Skyler Glasby


UPDATE 8/14/20 1 p.m.

Bail for this case against Skylar I. Glasby, 32, was set at $25,000 this morning in Walla Walla County Superior Court, and formal charges were filed for unlawful imprisonment as well as domestic violence crimes of threats to kill and assault in the second and fourth degrees.


A local man out on $150,000 bail and awaiting retrial on a reversed 2016 conviction for kidnapping and robbery was arrested Thursday in Waitsburg and had his first court appearance this morning in Walla Walla County Superior Court.

Skylar I. Glasby, 32, is currently being held on suspicion of unlawful imprisonment as well as domestic violence crimes of threats to kill and assault in the second and fourth degrees.

The Walla Walla Regional SWAT team raided the house on Main Street in Waitsburg with an arrest warrant for Glasby on Thursday, according to Walla Walla County Undersheriff Joe Klundt.

Walla Walla County detectives had been investigating reports of Glasby’s involvement in the assault and imprisonment of a woman he had been dating since his release from prison in February, according to court documents.

Records state Glasby might have been involved in an unreported assault in Dayton earlier this month, where he allegedly shot another man in the foot, which might have been witnessed by this woman. His arrest Thursday stems from reports that he might have wanted to silence her.

Photos the woman shared with detectives appeared to back up allegations that Glasby was abusing her, according to the arresting officer’s statement.

Glasby was released from prison in February after he successfully appealed a 2016 conviction for crimes the jury at that time found he committed the previous year in Milton-Freewater.

The Oregon jury found him guilty of first-degree and second-degree kidnapping, second-degree robbery, second-degree assault, unlawful possession of hydrocodone, third-degree escape and second-degree theft. He was found not guilty of first-degree robbery, second-degree robbery and unlawful use of a weapon.

He was sentenced to 15 years in prison.

But in December 2019, Oregon Appeals Court justices reversed the conviction and remanded the case for a new trial on all seven counts.

They found that Glasby had attempted several times over the course of the trial to get a new defense attorney, or even to represent himself, but he was denied.

“And, rather than weighing the request and determining on the record whether defendant’s decision was an intelligent and understanding one, the trial court erred by summarily denying his request without giving a reason,” according to the Appeals Court opinion.

“If the trial court had a valid reason for denying defendant’s request, that reason was not substantiated in the record. By summarily denying and ignoring defendant’s statements to represent himself, the trial court effectively precluded defendant from waiving counsel and representing himself,” justices determined.

Information on the status of that new trial was not available from the Umatilla County District Attorney’s office by press time today.

Glasby was also convicted in 2014 of leading deputies from Columbia and Walla Walla counties on a high-speed pursuit.

In 2012, he was convicted of forging $20 bills after a 21-hour standoff with Walla Walla police.

Editor’s Note: Glasby’s first name, Walla Walla detectives have confirmed, is legally spelled “Skylar” despite many reports over the years in connection with the man’s extensive criminal history of it being spelled “Skyler.”

Dian Ver Valen can be reached at or 509-526-8320.

Dian is editor of the Union-Bulletin and Lifestyles magazine. She received her bachelor's in journalism from Western Washington University in 2003. She received her master's in communication and leadership from Gonzaga.