Crooked River Ranch Man Killed in Crash During Freeway Chase After Missing Sentencing

Douglas Richard York, 54, died in a three-vehicle collision on Interstate 205 near West Linn, Oregon.

Published on Feb. 13, 2026

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A Crooked River Ranch man who pleaded guilty to the Halloween night masked holdup of a downtown Redmond cafe failed to appear for sentencing on Wednesday and was killed in a crash hours later while being pursued for speeding on a Portland-area freeway, Oregon State Police said.

Why it matters

This tragic incident highlights the risks associated with high-speed police chases and the challenges of the criminal justice system in dealing with repeat offenders. It also raises questions about bail reform and the need for better monitoring of defendants who are released pending sentencing.

The details

According to a preliminary investigation, Clackamas County sheriff's deputies had been pursuing a speeding white 2002 Lexus driven by York, who was heading south on I-205 near West Linn. York's car rear-ended a VW Golf driven by a 34-year-old Oregon City man. He then apparently lost control and the Lexus rolled, throwing him from the car. York was then struck by a gray Toyota Corolla driven by a 31-year-old Sherwood woman and died at the scene.

  • On October 31, York robbed Sassy's Cafe in Redmond, Oregon.
  • On February 2, 2026, York pleaded guilty to the robbery charges.
  • On February 12, 2026, York failed to appear for his sentencing hearing at 3 p.m.
  • On February 12, 2026, at around 7:10 p.m., the fatal crash occurred on I-205 near West Linn.

The players

Douglas Richard York

A 54-year-old man from Crooked River Ranch, Oregon, who pleaded guilty to the Halloween night masked holdup of a downtown Redmond cafe.

Clackamas County Sheriff's Deputies

Law enforcement officers who were pursuing York for speeding on Interstate 205 near West Linn, Oregon.

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What’s next

The investigation into the crash is ongoing, and authorities will likely review the circumstances surrounding the high-speed pursuit and York's failure to appear for sentencing.

The takeaway

This case underscores the need for a balanced approach to criminal justice, one that prioritizes public safety while also addressing the underlying issues that lead individuals to commit crimes. It also highlights the importance of effective monitoring and supervision of defendants who are released pending sentencing.