Meet the owners of the coolest, rarest and most valuable shoes at the largest sneaker show in Canada

Last weekend, hundreds of sneakerheads descended upon the Sheraton Hotel for Sole Exchange Canada, the largest sneaker show in Canada. We met a few of the collectors with shoes on display to get the backstories behind their rarest, priciest kicks—and to ask how much they’d sell them for (if they’d sell them at all).

1985 Nike Air Jordan 1, Chicago Colourway

Owner: Mark “Jumpman” Bostic Retail value: $85 (in 1985) Asking price: “I’ve had people offer me up to $10,000 U.S.”

“I’ve been collecting Jordans for 30 years now—I have 959 pairs so far. This pair was the first one I bought when I was 22. I wear them once, on the 1st of January of every year, and that’s it, I won’t put these ones up for sale.”

Adidas x Yeezy Boost 750, Triple Black Colourway

Owner: Ray Guo Retail value: $460 Asking price: $2,500

“I think these ones get the higher price because they were limited, and it’s Kanye West. These are the first release he did with Adidas.”

BAIT x Dreamworks x Diadora N9000, Skeletor Colourway

Owner: Jeff Smith Retail value: $288 Asking price: $590

“I won these shoes in an online international raffle. I just put my name and email in and then a couple of weeks ago I was contacted and told I had won them. This pair is one of 400 made. I’ll sell them if someone gives me the right price, but I’d rather keep them.”

Nike Air Max Lunar 90 SP, Apollo Moon Landing Colourway

Owner: Alvin Martinez Retail value: $220 Asking price: $980

“I got these because they landed at an outlet in Milton, and I was fortunate enough to get a pair at retail price.”

Nike Air Max 95 Premium DB “Doernbecher,” Colourway designed by Jacob Burris

Owner: Meredydd Hardie Retail value: $235 Asking price: $525

“Nike does this collaboration with a children’s hospital in Germany where they get kids to help design sneakers. This pair is from a kid named Jacob Burris, who they call the Bionic Kid because he has a heart condition. So the sneaker has all the circuitry pattern on it, his fingerprints, and Stan Lee’s signature. It’s my favourite pair from last year’s release. They never released in Canada, so I had to work really hard to get these shipped here.”

Nike Air Jordan 2, “Quai 54” Colourway

Owner: Earl Ortiz Retail value: $220 Asking price: $655

“There’s a street basketball tournament in France that Nike commemorated by releasing a set of shoes for the event, including these. Since they were only released in Europe, there are only maybe 20 of these in Canada, probably 10 in the GTA.”

2007 Nike Dunk High, “Year of the Pig” Colourway

Owner: McKeyra Peter Retail value: $364 Asking price: “Because of their sentimental value, the offer would have to be astronomical.”

“These are actually my girlfriend’s brother’s shoes. He has a disability and can’t really do a whole lot so he got into collecting sneakers. He was looking for these for a while and eventually ended up finding someone in Japan to help him get a hold of them and ship them here. They came out in 2007 to commemorate the Chinese Year of the Pig.”

Nike Air Force 1, “Look See” factory sample, “Maize” Colourway

Owner: Jaron Smith Retail value: N/A Asking price: $1,000

“These shoes are called a ‘look see’ sample. They’re one-offs from when Nike wants to experiment with a new colourway or a new collaboration on a style. These are ultra-rare and you can’t even Google them because they just don’t exist apart from these factory singles. They don’t even have a Nike stock number. I can’t really tell you how I came across these.”

Adidas Infant Yeezy Boost 350, Pirate Black Colourway Owner: Laith Karaki Retail value: $195 Asking price: $650 (quoted to a buyer en route to the sneaker show)

“I got to pick these up because I won a purchase ticket in an Adidas raffle. I put in two ballots for two different colourways. There were only 60 pairs in both colours at the Queen Street store.”

Extra Butter x Reebok Ventilator, Street Meat Colourway

Owner: Tristin Kennedy Retail value: $189 Asking price: $430

“These shoes are made to represent all the different components that go into the ‘street meat’ sold in New York City. All the colours mean something: The green is the lettuce, the yellow specks on the sole are for the fried rice, white for that yogurt sauce, red for the spice, and even some of the pink on the toe to show that sometimes undercooked meat you’ll get.”

Adidas Originals Wings by Jeremy Scott, Totem Eagle Colourway

Owner: Andrew Van Wynsberghe Retail value: $294 Asking price: $450

“One of my buddies contacted me about selling his whole collection. I ended up buying it and these were part of the lot. I had never seen a pair of these before and I haven’t seen anyone with a pair since.”

Air Jordan V, Bel Air Colourway

Owner: Aly Jamal Retail value: $240 Asking price: $600

“I love these shoes, I mean, I grew up on The Fresh Prince of Bel Air, so they’re probably my favourite shoe. I bought one pair of these at retail and I loved them so much that I bought a second pair from someone else at resale value.”

Air Jordan IV retro, 2013 “Fear” Colourway

Owners: Yaser Sagha, left, Kristian Tazbaz Retail value: $225 Asking price: $800

“These are a consignment sale, so we’ll get a cut for selling them. The guy who gave them to us is an old school collector. These are really rare and most of the time you’ll have to camp out for a day to buy them retail, but some shops do raffles for the purchase. I think we might be the only ones selling these never-used, with an original purchase receipt.”

Nike x Kanye West, Air Yeezy 2, Red October Colourway

Owner: Elvin Long Retail value: $320 Asking price: $6,000

“I have a friend who has a store here, who I asked to help me look for these shoes. After a month, he found a pair, and I purchased them for $4,500. I was able to get them because I sell shoes as well, so I don’t think I’ll ever sell these. Maybe if I buy a second pair.”