“We had a back and forth card game with Michael Jordan and Jay-Z”: Charles Oakley reminisces losing $50,000 and gambling with the Bulls and rap icons

Charles Oakley talks about gambling with both Michael Jordan and Jay-Z during the former’s birthday party. 

Michael Jordan built up a reputation for himself in the gambling space as time went on. By the time the early 90s had rolled around, Jordan was gambling on everything from card games to see who can toss a coin closest to the wall against a Chicago Bulls security guard. 

Essentially, if money was on the table, MJ would be damned if he didn’t partake. Even his part-time hobby of golf had racked up quite the bill for the 6x champ as Richard Esquinas wrote in his book titled ‘Michael and Me: Our Gambling Addiction-My Cry for Help’ that MJ had owed him over $1.2 million in golfing bets.

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Charles Oakley was someone who rolled with Michael Jordan all throughout his Bulls days and the two remained close even after Oak made his departure from Chi-Town and set out to be coached by Pat Riley on the Knicks. 

As most NBA players did back in the day, betting on card games was very much a part of the norm and MJ most certainly indulged in it with his teammates and/or friends. 

Charles Oakley on gambling with Michael Jordan and Jay-Z. 

On the Club Shay Shay podcast with Shannon Sharpe to promote his new book, Charles Oakley talked about betting with both Michael Jordan and Jay-z on the former’s birthday. He would also say that the most he’s ever lost while betting on cards was $50,000.

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Booray is a game that most players played back in the day and still do. However, Oak was someone who wasn’t all too fond of the game as he claims he liked to play Guts instead. 

‘The Enforcer’ didn’t specify on who won or who lost during this card game he had with Michael Jordan and Jay-Z and given Jordan’s history, it’s safe to assume it was anyone’s game.