Speaking to the Undefeated, Jamal Crawford told the WILDEST story involving pick up basketball, MJ, craps, and gambling debts.
Long story short, MJ’s trying to make an NBA comeback in 2001. He gathers some boys in Chicago, including Crawford who was then with the Bulls. They’re hooping, and then going to MJ’s restaurant across the street, in the back, to shoot craps and play cards. And bet thousands and thousands and thousands.
In Jamal’s words, he “got in a little too deep”. Starting off with 2k in cash, then at one point being up 10k, only to end the night down 100k. A few days later, Jamal’s agent gets a call from a middleman of MJ’s posse, to discuss the debts that Jamal owed. “You don’t understand”, the middleman said, “if he doesn’t pay now, these guys will kill Jamal.”
I imagine a dark room like Frank gets for his Vietnamese friends in Sunny, where MJ has secret passwords for anyone that wants entrance. Fingers are being sacrificed. Aaaaand of course MJ has some boys that crack down on people for their gambling debts. If you still have any doubt that MJ once bet on NBA games, you remain delusional. That’s not necessarily a bad thing. Because he bet on himself, no way MJ could ever bring himself to lose.