Law enforcement or soap opera? Race for Deschutes County sheriff keeps voters guessing

Thanks to their wives, the two men running for Deschutes County sheriff are both familiar with the hit Netflix show “Bridgerton.”

Part steamy soap, part period drama set more than 200 years ago, the fictional series revolves around an anonymous gossip columnist.

Under her pen name, Lady Whistledown risks it all to dish about the intrigues and betrayals of the cutthroat social season in Regency-era London.

Deschutes sheriff candidate Kent Vander Kamp said his local political race bears some unexpected similarities.

“It’s a lot like that, where you’ve got these mystery blogs,” he said.

Vander Kamp is a sergeant leading the sheriff’s office drug enforcement team. His opponent in the race is his longtime colleague William Bailey, a captain of the patrol division.

Whichever man Deschutes County elects in November will inherit a deeply divided staff. The agency has been embroiled in lawsuits brought by its own employees for much of the last decade. Reporting by the Bend Bulletin showed that, as the agency has drained its reserve fund since 2020, Bailey approved spending more than $3,000 on a slushy machine and the office dropped nearly $40,000 on golf carts last year.

As the public pays the costs, the twists and turns of personnel fights inside the office blur the line between law enforcement and soap opera, with Bailey and Vander Kamp now at the center of a drama fit for television.

Their campaigns have unleashed a bitter volley of accusations about lying, cheating and defamation. Ever since this election season got underway, a steady flow of criticisms have spilled online through an anonymous blog and social media account, DCSO Follies.

“Without further ado and with much joy and celebration, a tactical slushy machine was added to the Sheriff’s Office annual budget proposal. Yay!” reads one characteristically sardonic post.

The anonymously authored blog is often sympathetic to Vander Kamp, though he denies any involvement. Many of the posts take direct aim at Bailey.

“It’s all been lies, skewed to try to sell a message in the community that things are so unethical at the office and it is complete fiction,” Bailey said.

Bailey aims to continue ‘positive path’

Not all the criticisms in the blog are complete fiction.

For nearly a decade the sheriff’s office has been managed by Shane Nelson, a leader who has frequently been accused of retaliating against his own staff. Under Nelson’s leadership, the office has cost the county millions in legal fees and payouts for lawsuits brought by its own employees.

Nelson, who is retiring after two terms, endorsed Bailey. The patrol captain welcomed his longtime boss’ blessing.

“Sheriff Nelson has done good, really great things in our community, and he inherited a lot of personnel challenges that he had to address,” Bailey said, adding he is running “to ensure that our office stays in good hands and continues on a positive path.”

The 49-year-old captain has risen through the ranks of the sheriff’s office since becoming a reserve deputy 24 years ago. Before that, military records show he was honorably discharged from the U.S. Coast Guard after more than four and a half years of service. Bailey said he ended his second enlistment early, when he was 23, to deal with depression that he attributes to not knowing his biological father while he was growing up. He left military service, he said, “to get some additional help and support dealing with the years of stress and trauma.”

“I needed to go find my dad. I had to get some questions answered from him,” Bailey said.

During the campaign, anonymous social media posts implied Bailey left the service under more troublesome circumstances.

“I’d love to talk about policy and things I want to do in the future,” Bailey said. “But all we can seem to talk about is the past.”

If he’s elected, Bailey’s first priority, he said, is “healing the office.”

He also said he’s planning on a slate of internal promotions to support a new administration, followed by hiring to fill vacancies made by people moving up, while “making sure that we only bring the best people into an organization [who] help represent our mission and values.”

Vander Kamp’s October surprise

After endorsing Bailey, Sheriff Nelson launched an internal investigation into Vander Kamp.

In September, Vander Kamp became the fourth sheriff’s office employee this year to put Deschutes County on notice that he may sue over allegations of discrimination and retaliation at the hands of the current administration.

“It’s absolute tyranny, is what’s going on,” Vander Kamp said. “People are hiding underneath their desks just trying to make it through, day by day.”

The 51-year-old started with Deschutes County as a reserve deputy 20 years ago and is now a detective sergeant with the Central Oregon Drug Enforcement team. Outside of his work in law enforcement, Vander Kamp has controlled real estate and mortgage lending businesses registered in Oregon, including Oracle Funding Corp. In June, he announced on his campaign website he would suspend that business to focus on the sheriff’s race.

If elected, Vander Kamp said his first priority is to “get our money back in line,” and reign in overspending. He’s been endorsed by the office employees union and two county commissioners.

Vander Kamp claims an October surprise about his past law enforcement experience only shows the lengths his opponents will go to win an election.

But, recently revealed records do raise questions about Vander Kamp’s honesty.

The sheriff’s office investigation into Vander Kamp found that when he first applied to be an Oregon deputy in 2004, his employment application did not list an earlier stint as a reserve police officer in La Mesa, California. In September, Deschutes County officials obtained records detailing a La Mesa investigation into Vander Kamp’s conduct on the job in the mid-1990s.

Before these records became public, Vander Kamp sued the county and OPB to block the release. The records came out anyway.

They show that in 1997, La Mesa police officials wanted to fire Vander Kamp over what they called “serious incidents of misconduct,” including allegations of dishonesty. Vander Kamp has denied the city ever followed through with actually firing him.

“There’s no notice of discipline. There’s no due process documents,” Vander Kamp said. “They never terminated me.”

He said the controversy over his past is overblown, and blamed Nelson’s administration for distracting voters with “BS games and shenanigans.”

Sheriff’s office under scrutiny

Nelson stands by his decision to pursue information on Vander Kamp’s past.

“This is not election interference,” Nelson said in a prepared statement to OPB. “We have an obligation to determine if [Vander Kamp] was untruthful.”

While hired sheriff’s office employees are not allowed to engage in political advocacy on the clock, that’s not the case for their elected boss. State elections officials reached this conclusion late last year after reviewing a complaint about Nelson’s role in endorsing Bailey and appearing in campaign-related photos with him in uniform.

“ORS 260.432 allows for Sheriff Nelson to promote any candidate, while on the job,” state elections division compliance specialist Stephanie Darcy wrote in Nov. 2023 in response to a complaint.

Elections every four years routinely fail to check the vast powers of a sheriff, investigative reporter and lawyer Jessica Pishko argues in her recent book "The Highest Law In The Land."

The book explores the historical roots of sheriffs — they started in England as the muscle behind tax collection — and explores misconduct case studies across the U.S. today.

“There’s consistent problems of poor hiring, poor training, retaliatory hiring and firing, failure to promote women. All of these are really common in sheriff’s offices,” Pishko said.

The vast majority of sheriffs nationwide are white men, she said. Staffing at the Deschutes County Sheriff’s Office mirrors that trend: About 90% of sworn officers are men and 95% are white. Latinos, who make up about 9% of Deschutes County’s population, account for about 2% of its sworn sheriff’s officers.

A CBS News investigation recently found chronic abuses in sheriff’s offices nationwide, including deaths due to poor jail conditions or on-the-job shootings, are enabled by systemic failures. The consequences can be more dramatic than overspending or costly employment lawsuits, Pishko said.

Sheriffs who can’t control their office management, she said, “can’t control their deputies when they’re out in the field.”