During law school, Winston assisted the David Asper Centre for Constitutional Rights with its intervention before the Supreme Court of Canada in Henry v. British Columbia (Attorney General), the leading case on courts’ authority to award Charter damages against the Crown for prosecutorial misconduct. He also placed first in the Wilson Moot and won the award for best factum.

As a summer student at Torys, Winston was seconded to TD Bank. During his articling year, he was seconded to Ontario Power Generation, where he provided advice relating to litigation, mergers and acquisitions, and government relations. As an associate at Torys, Winston was seconded to the Litigation and Privacy group at Toronto Hydro.

Winston is the Corporate Secretary and a member of the Board of Directors of the First Generation Network, a non-profit that aims to reduce the barriers faced by law students who are the first in their family to complete post-secondary education.

Winston is a member of the Advocates’ Society, the Canadian Association of Black Lawyers and the Canadian Association of Urban Financial Professionals.

Winston serves on the Executive Committee of the Harvard Club of Toronto, an organization that fosters ties among Harvard alumni in the Greater Toronto Area. He also co-chairs the Club’s Schools Committee, which is responsible for interviewing candidates for admission to Harvard College.

Winston serves as a mentor and regular speaker with the Black Future Lawyers Program at the University of Toronto Faculty of Law, an initiative to provide supports and engagement opportunities to Black undergraduate students who aspire to become lawyers.