Michael Jordan is known as one of the fiercest competitors of all time, on and off the court. In part six of The Last Dance, it documented Jordan's love of gambling and the controversy it created for himself.
To Jordan, it was never about the money, he had plenty of it, to Jordan, it was about the competition. The ESPN documentary included an interview Jordan gave with Ahmad Rashad in 1993 where he explained his thought process.
"I don't have a gambling problem, I have a competition problem."
“It’s a hobby,” Jordan said. “If I had a problem, I would be starving, hawking this watch and my championship rings, selling my house. My wife would have left me, or my kids would be starving. I do not have a problem. I enjoy gambling. The media has taken it far greater than it is. Soon, whenever I walk away from this game, it’s going to be the only bad thing people say about Michael Jordan."
Regardless of how Jordan spun it, that's not how it appeared to the media and to a greater extent, the public. Sam Smith, an investigative reporter turned Bulls writer, wrote The Jordan Rules in the midst of the Bulls first three-peat. In its introduction, Smith discussed how Jordan would often play cards with Smith and other writers on road trips.
Beat writers were not the only ones Jordan saw an opportunity with, he bet his teammates as well. Jordan, Scottie Pippen, and Horace Grant were notorious for playing high stakes poker games in the back of the team plane. Thousands of dollars exchanged their hands, but sometimes Jordan took a break and made his way to the front of the plane. Upfront, other Bulls players engaged in dollar hands of blackjack, and Jordan wanted in.
“I want to say I have your money in my pocket,” Jordan told teammates John Paxson and Will Perdue when they asked why he bothered with their small-time game.
His gambling habits eventually became a bigger storyline. During the Eastern Conference Finals against the New York Knicks, Jordan found himself in the news cycle, and not just for his performance on the court. Following a loss in game one, Jordan needed to take his mind off New York, so he made a trip to Atlantic City for a night of gambling. It obviously didn't help, because the Bulls lost game two as well, and in game three, while the Bulls won. Jordan struggled. None of what Jordan was doing was illegal, but it simply created a bad optic and a reason for controversy. To the media, he was putting off-court vices ahead of basketball. To Jordan, he was just blowing off steam.
In addition to writers, and teammates, arena staff members also found themselves in competition with Jordan. John Michael Wozniak became an internet sensation Sunday night as part six progressed. A member of Jordan's arena security team, Wozniak is one of the surprise standouts of the documentary. He has been seen in several scenes thus far so it can be assumed that he spent significant time with him. Furthermore, the two were comfortable gambling together. Camera footage shows the two of them engaging in some friendly competition in the Bulls facility. The game is simple. Whoever can toss a quarter closest to the wall without actually hitting the wall wins. Wozniak bested Jordan and taunted him with the signature Jordan shrug. Jordan paid up, but you can tell it is clear that it was eating him inside.

It wasn't poker with his teammates, or quarters with staff-members that cost Jordan the most. Jordan was an avid golfer, and he enjoyed betting on his game. Unfortunately for him, he paid dearly for it. "Slim" Bouler was a golf hustler who eventually landed in jail for money laundering. When Jordan had to testify during Bouler's trial, it was revealed that Jordan wrote a check to Bouler for $57,000 for losses accumulated on the golf course.
Shockingly, that was not the biggest gambling debt that Jordan piled up on the golf course. Richard Esquinas, a golf partner of Jordan's, wrote a book about his gambling addiction. He lumped in Jordan as also being addicted and claimed that Jordan owed him $1.25 million from golf debts. Whether that is true, Jordan denied that debt was that much and the two settled for $300,000.
While the money he lost was a drop in the bucket for him, the media frenzy surrounding his gambling took a toll on Jordan. The Last Dance shows how Jordan became increasingly fed up with the media. By the end of their third title won, Jordan said he was mentally exhausted. While he was elated that they won their third title in a row, he was relieved the season was over. Parts five and six of the ten-part series were building up towards Jordan's first retirement from basketball in 1993. If the previous episodes are any indication, part seven should tell the story of his decision to step away from the game.
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