In November 2021, three young women came forward about sexual encounters they had with Barstool Sports’ founder, Dave Portnoy. These women told Insider the experiences with Portnoy turned frightening and humiliating and had taken a toll on their mental health. Two of the women also said Portnoy filmed their encounters without their consent.
Since then, three more young women have told Insider that Portnoy filmed them during sex without asking for permission. They ranged in age from 18 to mid-20s at the time.
One of these women, given the pseudonym Kayla by Insider, says Portnoy broke one of her ribs during an encounter that he filmed. A physician diagnosed the injury as an “assumed fracture.”
Many of these women who were filmed by Portnoy said they were scared to ask him to stop recording because of his aggressive behavior; some said the fact he then possessed these sexually explicit videos and photos discouraged them from doing anything in future interactions that might anger him.
A total of four women have now told Insider that Portnoy has sent them at least 19 unsolicited videos of what appears to be him having sex with other women.
Two of these videos, viewed by Insider, show women who appear to have difficulty breathing as they are being choked. One of the women interviewed also showed Insider an explicit photo from Portnoy of a woman’s body covered in red marks with an accompanying message boasting that he was responsible for the injuries.
Kayla, the woman who said Portnoy broke her rib, asked that Insider use a pseudonym to protect her from Portnoy’s fiercely loyal fans. Her identity, however, is known to the sports-media mogul as well as to his attorney Andrew Brettler.
After Insider approached Portnoy for comment for this article, he tweeted out a four-page letter from Brettler responding to Insider’s questions. Brettler represents several high-profile figures accused of sexual misconduct, including Prince Andrew, Chris Noth, and Armie Hammer.
The letter doesn’t deny that any of the alleged encounters took place, though it says all of Portnoy’s sexual encounters “have been entirely consensual.” The letter acknowledges Kayla’s rib injury and says she told Portnoy that sex with him was the most aggressive she ever had. Brettler says Portnoy “never filmed any sexual encounter surreptitiously or without the full knowledge and participation of his partners.”
The day after Portnoy tweeted his lawyer’s letter, Brettler wrote directly to Kayla and demanded that she renounce the statements she made to the Insider reporter Julia Black.
Courtesy of Kayla
“We demand that you immediately set the record straight with Ms. Black and retract the false allegations you made about our client,” the letter said. “Your failure to do so will expose you to substantial liability for defamation.” The letter also demanded that Kayla preserve all documents and materials pertaining to Portnoy.
Kayla has decided to move forward with telling her story.
“I know what happened to me, and I know what I experienced,” she told Insider. “I know what I went through, and I remember everything in those encounters so vividly, and I’m just very determined to speak up and share my story and hopefully encourage other women to feel confident to speak up.”
She added that she wanted to support the women who came forward in the first article.
“I have to stand up for these girls,” she said.
Kayla first messaged Portnoy on Instagram in the summer of 2017. Kayla, who was 21 at the time, was between her junior and senior years in college, living at her parents’ home in Connecticut. Portnoy was 40.
“I didn’t even think he would respond,” she said, adding that she was intrigued by Portnoy, who has millions of Instagram followers and a rabid fan base.
To her surprise, Portnoy replied within 24 hours. He sent her a direct message on Instagram, commenting on a photo of her posing in a bathing suit with her dog. “Mini Schnauzer and great ass. Nice combo,” he wrote. Kayla said she excitedly took a screenshot of this message — which she shared with Insider — along with other early ones from Portnoy when they popped up on her phone as push alerts.
Kayla and Portnoy continued to exchange flirtatious messages on Instagram and Snapchat for several weeks, Kayla said.
“I generally get what I want soooo,” he wrote in one Instagram message, urging her to come to his New York City home after learning her parents had an apartment on the Upper East Side.
“It was definitely exciting because he was famous,” Kayla said. “I was also obviously nervous, too, because I don’t know him and he was so much older than me.”
The two arranged to meet at Portnoy’s downtown apartment.
John Parra/Getty Images for Barstool Sports
An Uber receipt viewed by Insider shows Kayla was dropped off next to Portnoy’s apartment at about 10:30 p.m. that first night they met.
She took an elevator that opened directly into his apartment, and, soon, they had sex. It was more aggressive than Kayla anticipated. Kayla told Insider that at one point Portnoy began choking her so hard she couldn’t breathe and that she became frightened. He also slapped her on the butt so forcefully that it left red marks that lasted days. One of Kayla’s friends told Insider they viewed the red marks a few days later.
“I have never experienced that before,” she said. “Like, sure, it’s fun to get choked a little bit. It was just way too much. It was scary. I was getting no air. Not being able to breathe is one of the scariest things, and it sends you into such a panic.”
Kayla said she was too intimidated to try to push Portnoy off her.
“It’s hard to stand up for myself more. It’s like, ‘Oh, he’s so much older, he’s famous,'” she said.
Toward the end of their sexual encounter, Kayla said, she saw Portnoy holding his iPhone and recording her.
This was “odd and creepy,” she said, adding that the overall experience left her feeling “startled.” But she was willing to see Portnoy again.
Her friends, most of whom didn’t know the details of her sexual encounter with Portnoy, “thought it was kind of cool that I hooked up with him,” she said. She added that she enjoyed the attention he gave her.
So, about a month later, when Portnoy asked Kayla to come over to his New York City apartment again, she agreed. She said it didn’t even cross her mind that he might try to film her again or that the sex would become even more violent.
“Maybe I was being naive and hoping that something would be different,” she said.
“I just thought you know like: ‘He wants to see me again? How cool is that? He likes me. I’m good enough to get a second invite,'” she added.
Later, she would regret this decision. She says the sex during her second encounter was far rougher than she had anticipated or would have agreed to had she been asked.
“I always think back to it,” she said, “like, ‘Yes, it was technically consensual sex, but that was not the sex I consented to.'”
Kayla arrived at about 8:30 p.m. Early on, Portnoy and Kayla were standing in the hallway of his apartment talking when their conversation turned sexual, she said. Then, Kayla said, Portnoy suddenly slapped her across the face “full force.”
“I was like, ‘What the fuck?'” she said. “It just came out of nowhere. It wasn’t like a light slap.”
Kayla said she was shocked and afraid to speak up. “If he can hit me that hard, I was like, ‘I don’t want to make you mad,'” she recalled.
She started to panic and was overwhelmed with anxiety, she told Insider. “I’m in this guy’s apartment, he’s twice my age, famous, and I felt trapped almost,” she said. She worried that he could become forceful if she tried to leave and figured it was just better to go along with it all.
She ended up with her back on the living-room rug, having sex that she described as very painful. She said she could feel the skin on the small of her back “pulling away” during those moments. She developed a 3-inch-long rug burn.
“It really hurt,” she said. Photos viewed by Insider show layers of skin missing from Kayla’s back.
“It was literally raw flesh on her back,” said the friend who saw the wounds a few days later. This friend also recalled hearing contemporaneously about the slap.
Courtesy of Kayla
After several minutes, Portnoy and Kayla moved to the bedroom and started having sex on the bed. She said he attempted to have anal sex without her permission.
“He didn’t ask — he just like, tried to force it in,” she said, adding that she told him “no” three or four times because she “knew it would have been excruciating.”
“I really was trying to convince him, ‘I do not want that, that is absolutely not going to happen,’ but he kept trying,” Kayla said. Eventually, she said, he listened to her and “gave up.”
At one point, Kayla said, Portnoy was behind her and gripped her rib cage so tightly that she felt as if her body “was compressing in on itself.” Kayla believes this was when one of her ribs broke.
Shortly after, Portnoy placed his iPhone on the pillow in front of her. She said she felt too intimidated to ask him to stop recording.
Later, when he showed her the video he’d taken, she realized he’d been filming before she’d seen the phone.
When they were done having sex that night, Portnoy and Kayla went back to the living room to clean up the blood from her back wound.
Kayla spent the night at Portnoy’s but lay awake in bed. “I remember thinking: ‘I will not come back here. That’s it. I’m done,'” she said.
The next day, Kayla began experiencing pain and pressure in her chest as well as difficulty breathing. Embarrassed to explain to her parents why she would need to see a doctor, Kayla waited until she returned to college before visiting her school’s medical center. At that point leaning over, laughing, and working out had become extremely painful, she said.
A second friend saw Kayla in the days following her second sexual encounter with Portnoy. The friend said Kayla relayed the events to her in detail and said the experience “scared the shit out of” Kayla.
“We were 21. We were a little stupid, clearly,” the second friend said. “But I do specifically remember her being in a lot of pain.”
Insider reviewed a patient-visit summary dated September 4, 2017 — two weeks after Kayla said she and Portnoy had their last sexual encounter. The medical document said Kayla had “difficulty taking full breaths” and “specific site pain/swelling on chest bone.” The doctor didn’t order an X-ray, since most rib fractures heal on their own, but the provider’s assessment says “assumed fracture to left true rib #2” with advice to “rest and do deep breathing exercises to prevent pneumonia.” Kayla said she didn’t inform Portnoy about her diagnosis. Brettler’s letter said Kayla “joked about how she injured her rib during one of their sexual encounters and boasted to Mr. Portnoy that he ‘still holds [her] title for most aggressive sex.'”
Days after their second encounter, Portnoy texted Kayla three video clips of them having sex, which she says she eventually deleted.
She says she felt ashamed and hoped he wouldn’t share them with anyone else. But she also remembers feeling a lack of control.
“That really sucked, knowing that he had those,” she said, “and I felt like even if I told him to delete them, I would never trust him to actually delete them.” She said she tried to put the whole thing out of her mind.
In the months after their second encounter, Portnoy also sent Kayla at least three sexually explicit videos via Snapchat and text of him having similarly “aggressive” sex with several women, she said. Kayla said watching the videos, which appeared to show young women going through experiences similar to her own, was upsetting.
“He would text me or message me and be like, ‘Hey, I thought you’d like this,'” she said. “First of all, no I don’t like it. Second of all, I doubt that girl knows that you’re sending that degrading video to other girls.”
Annie Seifullah, an attorney at C.A. Goldberg PLLC, a national law firm that represents victims of privacy violations and sexual abuse, explained that in New York under a 2019 law, “Even if a person consents to having an intimate image being taken in the first place, it is still a violation of the law for someone to distribute that image without their consent” if there’s intent to harass, annoy, or alarm.
Portnoy made several attempts to meet Kayla in person again in the months following, but she refused, using her college schedule as an excuse, she said.
Courtesy of Kayla
Kayla says it took months to process what had happened to her.
“I think it takes some time and being removed from the situation to really realize how fucked up that all was,” she said. “It all felt very degrading.” Even once she came to terms with what had transpired, Kayla said, she was still too scared to talk about it publicly.
“It’s Dave Portnoy,” she said. “Everyone kind of knows if you go against him, it never turns out well. He’s basically built his brand around that idea. Like you don’t mess with him,” she continued, adding that the thought of widely sharing what happened made her anxious. “That just didn’t really seem like an option for me at the time.”
According to Brettler’s letter to Insider, Portnoy and Kayla texted again in March 2019 about a sexual experience she said she had with another celebrity in which the celebrity would “pin [her] down, choke [her] a little, slap [her] around a little, [and] bite [her]” (the letter included the bracketed text).
Kayla told Insider that she was no longer in possession of these messages because of an auto-delete setting on her phone but that the only other celebrity she’d had a sexual relationship with was a friend of Portnoy’s.
She described her sex with the celebrity as “the complete opposite of my experience with Dave” and said while they did engage in some of the acts described in the text, it was “respectful” and not nearly as forceful as what she said she experienced with Portnoy. She said there was communication with this celebrity about what she liked and she “never felt scared.”
Melissa A. Vitale, the communications director for NSFW, a sex-positive members-only club in New York City, told Insider that to safely practice BDSM — an abbreviation for bondage, dominance, sadism, and masochism — “both partners must give prior consent before performing any type of act or physically touching one another.”
“This includes discussing hard and soft limits of what each partner is comfortable with, agreeing on a safe word, negotiating pain levels, and checking in with your partner regularly throughout the process,” she continued. “Ultimately, any act should be pleasurable and desirable for both partners involved.” Things like hairpulling, choking, or spanking, Vitale said, don’t fall under the BDSM umbrella unless there’s consent and desire from both parties.
“He never hurt me,” Kayla said of the celebrity. “I felt confident. I felt good, which was not how I felt with Dave.” Kayla says this celebrity didn’t film them having sex.
According to Brettler’s letter, Portnoy said that shortly after Kayla messaged him about the celebrity, she wrote to him again saying Portnoy would “‘100% get laid’ if he helped her find a home for a certain rescue animal.” Brettler wrote that she also responded to a sexually explicit video Portnoy had sent her in which she wrote “fucking hot . . . miss that dick.” Kayla told Insider she didn’t recall writing these messages but usually answered sexually explicit videos he sent her with short replies meant to end the conversation quickly.
She also said she still felt intimidated by Portnoy and the fact that he possessed videos of the two of them having sex.
“It makes me scared knowing that he has those videos on his phone that I have no control over what he does with them, or how he uses them,” Kayla said.
“It’s really upsetting because it’s something that I can’t do anything about.”
Since its founding in 2003, Barstool has grown into a digital media juggernaut covering sports, gambling, and pop culture, with a mix of crude humor and barely clothed women. Portnoy himself has an estimated net worth of $100 million and has helped build Barstool into a $450 million empire that does business with brands including Dunkin’ and Walmart.
In the November article, one woman, given the pseudonym Madison by Insider, said she had sex with Portnoy at his Nantucket home last year that was so rough she was “literally screaming in pain.” Two of the women said Portnoy, now 44, both choked and filmed them without asking. The third, a woman given the pseudonym Allison, said she felt stressed and overwhelmed after her sexual encounter with Portnoy and the subsequent attention it got when her peers found out. Allison, who had depression, said she became suicidal three nights after the two had sex and was admitted to a hospital.
After that article was published, Portnoy acknowledged having sex with two of the women who were quoted but vehemently denied their characterization of the encounters. The day the article went live, he posted a nearly 12-minute filmed rebuttal on Instagram and Twitter, calling the allegations “100% not true” and saying he had “never done anything that’s remotely not consensual.”
On November 11, during an hourlong YouTube address, Portnoy speculated without evidence that Insider Inc. CEO Henry Blodget sought to profit personally by publishing the article on the day when Penn National, a public company with partial ownership of Barstool, was reporting its quarterly earnings. Portnoy went on to show anti-Trump tweets from Madison as proof she had an “agenda” since Portnoy publicly supported Donald Trump in the 2016 US presidential election and interviewed him in 2020. He also showed flirtatious messages from Allison after the two had sex but before she was hospitalized. Portnoy said he “did not film without advance permission.”
Tom Briglia/ Getty Images
On the day that article was published, he characterized Madison’s and Allison’s claims as not only false but also unique.
“Talk to all the girls I’ve actually hooked up with and known, you’re going to see just one after another, ‘great guy,’ ‘respectful,’ ‘yes, may like kinky sex,’ ‘yes, may send sext messages,’ things like that,” he said in his recorded statement, adding: “I’ve been pretty open about my sex life. None of the girls, besides this, have ever said a thing.”
When reached for comment for this article, Brettler, Portnoy’s attorney, argued that Kayla’s account lacked credibility because she continued to send Portnoy messages of a sexual nature two years after their last sexual encounter. He also characterized a second woman with whom Insider spoke as “unstable.” Brettler pointed to a yearslong history of sexual texts between his client and this woman, who was 18 when she first had sex with Portnoy, as evidence she couldn’t be telling the truth.
B.J. Cling, a clinical and forensic psychologist who specializes in sexualized violence, told Insider that after trauma, people often remain in touch with those who inflicted harm.
“By trying to contact the person who hurt you, you’re trying to undo in your own mind what really happened and make it into something else that actually it wasn’t because it feels better,” Cling said.
Following Portnoy’s publication of his attorney’s letter on Twitter, the woman who was 18 at the beginning of her relationship with Portnoy said she no longer wanted her experience detailed in the piece. “He has humiliated me and I can’t be part of it,” she wrote to Insider, expressing fear of what he might do if she continued to speak out.
In total, five women have now told Insider that Portnoy filmed them during sex without seeking permission.
Four of them said the sex that was recorded started consensually but then turned violent and frightening beyond what they would have agreed to had they been asked.
One of these five women had a different experience. She said the sex with Portnoy was rough, but consensual throughout. However, she told Insider that she never consented to Portnoy filming her during sex.
She said she saw the iPhone filming only when Portnoy yanked her hair back and repositioned his camera to capture her face in the moment. “I felt very anxious and embarrassed,” this woman said, adding that she tried to move her face out of the frame. She told Insider she asked Portnoy to delete the video but couldn’t say for certain whether he did.
She is certain that Portnoy has filmed other women during sex, though. She said he often sent her videos of himself having sex with different women, and she described some of the videos as “so awful” and “so degrading.” Eventually, she said, “I just stopped responding to him.”
In one of the videos viewed by Insider, Portnoy chokes a woman with both hands. One photo he sent, also viewed by Insider, shows a woman’s partially nude body covered in red marks. In an accompanying message, he claimed responsibility for the injuries.
Another woman told Insider she first sent Portnoy a direct message on Instagram in 2017 when she was 20 years old. After some flirtatious back-and-forth, she said, the conversation moved to Snapchat, where it became sexually explicit. Portnoy wrote that he wanted to have sex with her with “my hands pushing your face down into pillow so hard you can barely breathe.”
In another series of Snapchat messages viewed by Insider, Portnoy sent this woman a photograph of what appears to be his penis positioned in front of a woman’s face. In the photo he appears to be using his left hand to angle the woman’s face toward the camera. The woman has her hand over her face in an apparent attempt to block it from being photographed. “I dominated this girl,” he wrote. “Hahah,” he continued, adding: “I made her send this to all her friends while we were ducking.”
The woman who received the messages said that over several months Portnoy also sent her videos of him having sex with other women.
One video clip from Portnoy that this woman shared with Insider shows a close-up of an unidentified woman, who is red in the face and appears to be in pain, being choked. On several occasions, Portnoy offered to fly the woman he Snapchatted with to New York to have sex but she told Insider that, being as young as she was, she worried about what would happen. “I just made the decision not to. I had a gut feeling,” she said.
“When I saw your story come out I audibly gasped,” she wrote in an email to Insider. “It’s terrifying to know that I was one step away from potentially having that be a reality for me.”
Kayla says she’s fearful that Portnoy may still have videos of her, and of how he might use them if he does. She suspects there may be other women out there who share this fear.
“I can’t even imagine how many videos he has — how many girls have been through the same thing and they either don’t want to say anything about it because they’re scared or maybe they haven’t realized how messed up it really is,” Kayla said. “I’m sure a lot of them are younger girls, because that’s his type. So it might take those younger women time to come to terms with what actually happened.”
