Bill Simmons beat Pat McAfee to come out on top in the Sports Media Influence Olympics on Awful Announcing’s The Play-By-Play. The Ringer founder will never receive a ringing endorsement from Jeff Pearlman, however.
On Wednesday, Pearlman posted a TikTok captioned, “Bill Simmons is THE BIGGEST TOOL in sports media. It’s true.” The New York Times bestselling author gave several reasons why he feels so strongly about it.
“Bill Simmons is a loser,” Pearlman said. “And I know he’s a winner in that he’s made a lot of money, and he’s been successful, but he’s such a f*cking loser. And it actually drives me crazy.”
Pearlman cited Simmons’ recent flub on his eponymous podcast. He admitted to using his daughter’s boyfriend as a proxy to place sports bets, which predictably prompted swift backlash. “I learned my lesson,” Simmons said earlier this week. “Proxy betting is not allowed. I actually thought it was, but that’s fine.”
Simmons’ bets in question have since been voided, and the Massachusetts Gaming Commission is “currently reviewing the matter.”
“You’re a f*cking loser,” Pearlman said after reading one of Simmons’ quotes about how Hank, his daughter’s boyfriend, acted as his proxy. “Like, you’re a loser! First of all, Bill Simmons has done, to me, in my opinion, more to sort of [marry] gambling and sports than any sports media figure. Like, by far, the most.”
@jeffpearlmanauthor Bill Simmons is THE BIGGEST TOOL in sports media. It’s true. #billsimmons ♬ original sound – Jeff Pearlman
“He is in bed with gambling times a million,” Pearlman continued. “He doesn’t care how addicted one becomes. He doesn’t care about the negative repercussions of gambling; he doesn’t care. He doesn’t care about kids gambling. He doesn’t care about the ethics of gambling. He is in it for the money.”
Pearlman said he thinks it’s “insane” that Simmons would so brazenly admit to proxy betting. “Bill Simmons is owned by FanDuel, and it is just pathetic,” Pearlman said.
Pearlman also criticized Simmons’ bit of using ChatGPT to generate posthumous movie reviews from the late Roger Ebert on The Rewatchables. Simmons has come under fire for boasting ChatGPT as the “AI sponsor” of select podcasts for The Ringer.
“He just sucks, man,” Pearlman concluded, noting that he doesn’t want to hear any argument about gambling’s place in sports media. “He just sucks. He’s done a lot of amazing things in sports media. He’s a very talented guy, but he just has no soul. He has no soul. He is a f*cking ghoul. Like, all the sh*t with gambling, he just doesn’t care. He just doesn’t care. He took the money, and he ran with it, and he doesn’t care how it affects people. And I think it’s f*cking disgraceful.”
About Megan Armstrong
Since first getting published as a student by the Kansas City Star in 2013, Megan Armstrong has gone wherever curiosity and stories have taken her, specializing in sports, media, music, and culture coverage. She also has an extensive background in interviewing and profiling public figures. Her work has appeared in Billboard, Boardroom, Bleacher Report, Esquire, GQ, GRAMMY.com, NYLON, Newsweek, Teen Vogue, The Hollywood Reporter, UPROXX, and elsewhere.