Charles Barkley and Michael Jordan may have seen a rift in their friendship now, but the two have lived a lore to be spoken about for years. It is not just their on-court antics. Recent revelations assert that their shared gambling habit make up many good stories. From a test of their tennis skills to now a night at Vegas, Chuck and MJ give a good laugh.

During a recent All the Smoke episode, hosted by Matt Barnes and Stephen Jackson, Cedric the Entertainer recounted a memorable encounter in Las Vegas involving the two. When asked about gambling with the two NBA legends, Cedric revealed that he had only witnessed it once and, according to him, Michael Jordan used $150,000 worth of Barkley’s casino chips during a single spree.

“That’s one time. Let me get that s–t, very goddamn clear. They gamble on another level man,” he started. Chuck was supposedly playing in thousands when MJ just came in for some of the chips and not in a small amount.

“So MJ comes in, MJ just grab a stack of Barkley’s chips. Maybe like a $150000 or something and Barkley be like, hey man, ‘What you get?’ MJ said ‘does it matter? You know I got you’. Like whatever it is. Like ‘c’mon man, tell me what it is.’ ‘I’m MJ I got you. I just don’t wanna go and get chips,'” recalled Cedric during the podcast.

He was left shocked at the amount the two weighed in. $300,000 at one point even, according to the comedian. And it might not have been an exaggeration. Considering their gambling admission, it was sure a serious thing for the two icons.

Charles Barkley has been quite candid about his losses over the years. “There’s probably been seven times that I won a million dollars. But there’s probably been 25 times I’ve lost a million,” he previously admitted. Then in 2022, he revealed he had quit but not completely. It was only the bid that had reduced, from tens or hundreds of thousands to a thousand or so.

As for the Chicago Bulls legend, it was more of a hobby than a problem. May be why he so casually went in for a $10,000 bet with Charles Barkley during one of Kenny Rogers Classic Weekends. According to Tennis star Kevin Curren the two had bet the sum while arguing who the better athlete was. In the end, they would agree on a tennis game to settle the debate. But the results never came to light. But his opponent’s in a golfing bet did and it involved Cedric the Entertainer with tens of thousands.

When Cedric the Entertainer left gambling after a golf game with Jordan

Jordan’s passion for golf is almost as legendary as his basketball career. His love for the sport ultimately resulted in the creation of the Grove XXIII, which is an invite-only exclusive golf club. Moreover his love for the game also urged him to start gambling based on this sport. This turned out to be an eye-opener for Cedric.

During his appearance on The Late Show with Stephen Colbert, Cedric revealed that a golf game with Jordan ultimately made him realized the losses he was making with gambling. “That kind of took me from betting altogether. Mike likes to play golf, and then he bets throughout the game and it gets pretty serious. It got out of my pay range very quickly,” said Cedric during the show.

The catch of the bet was that for every ball that Cedric would put in a hole, he would get a $1000, but for every miss, he would lose the same amount. Unfortunately, the comedian ended up losing $18,000. For Cedric, that day on the golf course wasn’t just about losing money; it was about understanding the perils of gambling and knowing when to step away.