Jamal Crawford after gambling losses with Michael Jordan: “If he doesn’t pay now, these guys will kill Jamal”

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The legendary stories about Michael Jordan and gambling continue to perpetuate. Imagine if the social media, cell phones and technology of today, took place during His Airness‘ playing days? We already knew about players like Charles Barkley and Antonie Walker, but now, following up a story via The Undefeated, players like Jamal Crawford and Ray Allen, too, were part of these massive gambling sessions.

In fact, during a particular gambling session, Jamal Crawford — on his rookie NBA contract — became so far in the hole, that he was losing “15 grand” a roll. Fellow dice roller Ray Allen became even more entrenched having to borrow tens of thousands from Michael Jordan.

In between Crawford’s first and second year in the league, after the pickup games at Hoops the Gym, many of Jordan’s friends and associates would go next door to his contemporary American restaurant, One Sixtyblue. After hours, games of chance were set up – Vegas-style card tables, a separate corner for shooting dice.

He (Jamal 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.”

Then it was Ray Allen’s turn. And by the end, both players had much rougher nights than anything that ever happened on the basketball court.

As the evening went on, Allen came into the game. He represented fresh cash and became the shooter. Crawford bet on his roll. And lost again. Both their losses piled up, and Allen had to borrow tens of thousands from Jordan, according to one of the participants.

But Allen had made about $70 million in his career up to that point. Crawford was still on year one of his rookie deal, which guaranteed him $8 million over three seasons. As a colossal pit formed in his stomach, he remembered thinking, ‘What the hell did I just do?’

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. 

However, for Jamal Crawford, it was far from over. In fact, a call was placed to his agent demanding the young NBA guard pay his debt immediately or be killed.

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.

To help square the debt at the end of the second night, he walked out to his 2001 Mercedes-Benz S Class 430, an immaculate new grey sedan. Before he handed over the keys, he opened the trunk of the car. And took out his basketball.

The story continues on The Undefeated and is a really good feature of the life story of Jamal Crawford. It’s quite a long piece, but worth the read.

On the gambling side of things, if you’re a baller, you might want to stay away from MJ…just ask Antoine Walker.