Muhammad Ali came out of retirement or semi-retirement at least four times. Charles Barkley retired from the NBA in 2000, claimed he’d retire from his TV job in 2015, almost left TNT in 2022, announced his retirement during the 2024 NBA Finals, and cancelled retirement within a few months. So Bill Simmons is well within his rights to rib his friend after he outdid Muhammad Ali.

Charles Barkley was on The Bill Simmons Podcast once more and the discussion inevitably went back to TNT. ICYMI, Chuck called off retirement in early August, right after the NBA turned down TNT’s offer to match Amazon. He gave The Ringer mogul the chance to slap him with, “The most impressive thing you’ve done, I think, you broke Muhammad Ali’s record for most times retiring.”

Barkley almost missed the punchline claiming he’s glad Simmons brought up the ‘question.’ To which the podcaster stated, “It’s not a question, it’s a fact.” 

The sports media veteran foreshadowed TNT losing the NBA on the show. A few times he said that Chuck and the Inside Guys would become the most in-demand media free agents. He compared the possibility of Barkley leaving TNT to David Letterman’s historic shift from NBC to CBS. Yet Simmons was also confident that Chuck would never retire.

Still, Sir Charles is a little defensive about the fact. When Barkley doubled down that he told TNT he’d retire, Simmons also repeated, “You’re not retiring,” and “What are you gonna retire for?” Chuck did have a vague response for that.

Charles Barkley keeps proving Bill Simmons right

Just before he renewed his TNT contract in 2015, the 76ers legend said he’d be a fool to be working till he was 60. He now says he’d be a fool to work till he was 70. He’s got a decade in him, maybe longer, but Chuck tells Simmons he’d remain at TNT for about two years.

Turner needed him to put off retirement while they negotiated the NBA media rights deal. Because, obviously, Inside the NBA was the USP. “Little did I know they were gonna f*** that up,” Barkley says.

He would’ve stuck to his plan anyway. However, the TNT market reps told Barkley that if he stayed, it would be ideal for him since then he’d not have to walk to another network. And not wanting to start over after 25 years was a big deterrent for Chuck taking up NBC or ESPN’s offers.

The biggest incentive for Barkley is that he got to save thousands of jobs that were put in jeopardy with TNT losing the NBA. Chuck reaffirmed his decision to stay at the network and develop new shows for them. And he implies he’d leave once he’s done that.

Barkley signed a 10-year contract worth $210 million in 2022. He repeats he has no intention to see it to the end. Yet Simmons makes another one of his prophecies. – “I don’t think you’re gonna retire.” And the score is Bill Simmons; 3, Charles Barkley;0.