Putting Charles Barkley and Skip Bayless next to each other is like leaving two live grenades on the floor. There is most certainly bound to be an explosion. Just as Bayless has been LeBron James’ nemesis, Chuck has truly been Skip’s greatest hater. And he has no qualms admitting to it. However, right now, some believe the two are in somewhat similar circumstances.

Don’t let Gilbert Arenas hear that because he would not stand for it.

In the July 17 episode of Gil’s Arena, the former Warriors star said there was no way their two situations were similar. We all know what’s going on with Barkley. It’s none other than the NBA on TNT’s final days, meaning the end of the glorious Inside the NBA crew.

As for Bayless, the Fox Sports veteran is reportedly leaving FS1’s Undisputed later this summer. As host Josiah Johnson brought this subject up for discussion on Gil’s Arena, he phrased it this way: “Skip been in the game a long time, obviously done a lot of good work. [he] was making a lot of bread – one of the highest paid sports media figures leaving, but it kind of follows in the same tone of Charles Barkley leaving TNT.” Johnson did not get further before ‘Agent Zero’ interrupted him.

“No. No. Not even the same. Don’t even put him… One is getting canceled, one is leaving. We don’t know why he’s leaving; we don’t know what he’s gonna do. He might go to ESPN, he might go to another network.” All the Inside the NBA fans can perhaps relate to the emotion behind those words. Barkley has no choice or say in the matter, while Bayless is taking a decision wholly on his own. There weren’t any outside factors that pressured him into the exit (except maybe the money? Speculation, of course). It could be similar to what’s happening between Stephen A. Smith and ESPN.

With Smith’s deal with the company ending in the summer of 2025, ESPN insider James Miller revealed, “I think there have been preliminary talks already that have started. He’s looking for a big, big number.” Implying that the analyst could get offers from practically anywhere he wanted, Miller explained that ESPN would want to do everything it could to keep Smith there. “At the end of the day, it’s $20 million a year.” This sum would make him the highest-paid person in sports media. Seeing as ESPN lost the rights to the UFC, it could potentially make room for Stephen A. Smith’s mammoth contract.

When it comes to Charles Barkley and Inside the NBA, it’s likely that had it not been for the media rights war TNT has been in, Chuck (and us!) would still be having the time of his life with his goofy gang of Shaquille O’Neal, Kenny Smith, and Ernie Johnson. If he could have his way, fans would be in for many more fun-filled banter sessions between ‘Sir Charles’ and Shaq (unlike what it was with Skip Bayless and Shannon Sharpe). So, Gilbert Arenas immediately pointing out the difference is understandable. But why the sudden move from Fox?

As opposed to Charles Barkley, Skip Bayless could very well remain at Fox

After 12 years with ESPN, Skip Bayless moved to Fox Sports in 2016. And even though the former media mogul tried to lure the pundit back in 2021, Fox retained him with a 4-year, $32 million deal. The 72-year-old arrived to be the co-host of Skip and Shannon: Undisputed. However, the two were incompatible, often engaging in fierce back-and-forth on air. And it was nothing like the light-hearted ones between Barkley and Shaq on Inside the NBA. These were full-blown fights they had.

One of these instances was a couple of days after Week 17 of the 2022 NFL season. In the game between the Bills and the Bengals, Damar Hamlin collapsed on the field, and Skip Bayless tweeted his thoughts on postponing the game (before it was canceled). However, Sharpe disagreed with the tweet but didn’t say so until he returned after taking a break the morning after the game. So, when the NFL legend addressed his absence and the tweet in his monologue, Bayless interrupted him, and they fought on live TV. Things like this kept building up one after the other, prompting Sharpe to leave Undisputed last summer.

As Sharpe decided to become a part-timer for ESPN, Fox let him. Clearly, Fox considered Skip’s presence more valuable to the network than Sharpe’s. So, the sudden reported leave-taking has many scratching their heads. However, after the NFL legend split with Fox, Undisputed’s ratings took a dive, which could’ve been a possible reason for Bayless calling it quits, too. Unfortunately, though, there have been no official updates as to the reason or the next step for the media veteran. But retirement seems an unlikely scenario. Why?

Simply because of a statement in a 2022 episode of Bayless’ podcast. “I’m not going to stop. I told [my wife] I don’t even want to hear the word retirement because I associate it with death… I’m not ready to stop. It would be a waste for me to stop,” he said. While those in the media world who make use of his services would wholeheartedly agree with the last part, there would at least be a few who wouldn’t consider Skip’s retirement a “waste.”

What about another ESPN reunion? Unfortunately for the enfant terrible of hot sports takes, an ESPN spokesperson dispelled any such notions early on via a statement to Front Office Sports. “We are set with the current First Take rotation, and wish Skip the best on his future endeavors.” So, there goes that!

Well, what do you think? Could Skip Bayless have a change of heart and consider retirement? Or will the man surprise everyone with another card up his sleeve? Let us know your thoughts on the matter!