Tommy Davidson shared another legendary gambling story involving Michael Jordan, and this one perfectly captured just how competitive Jordan becomes once money and pride are involved.
Speaking on the Art of the Dialogue podcast, Davidson recalled playing against Jordan during a celebrity Texas Hold’em tournament. Davidson, best known for his work on ‘In Living Color’ and films like ‘Booty Call,’ explained that the event had multiple poker tables where players had to advance round by round to eventually earn a seat at Jordan’s table.
“You know, we gambled. We played Michael Jordan in Texas Hold’em. I’m going to tell a story. It was a celebrity tournament, right? There were all these tables, and you had to play your way to the Jordan table.”
“When I got to the table, he was talking to Robin and a couple of people. He saw me and said, what’s up, man? Glad you made it out. Then he asked, what you doing over here? I said, I won to get up here. He said, oh, okay. Well, that part’s over. Then he started talking to his friends. I said, ‘Hey Mike, just because you said that, you might lose. He said, yeah, good luck to you.'”
“So we get back, and the game’s going. He didn’t know I brought in one of the dealers from the casino. It came to me, and he was getting broke, and I could get him out of the whole game. But he had to bluff me. My dealer was like, he ain’t got nothing.”
“So I leaned into him because I had to get him to put out. I said, hey Mike, if you’re in the national championship against Georgetown Hoyas, and that Georgetown player didn’t throw the ball to Worby by accident, do you think you still win that game? He went boom. Everybody was like, whoa, whoa, whoa. He was mad too. Michael, chill out, man. My glasses flew off.”
“Then later that night I was shooting pool, and he came over. Boom. Boom. He took the ball out. 20,000 a ball. I said, I ain’t messing with you, Mike. I already showed you what I could do. He started laughing and asked, how you do that, man? I said, Michael, you dunk basketballs. I dunk minds. That’s my man, though.”
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Stories about Jordan’s gambling competitiveness have become almost mythical over the years. Charles Barkley once joked that Jordan’s gambling strategy was hilarious because “he didn’t realize we were all rich.”
Vince Carter has shared stories about Jordan casually losing huge amounts of money without blinking. Drake even called Jordan the ‘gambling GOAT’ after telling a wild ping-pong betting story involving the six-time champion.
Jordan himself has openly admitted his obsession is not really gambling itself, but competition. That mindset explains why stories like Davidson’s continue surfacing decades later. Whether it was poker, golf, cards, pool, ping pong, or basketball, Jordan approached everything with the exact same intensity.
Davidson probably explained it best with his final line:
“When it’s him and Derek Jeter in the room, forget about it. If you’re in the same room, just go home.”
