Portland’s newly elected mayor Keith Wilson shares vision for city, tackling big challenges

After the second release of preliminary election results from Multnomah County on Wednesday night, Keith Wilson maintained his lead in the mayoral race. The Oregonian has already called the race, and opponents Carmen Rubio and Rene Gonzalez have both conceded to him. Wilson is the CEO of a local trucking company and ran on a platform to end homelessness by 2026 by expanding shelter capacity and strengthening the city’s partnership with Multnomah County to tackle the crisis. Wilson joins us now to share more about his recent victory and vision for the city.

Note: The following transcript was transcribed digitally and validated for accuracy, readability and formatting by an OPB volunteer.

Dave Miller: This is Think Out loud on OPB. I’m Dave Miller. Portland is about to get a complete overhaul of city leadership and its system of government. We now know the baker’s dozen of Portlanders who are going to be at the helm at the beginning of this new chapter in Portland history. With the ballot drop last night, we finally have clarity on the makeup of the newly enlarged city council, which will include three members from each of four geographic districts, and we know who the next mayor will be. It’s Keith Wilson, who is in the studio with me right now. He is a born and bred Portlander and the CEO of a trucking company. On January 1, he’ll take over his first elected office as a chief executive of Oregon’s largest city.

Keith Wilson, congratulations and thanks very much for coming back in.

Keith Wilson: Thank you, Dave. What a great privilege.

Miller: One of the promises you’ve made a few times in the last few days – in a statement on Wednesday, in your acceptance speech yesterday – is that you’re going to approach this job with humility. What does humility look like in action to you?

Wilson: Well, that’s a learned value, since we’re talking about a CEO. I’ve got decades of experience and I know how to do things wrong, and humility now is about listening, recognizing that you do not have all the answers. Some of the best decisions I’ve made now are because I’ve listened to my team in all four corners of the three states we operate. Certainly, being a married person, you become humbled quickly when you’re having discussions with your wife or your spouse. But age has really allowed me to become humbled. I make better decisions, the more people I involve in those decisions. But they don’t paralyze me, they just make the decisions and the implementation better.

Miller: Who have you been listening to over the last few months that has made the biggest impact on you?

Wilson: So I have a national group of leaders who’ve helped me and a lot of them have ended unsheltered homelessness. Since that was that signature goal for my campaign, I’ve listened to them. And fortunately, their mayors, their county officials and their federal officials, they’ve done this before. And so they were with me that entire route and then I have local officials as well – Mayor Mark Gamba was a wonderful person to rely upon, a lot of our congressional delegates have been helpful. So I tell you, it’s been a community-wide effort, and everybody saw the message and understood the research. They just jumped all in. It’s been a proud moment.

Miller: I should say that there are plenty of other people that we have heard from who have very different ideas of the best way to approach homelessness. And I think we should focus on the signature promise you’ve made, that you want to set up an additional 20 to 25 nighttime shelters, churches and community centers, along with more daytime shelters. And then your promise is that you will, through this, eliminate unsheltered homelessness in your first year.

As you said, you developed this idea after traveling around the country, actually going outside the country as well. But there are plenty of folks who say that they would like this to work, but it’s a flawed model, that among the critiques is that it requires people to move every day. It makes it hard for them to have belongings. It doesn’t provide stability, they say, that could lead people to accept services. What is it that made you decide that this is the centerpiece of the right strategy?

Wilson: Well, let’s start with where we’re at. So I think that there’s a misperception. There’s this false choice between shelter or housing. And we think of shelter, we think about a four walled building that’s built, purpose, focus on shelter. It’s very expensive to do. I know one facility in Salt Lake City that just opened $37 million to build a shelter. It’s easy to see why people are apprehensive to believe in shelter because they feel that takes away from building housing, the long-term solution. That’s not what we’re talking about. That’s a false choice. We can’t allow people to suffer on our streets. That’s not Portland.

What this does is it takes a model that we perfected in Portland 30 to 40 years ago, and that most cities utilize tonight around the nation, to simply provide life saving care so those individuals can then be linked with needs. It’s low cost. You use repurposed assets, it’s immediate, you flex up, you flex down. Think about an earthquake. We would never let people live and die on the street if they’re in an earthquake. It’s a crisis. Let’s treat it like a crisis. We cannot move forward with people living and dying on our streets.

Miller: What is your estimate for the percentage of people who are currently unsheltered, who will voluntarily go to these new shelters that you hope to stand up?

Wilson: Well, I think it was cited by my opponents. One of them had noted that 70% did not accept shelter, but 30% would. So let’s flip that on its ears and say, well, goodness gracious, we know 30% will immediately. So let’s address that. That’s a win. That’s not a loss.

Now, 70% don’t accept shelter. What we do know, by setting up shelters, we can enforce our community safety laws. What we know is that you’re not going to be in a tent, you’re not going to be a makeshift shelter and you’re not going to be an RV because based on law, we have shelters available for those who are on the street. So therefore, it’s really hard to live outside to sleep on the street at night unless you have those resources. But when we provide those resources in some cases and allow those resources, we’re fostering that behavior, we’re removing all of those items, but we’re gonna provide life saving care when they’re ready to come inside.

Miller: Well, let me make sure … and I don’t have the number in front of me, but my recollection is something like 3,000 unsheltered people living in Multnomah County right now, or am I way off in the number?

Wilson: You’re right, but ...

Miller: To stick with that number – if you’re saying that something like 30% might accept shelter, and these are ballpark figures ...

Wilson: Exactly.

Miller: … But we’re talking about more than 1,500 people who might not. And are you saying that we can expect the police to say, OK, we’ve offered you shelter. If you don’t want it, then the next step is a fine or potentially jail.

Wilson: Yeah, I mean, you’re going to provide warnings. Certainly, you have the threat of arrest right there. But many people are going to come inside. But the reality is that you can’t set up a tent anymore. You cannot establish a campsite any more importantly, because we have a shelter for you.

And Dave, you’re right. These are ballpark numbers. What will happen is, we’ll start to slowly flex up the system – February, March, April, May, June – and then once we have 100 to 200 empty beds at night, you stop. You’re gonna allow people to come in. We’re gonna reunify people with their family and friends. We have people here from Arizona. We have people here from California, but we also have people that were couch surfing prior. We know the tents are no longer available.

We focus on aggressively reunifying people with their resources, but shelter may be one of those resources, And then we start figuring out what those needs are to then move them through the continuum, right? Move them into 24-hour shelter and then into housing.

Miller: What happens if the new city council doesn’t like your plan?

Wilson: Here’s what the reality is. I’ve spent nine months working with all 100 of them closely.

Miller: One hundred of the candidates?

Wilson: One hundred of the candidates. I brought in my national leadership team, we had a closed door meeting with 50 of them. They’ve already met the national team. I don’t wanna start this relationship thinking we’re gonna fail. Start from a position we’re going to succeed. They have all noted, they’re open minded. Now, I’m gonna work closely with them. Go out to their communities, their neighborhoods and explain how we’re gonna do it. They all want to address the suffering on our street. Not one of them has said I want the status quo to remain. They’re all with us.

Miller: Do you think you have six votes right now? And I say six, it’s 12. The power you’d have legislatively would be as a tiebreaker here, so you need six of 12, say, to authorize money for this change, right?

Wilson: It’s uncertain, Dave.

Miller: I mean, if you have those votes or if you need a vote?

Wilson: All the above. So we’re gonna work and collaborate with the council. You know, it’s a great question. So I’ve already talked to President Peterson at Metro. I’d like to have a resolution through them. I’d also like to have the CEO … you’ll have Jessica Vega Pederson on for the county here …

Miller: County chair.

Wilson: Yeah, I’d like to have a commission …

Miller: You called her CEO. It’s a good slip. We’ll talk about going from the private sector to the public sector in just a second. But you see her essentially as a CEO. Do you see yourself as a CEO?

Wilson: Well, you noted that at the top of the hour when you introduce the program that the CEO is of the largest city, the chief.

Miller: Fair enough, I did call you the chief executive.

Wilson: I do see it as somebody who’s going to be solely focused on executing the core values and the core services of our city, the enterprise.

Miller: OK. But I want to go back to what you said is an open question, which to me is a gigantic piece here. So you don’t know right now if you need city council approval to make your plan a reality?

Wilson: Not certain, but we are going to go through council for this, Dave. Regarding votes, there’s no reason to do vote counting yet. We don’t even know who the council is.

Miller: We have a pretty good … I mean, it hasn’t been certified, but based on the analysis of the Oregonian and others, it seems like we know who the council is going to be.

Wilson: You’re right. Then let’s cut to the chase. Yes, we’ll be going for council and it’s one of the first things out of the gate. I’d like to focus on unanimity with all the councilors to say, let’s end the suffering on the street.

Miller: And if you don’t get it. If for whatever reason, they’re not interested in supporting this idea, then what do you do?

Wilson: Well, we have a crisis on the street, Dave. We have got to address that crisis. There are so many issues on our street. It’s a false assumption to think they’re not going to want this. I mean, we have thousands of people on our street. We have got to care for our citizens.

Miller: It’s a false assumption to say that they’re not going to support a particular policy. I think the false assumption is that they don’t want homelessness to be addressed effectively. To me, it’s an open question of where a majority is going to think it makes sense to spend taxpayer dollars.

Wilson: Yeah, You know, I just go back. They don’t want us to squabble and point fingers, they want us to get things done. So I’m gonna work with them. Maybe I’ll answer it this way: Are they gonna want modifications and such? Absolutely. Will I entertain and bring those in? Yes. So let’s tackle it that way again. They’re gonna make it better. Whatever I bring to them, they are gonna make it better and fit their constituents in their districts.

Miller: Let me run by you a kind of bumper sticker version of what I think your promise to voters was. And tell me if you think this is accurate.

Wilson: Sure.

Miller: “The last two mayors have promised to end unsheltered homelessness – they didn’t. I will within a year.” Do you agree that that’s what you told voters?

Wilson: That’s exactly what I told voters.

Miller: OK. If you don’t, if a year goes by, it’s January 1, 2026, and you have not, let’s say, even made a sizable impact on the number of unsheltered Portland, will you decide to not run for reelection? Will you see, even just after one year, your term as mayor as a failure?

Wilson: Dave, that’s putting the cart before the horse. We’re not even a day one yet. I think that is a great question.

Miller: I wouldn’t ask the question in that way, if you had made this a central point and if you hadn’t basically said my two predecessors were failures and I can fix this. If you don’t … and I take it you’re such an optimistic guy and you want to be able to say, let’s not assume failure. I’m not assuming failure. I’m saying what if you can’t accomplish what you want, then what do you think voters should then be thinking?

Wilson: Dave, so here’s what I’ll tackle. First of all, my predecessors told Portland what they were going to do. I’ve shown Portland what I’ve done. We opened up a shelter this past Sunday – low cost, $16 per person per night. A Safe Rest Village is, per person per day, $189. We’re doing it at a tenth of the cost and we did it rapidly. And that’s open. Open day shelter six months ago to learn how to do it at a low cost and rapidly. Those are examples and those are the resources that I’ve learned how to do, and I’ve been doing this for four years.

Now, let’s talk about this next year. This former government is actually going to be different from the former government we once had. If we aren’t making measurable focus on that key goal, I have the ability to work seven days on this to make it and to address the problem solving. Now, I’m no longer a counselor. I’m not spending three or four days on developing policy, negotiating policy, voting on policy. We’ve got 12 very qualified counselors to do that. As the mayor, as the CEO, I can focus the time necessary to address this problem on the street. So we ensure nobody is suffering on January 1, 2026.

Miller: What about all the rest of your duties as mayor? I mean, police chief and everything else?

Wilson: I have a city administrative officer. We’re going to hire a qualified, experienced, seasoned person who knows how to run an enterprise well. That’s my focus on that. Certainly, the police chief will be helping as well, as far as the community safety laws. So we have the city and the structure set up. That’s what our charter reform did. They delivered a clear objective, a clear structure and we know who’s responsible, but that’s the promise I’ve made to Portland, and those are my friends and neighbors that are living on the street, Dave. This is not about us just having a policy on a piece of paper. These are the lives of our neighbors.

Let’s be clear, we cannot have people suffering on the streets of Portland any longer. It’s like quicksand, Dave. We can’t move Portland forward. If we have thousands of people living on the street. We have families leaving, we have businesses leaving, we have to be able to restore that community safety for us to move our city forward.

Miller: You’ve said you’re going to transfer ownership of your trucking company before the new year, since elected leaders in Portland cannot hold second jobs. In reporting, you’ve mentioned a couple of what it seems to me to be a couple of different versions of how to do that: a blind trust or selling it to employees. Have you decided yet which path you will pursue?

Wilson: So that’s where the city attorney comes in and that’s where my staff come in. I have some very trusted senior executives that have been with me for years, who have part ownership in a smaller portion right now. We’ll see what works best for them and what works best for the company. It’s a phenomenal business. Our job is to keep those families, those staff members and take care of them.

Miller: Your father, if I’m not mistaken, helped co-found what’s now called Titan Freight. And you say in your bio that it’s been a part of your life for as long as you can remember, long before you took over the company. What is it going to mean to you to relinquish control of something that you helped build and enlarge?

Wilson: Well, we’ve accomplished some extraordinary things: one of the lowest carbon footprint carriers in the nation; the lowest workforce injury rate in the state of Oregon; national innovator of the year for the last two years. That allowed me to get to this point to run our city. The love of Portland and the challenges we’re experiencing need somebody who’s ready to take on those challenges with a personal stake in this.

Miller: But my question is about losing the particular personal stake in that company. What’s that going to mean to you?

Wilson: I’ve enjoyed, you know … they’re going to continue on. Isn’t that the best part of it, that this will continue on but with different leadership. But Dave, it’s time to move on. I’ve made caring for our city the central point of my life for the last four or five years. That’s the goal right now, to turn Portland around.

Miller: It seems that one of the things that has endeared voters to you is your optimism. Where do you think your optimism comes from?

Wilson: A sense of hard work, a love for the city. You talked about our business. I really enjoyed the business because the team, we built the culture that we have. We’re gonna bring that to Portland. It’s just a dogged approach to work as hard as humanly possible, to overcome adversity. And our family was poor. My father and my brothers never graduated from high school. I did. I graduated and put myself through college. Every challenge that I’ve had, I’ve worked hard to get around. And I realize that every “no” that gets put in front of me is just an opportunity to learn a different way to get around that challenge. But it’s been beneficial to me and to others as well, along that journey.

Miller: It’s interesting because your answer, it’s a lot about work ethic, which strikes me as – maybe this is your philosophy – that if you work hard, you can accomplish good things. But it does seem that that’s different from a belief that things will work out.

Wilson: Yeah.

Miller: Which stands out to me maybe even more in my conversations with you. And I’m wondering why you believe that? What’s given you a sense that a better day is likely?

Wilson: Well, Dave, it’s hard work. So I met the daughter of Desmond Tutu two weeks ago. Desmond Tutu has always been one of those shining lights for me. He quoted at the Nelson Mandela Foundation … he said, “Don’t grow angry, improve your argument.” It puts the onus on me, instead of others. It puts the challenge on me. In other words, if someone doesn’t see what I’m trying to explain or the vision that I have, it puts the onus on me to explain it better because I don’t complain. I don’t need to complain on others. If they’re being negative or saying “no,” it just means I need to do a better job and more research to find a way around it.

But let’s tie it back to Portland. Portland’s suffering right now, right? People think that we can’t get out of this. So that’s, don’t grow angry, improve your argument. So that’s what I’m doing with our city right now. We’re gonna overcome this, Dave. So that’s the optimism – I’ve had some serious challenges in my life and I’ve always been able to find a way around it. And now we have a huge challenge in Portland. So let’s work together to find a way around it.

Miller: What are some of the serious challenges that you’re talking about when you say you’ve dealt with them already?

Wilson: Oh, I ran for city government four years ago and I lost my sister two weeks after announcing my candidacy. And it’s addiction. So I’m the only child in my family that hasn’t suffered addiction or mental illness. We struggle. I mean, we were a poor family living next to the Columbia Villa. Like many stories in North Portland, we’ve had adversity, a lot of adversity. But do I give up? Absolutely not. Do I care for my family today? Yes. Am I the caretaker for my brother? Absolutely.

Again, challenges to overcome, but cloister yourself around your family and friends, and they’ll always be there, and they always have been, and I’m going to be a part of that family. Whether it’s my family personally or whether it’s the family in Portland, we have got to care for one another right now.

Miller: The city administrator is going to be a hugely important piece of the day to day running of this city. And we’ve had a version of that already because Mayor Wheeler already has said, well, let’s not have it all start from scratch in 2025. But you’ll be the first mayor who fully is running this new form of government. Do you already have an idea who you’d like as a city administrator?

Wilson: Well, first of all, I’m an admirer of Michael Jordan.

Miller: The current city administrator?

Wilson: Yeah. He has been open minded. I’ve been meeting with him for this past year. So I give him all the credit because he’s taken this enterprise and he’s creating a wonderful structure.

Miller: Might you put his name forward?

Wilson: Well, he is, as an interim, he is and he will, and he’s committed to staying on short-term. He’s not long-term for the job though. And he’s told me that he wants to be a caretaker of this government. But, he hasn’t shown interest in the long-term. I think he’s at that point in his career where he wants to step back. And I applaud that. I’ll work closely with him.

So there’s the International League of City Managers, there’s a group of men and women around the nation that we’re going to look to the ranks to hire. Here’s what I’d like to see. I want somebody in a peer city, our size or larger, with a similar form of government, with a record of success, that we can hire and bring in, that can come in and see the city with a clear eye, but know how to operate day to day in a high performing, complex environment. Because I need that help, right? Now, the chief of staff or that person who’s going to be my right hand man or person, I need them to be able to help me with council. But we need somebody experienced who has institutional knowledge in Portland, so they can help the council and me with policy and development.

So it’s a matter of strength-based hiring. We need somebody with outside experience who’s already been successful to come in and hit the ground running.

Miller: What do you see as the significant differences between the public sector and the private sector? The differences that you think you’ll have to reckon with as you make the switch?

Wilson: Yeah. No doubt. As a CEO, you generally have your executive team, you generally have your board of directors, which is essentially what your council is going to look like. It’s going to be more intentional. We’re going to have to be very transparent. I do believe it’s going to be slower, and we’re going to have to have an awful lot more stakeholders at that and develop the policies and programs. We won’t be able to move as quickly as a private enterprise.

Miller: That sounds like it could be frustrating for somebody who has been the CEO in the private sector. Can you handle the Portland process?

Wilson: Let’s go back to that North Star when I talked to you about the quote: “Don’t grow angry. Improve your argument.” If people aren’t seeing that vision, then you have to double down and find it, but you also have to listen to those visions and change your policy. The more I’ve gained knowledge … I would come up with these corner office solutions for a facility in Spokane. I’d implement it in Spokane and then they wouldn’t work. That’s what I realized – go to Spokane, talk to the team, and they would develop the policy, and it always worked.

Same way it’s gonna be with council. I’ve got to involve them at the table early, often. Nothing about us, without us. I’ve been saying that for nine months. Yeah, we all want to just jump in and fix things tomorrow, but you do that, it’s not sustainable. And we need to make decisions that are evergreen, that are gonna last not only today but in 10 years,

Miller: Keith Wilson, let’s talk a lot more in the coming four years.

Wilson: Looking forward to it. Thank you, Dave.

Miller: Keith Wilson is the mayor-elect of Portland.

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