Horace Grant spent six seasons alongside the legendary Michael Jordan as part of the Chicago Bulls dynasty. He was an integral part of their first three championships from 1991 to 1993.
Grant had a front-row seat to Jordan's competitive side — far beyond games and practices. Jordan 's intensity didn't switch off when he left the court; it carried into everyday life and even into late-night gambling sessions.
Grant recalled one of them during his recent appearance on Speaking on the Legends in Session podcast.
Teams have different ways to kill time during long travel sessions in-between games. For the 1990s Chicago Bulls , card games were their go-to.
During one of the games, Jordan, who has a notorious love of gambling, apparently ran short of cash, so he turned to Grant.
"We were playing some poker and he asked me, he was like, 'Loan me a stack.' I'm like, 'Sure, s—t this is Michael Jordan., you go for it, '" Grant recalled. "He lose that, he was like, 'Can I borrow another one?' I'm like, 'Hell yeah,' That's another stack. And by the time he lose that, we're landing."
Jordan's competitive spirit has always been one of his signature traits. Off the court, especially in gambling, however, this never-say-die spirit has not fared well for him.
Jordan has had a long history of gambling. He even postponed his return from retirement because he was too busy playing spades. Not to mention the countless rumors of his gambling affecting his NBA career, with the popular one being that his retirement in 1993 was a front for a gambling suspension handed to him by the NBA.
For many people, gambling often leads to anger and frustration — especially after a loss. That's why it wasn't the wisest move for Grant to poke the bear right after watching Jordan lose the money he had lent him.
"Just to mess with him, I said, 'Yo, MJ, make sure you have my money in the morning,'" said Grant. "And I had never seen him that mad in a long time. Just the mere fact that I said out loud."
Suffice to say, the comment did not bode well for the easily-irritated Jordan. He made sure Grant would get his money in an instant, but not without first showing him that he didn't take kindly to his comments.
"When I walk in, he had two stacks of crispy $100 bills. And instead of just giving to me, he threw them at me and I just said, 'Thank you!'" Grant said, laughing.
Despite being one of Jordan's most effective teammates, Grant left Chicago to join the up-and-coming Orlando Magic in 1994 during the former's first retirement. The move wasn't only because the Bulls were weaker without Jordan; it was also because the Magic reportedly offered Grant more money.
Many rumors have surfaced that Jordan and Grant had tension despite their success. After years of being teammates, Grant was now on the opposite side with a legitimate contender, giving the Bulls' superstar a more concrete reason to hate him.
The hatred only intensified when Grant and the Magic handed Jordan his second playoff series loss in the '90s, after the Bulls defeated the Magic in six games in the 1995 Eastern Conference finals. Come 1996, however, after plugging the hole Grant left with Dennis Rodman, Jordan and the Bulls became unstoppable and ran through the league en route to their second three-peat.
This story was originally published by Basketball Network on Feb 22, 2026, where it first appeared in the Off The Court section. Add Basketball Network as a Preferred Source by clicking here.
