NBA legend Michael Jordan takes no prisoners both on and off the court. Be it an NBA Finals game or a round of golf with his friends, Jordan wants to win no matter the cost. His unbelievable drive to win no matter what has helped him become one of the best athletes ever. It has helped him win six NBA championships with the Chicago Bulls. It has helped him amass every individual accolade there is. Furthermore, it has made MJ a billionaire.

However, like many good things, his competitiveness has its downsides as well. It is no secret that Jordan liked to gamble with his friends and teammates. But sometimes it got out of hand. During his playing career, Jordan has had some controversies involved with gambling and betting. And there are some remnants of the old habit still present in His Airness.

The interviewer called out Michael Jordan?

In 2017, Michael Jordan sat down with Marvin R. Shanken for an interview with Cigar Aficionado. Shanken is the publisher and editor of Cigar Aficionado. During the interview, Jordan answered a variety of interesting questions ranging from his childhood, college career, NBA career, personal life, gambling, etc. In one instance during the sit-down of the Uncut version of the Interview released in 2020, Jordan revealed his bucket list for the future. It included playing golf with Shanken again and visiting Cuba. When the host was talking about it, Jordan was curious to know whether he won the game against Shanken.

When Shanken did not give him a straight answer, the Hall of Famer stated that it was a simple yes or no question. So Shanken responded, revealing actually what happened, “What happened was you insisted on playing for more money per hole than I wanted to play for. By a large amount.”

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Then Jordan said, trying to pacify the claim, “It’s not the money. I didn’t say how much did I win. I said did I win.” The host then admitted he lost the game. If it was not evident before, it was evident from this conversation how much winning matters to the five-time MVP. Even though it was just a round of golf with a friend, he wanted to win badly.

Jordan’s golf controversy

Michael Jordan does not mind putting his opponents under pressure by increasing the stakes, simply because he can afford it with his fortune. And this sometimes pushes his opponents into submission. However, it apparently backfired very poorly once when MJ once went on a golf betting spree with a man called Richard Esquinas.

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This time Jordan reportedly lost the game. Esquinas alleged the Chicago Bulls legend owed him $1.2 million. Esquinas even released a book about the whole ordeal called Michael & Me: Our Gambling addiction-My cry for help! in 1993. It was a huge controversy at the time. However, Jordan denied the claims and said he only owed the man around $300k.