2 longtime Clackamas County political fixtures face off in primary race for chair

For a little more than $5, supporters of Clackamas County Chair Tootie Smith can buy a ceramic 11-ounce mug with words that sum up her political philosophy: “Stop Portland Creep.”

Smith, a notably uninhibited politician who is hoping to be reelected as county chair, typically does not hold back when detailing how she feels about the state’s biggest city and the county in which it resides. Take, for example, a March 2, 2023, meeting: She was caught in a photo giving two middle fingers to depict how she believed the regional government, Metro, treats Clackamas County.

Related: OPB's Ballot Guide: Meet the candidates and learn what's at stake in Oregon's May 21 primary election

Later this month, she will face former Clackamas County Sheriff Craig Roberts, who served as the county’s sheriff from 2005 until 2020, in the May primary. The race is technically nonpartisan, but like most election campaigns, it’s quickly turned political.

When it comes to their neighboring county, Roberts is taking a different tact.

“If Portland is a failure, it will impact the entire tri-county region,” he said, adding he wants to see the counties improve their working relationship.

Smith has made it a point in her campaign to highlight what she sees as the contrast between her county and Multnomah. In a campaign blog post last month, she pointed to her county’s increase in police funding and success reducing the unhoused population. She also noted Clackamas County was growing while Multnomah was not. People favor the “Clackamas Model,” her website states, “over ideology and wokism.”

She might be right.

“If we asked people in Clackamas County if it’s heading in the right direction or not, most people are going to say it’s on the right track,” said John Horvick, vice president of the polling firm DHM Research.

And people’s perspectives are certainly shaped by being close to Multnomah County, Horvick said.

“Some of it is, ‘Oh gosh, how are we compared to that place that is in an overly bad spot?’” he said.

The state’s third-largest county is both politically and geographically diverse. It includes up-and-coming Happy Valley and wealthy Lake Oswego as well as smaller towns like Estacada. It stretches from Mount Hood to Milwaukie. Clackamas County has sent both conservative Republicans and more moderate Democratic lawmakers to Salem, and the county commission has vacillated from left- to right-leaning.

What the county has in political diversity, however, it lacks in racial diversity with a population that is more than 87% white. Voters in the district are closely divided between Democrats, Republicans and unaffiliated voters. In 2020, however, Smith won her seat for chair with about 53% of the vote.

This election, Clackamas County voters will have a choice between two fairly different candidates. Both have weathered some controversies, but have very starkly different personalities and politics.

Former state Sen. Bill Kennemer, R-Oregon City, was on the commission for more than a decade and served as county chair before heading to Salem.

“There’s more than 400,000 different opinions in Clackamas County,” Kennemer said, referring to a rough estimate of the county’s population. “No matter what pothole you step in, there is controversy.”

There is no doubt Smith has a knack for fanning the flames of controversy. She made national headlines during the COVID-19 pandemic for defying former Gov. Kate Brown’s isolation orders by proclaiming she would hold a Thanksgiving dinner “with as many family and friends” as she could find. She also said the governor’s orders were an attempt to treat citizens like “second-rate slaves.”

Her opponent is hoping to frame himself as more of a mild-mannered leader. Roberts called himself a patient man, a good listener and a collaborator.

“I have a unique talent for bringing people together and they might start out on opposite ends,” he said.

Like Smith, Roberts is a lifelong Clackamas County resident. The two have been fixtures in the county’s political world for decades.

Metro Councilor Christine Lewis, whose district includes Gladstone, Lake Oswego, Milwaukie, Happy Valley and Oregon City, said she wouldn’t mind a shakeup at the chair level.

“With Craig Roberts you know what you’re going to get,” Lewis said. “With Chair Smith, it depends on the context, the subject, the day, whether the meeting is open door or closed door, whether the camera is on. Consistency is important to me.”

But Smith has garnered her fair share of support — she’s even nabbed the endorsement of the Clackamas County Peace Officers’ Association, which represents more than 400 law enforcement officials from deputies and sergeants to crime scene investigators in the county.

And she’s received a positive assessment from an unlikely source, the only Democratic commissioner on the county board, Martha Schrader.

“I actually really enjoy working with her,” Schrader said. “We don’t agree on everything, for sure, but by and large, I find her really fun to work with … and we come from extremely different backgrounds. She’s a farm girl from Molalla. I grew up outside New York City in an urban area.”

A third candidate, April Lambert, is also running and focusing on issues of inclusion.

Her goal, according to a campaign website is to “ensure that all historically underserved communities are receiving equitable services.”

Earlier this year, Clackamas County commissioners closed its equity and inclusion office.

Housing

Last year, Smith surprised a lot of people when she voted against a transitional housing project for people experiencing homelessness.

The project, part of a broader, state-backed approach known as Project Turnkey, was an effort to turn a 110-unit Quality Inn into housing. As it was set to move forward, Smith reversed course and became the decisive vote against the project.

“We have heard from the public that they wish to be engaged, that they needed more time,” Smith said in explaining her change of vote at the time. “Now you have it.”

At the time, Gov. Tina Kotek said she was “stunned” by Smith’s vote. Project Turnkey was a project the governor championed while serving in the state Legislature. The governor told the Oregonian/OregonLive at the time that the vote was a “step backward” when everyone needs to be doing more to solve the housing crisis.

State Rep. Mark Gamba, D-Milwaukie, who previously served as the mayor of Milwaukie, said the county had already put down earnest money and the project was going to be state-funded.

“It wasn’t going to cost the county a penny, the county is already spending money to keep homeless people at the hotel at a much higher rate than if they owned it,” Gamba said. “Because of the political pressure Tootie got from the far right, they walked away from the deal.”

Smith declined to talk to OPB for this story.

Smith has stated that her county has reduced homelessness by 65% while she was chair. She is basing those numbers on a point-in-time count.

Gamba, who is supporting Roberts, said he doesn’t buy it.

“They are using a bad point-in-time count and walking around and banging a drum and saying they’ve solved homelessness,” he said.

Clackamas County Courthouse

Another big issue in the race is the effort underway to build a new Clackamas County Courthouse, which is expected to cost upwards of $300 million. About half of the cost the state is expected to cover, leaving the county on the hook for the other half.

Smith, who also served as state lawmaker, credited her time spent on the state budget writing committee as helping her understand and identify government waste. She said that’s helped tackle Clackamas County’s budget.

“What I learned was how government budgets worked and I learned how they didn’t work,” she said on X, formerly known as Twitter. “I’ve been able to take that experience and knowledge to Clackamas County and find waste, redundancies and holes that needed to be fixed.”

Related: OPB's ballot guide for the 2024 Oregon primary election

Roberts said he doesn’t trust it.

“They do need a new courthouse. They do need a new jail. And my concern is how are you going to pay for it?” Roberts said. “I was sheriff for 16 years and there was never an easy budget. So when they talked about this enormous expense … I do believe wholeheartedly there is a financial tsunami coming and the numbers don’t add up.”

Schrader, the Democratic county commissioner, said the county brought in a whole finance team that ensured the county was on track when it came to financing the courthouse.

“He’s a good sheriff and a good guy,” Schrader said of Roberts, adding she is not someone who likes to speak poorly of anyone. “If he gets elected, I’ll go through the [financial model] on the courthouse with him.”

Tolls

While county chair, Smith has vehemently opposed the push to toll drivers along I-205. Smith said she “led the fight to fight tolling” and after Gov. Kotek said the effort would be paused, Smith made it clear she would push to end it forever.

Controversy

While campaigning, Smith has been quick to point out she’s not the only one known for having some controversies under her belt.

During Roberts’ tenure as sheriff, the county settled a wrongful death suit for more than $1 million after an off-duty sheriff’s sergeant fatally shot his wife, two of her friends and himself. The lawsuit said Roberts knew the sergeant was unstable. Another detective under the sheriff was accused of ignoring a vast number of cases, some involving sexual assault of children. The detective was convicted of two misdemeanors for failing to investigate reports of child abuse. A report later determined the sheriff’s office was slow to act when it was alerted the detective was not doing his job properly.

During both instances, Roberts said, he acted in a transparent fashion and made a number of changes to ensure the office was doing everything in its power to prevent anything similar happening in the future. Roberts noted when it came to domestic violence, it was something he worked much of his career to combat.

“As a leader it’s important to be transparent. I was transparent and learned from it and found what improvements we can make,” he said.

Ballots are due May 21. The job pays $127,587 per year.