What Portland’s new government looked like for the city administrator

After months of searching, Portland has officially named Raymond Lee as the first long-term city administrator. The position, which was created with the city’s new form of government, oversees thousands of city employees and the day-to-day public services including public safety, public works and city operations to name a few. But Lee isn’t the first city administrator. Michael Jordan has filled the role in the interim since 2024. In this time in the position, he has responded to federal actions, made recommendations for the city’s budget and more. Jordan joins us to share more on what his time was like as Portland’s first city administrator, advice for his successor and what the city’s transition to a new form of government has been like.

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 has officially named Raymond Lee as the first long-term city administrator. The position was created as part of the city’s new form of government. Lee will oversee thousands of city employees who are responsible for day-to-day services like public safety and public works, but Lee won’t be the first city administrator. Michael Jordan has had that role on an interim basis since 2024. He joins us now to talk about his tenure. It’s great to have you back on the show.

Michael Jordan: Thanks for having me, Dave.

Miller: Your contract was supposed to end in June of this year and then, soon after he was elected, Mayor Wilson asked if you would stay on for at least another half year and perhaps up to a full year past that contract, but it ended up just being that extra half year. How did the timing exactly shake out?

Jordan: I think the mayor, with 20/20 hindsight, he was absolutely right. Going into 2025, him being newly elected, not having ever served as a public official before, a new council, a new form of government and a challenging budget year that he had to dive right into at the beginning of the year. He was right to say let’s wait ‘til the second half of the year to start recruitment for the permanent city administrator rather than try to do that recruitment at exactly the same time we were trying to onboard everybody and do a tough budget. So that was how the timing worked out.

Miller: As the months and weeks have ticked closer to January 2nd, when you’ll officially be out, has any part of you said, why didn’t I apply for this job on a permanent basis?

Jordan: No.

Miller: None, not at all.

Jordan: No part.

Miller: No part of you.

Jordan: No, I mean, I’m being a little bit facetious, but in August, I’ll be 70, Dave, and this is a younger person’s job. It’s high energy, it takes way more than 40 or 50 hours a week. You basically have to be everywhere, inside, outside, managing up to council, managing up to the mayor. So it’s an up, down and sideways job. This is my 41st year in public life, and it’s time for somebody else to take this on and give it the energy it deserves. It’s a high energy job.

Miller: What are you most proud of from this last chapter, it seems, of your public service career, from your time as city administrator in Portland?

Jordan: This last chapter really started when I started working directly for Mayor Wheeler in the spring of ‘22, prior to the election for the charter change. When he asked me if I would come take what was then the chief administrative officer job, I said, no, thank you very much, it’s the second worst job in Oregon politics, and yours is the worst, mayor, at the time, under the commission form of government. And we talked about it, and I said there is one thing that, if it happens, I would be really interested in doing, and that is if voters do change the form of government in November of ‘22, then I would be really interested in trying to help make that transition and get the city ready for this new form of government.

And so, I would say the last three years have really been the last chapter. While, again, with 20/20 hindsight, there are no doubt there’re some things that I, with more information, would have done differently. However, I’m very proud of the fact that everything happened on time, all of the technical things that had to happen, so that a November ‘24 election could go off without a hitch, and you could get a new city council.

The remodeling of City Hall, getting everybody ready, restructuring the government so one person could feel comfortable being held accountable for it, and redesigning the management structure of the government. I tell people all the time I’ve been matriculating for 40 years, and this is my capstone project. I’m very proud of the last three years.

Miller: What are your regrets?

Jordan: Nothing major. I think the two years in preparation for that ‘24 election and a new set of elected officials, we were constantly making a decision about everything we talked about. How much do you bake it before they get here, and how much do you leave it so they can put their fingerprints on it? And if I made a big mistake on those, I tended to lean towards baking it too much and not leaving things so they could put their fingerprints on it. I think the council, they were apprehensive about the fact that we had made decisions that they wanted to be involved in, and that was a tension right from the beginning.

One particular one was the staffing of their offices and their budgets as individual elected officials. The year prior we were in a difficult budget also, and the then-council of five and the mayor only gave them one staff person in the budget, and of course they were right to believe they needed more, and that was one of the early tensions.

Miller: Before the city council unanimously approved the appointment of Raymond Lee to be your long-term successor, they peppered him with some questions for a couple of hours not long ago, some of which were about existing tensions in city government. Councilor Candace Avalos said this: “I hope you will help be a bridge between our two branches of government. As you can hear, we don’t feel like that bridge is strong right now.” You’re nodding a little bit as I’m saying this. What’s your response to that?

Jordan: I don’t think it’s any big secret that there are challenges. I think those challenges are really – and I’ve been saying this for about three months now – and that is that I have grown to believe, and I should have recognized this earlier, given my tenure, but there are really three branches of government. There’s the mayor as the executive. There’s the council as the legislative, and there’s the administration that exists under the authority of the city administrator.

Miller: And I should just say, already, that what you just described is confusing for students of American civics. We’re very used to three branches of government, but one, the executive, is turned into two in what you’ve just said, and then there’s the judicial, that you didn’t mention, that says yes, you can or can’t do this, according to, say, the charter.

Jordan: Yeah, absolutely.

Miller: But to go back to what you’re saying, what do you see as the challenges of the system that you’ve just described?

Jordan: What has become evident is that the mayor is a political player, has an agenda, and is trying to get things done at a citywide scale. The legislative branch, all of the councilors, they have things they’re trying to do also. And all of them are looking to the administration to be the unbiased professionals. To provide them with data, to provide them with research, to provide them with information, so that their ideas can go from idea to the legislation that the legislative branch can deliberate on and make a rational decision about.

What has happened over the first seven or eight months, for sure, and even lingers on today in the form of Avalos’s comment/question, is that the administration has been viewed as being very connected to the mayor, and not connected to the legislature. That’s created some lack of trust, some tension, between the administration and the legislative branch.

I think that can be fixed, but I think that it is going to take a mindset of everybody in this discussion, that the people who operate city government in the administration are not politically motivated folks. They’re there to support the people who get elected. Nobody elected us. Our job is to support them equally. Our job is to get them all information and support them as best we can.

Miller: The information part is one piece of it, and that’s maybe more where clearly – and there’s been some pushback about, why didn’t we know about this pot of money earlier – but I don’t want to get stuck in those details, I guess I wanna think in the bigger picture, because the sharing of information seems very different to me than, in the end, the governance, where I do think of that as the executive branch role. I thought the idea was that the city council approves a budget and passes new ordinances, laws, but it’s the mayor, through you or soon your successor, who says, OK, but this is what it’s actually gonna mean in practice. You’re the ones who execute that policy. Do you disagree?

Jordan: No, I don’t disagree with executing the policy. I do maybe take a little bit of exception with the interpretation. The mayor certainly has the right, as the executive, to try to implement policy as passed by counsel or as appropriated by council in the form of the budget. But the council also has a right to interpret their own legislation. We are running into some of these challenges right now. We have some adopted legislation by council, where I think there will be significant disagreement of what it means to implement it.

Miller: So you said this can be fixed, but it’s going to take some work. In your mind, is it just people of good faith getting together and talking about things? Or is it something much more profound, a kind of new wording in the charter to say very clearly, this is the role of the city administrator, this is the role of city council members, this is the role of the mayor, that these are the powers that are delegated to them.

Jordan: I would never say that it wouldn’t be helpful to have more clear language in the charter. I think that’s true no matter what. Charters generally are written at very high levels and don’t have huge amounts of detail. I also can tell you that you can’t write enough detail to not have the success of this government rest on people of good faith working together to try to make it work.

I think we’re still really young in this form of government. The last one was here 113 years or so, and this one’s in year one, just wrapping up year one, so I think everybody has learned a lot. When we started, back in January of this year, I think there was a fairly strong laissez-faire notion to how this was going to work, and people of good faith could just talk to each other and everything would work.

Well, we have at least 13 different opinions on the elected side about how it should work, and 7,000 of us on the administrative side. Without more firm rules of the road about how we do things and how we interact with each other, then what we’ve run into this year is a little bit of chaos. People are working through it, and it is better than it was in January, by far, believe me. But I think we’re still working through what are those appropriate rules of the road that don’t infringe on an elected official’s ability to represent their constituency.

On the other hand, there are some clear pathways to go from idea to legislation to administrative rule to implementation. How does that work with the structure we have? I think it’s just a matter of continuing to work on honing the rules of the road so that everybody’s on the same page, not necessarily about “what.” We’re going to argue politically about “what” – or the elected officials will – but “how” you move through this and implement and serve Portlanders.

Miller: What advice have you given or will you give to Raymond Lee specifically about this?

Jordan: I’ve told him that we’re in an evolution, and we’re not mature yet and there are these issues, in my view, a lot of it has to do with agreements about how we’re going to hold each other accountable.

Miller: And how the public can know who is accountable.

Jordan: Exactly. And when you don’t have accepted rules of engagement then it’s fairly easy to point fingers at each other, because there aren’t any accepted rules where we hold each other accountable for things. I think that’s the evolution we’re in, and the maturation of the form of government.

Miller: Mike Jordan, thanks very much.

Jordan: My pleasure. Thank you, Dave.

Miller: Mike Jordan is the outgoing Portland city administrator.

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