Back when he was on the Bulls in ’01, Jamal Crawford used to run with Michael Jordan at pickup games as MJ contemplated a return to the League.
According to a an excellent profile on Crawford done by The Undefeated, pickup games led to dice games at Jordan’s restaurant, One SityBlue, which was located next door to the gym where they worked out.
One night, Jamal found himself deep in the hole and ran up a major debt with professional gamblers while playing Craps:
Two participants, on condition of anonymity, recounted one particular night when Jordan and Antoine Walker were among the card players and Crawford and Ray Allen were among the players shooting dice.
[Crawford] brought about $2,000 in cash that night and remembers being one of the first shooters. There were maybe a half-dozen players, most of whom were professional gamblers. Crawford was up and down for a while, once holding about $10,000 in cash, more than he had ever won before.
Then he went down. Way down. Into a hole there was no coming back from. He began making bets with money he didn’t have on hand with a group of professional gamblers used to getting paid on the spot.
“They would be like, ‘OK, you bet two grand on this one, OK lost,” Crawford recalled, agreeing to discuss his own role that night but refusing to confirm the identity of anyone else involved. “Then they’d say, ‘Now we will bet three on this one [roll]. Oops, lost. Now you down 15 [grand].” So it wasn’t like cash was coming out, it was like air money. But it was money I was going to have to pay somehow eventually.”
Crawford soon found himself down $100,000–others say it was in the hundreds of thousands. Regardless, a call was placed to Crawford’s agent, Aaron Goodwin, and the three-time Sixth Man of the Year’s life was threatened.
Over what is believed to be a two-day span, he said, he lost in the neighborhood of $100,000. A person with intimate knowledge of the game claims Crawford lost several hundred thousand and Allen lost even more. And that, days after the dice game, a call was placed to Goodwin, Crawford’s agent, to inform him that Crawford had not yet squared his debt with one professional gambler.
“OK,” Goodwin said, according to the person with intimate knowledge of the game. “What does he owe? Jamal is good for it.”
“No, you don’t understand,” the go-between said. “If he doesn’t pay now, these guys will kill Jamal.”
“Kill Jamal?!! He’s an NBA player. He gets paid as soon as the season starts. Give me the dude’s number.”
The person with knowledge of the game said Goodwin called the man Crawford owed money, set up a payment plan and resolved the issue without incident.
The situation was fortunately resolved without any violence, and Crawford has said that he has not gambled outside of a legal casino since.
The entire profile is worth a read and can be done so at The Undefeated.