William Bailey, a once-rising star in the Deschutes County Sheriff’s Office, has been fired.

Bailey, who was fired last week, saw his 25-year career ascension at Central Oregon’s largest law enforcement agency take a sharp downward turn after he unsuccessfully ran for sheriff in 2024.

In the wake of that loss, Bailey criticized the newly-elected leader on a local radio show — remarks that ultimately led to his dismissal. The firing comes amid a fresh election cycle featuring two first-time candidates who promise to change the culture at an office with a long history of allegations of discrimination and retaliation.

Bailey, who has until March 17 to appeal, declined to comment to OPB.

Bailey’s termination is not the first time county officials have dismissed an officer who ran for sheriff and didn’t win. And last time, the fired deputy’s lawsuit cost taxpayers more than $2 million.

Redmond City Councilor Clifford Evelyn, a former law enforcement officer, said the process leading up to Bailey’s firing sets a concerning example.

“He had no progressive discipline. He has no past disciplinary history. You get to have freedom of speech, even if you work for the sheriff’s department,” Evelyn said.

Radio appearance leads to an investigation

The events that culminated in Bailey’s recent termination began last year, when he criticized Kent van der Kamp — the man who beat him in the sheriff’s race – on live radio.

During the appearance on KNCP’s Muddtoe Radio show on June 20, Bailey alleged he and his supporters faced retaliatory practices within the office after losing the election. Bailey said van der Kamp attempted to demote him while promoting those who supported the new sheriff. Bailey described office morale as “broken.”

Van der Kamp launched an internal investigation into whether his former political opponent’s radio appearance violated department policy.

An outside investigator hired to conduct that review found in July that Bailey violated multiple office policies around speech and expression, such as making “statements that discredit or adversely affect the reputation” of the office, according to a copy of the findings OPB obtained through a public records request.

But van der Kamp resigned weeks later, just seven months into his term. State and local investigators found he had a history of serial dishonesty and lying about his background. Because of the investigations, the Deschutes County District Attorney disqualified van der Kamp from testifying in criminal cases and state certification officials later banned him from being a law enforcement officer.

His replacement, interim sheriff Ty Rupert, shelved the initial probe into Bailey’s comments and asked the Deschutes County Administrator’s office to oversee a new investigation. It’s the first time the County Administration has handled an investigation on behalf of the sheriff’s office, according to county officials.

Bailey was on paid administrative leave during the seven-month investigation, which cost the county more than $100,000.

A second investigation

The second investigation, conducted by a different consultant reporting to the County Administrator’s office, ultimately arrived at the same findings, according to county records, and centered around the sheriff’s office policy dictating speech and expression.

Rupert declined to comment when reached by email. The interim-sheriff told OPB last fall that he moved the investigation out of the sheriff’s office to sidestep any concerns about objectivity. Rupert was a vocal van der Kamp supporter and was promoted to captain by him after the election.

County Administrator Nick Lelack ultimately made the decision to fire Bailey. He declined to comment on the case. Kim Katchur, a county spokesperson, told OPB that the county handled the case “to provide Capt. Bailey full due process.”

Jennifer Stephens, Bailey’s campaign manager during his 2024 run for sheriff, said in an email that, “William Bailey was speaking up at the request of community members, and those internally at DCSO, who felt they couldn’t speak up.”

And, she added, “It cost him everything.”

A previous firing

The Deschutes County Sheriff’s Office has seen fallout from its elections before.

In August 2021, former deputy Eric Kozowski was awarded over $1 million dollars by a federal judge, who ruled then-sheriff Shane Nelson unjustly fired the deputy as retaliation for running against Nelson. The county spent another $1.2 million fighting the lawsuit, according to reporting from the Bulletin.

In an interview this week, Kozowski drew a distinction between his wrongful termination case and Bailey’s firing, saying that in his case, Nelson initiated internal investigations into him during the campaign. Nelson was accused by multiple employees of discrimination and retaliation throughout his nearly ten-year tenure.

Nelson endorsed Bailey as his successor, and Bailey welcomed the support at the time, telling OPB in September 2024 that Nelson “inherited a lot of personnel challenges that he had to address.”

Kozowski said he didn’t know enough about Bailey’s firing to draw parallels, but he hopes the county learned from his lawsuit.

“After what happened in my case, I would assume that the county would perform a lot more due diligence and be more careful in their actions,” Kozowski said.

Deschutes County Commissioners Phil Chang and Tony DeBone declined to comment on the specifics of Bailey’s firing.

Chang cited the appeals process, saying that if Bailey chooses to appeal the firing, he would come before the county commissioners’ board.

DeBone said that overall, he supports Rupert’s decision to relinquish control of the investigation to the county and he supports “the tough decision” that County Administrator Lelack made.

News Source : https://www.opb.org/article/2026/03/10/deschutes-county-law-enforcement-william-bailey-sheriff/