A longtime law enforcement officer in Deschutes County is appealing his dismissal following a controversial internal investigation.
William Bailey, a former captain with the Deschutes County Sheriff’s Office, was terminated on March 2 after more than two decades of service. Officials have not publicly commented on the decision.
Bailey is now seeking to challenge his firing, with the appeal expected to be reviewed by the Deschutes County Board of Commissioners.
Background behind the firing
The events leading to Bailey’s termination trace back to his unsuccessful 2024 campaign for sheriff, where he ran against Kent van der Kamp.
In June 2025, Bailey appeared on a local radio program and criticized the leadership within the sheriff’s office, describing internal morale as “broken.” His comments came during a period of controversy surrounding van der Kamp, who faced allegations related to misrepresenting his educational background. The situation led to restrictions on his participation in certain legal proceedings.
Following Bailey’s interview, an internal investigation was launched to determine whether his public remarks violated departmental policies. The inquiry concluded that policy violations had occurred.
Further developments and leadership changes
Shortly after the investigation began, van der Kamp resigned amid ongoing controversy, and his law enforcement certification was later revoked by state authorities.
Interim Sheriff Ty Rupert ordered a second review of Bailey’s case through the county administration. That investigation reportedly reached the same findings as the first.
Despite the conclusions, Bailey’s supporters argue the termination was unjustified.
Jennifer Stephens, who previously managed Bailey’s campaign, said his public comments were intended to address community concerns during a time of uncertainty and to help rebuild trust.
What happens next
Bailey’s appeal will determine whether the termination stands or if further action is taken. Meanwhile, the sheriff’s office has declined to provide additional details on the case.
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