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Omar Khadr answers questions during a news conference after being released on bail in Edmonton on May 7, 2015.

Dan Riedlhuber/Reuters

Legal experts say the widow of a U.S. soldier killed in Afghanistan will have an uphill battle when her bid for a freeze order on Omar Khadr's $10.5-million payout from Ottawa hits a Toronto courtroom on Thursday, but the outcome is hard to predict.

A lawyer for Tabitha Speer, the widow of U.S. army Sergeant Christopher Speer, and for Layne Morris, a U.S. soldier partly blinded in the 2002 firefight that ended in Mr. Khadr's capture, is seeking a freeze order on Mr. Khadr's assets.

The federal government officially apologized to Mr. Khadr last Friday for the role Canadian security officials played in abuses he suffered as a teenage prisoner of the U.S. military at Guantanamo Bay, Cuba. Ottawa paid $10.5-million to the former child soldier to settle a $20-million civil lawsuit over violations of his rights as a Canadian citizen.

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Campbell Clark: In the court of public opinion, Canadians say Trudeau got it wrong on Omar Khadr settlement

Ms. Speer and Mr. Morris are seeking the freeze order until the Ontario Superior Court can rule on their request to recognize a 2015 Utah civil court default judgment ordering Mr. Khadr to pay them $134-million (U.S.) for his actions in Afghanistan.

Mr. Khadr pleaded guilty in a plea deal to throwing the grenade that killed Sgt. Speer, but has since recanted.

Vaughan Black, a retired law professor from the Schulich School of Law at Dalhousie University in Halifax, says that to get a freeze order, Ms. Speer must show a "real risk" that Mr. Khadr will try to hide or move his money, or otherwise shelter his assets from his potential creditors.

"We don't go around freezing assets unless there is a fair likelihood that they will be dissipated or hidden in the meantime," Mr. Black said.

In court filings, Ms. Speer's lawyer cites media reports to suggest Mr. Khadr may try to make it difficult to access his assets or hand his money to his "extremist" family.

Mr. Khadr and his siblings spent their youth in the 1990s in Afghanistan living in a mud-walled compound with Osama bin Laden. However, it has been years since any government official has publicly accused any member of the Khadr family of lending support to al-Qaeda. Most of the siblings are in their 30s, have started families and live uneventful lives in Canada.

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Aly Hindy, imam at the Salaheddin Islamic Center in Scarborough, has known the Khadrs since Omar was 10 years old. Members of the family who live near the mosque visit regularly, he said.

"I don't think his family is different from any other family, they were just there in the wrong time in the wrong place, but they are ordinary people and they are good Canadian citizens and they will prove that," he said.

Mr. Hindy sees Mr. Khadr, who lives in Edmonton, when he comes to Scarborough to visit his family.The Guantanamo Bay plea deal Mr. Khadr signed in exchange for gradual release obliges him to live under restrictions until October, 2018.

Initially, the conditions limited his communications with his immediate family members – but most of these have been lifted. However, he can contact his sister, Zaynab Khadr, only by phone or video in the presence of a supervisor.

In 2002, Ms. Khadr came to Canadians' attention as an unapologetic firebrand during interviews for a CBC documentary titled An Al Qaeda Family. Since then, she had been living in Toronto and mostly out of the public eye until last year, when reports emerged that she had spent several days or weeks in Turkish custody after moving abroad. The circumstances remain unclear, but no charges have been publicized.

When the matter comes to court on Thursday, the plaintiffs will have to show that they have a strong chance of success in their goal of seeking the payment that a U.S. court says Mr. Khadr owes them. While they may clear this hurdle, a win in the final hearing on their case could be difficult, says Tanya Monestier, a Canadian who is a jurisdiction expert and a professor at Roger Williams University School of Law in Bristol, R.I.

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Before approving a foreign judgment, a Canadian court is supposed to determine if the court asserted its jurisdiction in the way a Canadian court would have. Prof. Monestier said the Utah ruling against Mr. Khadr might face a "steep threshold."

As she points out, he did not show up to defend himself as he was in prison and his alleged actions were in Afghanistan, not Utah.

The plaintiffs have cited Canada's 2012 Justice for Victims of Terrorism Act, which appears to support their case, along with a recent Ontario Court of Appeal ruling siding with U.S. victims of terrorism who sued the government of Iran.

But Prof. Monestier said the ruling is likely headed to the Supreme Court of Canada, although it applies for now. And she says the terrorism act still stipulates that foreign judgments have to meet Canada's standards of jurisdiction.

"We don't care whether under U.S. law they had jurisdiction," Prof. Monestier said. "We care about, under our principles did they have jurisdiction."

University of Western Ontario law professor Stephen Pitel says the U.S. plaintiffs may have trouble arguing that Mr. Khadr is sheltering his money, as they appear to base their case solely on an anonymous source cited in a report in The Globe and Mail.

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"I would struggle to see that that satisfies the evidentiary hurdle of showing a real likelihood that these assets are going to be somehow dissipated and not available," Prof. Pitel said.

He also predicts that even if the plaintiffs win their freeze order, they could lose their underlying case.

"I think it is going to be a highly contested argument," Prof. Pitel. "I don't know if I would pick a winner. … I think it could go either way. It's a discretionary call by the judge."

With a report from Colin Freeze

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