This Bay Street partner is a gifted skateboarder

Matias Milet is out at the skatepark up to six days a week
Matias Milet mid air on his skateboard
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When Matias Milet was maybe 10 years old, a boy from California carrying a state-of-the-art skateboard transferred into his Montreal classroom and sparked a deeper love for the sport. Milet had dabbled before in department-store skateboards, but this board was far better — and way more fun. It felt like gliding on asphalt. He began riding everywhere: empty swimming pools, crappy skateparks, ramps built out of found (or pilfered) plywood. 

Lawyer Matias Milet dressed in casual clothes, mid air on his stakeboard

Matias Milet

Osler, Hoskin & Harcourt LLP 

A couple years passed, and Milet, tired of skateboarding’s bro-y culture, dropped the pastime; more time went by, and he went to law school before practising tax law at Osler, Hoskin & Harcourt LLP, where the 55-year-old is now a partner. Then, in 2020, the pandemic hit, and Milet’s gym shut down. He needed to stay active. His 12-year-old daughter, captivated by the Instagram videos of the young British skateboarder Sky Brown, decided to give the sport a try. “It was just happenstance,” says Milet. “But it completely revived skateboarding for me.” 

At first, he joined his daughter twice a week. But Milet concedes he’s a little obsessive, and now he’s at Toronto’s Underpass and Ashbridges Bay skateparks, with or without her, four to six days a week. He’s often absorbed in technical tricks like heelflips and kickflips, moving on to a new skill only after he’s mastered the previous one or finds himself so stymied that the wisest counsel is to try something else. Milet also logs time in front of YouTube, watching videos not just of people doing tricks right but also doing them wrong, so he can understand where he’s gone wrong, too. In that respect, skateboarding isn’t altogether different from tax law: “You’re very engrossed in a problem, and you have to find a solution,” he says. “Luckily, I find solutions in law faster than in skateboarding.” 

But when he lands that kickflip? “It just fills me with a really intense pleasure,” Milet says. He’ll drive home from the skatepark with his daughter, music blaring, high on the adrenaline of nailing their respective tricks. “We just turn to each other and grin.” 

This is a story from our Winter 2021 Issue.

Photography by Steph Martyniuk.