Rock, paper, Scissors- Michael Jordan would bet on anything, Jordan’s former teammate Jay Williams had said. Not far behind is his long-time friend Charles Barkley.

Barkley would not have left the table before either winning a million or losing it! It is no surprise that beyond the basketball court, gambling would be something where the two legends would cross roads.

One such has recently come to light in a May 28 article by The Athletic. The story covers the Kenny Rogers Classic Weekends hosted by the country singer from 1988 to 1990. About 15 celebrities, across all arenas, gathered in Rogers’ lavish accommodation – the 1200-acre Beaver Dam Farms to compete in basketball, tennis, golf, and fish bassing. One among them was Michael Jordan, keeping interests up through his games and bets.

Understandably, Jordan was impressive in basketball. But it wasn’t the only sport where everyone was in awe of him. Tennis star Kevin Curren recalled in the article by The Athletic how good of a player he saw Jordan to be in his sport despite his inexperience – thanks to his athletic ability and confidence. “It was the absolute dream to play basketball with Jordan, and then I played tennis with him. That was even more fascinating to witness his movement on the court,” recalled Curren, who won doubles titles at Wimbledon and the U.S. Open.

It was here that Curren also recalled that those very abilities helped him win a bet against Charles Barkley. According to the article, in one year of the Kenny Rogers Classic Weekends gathering, Curren found Jordan and Barkley arguing over who was the better athlete. To put an end to the debate, they decided to play a set of tennis for $10,000. Jordan won easily, Curren recalled.

While this could’ve been without getting money involved, not making a bet when the opportunity presents itself is not something either of them would do. And it’s not as if either of the stars has not admitted to the habit. In an interview back in 2022, Charles stated that he won close to a million, about 5 or 6 times. But also admitted to losing a similar amount around 10 to 20 times. “It got out of hand. I quit for like 2 years,” Chuck had said.

via Imago

However, he admitted he’ll probably continue doing it but not to a great extent. “”Do I have a gambling problem? Yeah, I do have a problem, but I don’t consider it a problem because I can afford to gamble. It’s just a stupid habit that I’ve got to get under control, because it’s just not a good thing to be broke after all these years,” he had said in an interview in 2006. He also had a way out to keep that check. He said he would go to bet with only $1,000 a hand instead of $20,000. So he would be losing only $50,000 instead of millions.

As for the Chicago Bulls legend, he stated gambling is a hobby for him rather than a problem. He once accepted that things getting a bit out of hand with this hobby.

“I think I have a very positive life. Naturally, there have been some things that I have done wrong, and most people have. The gambling thing is something that kind of get out of proportion,” he said. Indeed it has landed him in a problem, at times quite grave.

Back in 1992, while investigating a money laundering and drug trials case, police found that Michael, one of the wealthiest sportspersons, had written a drug dealer for $57K to clear his golf gambling debts. But, according to some reports, Jordan’s biggest loss in gambling came in Las Vegas. lost $5 million at the craps table on one night. Interestingly, his gambling tales in golf are also legendary.

Michael Jordan’s way of gambling: hundreds and thousands of dollars a hole

Back in 2017, on Dan Patrick’s show, Barkley gave a glimpse of Michael Jordan’s lavish betting ventures in golf. “We’d be playing golf with certain people, and we’d be playing a couple hundred dollars a hole, and he’d be playing some guy for, like, a $100,000,” Barkley had said. His revelations also found support from Cedric the Entertainer.

Cedric had shared this instance on an episode of The Late Show with Stephen Colbert. He shed light on Mike’s love for golf and how his bets throughout the game got pretty serious. The 60-year-old shared a particular moment that quickly got him out of his pay range.

“The time I played, (Charles) Barkley was with us, and they were playing like ten thousand a hole, $10,000 a hole,” he recalled. The stakes kind of scared Cedric, which should’ve been the case with most individuals. And more so considering Jordan wanted Cedric also to play.

However, the stand-up comedian tried avoiding it by hilariously stating he would have to open a second line of credit just to play golf with them. But Mike still got him to agree to put $1,000 on each hole. Little did Cedric realize it was 18 of those, and he lost every one of them.

This is still one of the many instances when Charles Barkley and Michael Jordan bet against each other until the two drifted apart after Buck’s one take on live TV. The two haven’t spoken in years for Barkley’s remark on Charlotte Hornets, a team owned by Jordan. Now, if the two were ever to reunite, it is up to the latter, because Charles is all in.