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Keith Wilson is a serious man, running a serious business, whose campaign to become Portland’s next mayor is centered on the most serious problem in the city: homelessness.
Wilson has unlocked $100,000 in matching taxpayer funds for his campaign, making him one of just three mayoral candidates, along with City Commissioners Carmen Rubio and Rene Gonzalez, to qualify so far. A relentless campaigner, he received more individual contributions last month than any other candidate.
Wilson, 60, owns the state’s first fossil fuel-free trucking company, sits on a national transportation board, and was one of two Oregonians appointed by the Biden-Harris administration to vote on the agenda at the Democratic National Convention last weekend.
Paige Richardson, a longtime political consultant, says she’s “never seen anybody who can get as much done, or do as many things.”
Yet his bid for mayor is not being taken entirely seriously.
The reason, by the telling of political consultants and others familiar with the mayoral race, reveals a certain irony: While voters complain that city and county leaders have been sloppy and slow to make a dent in the problem, Wilson’s plan to end unsheltered homelessness in just 12 months is too ambitious.
“We have communicated directly to Keith that while we appreciate his urgency, we are deeply concerned that his promise to end unsheltered homelessness in a single year falls into the same pattern of so many failed plans of the past,” says Jon Isaacs, executive vice president of public affairs for the Portland Metro Chamber.
Which poses the question: Is it possible to be too ambitious on homelessness?
Wilson says no. “Why is keeping the failed status quo,” he asks, “considered ‘more serious’ than learning from what works?”
THE MAN
Wilson grew up in North Portland, one of seven children in a low-income household. He put himself through Oregon State University, then went to live in New York City, where he worked in sales at NBC and for a short time lived in a terminal at LaGuardia Airport. He returned to Portland in 1990 to help his father with his small packaging business and to earn an MBA at the University of Portland.
He grew his dad’s business into Titan Freight Systems, which generates $10 million a year in revenue, operates in Oregon, Washington and Idaho, and currently employs 70 workers. It’s the first trucking company in Oregon to operate a completely green fleet, free of fossil fuels.
He sprinkled his energies just about everywhere else, too.
He’s the vice chair of Word is Bond, a Black-led nonprofit that fosters leadership in young Black men. Wilson leads a group of these teenagers on a wilderness camping trip every year, typically the only white guy who goes.
He serves on a national committee advocating for high-speed rail and, in 2021, founded a political action committee to advocate for a slate of green energy bills in the Oregon Legislature, making between himself and Titan $125,000 in contributions.
But perhaps most importantly, Wilson is obsessed with ending unsheltered homelessness, a passion he took up in earnest after his failed 2020 campaign for Portland City Council.
Wilson self-funded what he called “fact-finding” trips to cities like New Orleans, San Diego, Los Angeles and Salt Lake City, as well as Rockford, Ill.; Gulfport, Miss.; Boise, Idaho; and the nations of Portugal, Greece and the Netherlands. There he’s talked to homelessness experts and local elected officials about what they’ve done.
Mark Johnston, who worked in various U.S. presidential administrations on homelessness for 30 years, including as a deputy assistant secretary in President Obama’s Department of Housing and Urban Development, met with Wilson five years ago after finding it remarkable that a man would self-fund trips to learn about homelessness.
“I couldn’t believe it,” Johnston recalls. “You meet him and you think, he’s in too deep. But he’s done more research than any other person I’ve ever met.”
Wilson’s trips and research culminated in him founding a nonprofit called Shelter Portland in 2023. Under that umbrella, he gathered homelessness experts, state lawmakers and nonprofit directors to help craft a plan to end unsheltered homelessness in 12 months.
“What you’re seeing right here,” Wilson says, “is an absolute, clear plan researched over years.”
THE PLAN
Wilson’s plan is as straightforward as it is ambitious: By June 30, 2025, in three months’ time, create 2,300 nighttime shelter beds across a constellation of churches, community centers and businesses in the city. By Wilson’s calculus, that’s enough beds for each unsheltered person in Portland that doesn’t already have access to a county or city shelter bed. Each shelter would host anywhere from 50 to 200 people a night. Across all those shelters (an estimated 20 to 25 in total), the city would need only 150 staff to run them.
Upon arrival at around 8 pm, each unhoused person would receive a snack and a sleeping mat. There would be no assigned beds.
“You just line up at 8:30 pm, you’re in at 9 pm, and it’s very respectful,” Wilson explains. “This is not a concrete shelter where you get bed 4A and your friend is in 20B on a bunk bed. You’ve got to keep that social network together.”
In the morning, everyone would get a light breakfast—a breakfast burrito, perhaps. Then they’d leave.
Wilson says no capital costs would be necessary; the city would just pay the host organization rent of $80 per person each month. So if a church accepted 50 beds, it would get paid $4,000 a month from the city. The city would partner with nonprofits to run the shelters, Wilson says. But not five-year contracts, like the Joint Office of Homeless Services normally signs with nonprofit service providers; these would be more like six-month contracts, Wilson says.
Wilson thinks he’ll have no problem finding 25 churches and community centers to agree to serve as nighttime shelters. He says he’s in active discussions with 13 places already prepared to assist. “It’s not been hard at all,” he says.
Plus, Wilson says, it’s really just a numbers game: “I doubt if 50% of the beds are going to be utilized.” What he means: If the city had enough shelter for every single person living on the streets, the city could enforce a 24-hour camping ban while complying with Oregon state law. “We have to meet the spirit of the law,” Wilson says.
(Shelter Portland pays $3,000 a month in rent to a church on Southeast 82nd Avenue for a day shelter, which partially covers operating costs.)
The annual cost of Wilson’s 2,300 shelter beds: $25 million. (Another prong of Wilson’s plan: abundant daytime shelters.)
Once unsheltered homelessness dramatically subsides under the plan, Wilson says, the $300 million spent by the city annually on the associated costs of dealing with homeless camping (police overtime, tent-barring boulders underneath highways, camp sweeps) would taper off.
Wilson calls the $300 million (a figure Mayor Ted Wheeler’s office cited earlier this year) “system waste” that should be spent on critical city services—not the damage caused by homelessness.
And Wilson believes he can only implement his plan if he’s in the most coveted position in the city: “The only way we could end homelessness is to have that most critical operating position, which is mayor.”
THE FEEDBACK
Indefatigable. Fucking relentless. Boundlessly optimistic. A man on a mission.
Not coachable. Myopic. He buys what he’s selling.
These are the words that four political professionals used to describe Wilson, speaking on background.
Longtime consultant Richardson, who’s launching an independent expenditure campaign to support Commissioner Rubio’s run for mayor, says Wilson is making a common mistake of CEOs-turned-candidates: conflating work as the chief executive of a private company with service as an elected official.
“Private sector is like being a captain of a speed boat, and the government is more like being a captain of an ocean liner,” Richardson says. “You can’t turn it as fast, it’s more complicated, it takes more space and time to move it, but it can carry a lot more people.”
Another political consultant who’s currently working on city races says Wilson is “not realistic in his appraisal of ideas. He continues those appraisals in the face of allies saying to him, ‘I don’t think that’s going to happen.’”
Commissioner Rubio, who is also running for mayor, called Wilson’s plan “naïve at best and dangerous at worst.”
“Believe me, I would love a magic wand solution to homelessness,” Rubio said in a statement. “To win this fight we have to get real about the complex nature of the challenge.”
But Wilson also has his cheerleaders, and they’re no chumps.
Some of them serve on Shelter Portland’s board or on its leadership council, including state Rep. Maxine Dexter (D-Portland), who sits on Gov. Tina Kotek’s Housing Production Advisory Council; Rep. Dr. Thuy Tran (D-Portland); and former Boise Mayor Dave Bieter.
Another admirer is Dan Steffey, who, under Mayor Bud Clark in the late 1980s, quickly stood up hundreds of nighttime shelter beds. (It’s the model Wilson aims to emulate.) Steffey is a special adviser to Shelter Portland’s board, which includes mostly shelter nonprofit leaders.
Steffey says the plan may be overly ambitious, but it’s not impossible.
“I don’t know about 12 months, but it’s damn sure feasible if it has the unflinching leadership it needs,” Steffey says. “You cannot look at what Keith has done, in building that plan and the research he’s done around the world, for God’s sake, and believe that he won’t provide the leadership.”
Another supporter is Johnston, the former deputy assistant secretary in the Obama administration: “Most politicians don’t want to try anything because they’re scared of getting criticized. That’s why we don’t get much done in this country, and Portland is about as bad as it could get.”
Perhaps Lance Orton, executive director of the housing nonprofit CityTeam, captures Wilson’s ethos the best: “I believe that he believes in the plan.”
Correction: A previous version of this story incorrectly stated that Wilson earned an MBA at Portland State University. That’s incorrect; he earned it at the University of Portland.