Bill Simmons said he believes that Jon Stewart quitting over the cancellation of 'The Late Show with Stephen Colbert' is 'in play.' Screen grab: ‘The Bill Simmons Podcast’

Bill Simmons doesn’t think that Jon Stewart will quit on-air following the cancellation of The Late Show with Stephen Colbert.

But he also isn’t ruling it out.

On the latest episode of The Bill Simmons Podcast, The Ringer founder discussed the circumstances surrounding the impending end of The Late Show with Puck’s Matthew Belloni. And after stating that Monday’s episode of The Daily Show will now be one of the most highly anticipated late night programs since the David Letterman extortion scandal, Simmons revealed he believes it’s at least possible that Stewart could publicly re-sign in protest of Paramount Global’s decision to cancel Colbert’s show.

“I think it’s in play,” Simmons stated after Belloni brought up the possibility of Stewart quitting on-air. “I think it’s actually a must-watch show. It comes on at eight o’clock here. Like, I’m definitely watching that live. One hundred percent.”

Belloni agreed, although he also noted that The Daily Show is taped, which would make the logistics of such a stunt easier said than done. Simmons then added that he doesn’t think that’s ultimately how this will play out, but remained steadfast in his belief that Stewart will take a stand over the cancellation of The Late Show, which comes on the heels of Paramount Global paying President Donald Trump $16 million to settle a lawsuit regarding the editing practices on 60 Minutes.

“I don’t think he’ll do that because he’s got a whole staff working for him,” Simmons said. “But I also think he’s gonna have to stand up and I think everybody would have his back about how he’s gonna feel about this. If they canceled [The Daily Show], I think he’ll be fine. I don’t think it’ll be fine for a lot of people that work for him and I think he’ll feel bad about that. But this is the whole point of this show is he has to stand up to this. This is 25 years of him on Comedy Central, basically. He’s not sitting this one out.”

While there has been plenty of reporting — including by Belloni — on the economics of The Late Show‘s cancellation, many have been quick to connect the news to the recent settlement with Trump and Paramount Global’s impending sale to Skydance Media, which still needs approval from the U.S. Federal Communications Commission. That includes Simmons, who took to social media late last week to mock CBS’ statement on the matter and reiterated on his podcast that he believes there’s more to this story than the amount of money The Late Show was losing.

Adding another layer to all of this is the personal connection between Stewart and Colbert, who first rose to prominence as a correspondent on The Daily Show. It’s also worth noting that both late night hosts share an agent with Simmons in James “Baby Doll” Dixon, although the ex-ESPN columnist stated that he hasn’t discussed the situation with any of the involved parties.

Regardless of how much of a role the Trump settlement and/or the impending sale to Skydance did or didn’t play in the decision, Simmons isn’t wrong there will be more eyeballs than usual on Monday night’s episode of The Daily Show. And even if Stewart doesn’t quit on-air, it’s a safe bet that he’ll have plenty to say.

About Ben Axelrod

Ben Axelrod is a veteran of the sports media landscape, having most recently worked for NBC's Cleveland affiliate, WKYC. Prior to his time in Cleveland, he covered Ohio State football and the Big Ten for outlets including Cox Media Group, Bleacher Report, Scout and Rivals.