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.

19. Game-Worn Converse Fastbreak ($190,373)

1984 was not only Michael Jordan’s rookie year in the NBA, it was also the year he and Team USA won gold at the Olympics in Los Angeles. At this early stage in his career, MJ was yet to make the switch to the Swoosh and was still rocking Converse as a hangover from his college sponsorship. In June 2017, a pair of Converse Fastbreaks signed by the then-rookie – and said to have been worn on-court at the Olympics – came up for auction. They were expected to sell for around $100k, but when all was said and done, they reached a staggering $190,373 – the highest ever price for a pair of game-worn sneakers at that time.

18. Nike Mag 2016 Auto-Lace ($200,000)

The first shoe that springs to mind when the question of selling a kidney comes up has to be the 2016 version of Nike’s Air Mag. The sci-fi sneaker was first imagined in the late 80s and presented on the silver screen in Back to the Future Part II. Of course, the lights and auto-lacing feature were originally achieved using cinematic tricks – it took almost 30 years for technology to catch up with the concept.

The release of the battery-powered, motor-driven sneakers was limited to fewer than 100 pairs, which were doled out via raffle to sneakerheads, cinephiles and pop-culture aficionados. Wide-ranging appeal, scarcity and technological significance have made it one of the most sought-after sneakers out there. While the Nike Mag Auto-Lace of 2016 was originally made available via raffle, one final pair was auctioned for $200,000, with all proceeds going to the Michael J. Fox Foundation for Parkinson’s Research.

17. Game-Worn Air Jordan 13 ($204,000)

Another grail worn during the Chicago Bulls 1997-98 Championship season, this pair of Air Jordan 13s actually came with a team letter confirming the shoe’s legitimacy: ‘Thank you for your interest in the Chicago Bulls. Please accept this letter to confirm authenticity of the Michael Jordan autographed game-worn black shoes in your possession. Michael wore these shoes during the 1997-98 Championship season. The autograph is authenticated by Upper Deck and includes the matching UDA certificate.’

The coding above the size information indicates production between May and July of 1998. Wear and tear was also generally light during this era, as Michael Jordan typically wore a new pair of Air Jordan 13s every half.

16. Game-Worn Nike Air Zoom Generation ($222,000)

The first signature shoe from LeBron James on the list, the Nike Air Zoom Generation is still a favourite among hoops-heads. Worn during the rookie’s second ever NBA game, the Air Zoom Generation accompanied LeBron on his way to 21 points against the Phoenix Suns in 2003. Earlier that same year, LeBron James signed a $87 million deal with Nike, a partnership that has extended throughout his entire career.

15. Bill Bowerman Handmade Track Shoes Prototype ($315,000)

Now this is one for the history books. A grail from the late 1960s, these handmade shoes by Nike co-founder Bill Bowerman were made specifically for Canadian Track and Field sprinter and Olympian Harry Jerome. Jerome set a total of seven world records over the course of his career.

Remarkably featuring four prototype logos (which bear striking similarity to the Swoosh logo), the shoes also feature the iconic Waffle soles – introduced by Nike via the Moon Shoe at the 1972 Olympic Trials.

14. Louis Vuitton x Nike Air Force 1, with Pilot Case ($352,800)

The sneaker industry is still reeling from the tragic loss of Virgil Abloh in November 2021. Longtime Kanye West collaborator and founder of the triumphant Off-White label, Virgil seized the reins at Louis Vuitton in 2018. The collection of Louis Vuitton x Air Force 1s are still among some of his most prized designs, with a 200-lot auction going live at Sotheby’s in 2022. With final prices smashing estimates in a $25.3 million auction war, it was Lot 1 that garnered the most attention, selling at an astronomical $352,800.

13. Game-Worn Air Jordan 13, Utah Jazz Game 5 ($378,000)

Game-worn Air Jordans continue to serve as the jewel in the crown for sneaker collectors the world over. Heralding Michael Jordan’s final season as a Chicago Bull, this dual-signed, game-worn Air Jordan 13 was laced during the first two quarters of Game 5 against the Utah Jazz. The Jazz won Game 5 83-81 before Michael Jordan and the Chicago Bulls shut the door 4-2 and secured their sixth NBA championship trophy.

12. Game-Worn Air Jordan 7 Olympic Dream Team ($420,000)

They were the most feared team in all of sport. In 1992, the USA ‘Dream Team’ descended on Barcelona for the Summer Olympics, a lineup loaded with Michael, Magic, Bird, the Mailman, the Admiral, Stock, Charles, Scottie, Clyde the Glide, Big Pat, Mullin and Laettner.

Pictured above is Karl Malone’s special pair of game-worn Air Jordan 13s, signed by Michael Jordan. Hiding in plain sight for a number of years, the Air Jordan 7s were actually on display at the Mailman’s own car dealership in Utah.

11. Game-Worn Air Jordan 1 ‘Broken Foot Game’ ($422,100)

‘The worst possible scenario for the Chicago Bulls, their greatest fear, became a cruel reality Monday when X-rays revealed that Michael Jordan, the heart and soul of this up-and-coming franchise, has a fractured bone in his left foot and will be out for at least six weeks.’ Reported by the Chicago Tribune, it was the news that devastated Bulls fans on November 5, 1985.

The shoes pictured above were the black and varsity red model worn during the fateful night MJ sustained his foot injury. During that fateful game, Jordan scored 12 points in 18 minutes prior to his injury, which was enough to help the Bulls win the game 111-105. He was sidelined for six months, and the Bulls fell to a 24-43 record without their superstar recruit. Eventually making his return on March 15, 1986, Jordan finished the season playing 14 regular season games and all three Playoff games against the Boston Celtics.

10. Nike Moon Shoe ($437,500)

Part of the Stadium Goods x Sotheby’s ‘Ultimate Sneaker Collection’, the out-of-this-world ‘Moon Shoe’ was so coveted that it was auctioned off separately to the rest of the $850,000 assemblage. The Nike Waffle Racing Flat, also known as the ‘Moon Shoe’, was reportedly one of just a dozen pairs ever created – and believed to be the only DS pair in existence. Cobbled by early Nike employee Geoff Hollister for runners at the 1972 Olympic Trials, the Moon Shoe is constructed from nylon and sewn together with fishing line. Sweetest quirk? The soles were literally moulded with waffle irons!

9. Game-Worn Air Jordan 1 From Rookie Season (486,000)

Another pair of game-worn Air Jordan 1s worn during Michael Jordan’s rookie year, these sold for $486,000. Coming with the customary size 13 left foot and size 13.5 right foot (based on the specific requests from Michael Jordan), the shoes came with a letter of provenance from Bulls/Bucks trainer Mark Pfeil that said the model was obtained during the spring of 1985.

8. Game-worn Air Jordan 1 ($560,000)

At first glance, it looks like a ‘Chicago’ AJ1 dressed in its legendary red, white and black colour scheme, but closer scrutiny reveals custom touches. The ‘TYPS’ printed inside the ankle collar stands for Tong Yang Player Sample, confirming these were indeed for MJ. Also, they’re mismatched sizes – any Jordanhead would know he wore a size 13 left shoe and a size 13.5 on the right. Secondly, the ankle height is modified shorter than the regular high cut of the time, but it retains nine eyelets.

Additionally, softer leather and materials – even better than what was being used at the time – feature on the uppers on his personal pairs. They’re signed by the man himself, and all the relevant paperwork is included. Bolstered by the spectacular The Last Dance documentary, the price of the pair skyrocketed to $560,000.

7. Game-Worn Air Jordan 1 ($615,000)

Incredibly, these Air Jordan 1s were autographed mere hours before Michael Jordan and the Chicago Bulls secured their first NBA Championship in 1991. San Antonio sportscaster Rick Lozano asked Michael Jordan to sign the shoes with a blue sharpie while on camera, flouting media conventions regarding reporters seeking autographs from players. Jordan signs both toe boxes, adding the notation, ‘1st pair.’ The Chicago Bulls defeated the Los Angeles Laker in Game 5 of the NBA Finals, 108 – 101.

6. Game-Worn Air Jordan 1 ‘Shattered Backboard’ ($615,000)

While playing in an exhibition game in Trieste, Italy in 1985, Michael Jordan played a dunk so powerful, it shattered the backboard. He did so while wearing the above pair, an OG AJ1 ‘Chicago’ edition. Real glass from the backboard is still lodged in the sole of the AJ1, and in typical MJ fashion, Jordan autographed the sneaker after the game before handing it over to a player of the opposing team.

5. Game-Worn Air Jordan 1 With Dunk Sole ($675,000)

This game-worn, signed pair of Air Jordan 1s were worn in 1986 at MECCA Arena in Milwaukee. Still nursing a broken foot, Michael Jordan came off the bench to score 28 points in just 26 minutes. Interestingly, the soles were swapped out for this pair, which were both softer and wider. This was to mitigate the risk of further damage to Michael Jordan’s healing bones. Another interesting manufacturing tidbit: there was an uneven count of eyelets on the right shoe!

4. Game-Worn Air Jordan 12 ‘Flu-Game’ ($1.38 million)

It was one of the many moments that defined Michael Jordan’s immortal legacy. Battling food poisoning, Michael Jordan nevertheless dragged the Chicago Bulls to a win in Game 5 of the 1997 Finals. His Airness willing himself to 38 points, including 15 in the fourth quarter.

‘Probably the most difficult thing I’ve ever done,’ Jordan said, later adding, ‘I didn’t want to give up. No matter how sick I was or how tired I was or how low on energy I was. I felt the obligation to my team, to the city of Chicago, to go out and give that extra effort.’

On his feet were a pair of black and varsity red Air Jordan 12s. Known in sneaker circles as ‘Flu Game 12s’, the signed pair were originally gifted to Utah Jazz ball boy Preston Truman.

3. Game-Worn Nike Air Ships ($1.47 million)

A pair of game-worn Nike Air Ships worn by Michael Jordan during his rookie year sold at Sotheby’s for $1.472 million in 2021. The shoes were originally worn during Jordan’s fifth-ever NBA game for the Chicago Bulls against the Denver Nuggets on November 1, 1984. At the time, it was the most expensive sneaker ever sold at auction. According to a statement by Sotheby’s, the auction winner was Nick Fiorella, a sports trading card collector who has previously paid $4.6 million for a Luca Doncic card – the fourth most expensive card ever sold.

2. Kanye West’s Grammy-Worn Nike Air Yeezy 1 ‘Prototype’ ($1.8 million)

Records were shattered when auction house Sotheby’s attracted a $1.8 million winning bid for Kanye West’s Nike Air Yeezy 1 ‘Prototype’. The enormous sum instantly made it the most expensive public sneaker sale at the time when the hammer fell in April 2021. The size 12 pair was worn by Kanye during his performances of ‘Hey Mama’ and ‘Stronger’ at the 2008 Grammy Awards, and was the exact shoe that announced Nike’s prospective Air Yeezy project to the wider sneaker world.

Designed by Kanye and Mark Smith, the sneaker features a soft black leather upper with perforated detailing, a tonal Swoosh logo on the overlay, and the familiar forefoot strap seen on all Air Yeezy models.

1. Game-Worn Air Jordan 13 ($2.2 million)

In 2023, Sotheby’s obliterated the record for the most expensive sneaker ever sold at auction with the game-worn Air Jordan 13 netting an incredible $2.2 million. Lacing them during Game 2 of the 1998 NBA Finals, Michael Jordan scored 37 points as the Chicago Bulls beat the Utah Jazz, 93–88. After the game, Jordan gifted the shoes to a longtime Jazz ball boy who maintained the visitors’ locker room. Michael Jordan and the Bulls would go on to win the 1998 NBA Finals for their sixth title of the decade.

‘Today’s record-breaking result further proves that the demand for Michael Jordan sports memorabilia continues to outperform and transcend all expectations. Sotheby’s is extremely proud to hold the world record for most valuable game-worn sports memorabilia at auction and the most valuable sneakers ever sold, both of which – to no surprise – are directly tied to the global icon, Michael Jordan,’ said Brahm Wachter, Sotheby’s Head of Streetwear and Modern Collectables.

For more on some of the most coveted sneakers across the globe, make sure to check out our interview with Sotheby’s Head of Streetwear.