Jamal Crawford Shares A Story When Michael Jordan Wanted To Flip A Coin For $100K With A Street Dude

Michael Jordan's gambling stories are pretty incredible. While the public record knows Jordan didn't have a 100% success rate in the world of gambling like he did in the NBA, he was quite the whiz. 

Charles Barkley, Magic Johnson, and many more have some incredible stories of Jordan gambling, though those usually involve playing with cards.

The World Came Out To Watch Jordan And Crawford Play Pick-Up

Crawford and Jordan connected in the summer of 2000 after Jamal was drafted by the Chicago Bulls. As a Bulls rookie, Crawford was given the opportunity to work out alongside Jordan after his second retirement in 1999. 

The pair started playing pick-up basketball in Chicago together, with Crawford allegedly beating Jordan and his team in a game. This prompted a visibly frustrated Jordan to silently align himself with Crawford before embarking on a legendary run that left multiple NBA players in their prime defeated. 

"The first time we actually played against each other, different teams, not one-on-one, and I think our team won. And I saw how mad he was, like he was pissed off and he went and sat in a corner, and he just sat there. He reacted as if he had lost a Game 7... The next day this run starts at 2 o'clock because young players have to work out with their team first and then can go do what they want. Grover's blowing up my phone, yo where you at, I'm like, ‘bro it's 1 o’clock.' ‘MJ's waiting on you, where you at, we ain't starting until you get here...' From that moment on we played together and we never lost.”

The games became so popular that everyone had to drop by Chicago to watch them take place, including Jay-Z and Beyonce.

"It got to a point through the summer, you got Jay-Z and Beyoncé sitting courtside at a pick-up run, bro, just watching him. Like, this is Jordan. It was crazy; we had everybody come through the gym."

(Starts at 25:54)

These pick-up games happened in the pre-social media age so we don't have any footage of them hooping together. Crawford inadvertently helped Jordan get in shape to return to the NBA, as he undid his retirement to play for the Washington Wizards until 2003.

Crawford didn't succeed Jordan as a superstar in Chicago but retired as one of the greatest sixth-men and ball-handlers in NBA history.