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Charles Oakley Recalls His Time Gambling With Michael Jordan And Jay-Z, Losing $50K In One Night

Charles Oakley Recalls His Time Gambling With Michael Jordan And Jay-Z, Losing $50K In One Night

If somebody has plenty of stories to tell from their active days, that's Charles Oakley. The New York Knicks legend wasn't the superstar that his close friend Michael Jordan was, but he knew how to become a valuable piece for every team he played for during his time in the association. 

Being friends with Michael had a lot of advantages, but it also comes with a lot of challenges from His Airness or those associated with him. Oakley, just like MJ, was a big gambler, and he didn't care to risk some money if that meant he'd have fun. However, things weren't happy all the time.

Talking with Shannon Sharpe on his 'Club Shay Shay' podcast, Charles recalled the times when he gambled with Jordan and legendary rapper Jay Z during one of MJ's birthday parties. Oakley said that he lost $50K that night, the most he lost in a single day. 

"[The most money I've lost] was about $50K," Oakley said. "We played Tonk. I like Guts, but I hate booray. So, we're at MJ birthday party, I had did all the cooking, did all this and that, so we had a poker game going on with MJ and somebody on the crew, we had another Guts game going with Jay Z and a few other guys. So I was back and forth 'cause I was doing the cooking. So I got in late in the Guts game, it lasted a few hours, by late 10 or 12, so it was coming to an end. So Jay Z won, I thought he capped pot on it, I was about to get in his a** because I think he capped the pot and didn't have any money. You call something, you gotta have it in front of you to call it. So, I was kind of heated, but it was a good night because it was my man's birthday."

Whenever they started gambling, things would get interesting. MJ used to do whatever it took to win and it seems like Jay Z adopted that move from him. Oakley wasn't having any of that and he almost get physical with the legendary rapper during that game session. Oakley wasn't having any of that, but now the story is a funny one to tell.