Deschutes County sheriff’s captain William Bailey fired after investigation into radio comments

BEND, Ore. (KTVZ) -- Deschutes County Sheriff’s Captain William Bailey has been fired following investigations into comments he made last year about the sheriff’s office and the department’s former elected leader.

According to reporting from Oregon Public Broadcasting, the events leading to Bailey’s termination began in June 2025 during an appearance on KNCP’s Muddtoe Radio show.

During the interview, Bailey criticized then-Sheriff Sheriff Kent van der Kamp, who had defeated him in the 2024 race for sheriff. Bailey alleged he and his supporters faced retaliation within the sheriff’s office after the election and described morale in the department as “broken.”

An outside investigation was launched to determine whether Bailey’s public comments violated sheriff’s office policies. That review found Bailey violated department policies related to speech and expression.

A second review ordered by the Deschutes County Administrator’s Office later reached the same findings.

Interim Deschutes County Sheriff Ty Rupert directed questions about the case to county administration.

“I must direct all questions regarding former Captain William Bailey to downtown county administration. I relinquished this investigation to downtown administration for complete transparency,” Rupert said in a statement to KTVZ.

KTVZ reached out to Deschutes County Administrator Nick Lelack for comment but has not received a response.

Kim Katchur, a spokesperson in Lelack’s office, confirmed that Bailey no longer works for Deschutes County as of March 2.

The controversy surrounding the investigation began during the tenure of former Sheriff Kent van der Kamp. Weeks after launching the investigation into Bailey, van der Kamp resigned from office after state and local investigations found he had been dishonest about his background.

KTVZ also reached out to Bailey for comment but had not received a response as of Wednesday evening.

Jennifer Stephens, who served as Bailey’s campaign manager during the 2024 sheriff’s race, provided KTVZ with the following statement:

“I was shocked to hear William Bailey was fully terminated for appearing on a radio show to address community questions and concerns of significant and serious public interest. William Bailey appearing on the radio show after an overwhelming number of requests to do so, in a time of chaos and uncertainty for the Sheriff’s Office, was a step towards reassurance and restoring public trust.

By the time William Bailey spoke on the radio show in June of 2025 it had been more than two months after news that Kent Vander Kamp had been placed on the Brady List became public, a recall campaign to remove Vander Kamp from office was forming, and complaints were being reviewed by DPSST which would ultimately lead to Vander Kamp being stripped of police certification for life. Also, the anonymous, self-proclaimed "satire" blog, which claimed to have insider information to hold the sheriff's office accountable, had been persistent in "publishing news" for 18 months. The DCSO Follies spread misinformation, personal and professional attacks by name and in detail, and fueled animosity internally and externally of the Sheriff's Office. Between Kent Vander Kamp's dishonesty and the DCSO Follies manipulation the public had ever-growing concerns and questions during and after the 2024 election.

William Bailey took on the risk and burden of running for elected office, and continued to advocate for what he felt was in the best interest of public safety and the Sheriff's Office, and it cost him everything. I do worry what repercussions this decision will have on current and future whistleblowers and honest, trustworthy leaders who are called to serve.

As a community member who values and supports public safety and first responders, I am deeply saddened we’ve lost a capable and trustworthy law enforcement officer and local leader. As someone who worked with William Bailey during his campaign for Sheriff and witnessed the actions of others to tear down the public image of the office in the name of politics was disappointing. But the inequitable enforcement of policy, the rampant double standards, is more than frustrating, it’s unjust.

Vander Kamp having an option to ‘retire’ during an active process of state decertification, and to retain retirement benefits even after decertification for life, is a failure of the system and only protects and rewards bad actors.”

Bailey has until March 17 to appeal the decision.