MAYOR CHARLIE HALES returned to Portland City Hall this year after something like a decade in the wilderness of the private sector, selling streetcars and density, and then more than a year on the campaign trail, reintroducing himself to a city that looks awfully different from the one he helped run as a city commissioner in the 1990s.

And later this month—on Friday, April 12, to be precise—Hales will mark his 100th day in office, a historically arbitrary milestone but one that's resonated in politics ever since Franklin Delano Roosevelt took office in the midst of one of America's worst economic crises.

Portland's financial struggles aren't nearly as legion. But they're no picnic for a new mayor working hard to scrub away the shadow of the old one, the controversial Sam Adams. So we figured this was as good a time as any to check in and see how things are going.

Some two-dozen observers spoke with us for this story. Other high-profile people were apparently too shy to dish a little—like House Speaker Tina Kotek, and Multnomah County Chair Jeff Cogen, and anyone from the Portland Business Alliance. The mayor's marks, so far, look promising—but that's just it. Promising.

Hales remains wrapped in a mist of good intentions—more than willing to change course when some of his few solid actions have blown back in his face. Bowing to the budget deficit he's inherited, he has set out to do less with less, although a budget plan that spells out how has yet to emerge. He's also promised a "culture change" at the Portland Police Bureau, but results will take months to show.

Like everyone else, we're intrigued by what we've seen—and waiting to see how the next 100 days play out.



Hales finds himself in the unenviable position of taking office right as Portland has fallen into its worst budget crisis in decades. And because of that, one number comes before anything else Hales might want to do: $25 million. That's the city's current best guess at a budget deficit—and solving it has become his top priority, the through line that connects every other decision he has to make.

To his credit, Hales has promised to do far more than slap a wishful bandage over the blood and pray for a miracle that economists say is extremely unlikely. Bureaus have been told to cut their budgets by 10 percent and then fight for whatever crumbs are left. He's put the fire and police bureaus on notice, for the first time in years, that deep cuts can't magically be averted. City employees everywhere are bracing for pay cuts at best and layoffs at worst.

And though Hales has gone to Salem with his fellow mayors to lobby for increased school funding, he's contemplating a world where Portland can't afford to do as much for its residents, including getting rid of paying for school kids' TriMet passes.

Nick Fish, city commissioner: He has been handed a unique set of challenges, right? He's managing a transition, he's inherited a $25 million budget hole. He's got at least six labor contracts that need to be negotiated. He's establishing working relationships with the second floor [the commissioners' offices]. He's breaking in a new staff. And he has an avalanche of work. I'd say that's a formidable set of challenges for any new mayor—someone who, unlike Sam Adams who moved up the ranks, has been away for 10 years.

Amanda Fritz, city commissioner: It's so different from the first 100 days of Sam. Sam had his 100-day plan set up because he won in May, and he was going to visit 100 businesses and he was going to do this and that. And we were right in the recession and looking for stimulus money. And then we had January 20 [in 2009, when Adams admitted lying about his relationship with Beau Breedlove] and there were major changes and a lot of focus on that issue.

Charlie Hales, mayor: Mayor Adams did a good job, and so did the council, trying to cut the budget over the last several years in ways that did the least possible damage. But with them having done that work, we don't have a lot of wiggle room now. Fortunately we've got some vacancies. But we will be laying people off. How many and in what bureaus? We don't know yet, but it's not like this will be just rounding errors and the size of the travel budget. This is going to be real reductions in stuff that we do that is very basic.

Alan Ferschweiler, president of the Portland Firefighters Association: It's difficult to know exactly where he stands. The one thing I've been impressed with is he doesn't over-speak on his position. It seems like he's trying to absorb a lot of information and make methodical decisions. Do I think he'd like to close fire stations? No. Do I think it's a bad budget season? I do believe that.

Hales: Now, if we actually close a fire station or two or three or four in this budget, believe me we'll hear from people if we're closing THEIR fire station. Anyway, that's how I'm approaching the budget. Keep the good people that we've hired on the payroll. Try to hold the level of service as close to what we did last year as possible. But we're not gonna do it with debt. We can't just borrow money and hope for a better day.

Mike Reese, chief of the Portland Police Bureau: It's going to be really difficult this year not to lay off police officers. He wants to find a way to use attrition to get to where we have to get without having to lay off officers. He's looking at strategies that will produce the budget number he needs to get to. The mayor is really interested in understanding how our system works and the challenges we face contractually, because this is a year when bargaining opens the door to new possibilities in how we manage the budget, so he wants to understand that.

Israel Bayer, director of Street Roots: Maintaining the social safety net is not only the right thing to do, but it creates an opportunity to make our streets safer for the police and people experiencing mental illness. Housing and homeless services are key to maintaining public safety for our community. If we can offer critical services without putting a strain on law enforcement, then everybody wins.

Rob Wheaton, representative for American Federation of State, County, and Municipal Employees, Local 189: We haven't spent a lot of time with Charlie and the mayor's office. Our understanding has been through collective bargaining. That's all I've been doing since January. Our financial packages are less than a percent apart. The problem is they're asking for a ton of language and rights concessions. Labor disputes happen over rights issues: seniority and subcontracting. It's hard to figure out what's coming from the mayor's office and what's human resources throwing stuff on its wish list. But it's clear that the mayor's office hasn't directed HR to cut the crap and get to a deal.

Richard "Buzz" Beetle, business manager for Laborers' Local 483: The biggest area of our membership is in parks. We haven't had a lot of clarity on parks. It's a lot clearer in transportation. He's talked about focusing on the frontlines. He seems to be doing that. He's looking at his overhead costs to find savings. Exactly what we want him to do. But the mayor's budget is not out yet, so we can't see on paper what his goals are. We'll see if he puts the rubber to the road. We hope Charlie's going to be a revenue mayor.

Hales: Can we go ahead and make some hard choices about grant making that the city has been doing over the years where we fund good things in the community that aren't really the responsibility of city government? I love schools, but scholarship programs funded by the city are not a core service when you compare them with mowing grass in parks. I love workforce development, and we need to develop our workforce and we need to have all kinds of partnerships between local government and business and labor and everybody else to do that. But can we get some of the other partners in that enterprise to pick up the tab for the next couple of years? Because we're short.

Carole Smith, superintendent of Portland Public Schools: He's put education at the front of what he's talking about and putting emphasis on. We've been in good solution-oriented problem solving with him about the [TriMet] YouthPass. That's looking like we're going to have it set up again next year. There's also been active conversation with him about how we maintain school resources officers. He's been very present. He's also been immediately in the mix, and that's what I need.

Fish: He deserves credit for the way he's opened up our budget process. That's the single most important thing he's done in his 100 days. In the past, frankly, there was a little more gaming of the system. And now everyone's being treated the same, so everyone must show where they would cut. As you know, bureaus are pretty good about resisting the idea that they can take cuts. But by treating everyone the same, it's literally changed the way council as a whole works on the budget. It inevitably brings all his colleagues along.

Fritz: The budget will be proof of whether we are going to act in a collaborative manner as a board of directors or not. It takes three votes to get there. The challenge is finding the money to do anything. There's not a pot of money that's up for grabs. Finding the money is job one. The second is how do you allocate that.



Hales' back-to-basics campaign mantra has appeared prescient at times. Within three weeks beginning in late January, the auditor's office released two audits on the Portland Bureau of Transportation (PBOT)—both taking a dim view of the department's penchant for pursuing shiny new amenities while existing assets languish.

Among Hales' first actions as mayor-elect was to do away with Transportation Director Tom Miller, a Sam Adams ally. Hales has panned Adams for not having conducted a national search for a transportation director, instead giving the bureau to Miller, his chief of staff, in 2011.

Hales installed John "Toby" Widmer, a retired city employee, as the bureau's temporary director. Widmer, the mayor said at the time, "came up through the ranks" and "could start up every piece of equipment in the maintenance yard and run it." Widmer was also a supporter, donating $1,650 to Hales' mayoral bid.

His mission was simple: Find money to pave city streets.

Hales, meanwhile, is no stranger to Portland's complex transportation system. As a city commissioner, he was a leading voice in the push for the Portland Streetcar and on transit issues, earning him the nickname "Choo-Choo Charlie."

Farrell Richartz, street cleaner in the city's maintenance bureau: I know it's early on for him, only a couple of months in, but we had a delegation that met with him in February. He took the time to talk for the better part of an hour. We talked about budget concerns and he didn't have an agenda. It was a good impression. [Hiring Widmer] has changed things. People respect him, the folks in maintenance. He's talking about things he knows about and it gives him authority. I know they're going to do a national search, since Hales said what he said about Tom Miller. It depends on who it is—hopefully somebody who knows their stuff and wasn't political.

Neil McFarlane, general manager of TriMet: He's a really strong partner in what we do. He understands the importance of public transit to the city very, very, very fully. In that regard we certainly give him high marks. I've had incredible access to him. I'm showing restraint myself, understanding the challenges he's got relating to the current budget. He's been very hardworking, diligent, and focused on that back-to-basics message. I think, at least in the transportation world of the city, morale is quite high.

Rick Gustafson, executive director of Portland Streetcar: Obviously, I worked very closely with Charlie when he was city commissioner. He's trying to help the city get back to the basics—certainly in transportation.

The pile of work ahead of him is so high he's having trouble getting to all of it. One of the things I was very impressed with was for [Portland] Streetcar he invited [City Commissioner] Steve Novick to work with us. Steve is serving on our Portland Streetcar Board, really on behalf of the mayor. I was impressed with that perspective of engaging the council effectively.

The road—like so many Portland byways—has not been without bumps. In late February, Widmer angered some with his proposal to do away with a long-awaited sidewalk on SE 136th. Eight days later, a five-year-old girl was struck and killed while crossing the street blocks away from the planned walkway.

A flurry of letters from active transportation groups and state lawmakers crossed Hales' desk. An online petition to save the sidewalk got hundreds of "signatures." Hales dithered briefly then came out in support of the project.

Shemia Fagan, state representative from East Portland: I came a little bit unglued when I learned about [the proposed sidewalk cuts]. I reached out to the mayor and his staff. To their credit, they didn't avoid me. They've returned every call. They met with me almost immediately. They've continued to reach out, which I appreciate.

The way I see it is PBOT tried to take the mayor in one direction—putting pavement ahead of people—and I pushed him in the other.

At this point I have to give him the benefit of the doubt. All I can measure him on is the fact his office has responded to me at times when they knew I was upset. He's also reached out proactively at times. He's shown himself to be the mayor of the entire city.

Rob Sadowsky, executive director of Bicycle Transportation Alliance: He's keeping a lot of things close to his vest—feeling his way a little bit. He's taking little steps to test different things and different ideas. We have yet to see a clear framework in transportation. That has to do with not having a permanent director or commissioner in the position. That gives us a [lack of] clarity at best.

One thing that's clear is we don't have to spend a lot of time educating Charlie. What he's learning, I think, in this first 100 days, is the impact that fatalities and near-fatalities have. In some ways, it's not something you can put a price tag on or clear returns in terms of x and y. It's not as easy as saying we need to fix potholes and that's all we're going to do.

Steph Routh, executive director of Oregon Walks: If the first 100 days of Charlie Hales were a TV theme song, it would be the Jeopardy! theme song. I'm on pins and needles.  

This is a really tough time, particularly in the budget. There are a lot of priorities that are trying to tell their stories. I would say normally the first 100 days in a mayoral tenure is the time when you really see those priorities take shape. In Mayor Hales' case, given the budget climate, it's the second 100 days that we'll really see where the priorities of the mayor and this city council fall.



Hales, on the stump, squarely took on a goal that Portland mayors have been chipping away at for years: reforming the Portland Police Bureau.

And Hales, budget challenges notwithstanding, has his work cut out for him.

Even though Adams helped sketch the rough outline of a US Department of Justice settlement that found our cops unconstitutionally roughed up people with mental illness, seeing the thing through falls to Hales.

Hales also must work to keep the trust of accountability advocates while rebuilding what had been a frayed relationship, under Adams, with the Portland Police Association. His presence at the premiere of Alien Boy, the documentary about James Chasse Jr.'s 2006 death by police, was noted. His hiring of Baruti Artharee, a city business leader and fixture of Portland's black community, to serve as public safety director has been applauded.

David Fidanque, executive director of ACLU of Oregon: We've been impressed with his staff. He's made some excellent choices. Gail Shibley [a former lawmaker, among other things, serving as Hales' chief of staff] certainly stands out. We have a long history with Gail, and that relationship is very strong. And we met Baruti Artharee. We're impressed with him as well. His staff seems to understand the issues, but there's a very steep learning curve. Trying to change the culture of the police bureau is not an easy task. But the mayor made it clear that's his goal. There's no question. He understands.

Dan Handelman, Portland Copwatch: It doesn't seem like an office that says, "We have this agenda and you all don't worry about it, we'll handle everything." They're open to hearing ideas, especially from an organization that's been around as long as us. But it's unfortunate how much there is on his plate.

Jason Renaud, Mental Health Association of Portland: Two good hires: Gail Shibley and Baruti Artharee. But so far, just smiles.

JoAnn Hardesty, steering committee member of the Albina Ministerial Alliance (AMA) Coalition for Justice and Police Reform: I just had my first meeting with him as part of the AMA coalition since he was mayor. He at least appears to have staff that's studied on the issues. He seems to be knowledgeable about it. But the jury's still out. With so few staffers, I'm worried.

Hales: No matter how many bureaus you have, if you have the police bureau, it's half of your attention span. So, in other words: Sorry, other bureaus. It's certainly the case now, since I want to be a change agent. We have a Department of Justice mandate, we had a series of terrible tragedies like [the deaths of] James Chasse and Aaron Campbell. So there was never any question that I was going to be putting a lot of time and political capital into the police bureau.

Hales has had to forge a fast partnership with a police chief, Reese, who almost ran against him. Tension in that relationship, as he pulls Reese along with him, could significantly hamper Hales' reform efforts. But the mayor's support for the chief has appeared unflappable, even in the face of a scandalous resignation in the bureau and embarrassing discipline cases at the highest levels.

Hales: I have a good working relationship with the chief. We will argue and debate a little bit—had a little pushback yesterday about overtime. To be continued.

Reese: He's really good at asking questions, very insightful questions, trying to understand the public safety system. He's gone on frequent ride-alongs. He's very hardworking. I like the fresh perspective that he has. His lens on the world allows us the opportunity to look at problems in a different way.

Daryl Turner, president of Portland Police Association: The mayor and I have met and we've had good discussions. That's really as far as I could go. For the most part, we have no problem with his approach thus far on police issues. I feel comfortable with the way things have gone.

Hardesty: The people making decisions on public safety are making bad choices, and there's no accountability for that behavior. He says he wants to change the culture. But you can't change the culture under the current leadership. Until he gets a new police chief, I can't expect much change.

Handelman: When Mike Kuykendall [the bureau's civilian director of services] resigned [over text messages mocking another cop, who was in a discipline case about his affinity for Nazi German soldiers], there was a chance to reach out to the community to hire a person of color, as had been asked for, and Hales didn't do that. I don't know whether the mayor had any input in that process at all. The mayor didn't have the history. If Kuykendall had resigned three months from now, I don't know if that would have happened the same way.

Hales: I'm very vigilant. I read the discipline cases word for word. Baruti and I talk about them. We then question the chief about many of them and he knows that we're watching carefully and that we very strongly support a move to a more matrix approach to discipline where, if you do this, that happens.

And we've listened closely to Mary-Beth [Baptista, independent police review director] and her staff. What's the old Ronald Reagan quote? "Trust but verify." I trust the chief and verify what he does, and he knows that and obviously he's willing to work under those conditions.



Three months is awful long for a honeymoon, but Hales and his colleagues on the council are clearly still basking in one. Everyone talks a lot about Hales' flexibility and willingness to listen. Not that there haven't been some missteps. And all the kind words might dry up in a few weeks or so, when Hales issues his first pass at a budget and the long knives come out.

But for now? Commissioners and others are reveling in the changed winds blowing from the mayor's office. Hales has purposely scaled back the weekly parade of policies on the city council agenda, a shift from the frenetic pace set by his big-idea-driven predecessor.

Eric Fruits, Portland State University economics professor and president of the Laurelhurst Neighborhood Association: The feeling I get is that dad's home and the party's over and he's got out the broom and he's cleaning away the beer bottles.

Dan Saltzman, city commissioner: Having worked with Charlie before, I was very pleased to see that in many respects he hasn't deviated much. I mean it in a good way. He's somebody who's independent-minded but also has a passion for the city and knows how to get things done. He's gone off and had 10 years working for HDR and that makes him all the better. It's been a very calm transition from my perspective. He seems to have gotten good staff people—fewer people—but they seem to be getting the work done.

Fish: I've had a chance to sit down with him and have very direct conversations about complicated things. I have found him to be a very good listener. He brings a lot of life experience to the job, both public and private, which explains why he seems to be calm in his approach to the various crises engulfing him.

Steve Novick, city commissioner: We heard taxicab permit appeals recently, and we had a spirited discussion, and Charlie said, "I want to postpone a vote. I haven't studied the record as well as I should." And said that in public. He didn't bullshit about it. He just said he wanted more time. It showed a great deal of self-confidence.

LaVonne Griffin-Valade, city auditor: I've issued three audits, with a fourth due this month, and his staff has been really responsive, very positive. He's read them, and that's a big change right there. They've also taken an interest in past audits. And that's spilled over to the rest of the commissioners.

That comity is helping smooth Hales' transition back to city hall after a decade working in business. And he's needed the help.

Hales also drew a contrast from Adams by hiring half the number of staffers and giving them heaps of work—which is the fallout of Hales also deciding to grab back every single bureau during budget season. After four years of a reprieve under Adams, who didn't bother with the takeover, commissioners and staffers found themselves stymied by the sudden free time and equally sudden lack of access upstairs.

Hales: City commissioners have been detached from their bureaus temporarily. That created a little disgruntlement, but they knew that was coming. I haven't asked them, "Well, how's that feel?" My sense is that they are appreciating the freedom that it brings to ask hard questions about all the bureaus, regardless of whose name used to be on the stationery.

Griffin-Valade: Right now there's an opportunity for some real direct and probing discussions and clearing up assumptions and hearing information he didn't know. And that opportunity might not exist once bureaus are assigned to other council members. I really hope he considers shaking things up a bit, giving commissioners a chance to manage bureaus other than the ones they desire or expect to be in charge of, to move folks out of their comfort zones. Maybe they're all open to that as well.

Ferschweiler: It's time for him to give back the bureaus. He has really concentrated on a lot of the major issues that are going on with the city. With such a limited amount of staff and limited amount of time, we have seen some of the smaller stuff falling off the plate. A grievance or a disciplinary issue we could get done with a commissioner—those types of issues.

Miscommunication woes, charitably speaking, helped fuel perhaps the most intense conflagration of Hales' tenure—outrage sparked by the city's shifting response to a controversial no-parking apartment project at SE 37th and Division. Hales gave the okay for a revised permit, then pulled back, directing officials to once again put off vetting the project until city council tackles parking policy.

Fruits: Yes, he's stepped in the bucket once or twice now. The issue on Division with the no-parking apartments, that seemed to be very poor communication or some very nefarious backdoor dealings. But it seems like he's trying. I couldn't imagine Sam Adams even having a discussion about changing the arts tax [another effort Hales is leading] at this point. That says a lot about what he's doing.

Anonymous political insider: He's learning you can't have half the staff and twice the work. They're good soldiers. But it's asking a lot of an office that's as understaffed as his to handle as much. The amount of time he spent recovering from the 37th and Division issue is not sustainable. He can't stop and spend that much time on one issue. I also don't think he thought through what it meant to have people like Fritz and Novick without full portfolios. People like to fill their plate. City hall works well when people are fully engaged.

Gustafson: There's just so many different agendas on the table here. It makes it very challenging for him to keep up with all of them. That's just part of being patient. We all have our panics of the day that we always need the mayor's help on. We're always better off when we have the direct understanding of the mayor, but we have to be patient.

Hales: This is going to sound egotistical but I have a hard time thinking of another misstep. There are some things I'm really happy about. I went out to this Westside Economic Alliance, apparently the first mayor ever to accept their invitation and show up and speak to a bunch of business leaders and elected officials in the Washington County suburbs and they treated me like a rock star. I got a standing ovation. I think my speech was fine but frankly I don't think it was the speech. I think it was the fact I paid enough attention to show up. Woody Allen, you know. Eighty percent of success in life is just showing up.  

The mayor also has shown flashes of the pragmatism that's served as the main lodestar of his political career. Beyond quickly reversing course amid outrage about the SE 136th sidewalk, or on the SE Division project, or also on a widely panned plan to cut funding for at-risk minority kids' internships, Hales risked the ire of the business community that helped elect him by standing by while Commissioner Amanda Fritz pushed an overdue proposal for paid sick leave in Portland.

Sick time is really the only signature policy effort to emerge from Hales' first 100 days. And even then, Fritz and Saltzman marshaled it through. Hales was notably content to let them have the reins.

Saltzman: On the sick-leave issue, he was very supportive of the approach we followed, doing the hybrid thing with the first reading of the ordinance and then the task force. Without his tacit support for that idea, it might not have occurred the way it did. It was the invisible hand working on the sick-leave process.

Hales: I knew there would be occasions where even though I've got good business support that I would make them mad and this was one of those. But my goal—and I think we achieved this—was to be as thoughtful and as open as we could be in developing the policy. You heard Bernie Bottomly [chief lobbyist for the Portland Business Alliance] and his testimony at the last hearing. They were saying, "Well we oppose this, but we really appreciate being given the time and given the opportunity to react to the details and change some of them." If you've got an opponent who's saying something like that, that's a pretty solid victory.

Fritz: It's a good example of how we have a commission form of government and it's not the mayor always setting the agenda. It's my project, and everybody in this building contributed to it. And it's a better project because of that. But I steered it. And I appreciated the mayor's support. Clearly if he had said, "Now, let's wait on this for six months," then that would have been difficult. Because I don't think I would have. I'm sure I wouldn't have.

Saltzman: Charlie's a guy who ran in a very hard race for mayor and worked very hard. I don't think he's going to be letting the reins be diffused or blurred. He's the one in charge.