“To me, gambling is like going to the edge of a cliff and then calculating what the choices may be,” Michael Jordan once said when he addressed his gambling issues. Jordan, apart from being arguably the greatest basketball player, was also a renowned gambler. There are enough anecdotes of MJ putting a wager everywhere including dressing rooms, golf courses, and casinos. The Chicago Bulls icon brings the same energy that we see on the court to the casino table.

Often, the former Chicago Bulls superstar has clarified that he did not have a gambling addiction. But one thing was certain. Whether it was a basketball game or a wager; he hated losing. There have been intriguing stories of him engaging in bets on every sport or play possible. And here at EssentiallySports, we exclusively got to hear one such story.

Recently, our NBA enthusiast Vishal Kolar had another conversation with Leonard Armato, ex-agent of Shaquille O’Neal. Armato shared some fascinating Michael Jordan anecdotes. And it is the first time this story about His Airness is revealed.

Vishal: “I think a good topic to end on which I realized, I missed this question before but we were talking about Shaq and Michael Jordan, now everyone has their one Michael Jordan story. Now, you got to give us the one Michael Jordan story you remember from an interaction with him.”

Armato: “All right, so I’ll take you back to the USC Texas football National Championship game at the Rose Bowl. Reggie Bush, Vince Young and I’m in the Gatorade Suite now. In the Gatorade Suite, I’m in there with my wife Holly McPeak…Magic Johnson, it was, um, Lance Armstrong, it was Sheryl Crow, it was, it was Nomar Garciaparra and Mia Ham. It was Matthew McConaughey, it was unbelievable who was in there. Danica Patrick. We’re on the Gatorade suite and in walks Michael Jordan.”

Michael Jordan used to carry his own bottle of Grey Goose as he enjoyed it, according to Armato. Jordan and he shared a cordial relationship since MJ knew about Armato being Shaq’s agent. Seeing the room full of people, the 6x NBA champion asked him if he would wager on the game. It was not on the results, but the small plays that were happening. Armato rejected it since he was a no-betting man. But his friend couldn’t reject the offer.

Chris McGee was standing next to Armato and was already in awe seeing all the superstars stacked in one suite. Jordan asked him if he wanted to bet and McGee instantly agreed. MJ said, “I got a $100 that they convert this third down,” and McGee replied, “Okay $100 that, that they don’t convert the third down.”

Armato further added, “They converted the third down. Michael Jordan grabs the $100 of the guy, laughing and screaming like he’d won the, you know, NBA championships. He was so happy. Then they bet again. Michael Jordan kept taking money from him, taking money from him. The guy lost like, I don’t know, 500 bucks to Michael Jordan. Nothing massive. So, I go walk into the bathroom and my guy (McGee) comes next to me. He goes, ” This is the greatest day of my life. I just lost $500 to Michael Jordan.’ He was so happy but Michael Jordan was happy, so happy to win a hundred bucks from a guy as he was to like, you know, win the NBA championship. He was just that kind of person but he was so gracious and so nice and it was it was really fun hanging out with him.”

The competitive nature in Jordan always got the best out of him on court. He couldn’t say no to a challenge. When Jordan and the Bulls lost one game against the Celtics in the 1980s, MJ found a way to call himself a winner. The Bulls teammates were playing cards at the airport and no need to guess who came out as a winner. “This is fun! We just lost to the Boston Celtics, but guess what? I’m winning!” But these are not the only stories of Jordan winning wagers.

Michael Jordan had a peculiar habit

Michael Jordan always found a way to make things interesting. Rather than just winning, he was also motivated by any chance he had of winning outside the pitch, too. The NBA icon consistently placed competitive bets even during his early days in the NBA. In Roland Lazenby’s book Michael Jordan: The Life, former Chicago Bulls Senior Director of Premium Tickets, Joe O’Neil shared a gambling story featuring a young Jordan.

According to O’Neil, MJ used to hang out at their office to kill boredom during his rookie season. They would play a little golf game with not-so-little wagers – $20 (but this was back in the 80s). He said Jordan wouldn’t let them win and never let them slide every time they lose.

Jamal Crawford also shared a hilarious story of when Michael Jordan was willing to bet $100K against a street dude. MJ had to kill time when he was with his friends. Suddenly, “one street dude came up there with a bag of $100,000. ‘MJ, let’s gamble.’ MJ looked at him, ‘I ain’t got a lot of time. Flip a coin for it, heads or tails?…’ The dude looked at that money like you could tell he had all the hood’s money. He was like, ‘Man, I can’t do this. I have no flip.’ He looked, ‘I’m good,’ and left.”

MJ’s competitive spirit, which helped him win 6 NBA championships, was also the reason for his gambling habits. Pretty sure he won’t be too disappointed about it.