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A man who contends he was wrongly convicted of murder in a “Mr. Big” investigation nearly 20 years ago is asking the Supreme Court to reopen his case, saying the federal Justice Department’s last-resort review system is broken, with files left dormant for years.

The extraordinary application this month from Kevin Simmonds – to a court that refused to hear his appeal in 2003 – says his confession to undercover police would be “incontrovertibly inadmissible” today, because the tactics that elicited it are now seen as legally questionable.

If Mr. Simmonds, 52, succeeds in obtaining a new hearing, it could help open the floodgates to similar cases. Hundreds of people have been convicted of serious crimes because of Mr. Big investigations, in which police create a fake criminal enterprise to lure in a suspect. But in 2014, the Supreme Court ruled in R v. Hart that confessions produced this way should be presumed to be false.

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But, rare though it may be, approaching the country’s highest court directly to reopen a murder case is preferable, Mr. Simmonds’s lawyers say, to seeking the help of the federal justice department’s Criminal Conviction Review Group.

The CCRG was set up in 1993 after two of the country’s most notorious wrongful convictions, of Donald Marshall and David Milgaard, raised concerns about the timeliness of reviews by the justice minister. The review group is considered the last resort of the wrongly convicted, and has its roots in the ancient tradition known as the royal prerogative of mercy. The CCRG advises the justice minister, who has the authority to order a new hearing or trial.

But the CCRG has just three or four staff lawyers, while a similar unit in Britain has 40, says Alan Young, who teaches at Osgoode Hall Law School in Toronto, in an affidavit filed with the Supreme Court on Mr. Simmonds’s behalf.

And in three cases Mr. Young has sent for review to the CCRG, the earliest dating from August, 2016, not a single one has had a caseworker assigned yet, he said in his affidavit. (Mr. Young is a founder of the Innocence Project at Osgoode Hall, a student clinic aimed at securing the release of the wrongly convicted.)

“To put it bluntly, the CCRG appears incapable of reviewing files in a timely manner, and the recent delays border on intolerable,” Mr. Young said in the affidavit.

The government says it is committed to ensuring it has effective mechanisms to identify and respond to potential wrongful convictions.

“We closely monitor the resources allocated to the Review Group to ensure that they are equipped to carry out this important function, Dave Taylor, a spokesman for Justice Minister Jody Wilson-Raybould, said in an e-mail.

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In 1995, the body of William Bedford, a cocaine dealer, was found duct-taped to a tree in Hope, B.C. He had been shot in the head.

Three years later, undercover police set up a fake criminal organization and gave Mr. Simmonds, then homeless and drug-addicted, $1-million in cash as a demonstration of the enterprise’s seriousness, his affidavit says. They brought him to the supposed crime boss – “Mr. Big” – to supply details about the killing of Mr. Bedford as a condition for becoming a member.

In 2000, a jury found Mr. Simmonds guilty of first-degree murder, which carries a mandatory sentence of life in prison with no chance of full parole for 25 years. In 2002, the B.C. Court of Appeal upheld the conviction. The Supreme Court refused a year later to hear his appeal. At no time did Mr. Simmonds raise issues of being illegally manipulated by the police tactics because, his lawyers say, there was no legal basis at the time for doing so.

In 2009, he applied to the federal review group. It rejected his claim of a possible wrongful conviction, replying that the Supreme Court had upheld the constitutionality of the Mr. Big technique.

But then in 2014, the Supreme Court said it had grave doubts about the use of Mr. Big schemes. It said that while the technique had produced convictions in hundreds of serious cases that would otherwise have remained unsolved, those convictions came at a price.

“Suspects confess to Mr. Big during pointed interrogations in the face of powerful inducements and sometimes veiled threats – and this raises the spectre of unreliable confessions.” It said the confessions should be presumed inadmissible, unless the Crown can demonstrate their reliability.

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Mr. Young says Mr. Simmonds was vulnerable to inducements, and repeatedly told Mr. Big he hadn’t committed the killing, before ultimately changing his story and confessing.

“His unique fragility forms the basis for establishing an abuse of process,” Mr. Young’s affidavit says.

In 19 Mr. Big cases since that point in Canada, three confessions were ruled inadmissible, the affidavit says.

Mr. Young likens Mr. Simmonds’s situation to that of an abused woman jailed for an act of violence committed in self-defence before the court recognized “battered-women’s syndrome” – fear of imminent death based on repeated abuse – in a 1990 case.

Following that ruling, the federal government asked Justice Lynn Ratushny to review battered-women’s cases. Of 98 cases, she found that seven deserved some form of action, such as a new hearing.

Mr. Young asked Ms. Wilson-Raybould in 2015 to establish a similar review for Mr. Big cases, but she rejected the request, and referred him to the CCRG.

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“I wanted to do that and I was doing it,” he said in an interview, “until I realized they do nothing.”

In 1995, the Supreme Court allowed Réjean Hinse of Quebec to appeal a lower-court ruling, after previously denying his request for leave to appeal. It is the only case Mr. Young is aware of that provides a precedent for Mr. Simmonds.

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