Jamal Crawford is never the one to back down from a challenge. And he, readily accepting rapper Gillie Da Kid’s 1v1 challenge back in 2023, testifies this. Notably, the challenge is now more of a good-cause-bet of $50,000 to the winner’s charity. However, the bet never actually came into the play, and it has almost been a year since then. But recently, both ends have reignited the sparks of the challenge again.

“He (Gillie) been running since the word “go” lol!! I’m back in the gym ready whenever!” Crawford posted on X. This came in response to a discussion held on Shaquille O’Neal‘s podcast. The discussion started with podcast co-host Adam Lefkoe reading out J-Crossover’s recent message for Gillie. Jamal Carwford stated in his message that he is now back at working out just for Gillie, so he needs to stop running.

The hilarious part of the discussion on Shaq’s show was Wallo already giving up on his cousin Gillie. He even made Lefkoe read out a text he had sent to Jamal Crawford. “Please don’t pay my cousin any attention. He smoked some bad w**d when he called you out. Legend, please give him a pass. He’s only 4ft, 9.5. Thank you for your time,” read the text by Wallo. However, although in good humor, Gillie exuded great confidence in himself regarding the challenge.

He portrayed himself as a threat to the ex-LA Clippers star with a wordplay fusing his name with some of the NBA greats. “There’s no way Jamal gonna beat Damian Gillard, Shai Gilldeous Alexander, Manuel Gillnobili, Shagille O’Neal, and if I’m really on, I’m Mike Gill Jordan,” he stated. Now it is to be seen that when the challenge actually comes into play, now that both sides seem ready. However, this is not the first instance where Jamal Crawford will indulge in a 1v1 challenge.

The time Jamal Crawford suffered a major loss in a shooting contest with Michael Jordan

There were rumors of Michael Jordan being in love with gambling during his time in the NBA. Although some suggest it was Jordan’s urge of self improvement that made him bring things to stake in order to bring a competitive factor in play. One such instance was a 1v1 shooting contest between Mike and Crawford.

The contest started with Jamal challenging Mike at a three-point shootout for $1000. Jordan won the round, and subsequently, the stakes were raised. The two players played the next round for $5000 in which Jamal emerged victorious, thus promoting to up the stakes even further.

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“He (Michael Jordan) asked which car I’d come in to training. I replied ‘In a Mercedes’, he then said ‘I came in a Ferrari, shall we play for it?'”, Crawford detailed, as per a 2022 article by Marca. Though Jamal Crawford agreed to the bet, it did not end well for him as he lost his car to the 6x NBA champ.