Redmond city councilor alleges ‘systemic culture of corruption’ at Deschutes Sheriff’s Office

Former sheriff’s officer Clifford Evelyn has spent his recent retirement years serving on the Redmond City Council, shaping policies and weathering conflicts in the fast-growing Central Oregon city. All the while, he said, his trust in the region’s largest local law enforcement agency withered away.

This month Evelyn escalated his concerns about the Deschutes County Sheriff’s Office to state police watchdogs, filing a complaint with the Oregon Department of Public Safety Standards and Training that calls for an investigation into “an unchecked, systemic culture of corruption.”

His complaint calls into question the involvement of both Deschutes County Sheriff candidates appearing on the November ballot — Interim Sheriff Ty Rupert and Lt. James “Mac” McLaughlin — may have had in leaking confidential information about employees in order to shape public opinion during the last race for sheriff.

McLaughlin did not respond to requests for comment. Rupert, who was appointed sheriff in July 2025 after a 20-year career with the office, said in an interview with OPB that he agrees the office has historically been a “good old boys club” but he denies contributing to that ethos or providing any insider information to people outside the agency.

Both men have campaigned on promises to change the office culture and rebuild public trust after years of leadership controversies. But once again voters in Deschutes County are navigating an election season filled with accusations of wrongdoing among the agency’s leaders that echoes the last election cycle, which turned off many voters altogether.

Nearly one out of every four Deschutes County voters – 22% – opted out of the sheriff’s race in 2024, a much higher percentage than in the previous election. That’s despite the sweeping power of the office to run the county jail, enforce laws, and set standards for the deputies they supervise.

It’s a problem rural counties across the country face, where a sheriff has vast discretion over what law enforcement policy looks like in areas without other police departments. More than 3,000 sheriffs across the country hold these elected positions, said Mirya Holman, a professor with the University of Houston and co-author of “The Power of the Badge: Sheriffs and Inequality in the United States.” The book explores how sheriffs approach running jails and overseeing more than a third of the nation’s law enforcement employees.

“Deschutes is a really interesting example because it’s a large population county, but the sheriff has a lot of law enforcement capacity within the county,” Holman said. And the impact of a sheriff’s decisions can matter greatly in everyday life.

“So if you think about something like rules about car chases or rules about SWAT or rules about the use of dogs – these have all been issues in Deschutes – those policies are set by the sheriff and then also implemented by the sheriff.”

‘So much nonsense’

Evelyn worked at the Clark County Sheriff’s Office in Washington for more than 20 years before moving to Central Oregon in 2017. Since then, controversies at the top of the Deschutes sheriff’s office have become so numerous they’re difficult to track.

Under former Sheriff Shane Nelson, who served from 2015 until 2024, the agency weathered accusations of retaliation, bullying, and discrimination, all while the county spent millions defending or settling costly lawsuits from employees. The next elected sheriff, Kent van der Kamp, resigned in 2025 less than a year into his term, after state investigators found he lied about being previously fired from a law enforcement agency. Two candidates who ran for sheriff and lost were fired shortly after their respective elections, in 2020 and 2024. One sued and got a settlement topping $1 million in 2021. The other is currently appealing his termination. This year, Sheriff-hopeful McLaughlin is campaigning while on leave because he’s being investigated internally over allegations of misconduct and dishonesty stemming from a SWAT action he led.

“There’s so much nonsense going on here,” Evelyn told OPB, “And one of the most troubling things is that it’s at the top, the leadership.

His complaint isn’t “against any one person,” he said. “I filed it against the Sheriff’s Department’s top administration and it’s because they’re not holding anybody accountable.”

Evelyn’s expansive state complaint covers years of reported problems within the beleaguered agency, with more than 300 pages of records and media reports included. Many of his claims focus on allegations that McLaughlin and Rupert violated department policy by leaking confidential information about employees and internal investigations in order to seed an anonymous blog.

The state has, thus far, kicked Evelyn’s call for an investigation back to other local elected officials on the Deschutes County Commission.

“The county is not in a position to comment,” said Deschutes County spokesperson Kimberly Katchur.

According to the state, the county has until Nov. 2 — the day before the election — to respond, said DPSST spokesperson Sam Tenney.

However, public policy expert Holman said the unilateral power baked into being an elected sheriff makes oversight by an outside agency unlikely.

“It’s not like the county board of commissioners is the boss of the sheriff,” she said, adding that she would be “shocked” if the board “was granted the legal power to do anything in this circumstance.”

‘Follies’

The county government did take the lead on firing a captain this year who ran unsuccessfully for sheriff in 2024.

Captain William Bailey’s decades-long service came to an end in March following remarks he made on a local radio show about his employer.

Rupert, the interim sheriff, bowed out of investigating or disciplining Bailey, handing decisions off to the county’s administrator. Bailey is currently appealing his termination through an arbitrator.

Evelyn’s complaint, which was compiled with the help of Bailey’s former campaign manager, alleges the sheriff’s office applied a double-standard by allowing Bailey to be fired while turning a blind-eye to Rupert and McLaughlin allegedly divulging confidential information that showed up on an anonymous blog.

The blog, DCSO Follies, gained a lot of attention in 2024 for airing insider information about conflicts at the agency, with posts often skewering leaders over finances and management decisions. The mystery writer or writers have never been publicly revealed.

One controversy featured in the Follies became the subject of an Oregon Department of Justice investigation last year. The state justice department probed allegations that a deputy, who has since retired, was fraudulently filing for overtime pay. In the course of the investigation, a former reserve officer, Ross Dargahi, told DOJ investigators that Rupert had provided him with incriminating information about the deputy, which could violate the sheriff’s office policy around disclosing personnel information outside of the agency.

Rupert said this week he did not provide any information directly or indirectly to the blog. “Absolutely not,” Rupert said. “I have no idea who the Follies are.”

Dargahi could not immediately be reached for comment. In 2024 he personally donated $25,000 to the sheriff campaign of van der Kamp, who resigned less than a year into his term and later received a lifetime ban from serving as a law enforcement officer in the state.

Rupert said this week that he remembered the DOJ investigation but did not recall specifics from his interview with the investigator in February of 2025.

“I was made aware of a complaint that had come in through DOJ. And if I remember right, Dargahi called and asked what the status of that complaint was,” Rupert said. “That’s the only communication that I recollect right now.”

With the election less than two months away, the region’s newspaper, the Bulletin, has already run an op-ed from an advocate urging voters to sit out the sheriff’s race. For his part, Evelyn said he plans to write in his own name in protest.