Bend-area Robber Escapes Prison, Dies in Crash on I-205

Douglas York was scheduled for sentencing in a Redmond cafe robbery when he fled and died in a high-speed chase on the interstate.

Published on Feb. 13, 2026

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Douglas Richard York, a 54-year-old man from Crooked River Ranch near Bend, Oregon, died in a crash on Interstate 205 in West Linn just hours after he was supposed to appear in court for sentencing in a Deschutes County robbery case. York had escaped from prison and was fleeing from police when the fatal accident occurred.

Why it matters

This tragic incident highlights the challenges law enforcement faces in dealing with repeat offenders who continue to commit crimes even after being released on bail or conditional release. It also raises questions about the effectiveness of the criminal justice system in rehabilitating and deterring such individuals.

The details

According to Oregon State Police, deputies with the Clackamas County Sheriff's Office tried to stop York for speeding, but he led them on a pursuit. York then rear-ended another vehicle, lost control, rolled over, and was thrown from the car. He was then struck by a third vehicle and pronounced dead at the scene. York had previously been arrested in early December in connection with a robbery at a Redmond cafe and was out on conditional release pending his sentencing when the fatal crash occurred.

  • On February 11, 2026, York was scheduled to appear in court for sentencing in the Redmond cafe robbery.
  • On February 12, 2026, York failed to appear for his scheduled sentencing hearing.
  • On February 12, 2026, around 7 PM, York was involved in the fatal crash on I-205 in West Linn.

The players

Douglas Richard York

A 54-year-old man from Crooked River Ranch near Bend, Oregon, who had a long criminal history in the state and was out on conditional release when he died in the crash.

Clackamas County Sheriff's Office

The law enforcement agency that attempted to stop York for speeding, leading to the high-speed chase that ended in his death.

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What’s next

Authorities will likely investigate the circumstances surrounding York's escape from prison and the events leading up to the fatal crash, as well as review the criminal justice system's handling of his case.

The takeaway

This tragic incident underscores the need for more effective rehabilitation and monitoring programs for repeat offenders, as well as the importance of ensuring that the criminal justice system is equipped to prevent such tragedies from occurring in the future.