Barstool Sports founder Dave Portnoy has revealed that a significant business deal and subsequent move to New York City in late 2016 were the primary factors leading to the demise of his marriage to Renee Satterthwaite.
In his recently published memoir, "Cancel Me If You Can," Portnoy, 49, explains that the $12.5 million investment deal with the Chernin Group presented a turning point. The deal necessitated Barstool's relocation from Boston to New York, coinciding with a period when Portnoy had anticipated easing his work schedule. Instead, the investment required him to re-engage in an intense work cycle.
"Looking back on it now, if there was one singular event that I could point to that ended Renee's and my marriage, I would say it was the Chernin deal and this move to NYC," Portnoy wrote in his memoir. "Of course, nothing is that simple in retrospect, but it definitely played a major factor."
He elaborated that while he had worked relentlessly on Barstool for thirteen years and felt he could finally ease up, the Chernin deal meant "starting over." His commitment to making the investment work led to a never-ending work cycle, while Satterthwaite, who had left her job, found herself in New York with Portnoy working constantly, causing them to grow distant.
The couple separated in 2017, after eight years of marriage, but remained legally married. Their attempt to legally divorce in March 2023 was denied by a Massachusetts judge who found their proposed financial arrangement, which included Portnoy funding all of Satterthwaite's expenses and healthcare, to be "unacceptable" and not equitable.
According to Portnoy, the judge believed Satterthwaite should receive half of his fortune, an amount she did not seek. The couple ultimately agreed to continue their existing financial arrangement without formal divorce, meaning they remain legally married. Portnoy, who is estimated to be worth $250 million, and Satterthwaite continue to share a joint bank account.
Despite the marital separation, Portnoy stated that he and Satterthwaite remain close friends. "Going our separate ways was the hardest thing I've had to do in my life," he wrote. "There was no big fight. We still loved each other and honestly wanted the best for each other. But it just wasn't working anymore."
He also reflected on the Chernin Group deal, acknowledging that Barstool would not have achieved its current status without it, though he noted the negotiation process was nearly derailed. Portnoy recounted an instance where he threatened to walk away from the deal over a disagreement about $50,000 in legal fees. He insisted that the Chernin Group honor their initial agreement to cover these costs, emphasizing the principle of upholding one's word.
Since 2024, Portnoy has been publicly dating Camryn D'Aloia, who is 22 years his junior.