Michael Jordan was arguably one of the coldest NBA superstars of all time. His Airness had only one objective, to win. Likewise, making friends was rare for the six-time champion. However, there was one person Jordan grew very close with through all of their intense battles. It was none other than NBA Hall of Famer Charles Barkley. The two shared a comedic relationship, and in 1997, MJ took a shot at the now TNT analyst over not winning any championship.

Barkley is considered one of the best forwards to play the game. The former Phoenix Suns star was mentioned in the same breath as Jordan in his prime. In 1993, the 11-time All-Star won the MVP award. However, despite achieving nearly all the individual glory, the most important trophy never became his. Notably, Barkley is one of the NBA legends who never won an NBA championship.

Likewise, being friends with a talker like MJ came at an expense. While speaking about his relationship with Charles Barkley, Air Jordan flew in with his own joke.

Michael Jordan never failed to remind Charles Barkley of his success

Jordan thrived off competitiveness. The former DPOY could turn any activity into a contest. While on The Keenan Ivory Wayans Show, he went into detail about competing with peers even outside the NBA floor. In particular, he spoke about hanging out with his best friend, Charles Barkley. Leaving no chance to embarrass the Round Mound of Rebound, His Airness revealed his methods of motivating the 1993 MVP to win a championship.

“I Hate That Fat F—”: How Michael Jordan Once Bribed Charles Barkley the Night Before NBA Finals

Michael Jordan said, “When I’m hanging out with Charles, I can say whatever I want to Charles, they never won. He’s second-place finish.”… The Chicago Bulls icon continued, “I am motivating Charles to get on my level and win a championship.”

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According to Jordan, he wasn’t trying to put down his friend. Notably, he only brought up the topic when Charles Barkley spoke about winning. The pair often showed their love by insulting one another. Shockingly, their friendship snapped years after competing. Notably, Barkley showed doubt over Jordan taking over the Charlotte Hornets. As history has proven, Michael Jordan is known to hold grudges. Likewise, while on “Let’s Go! with Tom Brady, Larry Fitzgerald and Jim Gray” Barkley openly spoke about their broken friendship. According to the Hall of Famer, Jordan took offense to his comments, and they haven’t spoken for over a decade.

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It’s unfortunate to see such a special relationship go down in flames. Now years later, do you think there is any hope of them being friends again? Let us know your views in the comments below.