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Twenty years ago, Cosmo Jacobson was convicted of first-degree murder in the killing of a Crown witness who had been set to testify against him for charges in an earlier home-invasion case.

Last week, he participated as a speaker at a seminar for some judges on the Ontario Court of Justice in a panel about the treatment of inmates and conditions of life behind bars.

Now, some attendees are complaining. A written statement from Jason Gennaro, a spokesman for the court, said some had “expressed concerns about the panel.” Correspondence was sent to all 356 judges on the Court of Justice to acknowledge the concerns.

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Cosmo Jacobson, who was convicted of first-degree murder in the killing of a Crown witness twenty years ago, was granted day parole in May.Supplied

In May this year, Mr. Jacobson was granted day parole. He lives in a community-based residential facility. The Parole Board of Canada last week reviewed and renewed his release status. The 50-year-old works three part-time jobs.

The Ontario Court of Justice controversy highlights the tension between the deep decades-long pain that reverberates – and never fully abates – from brutal crimes, and society’s collective goal for most incarcerated people: rehabilitation and eventual release to rejoin the community.

Mr. Jacobson’s criminal history is detailed in the Parole Board of Canada decision dated Nov. 4 that renewed his day parole. It states he committed “extremely violent acts against three innocent victims, causing the death of one.”

In 2000, he and two accomplices robbed the home of a drug dealer. Shortly after, Mr. Jacobson interacted with a security guard, Roy Jones, later learning the guard was a key witness for the prosecution in the robbery case. Mr. Jacobson planned a murder and in early 2001, according to the Parole Board report, “You shot him a number of times and left him dead in the street.”

Justice Brenda Green, an eight-year veteran of the Ontario Court of Justice, expressed her concerns about Mr. Jacobson’s presence at the judges’ seminar in an e-mail to colleagues, as reported by the Toronto Star on Wednesday. She called his appearance an affront to the victim’s family and the community.

“Cosmo Jacobson is a convicted, ruthless murderer,” Justice Green wrote in her e-mail.

Justice Green, before she joined the bench, was an assistant Crown attorney and had worked in Durham Region east of Toronto, the same area where Mr. Jacobson committed his crimes.

Judges across Canada each year attend a number of continuing education sessions. Among them, they have opportunities to participate in events and even visits to jail that bring those on the bench – who levy sentences as severe as life imprisonment – together with the people who have been convicted of crimes and are serving, or have served, their time.

David Cole, a retired judge who worked for about three decades on the Ontario Court of Justice, said it is important for judges to make connections with current and former prisoners, to understand a major part of the justice system that is not seen or easily understood from the august perch on the bench in a courtroom.

“These are people with things to say that judges should know about,” Mr. Cole said.

He has long worked closely with the Court of Justice and the National Judicial Institute on programs that connect judges and jails.

“For years, we’ve had lifers speak at these programs,” Mr. Cole said. “There might be some individual judge who is unhappy about some guy speaking but most of the time the judges are just fascinated to hear.”

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The Parole Board’s report on Mr. Jacobson cited victim statements in 2022 and 2025. “They describe the ongoing distress, and the emotional and psychological harm they have suffered through your offence.”

But the report also notes that while jailed, Mr. Jacobson took part in numerous vocational and voluntary programs.

This spring, Mr. Jacobson was granted and completed two successful 15-day unescorted temporary absences from jail and in mid-May, he was granted six months of day parole. That was set to expire, and another six-month period was approved last week. The first six months were described as exemplary.

“It is the Board’s opinion that you will not present an undue risk to society if released on day parole, and that your release will contribute to the protection of society by facilitating your reintegration into society as a law-abiding citizen,” the report said.

It also noted Mr. Jacobson had been invited by a law professor to the speaking engagement for the judges. It noted his expenses would be paid and he would receive an honorarium.

Catherine Latimer, executive director of the John Howard Society, a prisoner advocacy group, said judges need to understand what life is like in jails and added it is unfair to discredit Mr. Jacobson’s experiences while incarcerated because of his crimes.

“No one is condoning what he did but he is certainly well-placed to comment on what happens behind bars,” she said.

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