The second candidate to enter the race for Deschutes County Sheriff is a lieutenant in the department who will face off against the appointed interim sheriff Ty Rupert.

Lt. James “Mac” McLaughlin’s entry into the race comes at a critical time for a sheriff’s department that has weathered a scandal that led to the resignation of its previous elected sheriff just seven months into his four-year tenure. The agency is also struggling to recover from years of complaints about a long-serving former sheriff whose conduct cost the county millions of dollars in legal settlements.

Rupert was appointed interim sheriff after the former sheriff Kent van der Kamp resigned last July. McLaughlin, an 18-year department veteran who had the support of the rank-and-file, had also applied to be the department’s interim leader and says he faced retaliation during the 2024 election for supporting van der Kamp.

Rupert was also a vocal supporter of van der Kamp, though both candidates have spoken out against the former sheriff since his departure.

Meanwhile, an ongoing investigation of a political opponent of van der Kamp threatens to overshadow the campaign season and become the voters’ primary focus.

Upon his appointment, Rupert scrapped van der Kamp’s investigation into his former political opponent Capt. William Bailey and moved oversight of the probe from the sheriff’s office to the county administrator, while putting Bailey on paid leave a process that’s thus far cost taxpayers nearly $100,000.

The investigation’s outcome, which could come in March, is poised to set the tone in a political race for one of Central Oregon’s most high-profile law enforcement jobs.

During the last election, the accusation-filled race for the sheriff’s office alienated many voters. More than 35% of eligible Deschutes voters skipped choosing a candidate for sheriff on their 2024 general election ballots, much higher than the countywide rate of no-show voters.

That low turnout came against a backdrop of distrust, as many officers who spoke out against the previous sheriff claimed they were retaliated against, investigated and demoted.

Politics on the job

McLaughlin joined the sheriff’s office in 2007. He was promoted to lieutenant by van der Kamp in February 2025 and worked in narcotics enforcement, SWAT command and investigations, according to the application he submitted for the interim-sheriff appointment last year.

County commissioners ultimately chose Rupert for the role, though McLaughlin was the top choice among members of the sheriff employee’s union.

“I want to make a generational change and a generational impact here,” McLaughlin said in an interview.

Rupert, who rose through the ranks of the department for 20 years before being appointed interim sheriff last year, has said that he is focused on restoring public trust in the agency. He made his case to voters using official sheriff’s office channels Jan. 27, the day after McLaughlin announced his candidacy, in a press release sent out by the department.

“This campaign is about who is best prepared to serve the public with integrity, transparency, and sound judgment,” Rupert wrote. “I am confident that my record of leadership, financial stewardship, and operational experience demonstrates that I am the strongest candidate to guide the Sheriff’s Office forward.”

Rupert’s decision to use the sheriff’s office for a political statement is reminiscent of complaints to the state elections division in 2023, when former long-serving Sheriff Shane Nelson weathered accusations he used the office for political advocacy. The Oregon Secretary of State’s elections division told OPB at the time that while hired sheriff’s office employees are not allowed to engage in political advocacy at work, the same rules don’t apply to the sheriff himself.

Asking the department’s public information officer to send out the press release was a “mistake,” Rupert told OPB.

“I didn’t think about it at the time and it won’t happen again,” Rupert said, adding that he wrote the release himself and that as a first-time candidate he is still learning the process.

Nelson’s nearly decade-long tenure, from July 2015 to December 2024, was marked by complaints from employees claiming he abused his power, with numerous allegations of retaliation and harassment leading to lawsuits and millions of dollars in awards and settlements.

For many in the department the next sheriff, van der Kamp, was seen as a changemaker. Bailey, who was endorsed by Nelson, faced criticism for defending his leadership style.

But after the 2024 election went to van der Kamp by wide margins, the Deschutes County District Attorney revealed van der Kamp would no longer be called as a witness because the DA said he had a history of using fabricated resumes under oath, and a state licensing watchdog found he lied for decades about his past law enforcement experience.

Rupert, initially a supporter of van der Kamp, has largely distanced himself but has continued to support an investigation into van der Kamp’s former political opponent Bailey. The interim sheriff outsourced the investigation to the Deschutes County Administrator’s office, which hired an out-of-area consultant for the work.

Rupert also put Bailey on paid administrative leave, a status now in its sixth month. As of January, the cost to the county to keep Bailey on the payroll and investigate him was just under $100,000, according to a public records request.

‘Internal matters’

Van der Kamp’s investigation into Bailey started after Bailey made disparaging comments on La Pine’s Muddtoe radio show after losing the sheriff’s race to van der Kamp in 2024, according to documents obtained through public records requests. In the interview, Bailey claimed he faced retaliation for running against van der Kamp.

When Rupert was appointed to replace van der Kamp, the interim sheriff threw out the initial probe and asked the county to redo the investigation into Bailey, a decision that seems likely to become a key issue for voters as he seeks to hold onto his appointed role.

Under van der Kamp, an internal investigator found Bailey had violated four policies around speech and conduct, records obtained from the sheriff’s office show.

Bailey declined requests for an interview, citing the ongoing investigation.

Rupert told OPB he decided to scrap those findings and start over because of feedback from employees who expressed concern about how the initial investigation was handled.

“They didn’t feel like it was being structured properly,” Rupert said in an interview. “As a new sheriff, it’s important for me to make sure that we give Captain Bailey the fairness and treat him fair and equitable.”

Bailey is a 25-year veteran of the department with no prior history of sustained disciplinary findings, records obtained by OPB show. Rupert put him on paid leave in August.

“It avoids people from in the office wanting to talk to those people. It avoids them from wanting to talk to other people” Rupert said.

Public records show Klamath County-based company, Mountain Lakes Employment Investigations, spent four months investigating Bailey’s radio appearance, in a probe led by attorney David Groff. The County received the investigative report in early January and expects to conclude a review and associated hearings by early March, according to county spokesperson Kim Katchur.

Groff was looking into possible policy violations around speech, public image, and loyalty, according to his report, allegations that carry more weight given Bailey’s position as a supervisor in the department.

He found that Bailey’s remarks “could have harmed integrity and fairness” of internal investigations and any connected legal proceedings as well as “engender workplace disruption or loss of public trust” when he veered from discussing the 2024 campaign and van der Kamp specifically, and spoke about issues within the office broadly.

Groff took issue with Bailey publicly discussing “internal office matters,” such as “pending internal affairs investigations, personnel matters, tort claims, and litigation involving the DCSO” the report states.

Within the 152-page report, Groff makes his case for why he believes Bailey’s remarks were problematic, but he stops short of making judgements on policy violations. That decision, along with any disciplinary action, will ultimately fall to the county administrator, a departure from how the sheriff’s office has dealt with its own in the past.

A history of public criticisms

McLaughlin said he’s watching the outcome of Bailey’s case closely.

“I think the investigation will come down to whether or not those comments were protected under the First Amendment in that they were a matter of public interest,” McLaughlin said. “My hope is that this would be handled appropriately above board with transparency and the right thing being at the center of the decision. Both for the organization and for the community.”

During the last election, numerous sheriff office employees aired grievances through tort claim notices against the department. None followed through on these threats to sue, but the notices served as a way to put their complaints in the public record without triggering investigations into law enforcement policy violations, like the one Bailey faces. McLaughlin filed a tort claim in June 2024 against the office.

Among the claims in the notice, McLaughlin said he experienced retaliation under Nelson, and that after giving a speech at a campaign event for van der Kamp he was told to “tone down” his support or risk “losing his career.”

If elected, McLaughlin said he’d want to institute stability in the office by making a handful of key leadership positions permanent within the department. Right now, he said, some of the highest positions in the office are filled on an interim basis by the current sheriff.

So far, Rupert and McLaughlin are the only two candidates for sheriff. The filing deadline is March 10. If more candidates file, voters will select the top two candidates in the May primary election. If no other candidates file, the race between Rupert and McLaughlin heads straight to the general election in November.

Editor’s note: During the 2024 election cycle, former Deschutes County sheriff Kent van der Kamp took OPB and Deschutes County to court in an attempt to seal records about his past law enforcement experience in La Mesa, California. A judge found the lawsuit lacked any reasonable basis. OPB continues to have active litigation to recover legal fees accrued defending itself from van der Kamp’s lawsuit.

This story was reported by freelancer Jen Baires. She can be reached at [email protected].

OPB is a nonprofit, statewide news organization with a mission to tell stories for communities in all parts of Oregon and Southwest Washington. As part of that goal, we work with partner news organizations and freelancers to identify stories like this that might otherwise go untold. If you have an idea for a story, live in an area outside Portland and want to work with us, send your freelance pitches to [email protected].

News Source : https://www.opb.org/article/2026/02/04/deschutes-sheriff-race-county-investigation/