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Prime Minister Justin Trudeau has a problem and an opportunity as he prepares to make his fifth appointment to the Supreme Court of Canada, replacing Justice Michael Moldaver, who retires on Sept. 1.

The problem is that Justice Moldaver is the court’s leading specialist in criminal law. Criminal appeals make up a large part of the court’s caseload – 55 per cent of the cases heard in 2021. Justice Moldaver was once a leading criminal lawyer, and then a trial judge. His rulings ring with conviction and nuance acquired during a lifetime immersed in criminal law’s intricacies. And all that expertise is walking out the door.

The opportunity: Mr. Trudeau can choose a judge who favours a broad, liberal approach to interpreting the rights protected by the Charter of Rights and Freedoms. The court has been moving to the right on Mr. Trudeau’s watch, and Justice Moldaver at times was part of that drift. Mr. Trudeau, whose father Pierre was the visionary behind the Charter’s founding, describes himself unequivocally as pro-Charter.

“The court is becoming more and more conservative,” Toronto-based constitutional lawyer Paul Cavalluzzo said. “This is a very important appointment for the representation of a more progressive view.”

The deadline for applying to replace Justice Moldaver was Friday. The process is open only to candidates from Ontario, which by convention has three members on the court. The Globe and Mail interviewed 10 members of the legal community and political insiders about the search process, but is not naming them so they could speak freely about judges they may one day appear in front of.

Mr. Trudeau is widely expected to appoint a woman. Doing so would restore the 5:4 male-to-female gender ratio left by his predecessor, Conservative Prime Minister Stephen Harper. The terms of reference of the advisory body tasked with creating a short list of three to five names are explicit: the group must support the government’s intent to have a gender-balanced court.

If Mr. Trudeau is looking for a lawyer with a strong background in constitutional law and a progressive tinge, plus a background in criminal law, Justice Jill Copeland of the Ontario Court of Appeal would be a leading candidate, two sources said. She practiced criminal law, and has presided as a judge over trials at both the provincial and superior court levels.

Justice Copeland was also the executive legal officer from 2007 to 2010 for Supreme Court Chief Justice Beverley McLachlin, under whose leadership the court vastly expanded constitutional rights. And Justice Copeland clerked for one of the most liberal Supreme Court judges of the Charter era, Peter Cory. What’s more, she can hear cases in both official languages.

Some controversy might attach to Justice Copeland, because last September she released a man on bail after he was charged with first-degree murder in the death of a police officer, who was run over by a car in the parking lot of Toronto city hall. The ruling was criticized by Toronto Mayor John Tory and Ontario Premier Doug Ford. Most details in it are covered by a publication ban. She has spent only a short time on the province’s highest court, the Court of Appeal, having been promoted by the Trudeau government in March.

Her talent is in “seeing the really important issues, being able to assess them and weigh them correctly – do the right thing, in other words,” said retired criminal lawyer Marlys Edwardh, who hired her as an articling student and worked with her for several years.

If Mr. Trudeau is looking for a generalist, candidates from the appeal court include Justice Katherine van Rensburg, two sources said, and Justice Julie Thorburn, several sources said. Justice Thorburn was commissioned by Ontario’s Attorney General to write a 2015 report on access to justice for French-speaking litigants.

The easiest answer to Mr. Trudeau’s criminal-law problem might have been Associate Chief Justice Michal Fairburn of the Ontario Court of Appeal. Friends expected her to apply, but she did not, two sources said. As a Crown attorney for more than 20 years, she was considered one of the top appellate lawyers in the province. A senior lawyer called her Justice Moldaver with a friendlier face. (Justice Moldaver can be gruff in hearings; Justice Fairburn won a civility award.)

The stumbling block was Mr. Trudeau’s bilingualism requirement. Justice Fairburn has been studying French over an extended period, two people who know her say, but has also been handling a heavy caseload and administrative duties.

Supreme Court appointments allow the legacy of a prime minister to live on. Justice Copeland’s mandatory retirement date, at age 75, would not be until 2043, while Justice Thorburn’s would be 2037 and Justice van Rensburg’s would be 2033. Mr. Trudeau is expected to make the appointment well before the court’s next session begins in the fall.

In his last Supreme Court appointment, Mr. Trudeau replaced a woman, Justice Rosalie Abella, with a man, Justice Mahmud Jamal, leaving just three women on the court. Justice Jamal, who was born in Nairobi, became the first member of a racialized minority group, and the first of the Baha’i faith, on the country’s most powerful court.

This time, other stated priorities of the Liberal government, such as increasing racial diversity or appointing the court’s first Indigenous judge, may take a back seat. A potential candidate is Justice Michael Tulloch, a source said, who would be the first Black member of the Supreme Court. He has been studying French, the source said, but is not on the appeal court’s list of 10 judges who hear appeals in French. (Nine of the 10 are women.)

The Indigenous Bar Association, or IBA, is endorsing two Indigenous applicants, Ontario Superior Court Justice Michelle O’Bonsawin of Ottawa, a judge since 2017, and Ontario Superior Court Justice Todd Ducharme of Toronto, who joined that court in 2004. Both are fluently bilingual.

“They understand the plight of Indigenous peoples,” IBA president Drew Lafond, a lawyer based in Saskatoon, said in an interview. “They carry that lived experience and they wish to bridge gaps between Indigenous perceptions of justice and the way the justice system has treated Indigenous peoples in the past. And we view them as being exceedingly well-qualified for the position.”

A dark-horse potential candidate is Cynthia Petersen of the Ontario Superior Court of Justice, a source said. She brings small-l liberal credentials, as a former social-justice advocate. The same source said Nathalie des Rosiers, the principal of Massey College and previously a law dean, general counsel to the Canadian Civil Liberties Association and Liberal member of the Ontario Legislature, has applied, giving the Prime Minister another option on the left.

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