Dave Portnoy’s new book recounts origin of feud with Bill Simmons

Dave Portnoy’s new book includes a candid account of his decades-old grudge against Bill Simmons and how he feels like he eventually got the last word.

In an excerpt from his new book, “Cancel me if you can,” Portnoy writes that if you wanted to pretend you knew Boston back in the day, you talked about Ben Affleck, Matt Damon, or maybe Bill Simmons, but if you were actually from Boston, you talked about Barstool. He’d never met Affleck or Damon, but Simmons was different. He was close enough to actually cross paths with, and important enough to Portnoy’s own development as a writer.

“I did have a well-documented feud with Bill Simmons,” Portnoy writes. “And when I say well-documented, it’s because I documented it.”

Simmons’ writing, Portnoy says, directly shaped the early style of Barstool. So when he tried to land an interview with him for the paper, the rejection stung more than it otherwise might have. Simmons blew him off roughly 10 times before agreeing to take questions, then reversed course and pulled out of the interview, telling Portnoy he didn’t want to do any additional media.

“I wouldn’t say it hurt my feelings, but it definitely pissed me off,” Portnoy writes, noting that Simmons had just left Jimmy Kimmel’s show for ESPN. “What do you mean you don’t want media attention? F*ck this guy then, I thought.”

Portnoy allows, with the benefit of hindsight, that Simmons probably had no idea who Barstool was at the time. He maintains anyway that while Simmons is “definitely a far better writer” than he is, nobody on earth would rather grab a beer with Simmons than with him.

I always say that during those days, if you wanted to pretend like you knew about Boston, you talked about Ben Affleck, Matt Damon, or maybe Bill Simmons. But if you were really from Boston, you talked about Barstool.

(Author’s note: Weirdly enough, I’ve never met with or spoken to Matt Damon or Ben Affleck. However, I did have a well-documented feud with Bill Simmons. And when I say well-documented, it’s because I documented it. When I launched Barstool Sports, Bill Simmons was the man; the best writer I had ever read. His writing style certainly influenced the early days of Barstool. I eventually reached out to interview him for the paper and he blew me off a few times. And by a few times I mean like probably ten times. Finally he got back to me and said to send over the questions, which I did. He then replied that he didn’t want to do any additional media, so the interview was canceled. I wouldn’t say it hurt my feelings, but it definitely pissed me off. He had just moved from Jimmy Kimmel to ESPN. What do you mean you don’t want media attention? Fuck this guy then, I thought. In hindsight, maybe I was a bit harsh. He didn’t live in Boston anymore and maybe he had no clue who we were. Either way, it knocked him down a few pegs in my book. The one thing that I always said about Simmons back then and still maintain now is that he is definitely a far better writer than I am. But there is nobody on earth who would rather have a beer with him than have a beer with me. Of course, I’ve never met the guy, but I’m pretty sure I’m right.)

The score, as Portnoy frames it in the book, eventually settled itself.

In 2025, Barstool signed Ryen Russillo away from The Ringer, the media company Simmons founded, where Russillo had called home for six years as one of its most prominent NBA voices. Portnoy writes that landing Russillo meant beating out Simmons specifically, the same person who once wouldn’t grant him an interview. The move ended one of the more reliable institutions in NBA podcasting: Russillo and Simmons’ Sunday night NBA pods had run every February through July for seven straight seasons, and Simmons had to scramble to fill the void, eventually pairing with Ringer colleague Zach Lowe for that Sunday NBA slot.

Russillo brought longtime Ringer producers Steve Ceruti and Kyle Crichton — Crichton happens to be Simmons’ actual nephew — along with him to Barstool, and has since said the arrangement has exceeded his expectations, crediting Portnoy’s transparency in contrast to his reputation.

Portnoy and Russillo’s connection predates any of this, too. The two met two decades ago through a mutual friend and former ESPN draft analyst, Todd McShay – now with The Ringer — back when Barstool was still a paper Portnoy distributed by hand around Boston, and the book notes that McShay and Russillo were both essentially working for free at the same small radio station Portnoy ran in those early years. McShay went on to ESPN stardom and helped bring Russillo to the network as well, before Russillo eventually left for The Ringer in 2020. The Barstool signing closed the loop on all three men’s overlapping early careers in a way that, as Portnoy tells it, was 15 years in the making.