
Michael Jordan spent 15 seasons playing in the NBA. Despite the comparison with LeBron James and Kobe Bryant, the Chicago Bulls legend remains the GOAT.
While there have been a number of fancy tales linked with the basketball great, one that first surfaced around 2019 still knocks his fans off with the details.
A hockey Hall of Famer, Jeremey Roenick, took down memory lane and explained how an extraordinary day in Jordan’s life went.
According to Jeremey, the Chicago Blackhawks and Bulls were concluding their respective seasons back in 1992 when he got a call from MJ. Jordan asked Roenick to go for a golf match and the hockey great affirmed almost immediately.
While the two sports legends played 18 holes for hours, Roenick was done around 10 AM. He was expecting Jordan to call it a day as the Bulls had a match with the Cavs. However, the 14x NBA All-Star insisted on playing for a couple more rounds.
As the former Blackhawks explained, he couldn’t say no to MJ as there was money on the line. Though he has made some bucks for himself after beating Jordan in the initial 18 holes. Interestingly, Michael picked it up against Roenick when he said he will put his money on Cavaliers from the day’s winning.
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“He goes, ‘I’ll tell you what. I’ll bet you that we win by 20 points and I have more than 40.’ I’m like, ‘Done.’ Son of a gun goes out, scores 52 and they win by 26 or something… after (36) holes of golf and having maybe 10 Bud Lights. The man, to me, is the best athlete that I’ve ever seen,” Roenick said.
Drake Says Michael Jordan Can Bet On Anything

It will be a really long article if we go about Michael Jordan’s gambling and betting on anything.
Recently, Canadian rapper Drake opened up about playing ping-pong against the NBA Hall of Famer during the 2016 All-Star Weekend in Toronto. Drake recounted that he managed to beat Jordan multiple times, which triggered Jordan’s competitive spirit and gambling tendencies.
According to Drake, after his victories, Jordan continued to bet against him, wagering tens of thousands of dollars.
“Gambling GOAT? To me? Controversial take but Michael Jordan. He’ll gamble on anything. I think I remember it was All-Star Weekend in Toronto, and he had an event to be at. I beat him at ping-pong, like, a couple times, and he just wouldn’t leave the ping-pong table. He kept just betting me, like, bands. 10 bands, 20 bands,” Drake said.
Drake reveals during an interview with Stake that he beat Michael Jordan for over $20k in ping pong 🏓 👀 pic.twitter.com/xQZ46sgKbU
— RapTV (@Rap) March 22, 2025
Despite not specifying the outcomes of the bets, Drake noted that Jordan is not someone who can digest a defeat, be it in any form of competitiveness.
However, Drake expressed admiration for Jordan’s gambling nature, ultimately reaffirming his belief that Michael Jordan stands out as one of the greatest gamblers.
Also Read: Michael Jordan’s Business Empire At Risk Of Taking Massive Hit Thanks To Nike’s Recent Issues