Michael Jordan bet on how many Jordans he would see during a car ride

Dan Santaromita
NBC Sports Chicago

Michael Jordan's frequent gambling and competitive nature were main topics in Episode 6 of "The Last Dance." Jordan competed at everything, even tossing quarters, as shown in the documentary.

That desire to play games and compete at all times remains to this day. Jason Hehir, the director of "The Last Dance," shared a story about that on "The Jalen & Jacoby Aftershow" on Sunday night.

Hehir said he believes that Jordan doesn't gamble for financial gain, but because he loves games. Hehir was the victim of one of those games the second time they met for the documentary.

Hehir sets the stage at the final round of The Masters in 2018. They met at a hotel in New York City where they had a drink in the lobby before heading to a game at the Barclays Center.

They get into an SUV to drive from Midtown to the Barclays Center in Brooklyn, and as they are pulling away, Jordan propositions Hehir a friendly bet.

"We close the door. We pull away. He says, ‘I bet you we see 10 pairs of Jordans from here to the arena,'" Hehir said. "There was no money on the line, but he's got a half hour where he's in a confined space. He wants to play a game. That's what he wants to do, and he wants to win the game."

Hehir agreed to the game and thought about the route to the stadium. He figured there was only a short stretch of the drive with pedestrians until they got to the highway, and then it was clear sailing.

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The only saw three Jordans before hitting the highway. Hehir thought he was in the clear, but Jordan had a trick up his sleeve.

"When we start to get close to the arena, it's the Jordan Brand Classic, so anyone attending that game has Jordans on," Hehir said with a laugh. "He's going, ‘four, five, six, seven, eight, nine, 10.' I said, ‘Well, that's not fair. We're at the Jordan Brand Classic.' He just turns and winks at me. He knew he was going to win before he started that. That's what it's about with him."

There are plenty of stories about Jordan losing bets, but in this case, even with no money on the line, he knew exactly what he was doing, and was able to pull one over on Hehir.

"He doesn't know my name, probably, at that point, but all he wants to do is win that game," Hehir said. "So the calculus in his head, he sat there and I'm sure thought on some level, ‘There's going to be a lot of people wearing Jordans at this thing. I wonder how many people are wearing Jordans on the sidewalk? Not many, but there's going to be way more there. Hey, let's play a game that I know I'm going to win with this kid in this car right now.' That was such a glimpse into his personality."

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Michael Jordan bet on how many Jordans he would see during a car ride originally appeared on NBC Sports Chicago

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