Billionaire and NBA legend Michael Jordan is so wealthy that he would casually wager $100,000 on the outcome of a friendly bet.
In an episode of “The Pivot” podcast, released on April 16 and hosted by former NFL players Ryan Clark, Fred Taylor, and Channing Crowder, guest Jamal Crawford — a shooting guard known for playing with multiple teams and earning three NBA Sixth Man of the Year awards— shared insights from his career and experiences.
Jordan took Crawford under his wing as one of his protégés when Crawford first entered the NBA in 2000 as a first-round, eighth overall pick. He was selected by the Cleveland Cavaliers but drafted to the Chicago Bulls. They would train together whenever they had the chance.
Jordan’s Penchant For Taking the Chance
Crawford in the interview describes Jordan’s tendency to go overboard with the betting.
Throughout a series of private games during the summer, in a refereed, sanctioned game of pickup basketball where Jordan and Crawford played against Penny Hardaway, Mike Finley, Tim Hardaway, Antoine Walker, and Paul Pierce, Crawford recalls that Jay-Z and Beyoncé were there, and he and Jordan never lost.
An incident occurred where a hustler approached Jordan with a stack of $100,000, expecting him to bet strategically and carefully. To the hustler’s surprise, Jordan was willing to settle the bet with a simple coin flip.
Crawford said, “This one dude, word got around, you know, MJ. We were all hanging out afterward, and one street dude came up with a bag of $100,000 and said, ‘MJ, let’s gamble.’ MJ looked at him and said, ‘I don’t have a lot of time. Let’s flip a coin for it. Heads or tails.'”
Crawford continued, “The dude with the $100,000 thought he was going to go back and forth with MJ, but MJ didn’t have time for that. MJ looked at him and said, ‘Let’s flip a coin for it. Heads or tails, which one do you call?’ The dude looked at the money, and 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 and said, ‘I’m good,’ and left.”
He added, “My man MJ would wear Jordans that probably still aren’t out, whole different color Jordan outfits, shorts to match for outside, even matching Lambos. Bro, he was on something totally different, totally different.”
In a separate incident, former Italian pro basketball player and current coach Gianmarco Pozzecco, who led Italy in international tournaments for the Italian Basketball Federation (FIP), recalls a bet Michael Jordan made with Jamal Crawford around the time Jordan was preparing for his comeback with the Washington Wizards, which was around 2001.
Jordan had bet his Ferrari against Crawford’s Mercedes in a shooting contest, which Jordan ended up winning, Brobible reported.
Essentially Sports also reported on Jordan’s off-court gambling activities, where his inclination towards high-stakes betting matches his intensity and confidence on the court.
Jordan’s gambling habits, according to the outlet, includes a range of activities, from betting on golf games to wagering large sums on casino games, and just like the coin flip, Jordan plays games like rock-paper-scissors for $100,000, as told by former NBA player Jason “White Chocolate” Williams.
There are numerous stories about Jordan betting thousands of dollars on a single hand of blackjack or a single hole of golf. The NBA legend competitiveness seemingly never turned off,
