Bill Simmons Charles Barkley Photos via TNT Sports and HBO. Edit by Liam McGuire, Comeback Media.

As Charles Barkley nears potential free agency on the sports media market, Bill Simmons believes Barkley could be on his way to a record salary if Warner Bros. Discovery loses NBA rights and Barkley moves to a new network.

Beyond Barkley being a singular talent in basketball media and one of the faces of the sport, Simmons argued in a recent episode of The Bill Simmons Podcast that Barkley also appeals to media suits because he brings prestige and entertainment to the brand of whatever network employs him.

“This is the show (Inside) that figured it out, and Barkley is at least what? 85 percent of it? Because he’s the best TV talent that we’ve ever had in sports. So wherever he goes, when you talk … about the shiny new toy thing, and is that worth it, what’s the price? It is worth it if you’re NBC or if you’re Amazon, because you have Barkley,” Simmons explained.

“You have this face you can put everywhere, you can trot out. It’s like buying the biggest, shiniest yacht in St. Bart’s, and I don’t even know what he’s gonna get. But it’s gonna be some nuts number. Because you get the legacy. You’re basically still getting Inside the NBA because of him.”

Everything is on the table for Barkley, from signing at a new network like ESPN to producing Inside himself and licensing it to the highest bidder.

Simmons believes networks will line up to pay Barkley top dollar because they can bring him on their other programming as well as at corporate events and marketing. The Ringer and Spotify boss compared Barkley going to ESPN, NBC or Prime Video to David Letterman launching The Late Show at CBS after years at NBC.

“It’s like a Letterman going to CBS type of situation, where you’re getting the show but you’re also getting this personality you get to put at the forefront of all these different things you’re doing,” Simmons said. “You could argue that TNT/HBO/Warner maybe didn’t leverage that quite enough.”

Letterman reportedly doubled his salary in his move to CBS in 1993.

Barkley is involved at Warner Bros. Discovery upfronts every year and recently hosted a weekly primetime talk show with Gayle King on CNN. While Barkley warned he has no intention of being overworked by the worldwide leader, certainly networks would love to have Barkley on call for their news shows, take over his podcast from WBD, and make him the face and voice of their basketball brand.

While we imagine how much Stephen A. Smith or Colin Cowherd might make on their next contracts, Barkley could break records himself given his experience and respect across the business as well as the leverage he will get from WBD losing the NBA.

[The Bill Simmons Podcast]

About Brendon Kleen

Brendon is a Media Commentary staff writer at Awful Announcing. He has also covered basketball and sports business at Front Office Sports, SB Nation, Uproxx and more.