Deschutes County Sheriff's Office Payouts near $5 Million - The Source

The Deschutes County Sheriff’s Office is still dealing with the fallout of alleged favoritism and retribution that has plagued the agency for years.

The sheriff’s office, and Deschutes County, are now at the center of a grievance of termination and administrative appeal by William Bailey, a former DCSO captain who ran for sheriff against Kent van der Kamp in the 2024 election.

In the appeal filed with the County March 16, Bailey alleges retaliation, bias among County officials and a “procedurally defective” termination process.

These contentions were scheduled to be considered by the Deschutes County Board of County Commissioners in a public hearing at the Deschutes County Services Building April 22. Commissioners could make the decision that day — or postpone to a later public hearing — whether to approve a neutral re-evaluation of Bailey’s termination.

Sam Tenney, the spokesperson for Oregon Department of Public Safety Standards and Training, which certifies officers, says being terminated by a law enforcement agency doesn’t disqualify an officer from being hired somewhere else. If an officer violates moral fitness standards, the agency may revoke those certifications, but performance issues or a policy violation don’t rise to that standard. Tenney confirmed that Bailey’s Oregon police certifications remain valid.

In his complaint, Bailey alleges the commissioners are biased against him because Phil Chang and Patti Adair endorsed van der Kamp for sheriff. Bailey says van der Kamp initiated the internal investigation into his conduct, stemming from critical comments he made about van der Kamp, while off duty, during a local radio show in June 2025. Commissioner Tony DeBone, Bailey noted, made a public statement in support of his termination.

William Bailey, a former captain with the Deschutes County Sheriff’s Office, has appealed his March 2 termination to the board of county commissioners. Credit: William Bailey

The County declined to make a commissioner available to answer questions for this story because the board is the governing body hearing the appeal.

When Ty Rupert began serving as interim sheriff in early August, he placed Bailey on paid leave while a second investigation into Bailey’s conduct was administered by a third-party investigator. That investigation, led by Mountain Lakes Employment Investigations, found Bailey in violation of personnel rules; his employment with DCSO was terminated on March 2.

In his appeal, Bailey contends that the County personnel rules that were applied to his termination case are invalid because DCSO policy framework, not the County’s, should dictate discipline and appeal rights. The buck, ultimately, stops with Sheriff Rupert.

Yet County officials told the Source that in the interest of ensuring that Bailey received full due process as a non-represented employee, it utilized existing investigative and disciplinary procedures under county personnel rules. Under that process, County Administrator Nick Lelack was identified as the appropriate decision-maker. He reviewed the investigation report and supplemental documents and met with Bailey and his representative before issuing a final decision, said Kimberly Katchur, the County’s spokesperson. Her staff didn’t recall of any other instances of County Administration handling any other investigations on behalf of the Sheriff’s Office.

At his April 22 hearing, Bailey will request that a neutral party rule on the appeal of his termination, which in his complaint he calls “procedurally defective, was signed by an official not identified in DCSO policy as the official to issue a proposed termination to a sworn deputy and was imposed after an irregular investigation process and a shifting use of policy frameworks.”

A flurry of payments

If Bailey isn’t reinstated to his post with backpay and the termination scrubbed from his record, he has the option to sue the County, as other former DCSO employees have for wrongful termination and other allegations. Any settlement or compensation he’d receive would add to the pile of about $4.6 million the county has issued in payments and litigation fees since 2006. (That figure doesn’t reflect legal fees since 2014; the Source will update the figure when the County makes that fee amount available.)

Among the 16 parties who received payments since 2006, eight are past or present DCSO employees, according to the County. Some of the biggest payouts pertain to high- profile allegations, such as those of Captain Deron McMaster in 2024, Deputy Crystal Jansen in 2021 and Deputy Eric Kozowski in 2021.

In 2024, McMaster was awarded $265,000 for retaliation by Sheriff Nelson regarding an alleged cover-up of a fellow DCSO employee’s misconduct. Jansen won $527,000 for gender discrimination and retaliation; Nelson was named in that suit because he was Jansen’s direct supervisor.

Eric Kozowki won a $1.06 million jury award for retaliation for running against Shane Nelson in the 2016 race for sheriff.

Kozowski’s claim of retaliation for campaigning against Shane Nelson in the 2016 election for sheriff won him a $1.06 million jury award and cost the county $1.2 million more in legal fees. Those fees included costs associated with ethics advice, legal defense and the trial, according to the County’s Finance Department. Additionally, DCSO directly paid Kozowski $10,000 in damages.
Beyond the top five settlements and Kowoski’s jury award, which total $4.63 million, the average payout among the remaining 10 parties totals $284,000. That’s about $28,400 per party.

The DCSO is funded by two voter-approved county service district property tax levies. Yet these settlements and awards don’t come from DCSO coffers, but instead from the County’s Risk Management Fund, says Erik Kropp, the County’s risk manager who oversees the fund. That’s because the County itself has self-insured against losses for general liability for claims up to $1 million since about 2008, Kropp said. That self-insurance covers claims stemming from workers’ compensation, medical, dental and unemployment benefits, along with other risks. At the end of the 2025 fiscal year, the County’s General Risk Management Fund’s final budgeted amount was $5.6 million, according to the County’s annual budget report. Because of the amount greater than $1 million, Kozowski’s settlement is the sole instance since 2006 that the County put a claim on its commercial liability insurance policy, which is presently provided by Government Entities Mutual and NLC Mutual Insurance Company. The county presently pays $317,070 for excess general liability, Kropp said.

Insubordination or whistleblowing?

The November 2024 sheriff race, for many voters, represented a changing of the guard at DCSO. Out with the we do things a little different ‘round here mentality, embodied by former Sheriff Shane Nelson and in with contemporary accountability and transparency. For many, including the Source editorial board, van der Kamp embodied that change; Bailey, after all, had been endorsed by Nelson, whose tenure as sheriff was marred by favoritism, retaliation and lawsuits. Van der Kamp won 60% of the November vote, assuming office on Jan. 1, 2025.

Former Sheriff Kent van der Kamp Credit: DCSO

While Bailey declined to comment for this article, he contends in his complaint that van der Kamp had explicitly given permission for DCSO employees to speak to the media. During the same period, local media had reported on the allegations of disorder, dishonesty and retaliation that had been trickling out of DCSO since the election year.

In his appeal, Bailey says “… Sheriff van der Kamp’s honesty and credibility had already become matters of public controversy, including public reporting that he had been placed on a Brady list and decertified in Oregon based on dishonesty findings.”

Jennifer Stephens, Bailey’s former campaign manager, declined to comment on the record, referring to a previous statement she made on Facebook: “I was shocked to hear that William Bailey was fully terminated for appearing on a radio show to address community questions and concerns of significant and serious public interest. In the weeks since, I’ve been stunned by the irregular undue process and inconsistency of policy enforcement unfolding.”

In the months leading up to Bailey’s June 20 radio appearance, van der Kamp’s name had cropped up in local media, including the Source.

In April, Deschutes County District Attorney Steve Gunnels placed van der Kamp on the Brady List — a compilation of officers barred from testifying in court, the Source reported.

In May, the Oregon police certification agency concluded an investigation, finding that van der Kamp failed to disclose a termination from a Southern California police department to the DCSO when he was hired as a reserve deputy. The agency also substantiated the Deschutes County District Attorney’s Office findings that van der Kamp, on numerous occasions, lied while testifying under oath.

During the radio spot, in which Bailey asserted that he was not speaking in his official capacity as DCSO captain, he said van der Kamp’s winning the race for sheriff “was one of the ultimate con jobs.” Bailey spoke frankly about van der Kamp’s decertification and his Brady Listing. He also said van der Kamp, newly in office, had promoted those who helped his campaign and that he himself faced the option of self-demotion to lieutenant, which Bailey refused.

Bailey’s public frankness precipitated an internal investigation initiated by van der Kamp, in which Bailey was accused of violating confidentiality rules in discussing personnel matters on the radio program. That investigation, in which Rupert was interviewed as a witness, was never completed, according to the County. When Rupert became sheriff, he declined to serve as the decision maker, since his being a witness created a potential conflict of interest, says Katchur.

Three days after the radio program, on June 23, van der Kamp announced his resignation from sheriff, effective July 31, the Source reported.

In his appeal, referring to the second investigation, Bailey says: “The confidentiality finding is similarly problematic. My media comments referenced matters that had already been publicly reported by news outlets and did not disclose nonpublic investigative facts, personnel records, or protected law-enforcement information. Even so, the investigation treated discussion of already-public reporting as disclosure of confidential or insider information. That conclusion is difficult to reconcile with the fact that the underlying subject matter had already entered the public domain through media coverage.”

In September, van der Kamp dropped his appeal of his certification revocation, according to the state police certification agency; letting stand his lifetime ban from serving as a police officer in Oregon.

Presently, there are seven litigation cases open with the Deschutes County Sheriff’s Office.