Bill Simmons and John Skipper.

It seems like it was eons ago when John Skipper and Bill Simmons were two of the biggest names at ESPN, but really it was just a few years ago. Skipper and Simmons were arguably the two names most synonymous with the direction ESPN was heading in the 2010s, with Skipper as the company’s president and Simmons as its most prominent personality with his podcast, Grantland, 30 for 30, and NBA coverage.

However, that era at ESPN came to an abrupt end all came to an end when Skipper announced in 2015 that the network would not be renewing Simmons’ contract. Simmons left to form his own Grantland-style website in The Ringer and signed on to do television work with HBO. That HBO work included his short-lived television show Any Given Wednesday as well as documentaries like the popular Andre the Giant film.

Skipper ended up leaving ESPN as well just two years later in an even bigger shock. Citing a substance abuse problem, Skipper stepped down from his post as ESPN president in 2017, ending his five year tenure. He’s now involved with the streaming platform DAZN.

Skipper and Simmons will always be linked together because of their time together at ESPN and in a stunning turn of events, the pair will be reunited once again. Skipper’s DAZN has bought sponsorship time on Simmons’ podcast and the former president will appear on the podcast of the man he once let go from ESPN, according to John Ourand of SBJ. I wonder if they’ll have anything to talk about…

This should be a must-listen, considering some of the feelings on display when Simmons didn’t have his contract renewed by Skipper at ESPN. Let’s take a brief walk down memory lane, shall we? Simmons told the Hollywood Reporter at the time of his release how he felt about the way his departure was handled and needless to say, he wasn’t happy about it.

He never would get that chance. Simmons woke up the next morning to a New York Timesreport that his contract would not be renewed. “This is not personal,” Skipper told Richard Sandomir of the Times. “It’s business.” ESPN had decided it would get ahead of the story in an attempt to control the narrative. Simmons, who had been at the company for 14½ years, was blindsided. “It was f—ing shitty,” he says, having caught the news, as many of his employees did, on Twitter. “By the way they handled it, you would think I played grab-ass with some makeup assistant or something.” His rage soon would turn to bitterness, and he never set foot in Grantland’s downtown Los Angeles offices again.

Skipper basically admitted that he blindsided Simmons at an ESPN Upfront presentation. Well, at least he didn’t deny the narrative that existed at the time to CNN.

It appears that Bill Simmons was as surprised as the rest of us to learn that ESPN wasn’t renewing his contract.

Shortly after ESPN announced that it was moving on from Simmons on Friday, reports circulated that the sports commentator wasn’t informed of the decision before the New York Times broke the news.

Speaking to reporters Tuesday, ESPN President John Skipper responded to a question about whether the report was correct.

“The narrative that you read is accurate,” Skipper told reporters following the ESPN Upfronts in New York. After a brief pause, Skipper chuckled and added, “I know I kind of dodged that, but I am going to.”

In 2016, Skipper was much harsher on Simmons. Much of the debate around Simmons’ ESPN exit revolved around his criticism of the NFL and Roger Goodell specifically. Simmons, of course, had been suspended by the network in 2014 for comments about Goodell. With ESPN in a multi-billion dollar relationship with the NFL, it’s easy to see why the questions would arise regarding whether or not the league tried to influence ESPN regarding Simmons’ place at the network. (Not that the NFL has ever put the squeeze on ESPN before or anything…) However, Skipper took full responsibility for Simmons’ ouster and dismissed his “conspiracy theories.” Skipper also denounced Simmons’ “repeated lack of respect” at ESPN in a statement to the New York Times.

“Bill would rather spin conspiracy theories and be perceived as a martyr than take responsibility for his own actions. Let me be unequivocal and clear and take responsibility for my actions: I alone made the decision, and it had nothing to do with his comments about the commissioner. I severed our relationship with Bill because of his repeated lack of respect for this company and, more importantly, the people who work here.”

With both parties now no longer at ESPN, perhaps this is all water under the bridge and ancient history. Or perhaps there are still some items left to be hammered out between the two. It’ll always be a great “what-if” question to see where the industry would be if both remained at ESPN. Whatever is the case, their podcast together should be a must-listen for those who follow sports media.

About Matt Yoder

Award winning sportswriter at The Comeback and Awful Announcing. The biggest cat in the whole wide world.