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Michael Jordan’s competitive streak has long been part of golf lore. Yet former PGA Tour veteran Peter Jacobsen believes one part of that reputation deserves a closer look, revisiting a story that puts the NBA legend’s money-match mystique under the spotlight.

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“During the Olympics, the Dream Team, we went and played in Portland because my buddy P.J. Carlesimo was the Trailblazer coach, and we would go out and play before the games, and we’d play for a couple hundred bucks, that’s it,” Jacobsen shared on the Dan Patrick Show. “I never lost to him (Jordan). I don’t think anybody’s ever lost money to Michael.”

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It echoed another long-running story about Jordan’s golf habits, which host Patrick even questioned. “Mike will tell you his handicap is better than what he really is, and therefore he loses money.”

Jacobsen’s memories of Jordan weren’t all about betting. Long before the six-time NBA champion became one of golf’s most recognizable celebrity players, he was simply an eager student determined to improve every aspect of his game.

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Jacobsen recalled that their relationship began shortly after Jordan signed with Nike. As MJ was developing his skills on the hardwood, he was eager to learn and improve his golf game.

“He was like a sponge. I would say, ‘No, no, when you hit a flop, wedge goes open, you swing left, you throw the head out.’ He would do it,” said Jacobsen. “I’ve never seen anybody accept instruction and actually replicate it like a Michael Jordan.”

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Previously, Jacobsen revealed another story of Jordan losing during a celebrity golf tournament and involving actor Bill Murray. In 1998, they played a celebrity tournament for five holes with one team eliminated after each hole. By the end, only two teams remained: Bill Murray and Peter Jacobsen against Michael Jordan and PGA Tour professional D. A. Weibring.

Again, in this story, Michael Jordan lost. Jacobsen’s team emerged victorious, and Murray donated his $10,000 share of the winnings to Big Brothers and Big Sisters of Chicago.

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Hobby during his college days at the University of North Carolina eventually became a lifelong passion. That eagerness to improve helped transform Jordan from a mid-handicap golfer into one of the better celebrity players in the game.

But apparently not enough to win bets against his friends. Patrick even suggested that Jordan would play off a handicap that’s lower than his actual ability. A lower handicap means putting himself at a disadvantage, but raising the stakes of his victory. That’s what the drive of Michael Jordan truly was.

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Pranav Kotai

3,132 Articles

Pranav Kotai is an NBA Writer at EssentiallySports, specializing in basketball coverage with a focus on trade dynamics and front-office decision-making. He previously worked on the Trade Desk vertical, where he brought clarity to how salary cap pressures and roster needs shape NBA transactions. His coverage of the Philadelphia 76ers' decision to hold firm on Joel Embiid amid trade speculation highlights how market context and team strategy influence major roster moves. Before joining EssentiallySports, Pranav built experience in professional writing, editorial work, and digital content creation. He holds a postgraduate diploma in digital media, where he mastered the tools to create engaging and credible content across various platforms. Known for his attention to detail, storytelling, and editorial expertise, Pranav combines deep basketball knowledge with sharp analytical skills to deliver clear, insightful perspectives on the complexities of NBA trades and team management.

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Cherry Sharma

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