Once upon a time, Jamal Crawford owed so much after playing craps that a gambler threatened to kill him, according to a profile for The Undefeated. And, of course, when you bring up the NBA back in the day, and gambling in the same sentence, you know who isn't too far behind, right? Michael Jeffrey Jordan.

During the summer of 2001, as Jordan mulled over the idea of returning to the league, and possibly playing for the Bulls, he asked Crawford to be his teammate for pickup games at the Hoops the Gym in Chicago. Obviously, Jamal accepted the invitation, and the two never lost. Where things got interesting was after the pickup games came to an end.

Typically, a group of Jordan's "friends and associates," would go next door to MJ's restaurant, One Sixtyblue, after pickup games. There, the establishment was set up with card tables throughout the room, and a corner meant for shooting dice. In between his first and second year in the league, Crawford went to One Sixtyblue, and played craps.

On this night, Crawford had $2,000 in cash on him. After a while, he was holding upwards of $10,000 before he lost it all...and then some. It got to the point where Jamal was betting money he didn't have with a group of professional gamblers, who didn't like to hear the phrase "I'll pay you later."