Every sneakerhead knows that there are grails, and then there are holy sh*t grails. This list no doubt belongs to the latter. From long-forgotten Nike Air Ships to immaculate Yeezy samples, the market for rare game-worn sneakers and archival gems continues to skyrocket. So grab your auction paddles, these are the most expensive sneakers ever sold at auction.

Going once, going twice, SOLD!

20. Game-Worn Air Jordan 1 ’Chicago’ ($189,000)

Get ready for some game-worn Air Jordan 1 grails! Manufactured in 1985 between the months of January and February, this pair of Air Jordan 1s was used lightly, shown through black paint scuffs on the outsole and back heel of the left shoe. The consignor acquired the pair from his grandmother, Carol Couch, who received them as a gift from Utah Jazz’s Jerry Sloan.