Deschutes County Sheriff’s Office Capt. William Bailey has been placed under investigation for comments he made on a radio show criticizing his former political opponent Sheriff Kent van der Kamp.

A public records request confirmed that the investigation is ongoing, but the agency declined to provide any documentation. The Bulletin attempted to contact van der Kamp seven times to confirm the investigation, but each call went directly to voicemail. On Thursday morning, Deschutes County Sheriff’s Office Public Information Officer Jason Carr confirmed that the probe pertains to a two-hour long interview aired on KCNP’s “Muddtoe Radio Show” on June 20.

During his interview, Bailey allegedly accused van der Kamp of being unqualified to run for sheriff, adding that the agency’s reputation has rapidly declined since he took office. Van der Kamp — who has now resigned effective July 31 — has faced intense public scrutiny since it was reported in May that he supplied false documents to Oregon State Police and lied while under oath during criminal cases in Deschutes County Circuit Court.

The investigation of Bailey was initiated on June 26, Carr said, just three days after van der Kamp submitted his official resignation.

With the position now vacant, it falls to the Deschutes County Commission to appoint an interim sheriff until a special election can be held in 2026, but Bailey announced he will not be applying.

“In talking to my family, and reflecting on the last nearly two years, I am not seeking to be considered for the appointment, nor will I run for the position of Sheriff,” he said in a Facebook post on June 25. “To my colleagues, this period of uncertainty and turmoil has been treacherous and difficult. I’m sorry for the unnecessary additional burden you’ve shouldered while putting public safety first.”

Bailey lost the November 2024 election to van der Kamp, garnering 40% of the vote. Bailey has declined media requests for comment.

Carr said that Bailey violated a new policy created by van der Kamp shortly after he took office in January about speech and expression. The policy states that “inappropriate personal communications in some instances may amount to an abuse of
authority and may have harmful effects on a member’s perceived integrity or bias towards others.”

During an informal debate between five of the interim sheriff applicants, recent media scrutiny of the Deschutes County Sheriff’s Office was cited as a point of unrest within the sheriff’s office.

“Everybody knows that we’re on the news quite often. We can’t be on the news quite often. I work with incredible people that do an incredible job and they get tired of being on the news for negative stuff that they didn’t cause — and a lot of times it’s been former command staff,” said interim sheriff candidate Ty Rupert.

The Deschutes County Commission aims to appoint an interim sheriff prior to van der Kamp’s departure July 31.

Those who have already applied for the position include Detective Gabe Burchfiel, Undersheriff Aaron Wells, Detective Lt. James McLaughlin and Capt. Ty Rupert, all with the Deschutes County Sheriff’s Office. Former Deschutes County Sheriff’s Office Capt. Deron McMaster and Central Oregon Community College Director of Campus Safety and Emergency Management Cory Darling have also announced their intent to apply for the position.

The Deschutes County Sheriff’s Office has a history of retaliation against employees. Former Sheriff Shane Nelson was found to have wrongfully terminated his political opponent in the 2016 election, Eric Kozowski, according to the verdict of a federal civil trail that awarded Kozowski $1 million. Later, a string of tort claim notices — the official notification to a public agency of a potential lawsuit — were filed alleging the sheriff’s office engaged in political retaliation against those who supported van der Kamp in the 2024 election cycle.