REGINA – A Regina street gang member with a long history of violent crime and institutional misconduct has been declared a dangerous offender and sentenced to an indefinite prison term.
Michael Riley Obey, 35, will remain in a federal penitentiary indefinitely, with strict supervision if ever released. The decision came after Saskatchewan Associate Chief Justice M. D. Tochor ruled in Regina Court of King’s Bench that Obey poses an ongoing threat to public safety.
“I am satisfied that only an indeterminate sentence will adequately protect the public in these particular circumstances,” said Justice Tochor in his July 16 written decision.
History of violence and gang activity
Obey, described in court by corrections officials as Saskatchewan’s most dangerous inmate, has spent most of his life in custody, first as a youth, then as an adult.
Evidence in court revealed a pattern of escalating gang-related violence, including assaults, riots, and escape attempts.
While incarcerated, Obey instigated multiple prison disturbances, including riots in 2018 and 2021 that required emergency intervention and caused more than $200,000 in damages.
Correctional staff labelled Obey as a “placement nightmare” due to his gang recruitment efforts, weapons manufacturing, and violent altercations with inmates and guards.
In 2021 alone, Obey was involved in 37 incidents, resulting in 29 institutional charges and three criminal charges. The following year, he was involved in 14 more incidents, including a gang-related assault where he attacked another inmate with a homemade weapon.
Dangerous escapes and confrontations
Court heard Obey’s violent behaviour extended beyond prison walls. In March 2021, while being escorted to a medical appointment in Regina, he assaulted two correctional officers, stole a vehicle, and led police on a high-speed chase before being recaptured. One correctional officer suffered a broken leg during a struggle.
During an MRI procedure, his restraints were temporarily removed. When officers attempted to reapply the shackles, Obey attacked, punching both CO's multiple times in the face before fleeing the treatment room.
Obey bolted into the parking lot and jumped into the passenger seat of a vehicle parked outside the clinic. He ordered the driver to drive away but she jumped out of the vehicle and fled. Obey got into the driver’s seat and drove away.
A Regina police officer quickly located the stolen vehicle, initiating a pursuit that involved the Regina Police Service and RCMP. Police deployed spike belts twice before a tactical maneuver forced Obey’s vehicle into a ditch just outside the city.
For nearly an hour, Obey refused to surrender, spinning the vehicle’s tires in an attempt to escape. Police deployed a K-9 unit, but Obey barricaded himself inside before finally getting out and surrendering.
Incarcerated since 2018
Obey has been incarcerated since his December 2018 arrest where he racked a loaded shotgun and pointed it at a Regina police officer. Racking a firearm refers to chambering a round by pulling the bolt or slide back and releasing it, which prepares the firearm for firing.
The police officer took cover and Obey fled, leading officers on a dangerous pursuit outside Regina, driving at speeds up to 130 km/h. At one point, while being pursued, he turned around and drove straight towards the police vehicle, forcing officers to jump out of the vehicle.
That evening, Obey was found driving a half-ton truck east of Regina. He was pursued by police and sometimes drove on the centre of the highway and sometimes on the wrong side of the road. When his truck ran out of gas he tried climbing into a semi-truck that was stopped on the highway. He eventually ran into a nearby field on foot.
He was later tracked by a police dog to a farmyard early the next morning. In the farmyard, Obey was driving a skid steer and drove the skid steer towards an officer approaching him, court heard.
Unprovoked prison attacks
Months after his escape attempt, Obey stabbed fellow inmate Jordan Ironstand multiple times in an unprovoked attack at the Saskatoon Correctional Centre. Ironstand, unarmed, was stabbed in the arm, chest, back, and head.
Gladue Factors and lack of rehabilitation
A Gladue Report detailed Obey’s traumatic upbringing, including exposure to violence, neglect, and the intergenerational effects of residential schools. Diagnosed with FASD, ADHD, and PTSD, he began abusing substances at the age of five.
Much of his youth, from ages 12 to 18, was spent in custody. Much of his adult life has also been spent in custody.
Indeterminate sentence deemed necessary
Justice Tochor said that Obey’s gang affiliations, violent history, and refusal to reform left no realistic chance for rehabilitation. While acknowledging the impact of his Indigenous background, the judge ruled that public safety required indefinite incarceration.
He said Gladue factors have some impact on Obey's moral culpability but must be assessed in the context of all the evidence and sentencing objectives.
“In these particular circumstances, I do not accept that Mr. Obey’s moral culpability for his violent behaviour is significantly diminished by Gladue factors. When I consider an accounting of his behaviour in the context of his Gladue factors, particularly the predicate offences, I conclude the nature, seriousness and timing of his violent behaviour – manifest in the pattern of both his criminal and institutional history – overshadow any suggestion that his moral culpability should be significantly reduced.”
The Gladue Report recommended Obey be held at Saskatchewan Penitentiary in Prince Albert or the Wilow Creek Healing Lodge.
Justice Tochor sealed Obey's Gladue Report, with only Correctional Service Canada, Obey's defence and the Crown permitted access without a court order.
