Thirty-minute jailbreak costs Headingley inmate one year of freedom

An inmate who escaped from Headingley jail, swam across the Assiniboine River and tasted freedom for a mere half hour has been sentenced to one year in custody.

Tyson Breland, 37, was handed the sentence, which amounts to time served, by provincial court Judge Mary Kate Harvie this month after pleading guilty to prison breach for the August 2025 incident.

Breland is still awaiting trial on more than two dozen charges stemming from a break-and-enter in Black River in which a woman and eight children were held at gunpoint on May 23, 2025.

While in remand custody in Headingley, he made a number of phone calls to his father and a former inmate, Joseph Swain, wrote Harvie.

“During these calls an escape plan, concealed as a ‘roofing job,’ was discussed with Breland offering Swain compensation for participating,” Harvie said.

On Aug. 2, 2025, Breland made several calls to his father, the last just after 6 p.m., during which his dad said that Swain was “at the job site.”

Just after 8 p.m., correctional officers spotted Breland running outside the jail fence, south toward the river.

Another inmate had held up the bottom of the fence for Breland to crawl under. He swam across the river to the south bank and tried to make a break for it.

RCMP officers were dispatched at about 8:15 p.m. and corrections officers from the jail began searching along the south bank.

Officers found Breland just before 8:30 p.m. hiding behind a large farm truck on private property. He was pepper-sprayed during the arrest.

He had cigarettes, cash and a lighter on him that he had stolen from a parked car.

Harvie noted that although no one was caught trying to help Breland after he got across the river, he “certainly attempted to have someone there.”

Breland was returned to the jail and later moved to the jail in Brandon. He was in custody since being officially charged with prison breach in September 2025, which the judge counted as his sentence.

He must hand over his DNA to law enforcement and is barred from possessing weapons for 10 years.

The Crown had sought a two-year jail sentence, while Breland’s lawyer had argued for one-year, with enhanced credit, counting as time served.

His lawyer argued that Breland has recognized the negative effect the escape had on himself and other inmates at Headingley, and noted he has been held at the jail in Brandon, where access to programs is limited owing to “serious overcrowding.”

It’s unclear, based on court records, whether Breland has applied for bail on the charges from May 2025. His next court date is in Powerview-Pine Falls next year.

erik.pindera@winnipegfreepress.com