Years After Golfing with Michael Jordan During the 1993 Finals, Charles Barkley ‘Insulted’ Comedian’s $40 Bet: “Get Rid of Them $1s”

Charles Barkley, much like Michael Jordan, has loved golf for almost the entirety of his career. Even in the middle of his one and only NBA Finals appearance in 1993, Barkley was found hitting the greens and playing a few holes with his then close friend and Chicago Bulls superstar, Jordan. That love for the game has famously kept going well into his retirement. Years after his 1993 NBA Finals appearance, the Chuckster made a $40 bet with a comedian, resulting in the most peculiar conversation.

When Barkley and Jordan played together, the former was always astonished by how much the latter would bet on games. MJ is a competitor through and through, and someone who famously loves gambling. As a result, he and ‘the Chuckster’ would frequently make shockingly high stakes bets on games. On one occasion, the amount even went up to $300,000 for a single putt. Fortunately, that wasn’t the case with Gerry Dee.

Comedian Gerry Dee got roasted by Charles Barkley for trying to make a bet with $1 bills

Charles Barkley and Gerry Dee were having a mean back and forth with each other back in 2009. Of course, they were only horsing around. Nonetheless, when the time came to show how much they wanted to bet on themselves in a golf game, Sir Charles wasn’t impressed at all by the comedian’s pockets. Here is what happened, as seen in the YouTube clip by Gerry Dee.

Charles: What’s your handicap?

Gary: 40… 36..4

Charles: “See, you’ve got no heart… Trust me, you better start getting rid of them $1 (bills), this ain’t a str*p joint.”

Barkley can always be trusted to be brutally, almost embarrassingly honest. And as the quote shows, this occasion was clearly no different. However, to his credit, that’s why he is universally beloved by the NBA community.

Barkley got back-to-back birdies

Getting a birdie alone in golf is not an easy task. And especially for Charles Barkley, whose form has been a laughing stock for golf aficionados for a while now, it was something akin to impossible. Yet, after 40 years of playing golf, the Chuckster finally got not one, but two birdies in a row. You can read about the NBA legend’s reaction to it here.