Dave Portnoy has finally spilled all on the deterioration of his doomed marriage – and why a $12.5million business deal was the final nail in the coffin.
In an explosive new memoir published Tuesday, the founder of Barstool Sports, 49, has told how the meteoric rise of his media empire ultimately precipitated the demise of his marriage to Renee Satterthwaite, who he wed in 2009.
Barstool’s headquarters, which were originally established in Portnoy’s native Boston, made the move to New York City in late 2016 following a multimillion-dollar deal with the Chernin Group investment firm – a deal Portnoy almost walked away from at the eleventh hour.
‘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, Cancel Me If You Can. ‘Of course, nothing is that simple in retrospect, but it definitely played a major factor.
‘I had been working on Barstool relentlessly for thirteen years – literally since the day I met her. I had finally gotten to the point where I could take my foot off the gas a bit. I could enjoy a weekend off without freaking out. We could take a normal vacation. But once the Chernin deal happened, in many ways it was like starting over.
Barstool Sports founder Dave Portnoy and his estranged wife Renee Portnoy
Renee celebrates the 2017 Kentucky Derby at an event in Nantucket, Massachusetts
‘I had made a promise to do whatever I could to make this investment work. That meant I was back to a never-ending work cycle right when it seemed like maybe I had been going to take it back a bit. And for Renee’s part, she had left her job and was now stuck in the middle of Manhattan with me working nonstop. We just started to grow distant.’
The couple split the year after the move to New York in 2017 – after eight years of marriage – but did not legally divorce. In fact, to this day, they remain married.
They attempted to legally separate in March 2023, citing irretrievable breakdown, but a Massachusetts judge denied their petition due to the couple’s financial requests.
Court documents obtained by the Daily Mail show the couple requested to maintain their joint bank account, which would be ‘entirely and exclusively funded by [Portnoy] for the payment of all expenses of [Renee] without limitation.’
Portnoy also wanted to commit to providing medical and healthcare coverage for his ex-wife.
But a judge denied their divorce petition in 2023, calling their proposed arrangement ‘unacceptable.’ The judge felt the arrangement was not equitable to Renee, believing she should receive half of Portnoy’s fortune in the divorce, the businessman explained in 2024.
Renee, however, did not want as much as half, per Portnoy, so the pair agreed to continue their fluid financial situation without legally divorcing.
As a result, the exes still remain legally married. What’s more, the Barstool chief, who is worth an estimated $250million, and Renee still share a bank account.
Portnoy at an Indiana Fever versus Connecticut Sun WNBA game in 2025 in Boston
Portnoy and his girlfriend, Camryn D’Aloia, at a Boston Celtics versus Dallas Mavericks NBA game in 2024
Portnoy’s memoir, released via Gallery Books
And since 2024, Portnoy has been in a new relationship with Camryn D’Aloia, who at age 27 is 22 years his junior.
Certainly, it is an unusual dynamic, but Portnoy claims he and his wife remain close friends.
‘Going our separate ways was the hardest thing I’ve had to do in my life,’ Portnoy wrote in his memoir. ‘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.
‘And if you’re wondering if we stay in touch, the answer is that we do. She’s always been there for me and vice versa even after all these years. She’s still my best friend.’
Despite it bringing about his split, Portnoy has admitted that Barstool would not have ‘become who we are without’ the Chernin Group deal – even if he almost did back out at the last minute.
‘I’ve gone back and forth over the years on whether the Chernin Group screwed us with that $12.5million offer,’ Portnoy wrote. ‘Do I think they knew it was wildly low? Yes, probably.
‘But at the same time, it’s not like any other investment companies were beating down my door. They were the only ones who showed any real interest. So for that, they get a lot of credit. And there is no chance we become who we are without them.
‘But I also wouldn’t trust them as far as I could bowl them in terms of any future negotiations.’
Portnoy and D’Aloia, who is 22 years younger than her boyfriend, attend Jake Paul versus Anthony Joshua Fight Night in 2025
Portnoy appears on the Megyn Kelly show in 2025
And it was one particular negotiation niggle that left the deal teetering on the edge of implosion.
Portnoy claimed that during the negotiation process the Chernin Group had agreed to foot the bill for his $50,000 legal fees in order to get the deal over the line.
However, once they reached said goal line, he alleged, Chernin renegaded on that promise, sparking a furious reaction from Portnoy, who put his foot down.
‘They also learned a very early lesson on how to deal with me during the final stages of closing this deal,’ he explained. ‘As long as you always do what you say and say what you do, I will always get along with you. I can take bad news. I don’t always need to get my way. But when you say something to me, it’s in stone.
‘I absolutely refused to move forward. I told them the deal was off if they didn’t honor their word. There would be no negotiations. I wouldn’t pay 50 percent or five dollars of it. They agreed to pay it and that was that.’
The Daily Mail has contacted the Chernin Group for comment.
‘In the scheme of things, it wasn’t that big of a number; it was the principle of it that mattered to me,’ Portnoy continued. ‘I doubt they’ve ever had somebody seriously threaten to walk away over something so minor, but I was 100 percent ready to torpedo the entire thing over it. Do what you say. Say what you do. Always.
‘Once we got past that last little snafu, we were off and racing. Somewhere along the way we all agreed that the new HQ would be in New York City.’
And, of course, it was there that Barstool flourished, and his marriage ultimately withered.
