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In the final weeks as the city of Portland’s top administrator, Mike Jordan sat down with a slate of TV reporters, print journalists and radio hosts to talk about the first year of the city’s new form of government.
It’s a year that’s been marked by drama in City Hall on a number of levels: Budget woes brought increasing division between the legislative and administrative branches; Mayor Keith Wilson rushed to open 1,500 shelter beds, sometimes with sloppy results; and the city waited in limbo as the state fought with President Trump in court over the deployment of National Guard troops to Portland.
Jordan was tapped first by former Mayor Ted Wheeler in 2023 to help transition the government after voters remade city government at the ballot box the year prior, and then asked to stay on board for an additional year by Mayor Keith Wilson. He sat down with WW for an interview last week. He discussed the turbulent first year of the new government, his reflections on what it will take for the council and the administration to get along, and his recommendations—and warnings—for the council and the mayor in the new year.
As the city’s top administrator, Jordan has been the witness to—and sometimes the arbiter of—the shifting dynamics and structural changes at City Hall. He’s found himself at times in the crosshairs of members of the City Council. At other times, he’s found himself crosswise with Mayor Wilson. And he’s had to navigate those relationships even as the council, mayor and the administration were left with no blueprint for how the new government structure should operate and who has the powers to do what.
Jordan is being replaced by incoming city administrator Raymond Lee, who hails from Greeley, Colorado. The City Council unanimously appointed Lee to the role earlier this month.
In his interview with WW, Jordan at times grew emotional, as he had with other reporters in December. He managed in nearly every interview to repeat a gentle recommendation to the council and mayor: Give each other more grace as they fumble through the first few years of the new government. Jordan tells WW that he came to that conclusion only during the last few months of his job with the city, as he was preparing to end almost five decades spent in local government.
“I spent most of my life doing this, in one way, shape or form. It kind of sneaks up on you sometimes,” Jordan said, seated at the end of a stately wooden table in one of City Hall’s conference rooms. “You learn things over that amount of time that you don’t even know you learned, and then when you realize you did, it just hits you pretty hard.”
But Jordan offered more pointed thoughts, too. In one, he offered a warning: The attitude at the top of city government eventually seeps down into the entire organization. And at the rate this council is going, Jordan says he fears that city staff—the ones who do the groundwork for the city—will begin to operate out of fear. In fact, he says some of them already have.
“They don’t get mad,” Jordan says. “They get scared.”
Jordan says he’ll be mostly off the grid for the next six months, spending time with his wife, his kids and his six grandchildren. But he says he’ll probably never really leave local government. After all, he says, it’s just too seductive to stay away.
Jordan’s responses have been lightly edited for brevity and clarity.
What’s the thing that’s made you emotional just now?
We think that this work is based in data and rational decision-making. What we forget more than anything else is that at the end of the day, this is an incredibly human endeavor. This is ultimately about people
If I had advice for everybody in this whole little endeavor, I’d tell everybody: Cut everybody a little more slack. Be a little more patient.
It feels you’re giving the council, the mayor, administrative leaders, a lot of grace. I’m curious if you’ve felt that all year, or if this has just hit you in retrospect.
This is not an irrational endeavor, but it is often non-rational. Which means that data and the facts, as they appear on the ground, sometimes aren’t the most important thing. It really is about people.
Has staff, council, mayor and deputy city administrators struggled to stay grounded in that this year?
Absolutely. We’re not patient enough with each other and it’s hard to sit in a room and confront people, and the power dynamics are uncertain. In the old commission form, you knew what the power dynamics were. Everybody knew. Not so much here. It just adds a layer of ambiguity to everything you’re doing.
You really have to remember that everybody around this table—staff, attorneys, mayors, councilors—we’re all human beings and we’re trying to make this place better. And we’re going to argue like hell—actually we don’t even argue about what very much, we argue about how—just a general recognition that we’re a lot more alike than we are different.
Has this been a more combative City Hall than you’ve experienced prior?
Anywhere. Governor’s office, state legislature, Metro Council, I’ve never experienced anything like it.
There’s two lines of thought. That combat is necessary because we’re figuring things out and it’s how democracy works; and that the combat is for no reason, and it just digs us into a hole of hard feelings and getting nothing done. Where do you land on that spectrum?
You can listen to deliberations of the City Council and you can, from sentence to sentence, from someone at the dais, you can feel like they’re making a really brilliant point, and in the next sentence from the very same person, you can feel like there’s a bit of vitriol. I think that’s a function of the ambiguity, of not knowing the power dynamics… So there’s a lot of making it up. I would say there’s very little malice, they’re more bumping into each other because they’re in a dark room and nobody’s turned the lights on.
Because there’s so much ambiguity, it’s difficult to build trusting relationships. With that lack of predictability and uncertainty, it’s hard to build trust. And without that, everything seems harder.
What it does is—what I’ve noticed—is that that atmosphere at this high level in the organization makes most everybody else run for cover. They don’t get mad, they get scared. And that’s not a good thing for an organization. You can’t play this game scared, at least not well.
So there’s been a trickle-down effect to city staff?
It’s permeated. I’ve noticed more people, very talented people at mid-management levels, tell me: I would have applied for that job but they had to deal with leadership. Both on the elected side and sometimes also on the staff side. The atmosphere, the feel of it, it doesn’t feel good. And that’s a more powerful motivator than, does it look good or did we make the right decision?
If it turns into a cultural norm, that’s a real problem. I don’t think we’re there yet, but I’m concerned.
Are we a better run city than we were 2, 3 years ago?
Yes and no. In the 18 months that administratively we’ve been trying to think about how to create a more accountable, more well-organized, more integrated approach to managing city service delivery—I think we’re further along than I would’ve guessed.
The other challenge we’re having is the amount of change, and another one is fatigue. There’s a brain drain going on. I tell people all the time, the last five years have been the hardest five years of my entire career. No question about it. COVID, civil unrest, homelessness, fiscal stress, a charter change, new government. I’ve never seen this much change in an organization in five years, ever.
Was this new form of government a good idea?
I don’t think there’s any question that the move to professional management of the organization was a good idea. The rest of it, I think the jury is out. This council and mayor and administration have until 2030 to make this work a lot better. And if it doesn’t, there will be a new charter commission and you can bet this will be top of the agenda.
I’m encouraged and hopeful that this group will settle in. I think in the last few months, there’s a broad acceptance among all the leadership players that we’ve got to get together and there’s got to be rules to the game. We gotta put some sideboards on how we’re going to interact and do our work.
There’s been a lot of distrust from the City Council, aimed at administrative leaders, the mayor, but also at bureaus. What are the consequences if that tenor continues from this new elected body?
I do feel like the administration is trying to dig themselves out of a hole with this group, no question about that. There is that kind of tone and you can almost hear it at the dais from sentence to sentence. The first sentence is some kind of rational, thoughtful thought, and the next sentence is laced with vitriol, and it oscillates.
What happens, I think, [in lower levels of the organization], is that staff don’t get mad, they get scared. And when people are working out of an element of fear, all those emotions come into play. The fight, the flight. And I think that’s a trend that everybody has got to start to recognize.
I’m not sure we’ve come to the common understanding that nobody gets to do their work without everybody else at the table functioning at a high level. One thing that gets in the way of functioning at a high level is this emotional undertone that creates things like anger and fear and avoidance.
Is the City Council showing discretion when seeking to change how the city operates?
It was 2022 with the charter change. People just thought City Hall was broken. We couldn’t do anything right. Voters thought, City Hall does not work, it’s broken, and I’ll vote for change. And they did.
Fast forward two years, we get a crop of brand-new officials, and they come into office with the underlying notion that nothing at City Hall works. Everything is broken. And oh by the way, you guys have been in charge of this for years. And not only is that broken, you’re broken. Now, that’s an oversimplification. But there’s this underlying notion that it’s broken and we got elected to fix it. So there’s this dynamic, and it’s an attitudinal dynamic, that puts the administration digging itself out of a hole at the beginning of a conversation without having even said anything.
As you said, the city is dealing with an existential threat with the federal government under Trump. How do you think they’re handling those threats?
I think the council has gotten a little distracted from their role of running a city.
They are reacting—rightfully so—to this incursion by the federal government, and are ready to do almost anything to show their constituency that they’re standing up to the feds. It’s an incredibly challenging public policy. What you can substantively do against the federal government is very little. I think they should spend more time thinking about the long-range health of the city.
I think if they spent a little more of their energy on, where is this city headed longer term? On things we do have control over, I think that would be a really good use of time.
Do you think how everything is going with the city, do you think it gives other jurisdictions pause in working with us or trying to work with us?
I think it depends. Discussions I’m in with other jurisdictions, I’ll be very blunt, there’s always the question of, “Does this have to go to council?”
So there’s a trepidation around council involvement?
There’s a trepidation. I get that question more often now than I used to. Our neighbors and fellowing jurisdictions, they’re watching.
Early indicators suggest the city is looking at another devastating budget hole next year. Economists say that problem will continue to persist. What should the city do with that?
There are some really big drivers that the city has to get its head around. One, the structural nature of local government financing in Oregon is broken. It can’t survive forever without major reformation. That may drive the city to look at more niche revenues that it can put in place locally, like a utility fee or a tax.
One of the big problems on the expenditure side is being driven by the fact that our cost per public employee is going up much faster than inflation. Healthcare, retirement, and a newly found power of organized labor. So that’s an issue that will challenge the city going forward. How can you constrain the growth in costs over time?
And the third one: the tyranny of the now overwhelms the long-range view of both the elected body and the administration on the issue of deferred maintenance. We’ve got a whole bunch of stuff that’s just falling down around our ears. To get at that, the council is going to have to find a way to reduce operational cost so that some amount—$50 million is probably not that far off—has to be redirected to maintenance on an annual basis. But you have to have a constant, predictable source of revenue to do it.
Mayor Wilson opened 1,500 shelter beds this year. It didn’t solve homelessness. Do you think the city’s investment in those shelter beds was a good use of money, and do you believe it was effective?
Will his approach ultimately be more successful than the others? I don’t know the answer to that. But the mayor is the first person in this whole discussion that I’ve seen willing to apply carrots and sticks in some kind of a measured way. You can argue whether that’s right or wrong, whatever. But he’s the first person I’ve seen willing to do it, and withstand the political heat that comes with it.
I will tell you, going into this budget year, I am concerned that the city can raise another round of one-time money to keep the entire shelter system going as it is. I also think providing a bed is only one part of the answer to getting people into housing. And that mostly involves Multnomah County, and they’re looking at significant deficits in their budget, too. If this is going to be successful at all, we’re going to have to get together and decide: which parts of this system are most effective? And we may have to eliminate some parts of the system. That’s going to be really tough.
