Where Damion Ryan Stands: 24½ Years in Manitoba, a First-Degree Murder Charge in Ontario, and a Murder-for-Hire Indictment in Minnesota (August 17, 2026)

This is a status file, not a news bulletin. Nothing happened in the Damion Ryan matter today. What follows is the consolidated position of a full-patch Hells Angel who is seven weeks into a Manitoba drug sentence while two other sets of prosecutors wait their turn — and a correction to a figure this site and much of the press reported earlier this year.

The Number That Needs Fixing First

Ryan’s Manitoba sentence is routinely described as 23 years. That is one component of it, not the total.

On June 26, 2026, Court of King’s Bench Justice Chris W. Martin sentenced Ryan, 45, to 23 years for conspiring to traffic fentanyl, cocaine and methamphetamine, plus a further 18 months to be served consecutively for instructing a person to commit offences for the benefit of a criminal organization. The total is 24 years and six months. After credit for time already served, Martin said Ryan would spend roughly the next 18 years in custody.

Crown prosecutors Kate Henley and Janna Hyman had asked for 23 to 25 years. The defence proposed 15, which the judge rejected in blunt terms as falling far short of what the conduct required. Martin described Ryan as the organizing figure: “Mr. Ryan was the kingpin.”

Manitoba: Project Divergent

The conviction came on December 15, 2025, on five counts including three of conspiring to traffic and one of conspiring to profit from the proceeds of crime as a member of a criminal organization — the network police and prosecutors call the Wolfpack.

The underlying investigation, Project Divergent, was a multi-year RCMP operation spanning several provinces. It produced roughly two dozen arrests in March 2022 and what police described at the time as the largest drug seizure in Manitoba RCMP history, valued at more than $70 million. Ryan was the only full-patch Hells Angel taken in it.

The case turned on a Winnipeg drug dealer who became a police agent, known in court as Agent 66. Ryan insulated himself behind a series of nicknames — court heard he went by Mr. Wolf, Polar Bear, Berzerker and Big Homie — and vetted anyone seeking a meeting, a caution dating to a 2015 attempt on his life at a Vancouver airport food court in which the gunman’s weapon jammed. He agreed to meet Agent 66 at a Montreal restaurant in 2021 anyway. Prosecutors alleged one of the intermediaries who brought them together was Ryan’s brother-in-law Denis Ivziku, known as Menace, whose own four-year flight ended with a capture in Mexico in May.

The trial was repeatedly delayed. Ryan went through at least five lawyers, most of whom he fired, and represented himself for part of the proceedings with a court-appointed assistant. For the longer arc of the club he belongs to, see our file on the Hells Angels in Canada.

Ontario: A First-Degree Murder Charge From Bolton

This is the file least understood outside Ontario, and it is the most serious one still ahead of him.

On April 1, 2026, the Ontario Provincial Police announced that Ryan, listed as 45 and of Ottawa, had been arrested as the fifth person charged in a 2021 killing in Bolton, northwest of Toronto, and in two related attempted murders in the Greater Toronto Area dating to 2020. He faces first-degree murder, attempted murder and conspiracy to commit murder.

The homicide occurred on January 18, 2021, when OPP officers were called to a shooting on Harvest Moon Drive in Bolton. Two people inside the home were shot. Giovanni Costa, 65, died at the scene. Police have said the intended target was his son Michael, who had been the victim in an earlier incident in Vaughan. Ryan made a first appearance in an Ottawa courtroom on April 13, 2026.

Two men charged in the same investigation remain at large. A Canada-wide warrant is outstanding for Waheed Barakziye, 48, of London, Ontario, who faces first-degree murder, two counts of attempted murder and conspiracy to commit murder. The Ontario government has posted a $50,000 reward. Caledon OPP continue to investigate under the direction of the OPP criminal investigation branch.

Minnesota: The Iranian Murder-for-Hire Indictment

The third file is American, and it is the one that moved Ryan from a Canadian organized-crime story into a national-security one.

On January 29, 2024, the U.S. Attorney’s Office for the District of Minnesota unsealed an indictment charging Ryan, Iranian national Naji Sharifi Zindashti and Canadian Adam Richard Pearson with conspiracy to use interstate commerce in the commission of a murder-for-hire. Prosecutors allege that between December 2020 and March 2021 the three plotted to kill two people then living in Maryland, one of whom had defected from Iran and fled to the United States with the other.

According to the indictment, the planning was conducted over the encrypted service SkyECC. Zindashti approached Ryan about work; Ryan brought in Pearson; and the parties settled on a payment of $350,000 plus $20,000 in expenses. The killings never took place.

On the same day the indictment was unsealed, the U.S. Treasury sanctioned Zindashti’s network, which American officials describe as targeting Iranian dissidents and opposition figures at the direction of Iran’s Ministry of Intelligence and Security. Zindashti is in Iran, and the United States has no extradition treaty with it. Ryan and Pearson were already in Canadian custody on unrelated matters when the charges were laid.

Standing of This File

What is verified. The sentence figures, the conviction date and the judge’s characterisation come from CBC News reporting of the June 26, 2026 sentencing hearing in Winnipeg. The Project Divergent particulars come from CBC coverage of the trial’s opening in September 2025. The Ontario charges, the Bolton victim, the outstanding warrant and the reward come from the OPP announcement of April 1, 2026 as reported by CBC News. The American allegations come from the U.S. Department of Justice press release announcing the indictment, a primary source.

What is corrected. Earlier Gangland Files material described the Manitoba sentence as 23 years. That figure is the drug-conspiracy component only and omits the consecutive 18 months imposed for instructing offences on behalf of a criminal organization. The correct total is 24 years and six months.

What is untested. The Ontario charges and the American indictment are allegations. Ryan has not been tried on either, is presumed innocent on both, and the co-accused named here are equally entitled to that presumption. The two men still sought in the Ontario case have not been convicted of anything.

When this will be updated. On any appeal of the Manitoba sentence, on the setting of a trial date in the Ontario prosecution, on the arrest of either outstanding co-accused, or on any movement in the Minnesota file.