It's common knowledge that Michael Jordan 's competitive nature was just on a different level. His drive to win was so intense that he needed an outlet when he was off the court, something he found in the game of golf. While the sport exudes serenity and calmness, Jordan's competitiveness brought a whole new level of intensity to the game.
Cedric the Entertainer, a well-known comedian and actor, was once invited by Jordan to play golf with him and another NBA legend, Charles Barkley. But little did he know that this game would turn out to be more than just a casual round of golf. As they started playing, Cedric quickly realized that he was in over his head.
A famous stand-up comedian, actor and television host who has starred in his fair share of hit movies, Cedric has earned millions of dollars in his career. But his wealth pales in comparison to the fortunes of Jordan (net worth of $3.5 billion) and Barkley (net worth of $90 million).
Despite that, he recalled trying to hold his own against the two basketball icons, daring to bet $1,000 per hole. It didn't take long for him to realize how much he could potentially lose if he lost on every hole.
"You know, I'm trying to act like, you know, I got something. 'Thousand a hole then!' We're doing the math, that's $18,000 — that's not one I can explain to the wife," he said during an appearance on the "All The Smoke" podcast, which sent hosts Matt Barnes and Stephen Jackson into a fit of laughter.
It turned out that what Cedric thought was a fair figure to bet was anything but. He revealed that Michael and Charles ended up betting $30,000 a hole — a staggering number but mere pocket change for the two NBA legends.
"They doing $30,000 a hole, they doing their billionaire s — t, whatever they doing. But I like, yeah, I'm like, trying to act like I'm somebody, that hurt," he added.
While there are countless stories of Jordan's gambling escapades, another one that made the rounds was when he met Wine Spectator and Cigar Aficionado founder Marvin R. Shanken in Chicago and went for a round golf. Shanken, a wealthy man who founded M. Shanken Communications, soon discovered that when it came to golf and betting, the Chicago Bulls legend was truly in a league of his own.
"The rumor is that he likes to play for a lot of money. He wants to play for more money than you can afford to lose," Shanken shared in an interview with GQ. "He thinks he has an edge that way. So he started off — I don't remember the number — but he wanted to play for so much a hole that I said, 'You're out of your mind! I'm not gonna play for that.'"
Although Jordan agreed to bring the amount down, Shanken was amazed by the lengths the former went to raise the stakes and make a casual golf game seem like Game 7 of the NBA Finals.
"That showed me the competitiveness that he had," Shanken stressed.
To Jordan, there's really no such thing as a casual game. In his mind, games are meant not to be just played, but to be won. Whether it's on the court or on the golf course, Jordan's fierce drive and determination know no bounds.
This story was originally published by Basketball Network on Jan 31, 2026, where it first appeared in the Off The Court section. Add Basketball Network as a Preferred Source by clicking here.
