Manitoba court news: a 37 year old inmate who crawled under a fence at Headingley jail and swam the Assiniboine River has been sentenced to one year of time served for the escape, and he is staying behind bars on older charges.
By Maplestime Manitoba Desk | Headingley, Manitoba | November 13, 2026
Sources: CBC Manitoba and Winnipeg Free Press | Last updated: November 13, 2026
Key Takeaways
- Tyson Breland, 37, pleaded guilty to prison breach after breaking out of Headingley Correctional Centre on August 2, 2025.
- He escaped by crawling under a fence while another inmate held it up, then swam across the Assiniboine River. He was free for about 30 minutes.
- He planned the escape in phone calls coded as a roofing job and offered a former inmate compensation for help.
- Provincial court Judge Mary Kate Harvie sentenced him to 12 months custody with enhanced credit for time served.
- Breland remains in custody after being denied bail earlier this month. His next court date is in Powerview-Pine Falls in January.
How the Escape Happened
While in custody at Headingley, Breland made a number of phone calls to his father and a former inmate from Headingley who had since been released, Judge Harvie wrote in her sentencing decision. He discussed an escape plan during these calls but concealed it as a roofing job, and he offered the former inmate compensation for his help.
Breland called his father several times on August 2, 2025, the last call ending with his father telling him the former inmate was at the jobsite. Correctional officers saw Breland running outside the fence of the jail shortly after, heading south toward the river. He jumped in and swam across to the south bank. It was later discovered that another inmate held up the bottom of the fence for Breland, allowing him to escape.
RCMP and correctional officers found Breland hiding behind a large farm truck about 20 minutes later. He did not comply with demands, and was pepper sprayed and arrested. His shoes were bound to his feet with rubber bands, and he had a small amount of cash and cigarettes, and a lighter stolen from a nearby parked car, on him. Harvie noted that no one was caught trying to help Breland when he crossed the river, writing that he certainly attempted to have someone there.
The Sentence
The Crown sought a sentence of two years without enhanced credit for time served, while the defence argued one year would be sufficient and that Breland should be entitled to credit for time served. Defence counsel noted Breland has been detained at the Brandon Correctional Centre, where access to programming has been limited due to serious overcrowding issues.
Harvie agreed Breland was entitled to enhanced credit and sentenced him to one year of time served. She wrote that she was satisfied that a sentence of 12 months custody adequately takes into account the circumstance of this offence and this offender, and is consistent with the length of sentence imposed in other cases.
Harvie weighed aggravating factors, including that Breland put a significant degree of planning and premeditation into his escape, enlisted others to help him, and was uncooperative during his arrest. On the other side, she noted his escape was brief and that there was no violence or weapons involved.
Related: Tiana Obirek Inquest: Standing Hearing Set Jan. 14, 2027
What Happens Next
Breland remains in custody after being denied bail earlier this month, according to court records. His next scheduled court date is in Powerview-Pine Falls in January. The sentencing decision did not go into details on the older charges he faces. An RCMP media release from May 2025 said Breland was wanted on numerous charges in relation to a break and enter in Black River First Nation, where a woman and eight children were held at gunpoint. Breland was arrested on those charges that month.
Maplestime will provide updates from this case as announcements are made.
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