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Charles Barkley can pinpoint one particular moment when it all went downhill between him and Michael Jordan.

The retired NBA icon Barkley appeared this week on “The Tom Tolbert Show.” During the episode, Barkley spoke out about his relationship with his fellow basketball great Jordan and when exactly it broke down.

Barkley said that his friendship with Jordan soured after he criticized Jordan’s ability as a general manager on TV.

“I remember he called me that night, and he went ballistic on me,” said Barkley of Jordan. “Telling me, ‘You supposed to be my best friend, and you’re going to do that bulls–t? Blah, blah, blah, blah, blah.’ I said, ‘Man, I gotta do my job.’

“And I said, ‘You haven’t done a good job as a general manager, and that’s my job, to be honest,’” Barkley added. “How can I criticize other people and give you a pass? When other guys make bad draft picks, I call them [out] on it too. And he just cursed me out up and down, and we have not spoken since that night. It was a very difficult thing for me because the guy was, like, really my best friend at the time.”

Barkley and Jordan, now both 62 years old, were contemporaries in the NBA and shared a very close friendship many years ago. But their relationship has been fractured for over a decade now as Barkley indicated all the way back in 2012 that Jordan was not happy about what he had said.

In 2006, Jordan became a minority owner as well as the head of basketball operations for the then-Charlotte Bobcats (now the Charlotte Hornets). While he later became the majority owner of the franchise in 2010, they only earned three total playoff berths and zero total playoff series wins during Jordan’s time in charge (including posting the single worst record in NBA history by going 7-59 in the lockout-shortened 2011-12 campaign). Jordan then sold his majority share in the team to Gabe Plotkin and Rick Schnall in 2023 but still remains a Hornets minority owner.

As for Barkley, he never had much of a filter as a player and still does not have much of one after having spent the last two-and-a-half decades as a commentator. So while it was very much on-brand for Barkley to bluntly criticize Jordan, Sir Charles is clearly still very bothered by the breakdown of that friendship. He also once revealed what bugged him the most about his rift with Jordan.