Portland mayor-elect Keith Wilson shakes hands after his official acceptance speech Thursday, at the Charles Jordan Community Center in Portland, Ore., Nov. 7, 2024. Wilson shared a hopeful view of the city’s future, speaking about ending “unsheltered homelessness and open drug use,” as well as restoring public safety in Portland.
Kristyna Wentz-Graff / OPB
Last month, Portlanders elected a political outsider to the mayor’s office.
To voters, trucking company CEO Keith Wilson offered an alternative to the status quo in City Hall. He also offered a hopeful promise: To move everyone sleeping on Portland’s streets into shelter within a year.
Here’s a quick primer on Wilson as he prepares to oversee Portland’s new form of government.
Who is he?
Wilson, 61, is a lifelong Oregonian who grew up in North Portland. After earning a master’s degree in business administration at the University of Portland, Wilson took over his father’s burgeoning freight company, Titan Freight Systems, which he grew into a multi-million-dollar business. At Titan, Wilson experimented with ways to reduce his trucks’ carbon emissions, like switching to renewable diesel as a main fuel source. He eventually turned Titan into Oregon’s first freight carrier to use electric vehicles.
Wilson has spent time lobbying the state legislature to phase out petroleum diesel sales statewide and make renewable diesel more available.
Wilson is also passionate about ending homelessness, after experiencing the challenges of navigating Portland’s social service programs firsthand when his older brother was homeless.
In 2022, Wilson founded a nonprofit called Shelter Portland, which advocates for solutions to homelessness and helps fund a few shelter programs.
He says he was drawn to politics to address homelessness, both to better the lives of unsheltered people on Portland’s streets and to restore all Portlanders’ love for their city.
“The people I care about, they’re leaving Portland,” Wilson said. “I want my friends to stay here. I want to retire here. I want this city to thrive again.”
How did he win?
This wasn’t Wilson’s first City Hall race. In 2020, he ran for City Council, only to land about 5% of the vote. This year’s race for mayor was different. That’s partially due to his opponents. Wilson’s top competitors were two current city council members — Rene Gonzalez and Carmen Rubio — who both struggled with controversies on the campaign trail. His win can also be attributed to his positioning as a political outsider: Numerous polls leading up to the campaign suggested that Portlanders were frustrated with city government and eager for new leadership.
He garnered support from Portlanders across the political spectrum, including environmental groups, business lobbyists, and labor unions.
Wilson is the first mayoral candidate to win in a Portland election using ranked choice voting. The 2022 ballot measure that changed the city’s voting system also overhauled the city’s form of government. That new model, which expanded the size of the City Council, created voting districts, and removed the mayor from the City Council.
What has he promised?
Wilson has promised to end unsheltered homelessness by 2026. Unsheltered homelessness is a term for anyone who is living outside a building, whether that’s in a tent or car.
It’s a familiar pitch: Mayor Ted Wheeler centered his 2016 mayoral campaign on a promise to move all homeless Portlanders into shelter by 2019. The city’s homeless population has tripled in the time since.
Portland mayors have been pledging to end homelessness, unsuccessfully, for decades.
Yet Wilson is confident that his proposal will break this pattern, due to the years he’s spent researching other cities’ ability to shrink its unsheltered population.
How will he do that?
The crux of his plan relies on swiftly converting existing buildings like churches, community centers, and vacant commercial buildings into temporary overnight shelters. He believes these shelters will create a path toward more permanent housing for people living outside.
Portland doesn’t have many night shelters, largely due to local government’s decision to shift funding to shelters open 24/7 over the last decade. Wilson said he thinks that’s a mistake.
“Overnight shelters are a valuable piece of the continuum for somebody to walk through so we can help care for them eventually with housing,” he said. “Right now, we’re missing that piece.”
Wilson proposes that the city staff these shelters with paid employees and offer assistance to guests interested in other social services or housing programs. He also said his plan will incorporate different types of night shelters, some requiring guests to be sober, others allowing drugs on site, to ensure everyone feels welcome. Staff will be trained to help people in mental health crises, according to Wilson.
Wilson estimates it will cost around $25 million — on top of what the city already spends on homeless services — to provide enough shelter to accommodate all unsheltered Portlanders in the first year.
So ... can he?
That’s hard to say. Wilson certainly has his critics, including people currently experiencing homelessness and longtime shelter providers. They agree overnight shelters aren’t a one-size-fits-all solution to a population as complex and diverse as those living outside. Others who study shelter effectiveness say Wilson’s cost estimate of $25 million is far too low to account for the scale of shelters he hopes to staff and open. The city currently spends nearly six times that amount annually on shelter and other homeless services.
Yet Wilson is confident his plan will be successful. He’s also open to making adjustments, whether that comes from the new city council members, Multnomah County leaders, and homeless service providers. Wilson’s wife, Katherine Wilson, said her husband’s open-mindedness is key to his success.
“He doesn’t think his opinion is the only one,” she said. “He will always hear people out and is open to new perspectives. That probably is the strength that will help him the most next year.”
Read more about Wilson’s path to the mayor’s office, personal motivation and leadership goals.
