Stephen Aylward // Precedent Setter Awards 2021

Portrait of Stephen Aylward
Meet the litigator who thrives in the most complicated cases

By Danielle Groen

On Tuesday May 25th, 2021

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Stephen Aylward

Associate, Stockwoods LLP
Year of Call: 2014
Law School: University of Toronto and University of Oxford

Six years ago, a 20-year-old single mother facing eviction was caught at Toronto Pearson Airport with a suitcase lined with cocaine. Cheyenne Sharma, a member of the Saugeen First Nation, had no criminal record; she’d transported the drugs for rent money. Thanks to a 1996 reform to the Criminal Code that was meant to reduce the over-incarceration of Indigenous people, she could have been considered for house arrest — except that the Harper government had banned conditional sentences for crimes like Sharma’s. She spent more than five months in jail away from her daughter.

Portrait of Stephen AylwardSharma challenged the ban on conditional sentences as an infringement of her constitutional rights. To help her make that case, Stockwoods LLP came on “low bono,” with the file partly funded by Legal Aid Ontario. Stephen Aylward, an associate at the firm, got to work, building the appeal around a simple argument.
“Once a program has been enacted by Parliament to mitigate racism, any bill that undermines it is a violation of Section 15 of the Charter,” says Aylward, referring to the section that guarantees equality under the law.

The court agreed. Last July, eight months after Aylward argued the case, the Ontario Court of Appeal declared the ban on conditional sentences unconstitutional. “Steve’s flat-out brilliance makes him a go-to person when you have a really challenging file,” says his co-counsel Nader Hasan, a partner at Stockwoods. Aylward applies that ingenuity to his entire caseload, which is divvied up between corporate, regulatory and constitutional work.

Aylward understands intimately that Canadian society is not built for everyone who lives in it: due to an inherited retinal condition, he is legally blind. He works closely with Fighting Blindness Canada, providing mentorship to young people with vision loss — and demonstrating that his condition won’t keep him from performing at the very highest level of his profession. “I want to prove it’s not a limit,” says the 33-year-old. “In many ways, having a disability is a driver.”


Don’t forget to read about our other amazing winners.


This story is from our Summer 2021 Issue.


Photography by Saty + Pratha; set design by Kristen Lim Tung; hair & makeup by Caroline Levin / P1M.