Following Game 5 of the 1998 NBA Finals, a Utah Jazz ball boy by the name of Preston Truman was given a once-in-a-lifetime gift: the sneakers Michael Jordan wore during the game. In 2020, in the wake of the release of The Last Dance and the uptick in collectors’ interest in Air Jordans, Truman sold the shoes to Grey Flannel Auctions for a little over $200,000. Just three years later, in early 2023, they sold again at auction for an incredible $1.38 million.

It helped that the shoes were worn during the legendary Flu Game, in which Jordan overcame a debilitating bout of food poisoning to deliver one of his most clutch performances ever. To this day, the black-and-red Air Jordan 12s are known as the “Flu Game,” which means that these sneakers are the OG version of one of the most beloved Jordan colorways of all time, too. Few game-worn sneakers have as much illustrious history attached to them.

The story does have a down side: Truman launched a lawsuit against Grey Flannel in 2023, claiming that they pressured him into selling the shoes. The lawsuit is still ongoing.

6. “Glass Shard” Air Jordan 1, $615,000

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In August 2020, as post-Last Dance Jordan hype was reaching record levels, a single pair of game-worn Air Jordan 1s turned heads when it sold at auction via Christie’s for more than half a million dollars. Worn by Michael Jordan during an exhibition game in Italy, according to the auction listing, they were actually estimated to fetch an even higher figure, closer to $850,000. (Still, the price was impressive.)

What made this particular pair of Jordan 1s so unique was what else was included with them: a shard of broken glass, embedded directly into the shoe and apparently caused by Jordan shattering the backboard during a slam dunk. (These, of course, are not to be confused with the “Shattered Backboard” Jordan 1s.) During the same auction, a pair of sneakers worn by Jordan during Team USA’s gold medal game at the 1992 Olympics fetched over $100,000.

7. Game-Worn Air Jordan 1, $560,000

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