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…

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