Inside Toronto's Thriving Underground Sneaker Resale Market

Calum Marsh
·4 min read

One of the best places to buy sneakers in Toronto is a deserted parking lot behind a laundromat in the west-end neighborhood of Parkdale. On a rainy afternoon in late August I rolled up there on my bike to meet David, who was standing by the trunk of his car wearing a pair of Rookie of the Years. I had connected with David over Kijiji that morning and arranged to buy some mildly scuffed-up Air Jordan 1s in the coveted “Turbo Green” colourway, and here he was, as promised, to make the deal. As we waited for my e-transfer to be completed—I was sending him a little over $300—a portly, middle-aged man in a business suit strolled by and nodded at the Nike box on the ground between us. “Got any other Jordans for sale?” he asked. “Lots,” David said. “What are you looking for?”

David is the proprietor of We Got Grails, a sneaker resale company he runs out of his living room with his brother in the Greater Toronto Area. Meeting up with eager local sneakerheads around the city, he buys, sells, and trades all kinds of new and used Jordans, Dunks, and Yeezys, advertising his wares on Facebook and Instagram and online marketplaces like Craigslist and Kijiji. The kinds of cash-for-kicks deals he coordinates with interested buyers like me are his bread and butter—and as the demand for rare sneakers continues to rise, businesses such as David’s are becoming more successful than ever. This is no longer about people lining up for shoes and flipping them on eBay for a tidy profit. The sneaker resale market has become a whole cottage industry, and in Canada, outfits like We Got Grails are cleaning up.

When I reach Tyler on the phone, he’s on the highway, “running around all day from store to store buying shoes,” as he explains it. Although most shoes sell out the minute they’re released, small numbers will still arrive to stores in dribs and drabs in the days and weeks to come. You just need contacts on the inside to clue you in. “You have to be well-connected,” he says. “Managers at Champs and Foot Locker will message me and say, ‘Hey, I just got this in, you have thirty minutes to get here.’ That’s how it works.”

While Tyler’s day-to-day business is much like Richard, Shawn, and David’s, he has an eye, in particular, on the long term. As he puts it, the sneaker resale market is more complex than it might initially seem. “It’s like the stock market,” he says. “There are different perspectives. There are quick sales and there are long-term holds. Long-term investment strategies work really well.” Shoes that might sell “for a decent amount right away,” such as Court Purple Jordans or the recent Tokyo JPs, will appreciate in value in time. “If you’re comfortable holding on to something like that for two years, you can realistically double the investment,” he says. “You just have to make that decision when you’re buying the shoe. Is it a quick flip or a long haul? You do the equation from there.”

Tyler says he would love to have the capital and the time to make larger shoe investments: he insists it would be a smart move to snap up as many Jordan 1 Off-White Sails as possible now and hold on to them for 12 to 24 months, as their current $2000 price tag will continue to balloon. His current operation, however, is oriented around quick turnarounds and smaller margins: “I prefer volume and consistency right now,” he says. “That’s the way to go.” He hopes to some day turn his reselling business into a full-blown retail storefront, and is considering moving to the U.S., where the sneaker market is much easier on consumers and resellers alike.

Richard and Shawn agree. “Our clients now are the average sneaker lover, and a lot of them are young kids and students who don’t have the cash flow to spend $2000 on a shoe,” Shawn says. “We want to stay in that market. If we had the chance to buy an Off-White at a decent price, we’ll move them. But we don’t want to move into the hardcore sneakerhead territory where we’re spending $2000 on a shoe and getting $2200 for it.” The average sneaker, Richard points out, is luxurious enough. “The Jordan 1s are still expensive. $400 is a lot of money for a pair of shoes,” he says. “But I’d rather move 20 of those for $400 than two pairs of Off-Whites for ten times the price.”

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