Air Jordan 10 OVO

We're starting this ultra-valuable spectrum of sneakers with shoes that were not owned or worn by Michael Jordan, unlike many of the Air Jordans on this list. Instead, in 2014, Canadian singer Drake gave out these Air Jordan 10 OVO sample shoes from his own collection to lucky fans. During a 2014 Raptors game in Toronto, it all happened on "Drake Night."

Because these sneakers had never been released before, the two pairs presented to fans were unique. The white pair went for $20,000 the next week on eBay (because of course they put them on eBay). The black pair, shown below, sold for $100,000 after 154 bids.

These Air Jordans were never meant to be worn in competition. They were given to Drake as a thank you for his Air Jordan cross-promotion during a performance tour.

Price: $100,000