.

Several additional TikTok videos, many of which have since been made private or taken down, purported to show private messages from Portnoy sent to women soliciting sex. When the poster of one of these videos — who was 19 at the time of posting — was reached for verification, she forwarded a screenshot of the message to Portnoy. He tweeted it out to his followers with the caption “Hard hitting research from @BusinessInsider dm’ing girls who follow me on insta asking if they’ve Dm’d with me.”

Portnoy later acknowledged on his podcast that he’d sent messages to this woman, though he said they never met up.

The Instagram influencer Ava Louise recalls messaging with Portnoy in August 2017. At the time, she had just turned 19, and he was 40.

A post shared by Ava Louise (@avalouiise)

“I never reach out,” he texted her in August 2017, in messages viewed by Insider. “I noticed you 2 weeks ago and was interested.” Later he wrote, “I thought about you a bunch last night. Not all wholesome all the time.”

“I wanna be famous so bad I’d be so good at it,” she wrote later.

“I’m a good start then 😏,” he replied.

Though she responded willingly at the time, Louise said she had come to see an inherent problem with “a man in power knowing he could take advantage of a younger girl.”

“It’s predatory,” she said.

Louise said it’s not just a problem with Dave Portnoy.

“It’s every man that has followers or status of any sort, and it’s kind of, like, terrifying in a way,” she said.

She says her parents were “really freaked out by it” when they found out she was thinking of meeting up with him and threatened to stop paying for her college if she followed through. Today, she’s grateful for their intervention.

“I probably would have let Dave Portnoy do whatever the hell he wanted to me,” she told Insider.

“Because I’m like, ‘Oh my God, it’s Dave Portnoy,'” she added. “I’m glad I didn’t have that experience.”

If you want to get in touch with Insider regarding Barstool Sports or Dave Portnoy, email featuretips@insider.com

Additional reporting by Kat Tenbarge.

If you or someone you know is struggling with depression or has had thoughts of harming themselves or taking their own life, get help. The National Suicide Prevention Lifeline (1-800-273-8255) provides 24/7, free, confidential support for people in distress, as well as best practices for professionals and resources to aid in prevention and crisis situations.