A political outsider faces a daunting task: Fix Portland’s homelessness crisis

A storm is bearing down on Portland, and its incoming mayor has placed himself squarely at its center.

As a windy, freezing bomb cyclone grazed Portland on a recent November evening, mayor-elect Keith Wilson handed out blankets to people planning to ride out the storm outside.

Wilson, 61, was volunteering at the Portland Central Church of the Nazarene, a Southeast Portland church that converts itself into an overnight homeless shelter during winter months. By 9:30 pm, the shelter’s 45 sleeping mats, spread across the floor of a large auditorium, were occupied. Wilson and other shelter workers were forced to turn a dozen people away at the door.

“There’s nowhere else for them to go tonight,” Wilson said in a nod to the city’s shortage of shelter beds. “We gave them blankets, but they’ll be sleeping in doorways, on sidewalks, in culverts … It’s just inhumane.”

Expanding night shelters like this one is a key part of Wilson’s lofty plan to end unsheltered homelessness in Portland by 2026, a proposal that helped propel the trucking company president to victory in last month’s mayoral race. His top three competitors were sitting City Council members, so Wilson offered Portlanders both an alternative to the status quo and a message of optimism often lacking in conversations about Portland’s future.

Yet now that he’s been elected, he also offers uncertainty. How Wilson, an unfailingly earnest political newcomer, will navigate a newly overhauled city government to swiftly resolve the city’s largest crisis — one several mayors before him have promised and then failed to solve — is unclear, even to those who know him well.

“The old way of doing things isn’t the path forward,” said Noah Siegel, one of Wilson’s top political advisors and a former aide to two previous Portland mayors. “Keith will have his own path. And we’ll see where it leads.”

At the Church of the Nazarene, two men chat near their sleeping mats before settling in for the night. One nods to Wilson as he walks past the door in a bright orange windbreaker.

“Who is that guy?” the man asks.

It’s a question Portlanders are eager to have answered.

Watching the system not work

Wilson grew up in North Portland’s Portsmouth neighborhood, one of five children in a low-income household, and was what he recently recalled as a “happy-go-lucky kid.” He played varsity basketball at Roosevelt High School, where he was classmates with Portland City Commissioner Dan Ryan.

“He was the jock, and I was the nerd,” said Ryan, who was senior class president.

After earning a business degree at Oregon State University, Wilson traveled the world, working in New Zealand, New York City, and London before feeling what he describes as a magnetic pull home. He started working at his father’s burgeoning freight company, Titan Freight Systems and studied for a master’s degree in business administration at the University of Portland.

Wilson eventually took over the family business in the early 2000s, and quickly grew the company’s reach and revenue. But that growth came with a cost. By the early 2010s, Wilson said, he found himself at a crossroads.

“I started realizing the real negative effects of the transportation sector on climate change,” he said. “As a responsible party, we had to do something.”

Inspired by other industry leaders, like FedEx and UPS, Wilson set out to cut Titan’s fleet emissions by 20% by 2020. But, despite upgrading truck engines and adding new features to improve aerodynamics and engine use, Titan only saw a 3% decline in emissions by early 2020. That wasn’t going to work for Wilson.

“We realized we could not get efficiency when still using petroleum diesel,” he said.

Wilson switched Titan’s entire Oregon fleet to renewable diesel, a product made from animal fats and vegetable oil that can be used in any diesel engine. In less than a year, Titan recorded more than 60% emission reduction. By 2023, Titan had, with the help of state and federal incentives, become Oregon’s first freight carrier to use electric trucks. Wilson said the company is now on track to be emission-free by 2030.

Wilson said he is driven by challenges like these, especially scenarios in which people tell him the outcome is “impossible” to achieve.

“Like ending homelessness,” he said.

Family drew Wilson into the trucking business — and into Portland’s homelessness crisis. Wilson’s older brother Carl, who struggled with addiction and a mental illness, experienced periods of homelessness in the mid-2000s. It was up to Wilson and his parents to offer Carl a place to stay on occasion and to navigate social services to get Carl help. Wilson said he and his mother worked hard to gain mental disability insurance for Carl to help pay for the condo he now lives in.

“Today, my brother is in long-term recovery, stable, and someone I am incredibly proud of,” Wilson said.

But, without the financial and emotional support of his family, Wilson doesn’t know where Carl would be today.

After helping get Carl stabilized in housing, Wilson started hearing more frequently about former classmates, friends, and other family members experiencing homelessness in Portland. Some of them had died while living outside.

“I started seeing that suffering on our streets in a new way,” Wilson said. “And I could no longer recognize our city.”

Much like his approach to business, he began researching other cities that had meaningfully reduced the number of people living outside or unsheltered. From New Orleans to Philadelphia to Boise, he met with city leaders to understand their approach. Wilson brought those findings back to Portland, where he met with local leaders to lobby for changes in Portland’s homelessness response to match other cities’ models.

Wilson said he was brushed off for trying to compare Portland to cities with different laws, population sizes, or other dynamics that make solutions hard to replicate. His proposals felt too idealistic and far-fetched to many who’d spent their careers trying to address Portland’s homeless crisis.

“It seemed like every time I’d meet with a politician, they’d tell me, ‘That wouldn’t work here,’” Wilson said. “They were always too busy for me.”

So, Wilson decided to become a politician.

Getting involved in civic life

Wilson lost his first campaign for City Hall in 2020. Running against incumbent Commissioner Chloe Eudaly, then-city employee Mingus Mapps, and former Mayor Sam Adams during a global pandemic, Wilson was unable to gain enough attention. He came in fourth, with 5% of the vote.

Wilson’s memory of that race is tainted not just by the growing anxiety brought by COVID-19, but the fact that his sister died from a drug overdose weeks after he announced his campaign.

“She was addicted, but I was caring for her at the time,” he said. “It was a lot to process.”

But he sensed enough public interest in his policy ideas on the campaign trail that solidified his burgeoning interest in politics. He spent the following years lobbying the Oregon Legislature to pass bills expanding access to renewable diesel through a political action committee and formed a nonprofit called Shelter Portland, which advocated for solutions to homelessness he had seen work in other cities, like temporary shelters.

Wilson also began joining nonprofit boards, participating in various community meetings, and showing up at all sorts of civic gatherings.

“Once I met him, I started seeing him everywhere,” said Lakayana Drury, director of Word is Bond, a nonprofit that offers leadership development for young Black men. Drury first met Wilson at a public forum on gun violence held at a North Portland community center. “I’m like, ‘Oh, this dude’s really doing stuff.’”

Wilson later joined Word is Bond’s board and offered apprenticeships at Titan to the young people involved. He also reserved his family’s camping spot on Lost Lake for a summertime retreat for Word is Bond participants.

“I learned quickly that he has a huge heart,” Drury said.

Many people who met Wilson during this time questioned his motives. Was it religion? Something he needed to prove? A savior complex?

“He just deeply, deeply loves Portland,” said longtime Oregon campaign consultant Paige Richardson, who advised Wilson during his 2020 council campaign. “He has a level of passion for strangers that is rare in this town … and a strong moral compass.”

Wilson’s wife, Katherine Wilson, said that compass was likely inherited from his mother, Avis. She spent much of her free time volunteering with the Special Olympics and other local organizations and instilled this drive in her children.

“She was always giving back and just a delightful person,” said Katherine, a special education teacher. “I think that’s where Keith gets it.”

It’s made Wilson a humble person, his wife said. On the campaign trail, Wilson rarely used the word “I” to talk about his accomplishments, instead referring to “we.” That also carries over to his personal life.

“He never once comes home and says, ‘What’s for dinner?’” Katherine said. “He says, ‘What are we going to do for dinner?”

Those close to Wilson also say he’s not driven by money. Despite running a multi-million-dollar company, Wilson doesn’t appear to embrace a lavish lifestyle.

He lives in a 2,000-square-foot home in Northeast Portland’s Alameda neighborhood that he and Katherine bought for $125,000 in 1995; it’s now worth around $700,000, according to Zillow. That’s unassuming compared to his predecessor, Ted Wheeler, who owned a $1.3 million home in Portland’s West Hills when he entered the mayor’s office in 2017.

Wilson frequently wears crisp suits in public, but those close to him are quick to point out that they never appear to be tailored — perhaps intentionally.

Maybe he’s just dressing for the unglamorous job he wants.

Several political veterans OPB spoke with claimed they were the ones who encouraged Wilson to run for mayor in 2023. But Wilson tells a different story. In December of last year, Katherine was preparing to undergo open heart surgery.

“At 5 a.m., she’s in the operating room and we’re having our hellos and wondering what the other’s thinking, and you’re so frightened, you know,” Wilson recounted to the crowd gathered with him on Election Night at Old Town Brewing. “But she looks at me and she says, ‘No matter what happens, you’re going to run for mayor.’”

Wilson describes Katherine as a counter-weight to his laser focus on challenging projects. Before getting married, the couple met with an adviser with the Catholic Church to test their compatibility. (Katherine was raised Catholic, Wilson wasn’t. She said neither practice a religion now.) After the adviser reviewed their answers to a personality test, he delivered a verdict.

“He said, ‘You guys are an incredible match,’ and then he turned to Katherine, ‘But he works a lot. And he needs a challenge to be satisfied,’” Wilson recalled. “And I’m sitting there like, ‘Wow, yeah, that’s on the nose.”

Their marriage comes with rules designed to tamp down Wilson’s workaholic tendencies: Wilson needs to call every three hours when he’s focused on a big project. He needs to make time for family — they have two college-aged children — amid a chaotic work schedule. Katherine said Wilson has always been skilled at balancing his work and personal life, whether that’s through coaching his son’s basketball team or going on bike rides to let off steam.

“He can step away,” she said. “But he gets energized from work.”

After Katherine recovered from surgery, Wilson made his announcement.

The benefits of being unknown

Much like his 2020 City Council race, Wilson ran as an outsider in a field with experienced politicians. But, in this contest, being relatively unknown improved his odds.

His win, in the city’s first election that relied on ranked choice voting, has partially been attributed to his opponents. The other leading candidates, city Commissioners Rene Gonzalez and Carmen Rubio, both struggled with numerous controversies on the campaign trail, ranging from campaign finance violations to unpaid parking tickets.

Numerous polls leading up to the campaign also suggested that Portlanders were frustrated with city government — and eager for new leadership.

“It’s reasonable to think about Wilson’s win as a reflection of voters’ anti-incumbency interests,” said Chris Shortell, a political science professor at Portland State University. “And individual challenges presented by other candidates for mayor made it easier for voters to say, ‘Let’s go with someone who has no connection to this government.’”

Wilson is the first mayor elected in Portland in nearly 40 years who has no background in politics.

But, as much as voters were driven by disinterest in his opponents, there was enthusiasm for Wilson’s leadership. Because of his background, he was able to draw support from groups often at odds with each other during election season: businesses, environmental groups, progressive activist groups, and labor unions.

“We are thrilled that our next mayor is a business leader whose core values reflect Portland,” said Andrew Hoan, CEO of the Portland Metro Chamber. “Sustainability, homelessness, public safety, and support of the private sector.”

Sunrise Movement PDX, a progressive group that advocates for policies that reduce climate change, endorsed Wilson for both his commitment to the environment and reducing homelessness.

“When we were looking at the candidates in the race, Keith was the only one who really had a plan … for anything,” said Jacob Apenes, a campaign organizer with Sunrise. “He has a vision, and he’s really hopeful about trying to see it through. He understands housing affordability impacts and is super knowledgeable about transportation and energy issues. We’re optimistic.”

Wilson also represents a welcome break from divisive leadership to many. In recent years, Portlanders have become accustomed to city and Multnomah County leadership bickering over their shared responsibility to oversee the region’s homeless crisis and public safety programs. The arguments have centered on philosophical differences in how to spend money to address homelessness but did little to move the needle on the region’s priorities, only delaying solutions.

That came to a head weeks before the election when city commissioners advanced a proposal to pull out of its partnership with the county to address homelessness. After early Election Night results showed Wilson in the lead, Wilson called the commissioners behind the proposal, mayoral candidates Gonzalez and Mingus Mapps. He urged them to drop the issue since he wanted to maintain a partnership with the county as mayor. They reversed the plan the next day.

“That went a long way to show he’s really committed to working together,” said Multnomah County Chair Jessica Vega Pederson, who has lobbied the city to remain in the agreement. “That’s refreshing.”

Related: What to know about the Portland proposal to leave city-county homeless services partnership

A very new job

Wilson steps into an office plagued by public dissatisfaction — and radically different from what prior occupants have experienced.

In the past 15 years, Portland mayors have repeatedly struggled to follow through on lofty promises, pitched unpopular policies, and became hampered by controversy. Most only served a single term and exited City Hall with low approval ratings. Wheeler broke the pattern of one-term mayors by winning a second term in 2020 but didn’t shed the negativity. A May poll by DHM Research found that nearly 50% of Portlanders surveyed disapproved of Wheeler’s job performance — making him the most disliked local politician at the time, according to those polled.

Richardson, Wilson’s former campaign advisor, sees Wilson breaking this pattern of disappointment.

“Keith charts his own course,” said Richardson, who worked against Wilson as a campaign advisor for Rubio’s mayoral campaign this year. “He knows who he is and what his values are, and he is willing to admit failure. Not many politicians in this city can do that. Keith knows it’s not personal, and he just keeps going.”

Oregon Rep. Mark Gamba (D-Milwaukie), whose focus on local climate issues led to his introduction to Wilson, said he also sees Wilson not bending to lobbying from wealthy donors or lobbying groups like some past politicians.

“When politicians are beholden to powerful entities, they make poor decisions,” Gamba said. “They’re not always asking ‘Is this good for the people or the planet?’ Keith is. I think his moral clarity is such that I don’t think it’s going to be an issue.”

Aside from his strong moral compass, Gamba said, Wilson isn’t entering the mayor’s office focused on being re-elected, a mission that would likely require the support of the city’s deep-pocketed power brokers.

“If somebody can come to him and say, ‘Hey, this is going to make things worse,’ he will listen,” Gamba said. “But if it’s just, ‘That’s gonna affect my profits,’ I think that’s going to be less of a concern for him.”

Much of the discontent around recent Portland leaders has hinged on their approach to Wilson’s top priority: ending unsheltered homelessness. For decades, mayors have pledged to address homelessness with detailed plans and partnerships, and fallen short. Like Wilson, Wheeler centered his 2016 mayoral campaign on a promise to move all homeless Portlanders into shelter by 2019. Instead, the city’s homeless population has tripled in size since his campaign. And the homeless crisis remains Portlanders’ top concern.

Wilson believes he can break this pattern of broken promises due to his years of research and relationship-building across the country.

“To me, it’s simply an operational challenge,” he said. “There are two types of politicians: You can be operationally focused, or you can be agenda focused. Well, the agenda has obviously gotten us in trouble.”

The homelessness promise

Yet Wilson does have a clear agenda.

His plan to end unsheltered homelessness within a year relies on opening a series of temporary nighttime shelters in existing buildings, like churches, community centers, and vacant commercial buildings. He proposes the city staff the shelters with paid employees, pay rent, and offer assistance to guests interested in other services or housing programs.

The nighttime shelter at Portland Central Church of the Nazarene is funded by Wilson’s nonprofit Shelter Portland and serves as an example of his vision for the city. The shelter mostly offers beds to people on a first-come-first-serve basis, but visitors are guaranteed a bed if they slept at the shelter the previous night. A social worker checks in with visitors to assess needs.

Matt Huff, lead pastor at the church, said the model gives people an entry point to programs that can help them leave homelessness behind.

“Once we get people in the door, you start building trust,” Huff said. “And then you can start figuring out the next steps.”

Wilson said his plan will incorporate different types of night shelters, some requiring guests to be sober, others allowing drugs on site. He said staff will be trained to help people in mental health crises.

Wilson has no public document outlining his plan. He has said it will cost around $25 million to provide enough shelter to everyone on Portland’s streets in the first year. The city currently spends nearly six times that amount annually on shelter and other homeless services.

Those who study shelter costs have balked at Wilson’s cost estimate.

“Yes, these types of bare-bones shelters will cost less,” said Marisa Zapata, director of Portland State University’s Homelessness Research & Action Collaborative. “But there’s still the cost of paying people, renting the space, shuttling people to and from the shelter … I just don’t think this is a realistic plan.”

Zapata’s incredulity is echoed by many employed by the city and county who work on the regional shelter system but who declined OPB’s request to speak publicly about Wilson’s strategy.

Portland used to have many more overnight shelters. But in 2017, the city and county’s Joint Office of Homeless Services chose to reroute any financial support to night shelters to shelters that were open 24/7.

“The thinking was, a 24/7 shelter really gives staff time to engage with people and connect them with services that are open during the day,” said George Devendorf, who worked as the executive director of homeless service nonprofit Transition Projects at the time. “People didn’t feel rushed, they could relax. There are real shortcomings in the overnight shelter model, where you have to leave at daybreak.”

The Joint Office surveyed people experiencing homelessness about shelter preferences and heard a resounding rejection of temporary nighttime shelters due to lack of stability and the unreliable nature of waiting in line for a bed each night.

“Part of personal dignity is to have privacy,” said Barbie Weber, who is the co-founder of waste-removal nonprofit Ground Score Association and describes herself as homeless. “There’s no privacy at temporary shelters. It’s a Band-Aid. We need long-term solutions.”

Weber knows Wilson well — they both sit on a nonprofit shelter board — but she worries he’s focusing too closely on just removing people experiencing homelessness from public view.

“Maybe we can get people off the street for a night, but what’s the end game?” she said. “But I don’t think he realizes how complex this issue is.”

While overnight shelters are the central pitch of his homelessness plan, it’s not the only facet. Wilson wants to keep funding 24/7 shelters and transitional housing to serve as a stepping stone between an overnight shelter and permanent housing.

“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.”

He sees this plan going hand in hand with the city’s new camping restrictions, which penalize people resting on public property who refuse to move into shelter. The city has been slow to roll out this new policy, in part due to the lack of enough shelter beds needed to accommodate its unsheltered population.

Wilson said he does not want to criminalize homelessness. But he believes the threat of arrest may help motivate people to accept shelter. He wants Portland police to give people five warnings before resorting to an arrest — and he doesn’t want police to start enforcing the law until there are at least 50 empty beds available, on average.

“It’ll be a slow process,” he said.

A new political calculus

It’s not certain if Wilson will have the political power — or political support — to advance his plan in City Hall due to new changes in city governance.

This course was set by a 2022 voter-approved plan to overhaul Portland’s government, which introduced ranked choice voting, expanded the size of the City Council, and created voting districts. It also changed the mayor’s role. Under the changes, which go into effect in January, the mayor will no longer sit on the council and will instead focus on running city departments and carrying out new policies passed by city councilors alongside a new city administrator.

Related: Portland is overhauling its voting system and government structure. Here’s what you need to know

New policies will need to be introduced and voted on by members of the City Council. Wilson is hopeful the majority of the new 12-person board will back his plan.

Incoming District 3 Councilor Steve Novick, who served as a city commissioner under the old form of government, said he’s optimistic about Wilson’s proposal.

“If we can solve homelessness with $25 million, we should do it,” said Novick. “We need to hear his case. Of course, theoretically, the council could ignore the mayor.”

But Wilson isn’t certain he would even need the council’s support to put his idea in place. Portland already has an anti-camping law on the books, he said, and his shelter proposal can be considered part of the plan to enforce that law.

“And, as mayor, it is my job to enforce all the laws,” Wilson said.

Those who know Wilson well say his ability to build collaborative relationships with councilors could be a weak spot.

“He’s a professional, and that goes a long way,” said Jeff Allen, the executive director of a nonprofit focused on expanding access to electric vehicles called Forth, who has known Wilson for years.

“But a big part of Keith’s work is going to be building coalitions and support on the council behind policy direction he wants to go, and I don’t know that he has as much experience there,” he said. “It’s not like running a company.”

That’s become apparent as Wilson begins meeting with city officials and staff before entering office. Several longtime city employees that he’s engaged with expressed concern to OPB about his governing blind spots and what they see as his private-sector mindset. That worry was amplified early this month when Wilson held a virtual town hall meeting with nearly 2,000 city staff and promptly announced a plan to mandate in-person work for at least four days a week.

Staff, who currently are only required to spend half their work week in the office, flooded the meeting chat box with concerns about how it could worsen their mental health, finances, and effectiveness at work. The announcement dropped in the midst of the city’s drawn-out, tense negotiations with three public labor unions. Labor leaders say Wilson’s proposal could worsen those talks.

It’s a new landscape for Wilson, who oversees a non-unionized workforce at Titan Freight.

“A reminder,” wrote one anonymous city staffer in the meeting chat, “Bad (management) makes great union members.”

Bringing the private sector to public work

Wilson is used to navigating disagreement.

Wilson’s work advocating for renewable diesel at the State Legislature went directly against the agenda of the state’s largest trucking lobby. Not only did he want to expand access to climate-friendly diesel, but he pushed for a bill to end the sale of petroleum diesel statewide.

The Oregon Trucking Association opposed this legislation, citing concerns about supply and costs of the relatively new fuel source. Yet it didn’t stop Keith from regularly meeting with Jana Jarvis, executive director of the Oregon Trucking Association, to hear her concerns and to continue paying member dues to the association.

“Keith is very open and willing to engage, even when the majority of the industry disagrees with his perspective,” Jarvis told OPB.

The bill to phase out petroleum diesel failed.

Even when Wilson loses, he doesn’t seem to lose his cool. No one who spoke with OPB who had worked closely with Wilson said they’ve ever seen him get angry or raise his voice when his plans don’t go as anticipated.

Wilson and Allen, the director of the electric vehicle advocacy group Forth, both sit on the state’s Road User Fee Task Force, a commission focused on finding alternative funding sources to the state’s gas tax as more Oregonians start driving electric or hybrid cars.

Allen said that he and Wilson are often in the minority on the board in their shared interest to incentivize electric vehicle use. Often, their ideas are dismissed for not being “realistic” or “viable,” according to Allen.

“It can be frustrating,” Allen said. “But he’s got an ability to just stay focused on the outcome. If there’s a setback, he’ll just look for another way to get there. He just keeps chipping away.”

“I haven’t really seen him express frustration,” he continued. “Maybe he goes home at night and screams into his pillow, but I haven’t seen it.”

Wilson is comfortable with accepting when he — or his industry — makes mistakes and changes plans when needed. Rep. Gamba recalls Wilson attending a public meeting with state leaders and department heads after a semi-truck driver killed a cyclist on SE Powell Blvd in 2022. While Titan wasn’t connected to the truck or driver, Wilson came to express support for street improvements as a trucking industry leader. Attendees discussed ways to make Powell, a main trucking thoroughfare, safer for pedestrians and cyclists.

“There was some push back from the state and city, they said it could never work for freight,” Gamba said. “But Keith was right there saying, ‘Actually it could, here’s how.’ I just found that extraordinary.”

Wilson’s ability to change course shows up in his personal life. His wife Katherine said one of the most “amazing” things about her spouse is open-mindedness. “A huge part of our success in marriage is due to the fact that he’s willing to change his mind,” she said. “He doesn’t think his opinion is the only one. 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.”

A tough job

Advancing his shelter plan is just one of many challenges Wilson will encounter when he enters City Hall in January.

He’ll also be expected to formulate which policies to lobby for during the state’s January legislative session and draft a city budget amid a period of serious revenue shortfalls across the city. Wilson is already getting to work, joining Wheeler in meetings with the city’s budget staff. He said his priority is getting the city to secure federal grants and other funding before Donald Trump takes office on January 20. He said that potential cuts to federal funding the city relies on under a new White House administration are a major concern.

Under the last Trump Administration, Portland was regularly used as a political punching bag by Trump and other Republican leaders who depicted racial justice protests, rising crime and homelessness as the byproduct of failed liberal leadership. Mayor Wheeler often took the bait, defending the city on social media or with other public statements. Those days are behind Portland, according to Wilson.

He’s confident that, with the improvements he has planned for the city, Portland won’t catch the same kind of national negative attention.

“We will not be Fox News fodder anymore in Portland,” said Wilson. “We’re not going to be a national symbol of disaster for President Trump to point to. We’re going to be a national symbol of a community working together.”

It’s not entirely clear how he will avoid Trump’s ire.

Wilson’s priorities stretch beyond homelessness. Cutting the city’s fossil fuel emissions. Lobbying for high-speed rail. Economic development programs. “But we have to focus on homelessness first,” Wilson said.

Another challenge: Leading a brand new form of government with no political experience. Wilson knows he can’t rely on his business background alone to be successful. He’s spent the weeks following the election meeting with potential candidates with government experience to join his staff.

“The uncertainty (of the new city government) is a threat,” said Wilson. “We have to address that by having experienced professionals on our team.”

Earlier this month, Wilson announced he’d hired longtime political consultant Aisling Coghlan as his chief of staff. Coghlan isn’t new to City Hall: She worked as former commissioner Dan Saltzman’s chief of staff in the early 2000s. More recently, Coghlan held a leadership position in the Democratic Party of Oregon.

Wilson will formally resign from Titan before the end of the year, as elected officials aren’t allowed to hold other jobs. But moving from the private to the public sector won’t strip Wilson of some of his leadership tendencies. He said he plans on working seven days a week at City Hall.

“You’re going to see my truck parked at City Hall late at night…you’re going to see it there on weekends,” Wilson said. “And that’s going to be your signal that somebody is manning the ship.”

(He promises that he doesn’t expect his staff to copy his blurred work-life boundaries.)

To Wilson, the work is “life or death,” as he hears of people experiencing homelessness dying on Portland’s streets. But he admits it’s also a little self-serving.

“The people I care about, they’re leaving Portland,” he said. “I want my friends to stay here. I want to retire here. I want my babies to come back. I want this city to thrive again.”