Sarah Iannarone started running against Ted Wheeler in the 2016 Portland mayor's race and she's never really stopped.

Last week, she landed an early uppercut in the 2020 rematch, when Wheeler announced he would give away $16,000 in previous contributions from President Donald Trump's embattled ambassador to the European Union, Gordon Sondland.

She says it shouldn't have taken until Sondland became a central witness in Trump's impeachment hearings for Wheeler to cough up the former Portland hotelier's money.

"What is the right thing to do and when is the right time to do it?" Iannarone asks. "I called that one, and there have been others."

Iannarone, 46, finished third in the 2016 primary, behind Wheeler and former Multnomah County Commissioner Jules Bailey, but neither she—nor some voters—accepted that result as final.

"People would say, 'Sarah, there's this homeless camp that's being swept,' or 'Sarah, there's this dangerous intersection,'" she says. "It was like my Twitter account was almost serving as a mini-City Hall for trying to address the problems Portlanders were facing."

This time around, she's qualified for public financing of her election campaign—a big change from her cash-strapped 2016 effort. And she's staked out positions far to Wheeler's left, hoping to surf the progressive wave that propelled Commissioners Chloe Eudaly (2016) and Jo Ann Hardesty (2018) to victories over more moderate opponents.

We caught up with Iannarone for an interview that has been edited for clarity and brevity.

WW: What is Mayor Wheeler doing wrong?

Sarah Iannarone: It's a top-down leadership style. It's a disconnect from the daily lives of Portlanders and a failure to listen to the people whose opinions and expertise matter most. A great example is the protest policy [which attempted to restrict when and where protesters could gather]. What would it have meant for him to listen to experts on that?

You've said TriMet should stop charging fares. How would you make up the lost revenue?

You could look at everything, including a congestion parking fee. We need to think about how we want to provide socialism in urban space. Right now, we have a high degree of socialism for the privately owned automobile. All over the city, there's free parking and free access to roads. There are people who could be taking trips downtown by transit, but if it's cheaper to park downtown than it is for a day pass on TriMet, then which option do you think people are going to take?

The first part of your platform you've published is your climate plan. Why have you made that a higher priority than housing and homelessness?

I don't think it's a higher priority. I think it's the overarching priority. If you talk to any Portlander, they're going to tell you the same things. Housing's too expensive. Traffic's too bad. I know those are the issues that are on Portlanders' minds, but when you talk about how we're going to address these things, making sure that we're taking an equitable approach and applying a climate lens to everything we're doing is how we're going to frame the solutions.

What's your assessment of Commissioner Eudaly's attempt to remake the neighborhood associations system?

It's noble in its aspirations. I do think dismantling structural racism is something Portlanders need to focus on explicitly and with urgency. The consequences for the neighborhood associations maybe snuck up on them. I think they were a little blindsided, and when you've got the most cohesive, politically empowered and vocal contingencies feeling under threat, you're going to have pushback. It's almost inevitable.

Your website says, "I'm uniquely positioned to be the visionary leader our city needs at this critical time." Please explain.

Well, I'm ordinary. We don't see people like me being the mayor of Portland a lot. I'm not entrenched in any particular party politics. I'm not entrenched in
establishment decision-making. I earn the median household income. I try to get around on my bike or by the bus. I send my kid to Portland Public Schools. I've lived the life Portlanders live, so that makes me uniquely positioned to make decisions that will work for everyday Portlanders.

Which Portland mayor do you hope to emulate?

Vera Katz, but without the police brutality. Kinder, gentler policing but with Mayor Katz's urban vision.

But you said you're an ordinary Portlander. She spent her entire career in politics. Did that help her be a better mayor?

Vera's leadership style was, "How do we try to get people on the same page, how do we know when there's enough process and when there's not and how do we move from A to B in a way where we can get as many people as possible as happy as possible?" Does political experience help with that? Yes, but so do other kinds of experience.

Why would your presence on the City Council make a difference?

It's about the kind of leadership you want, right? Maybe being a person who can run a room of five toddlers is more important than having been treasurer of the state of Oregon when it comes to wrangling how things are going to go down in that building.

I had a child care co-op and a food co-op in my early days when I was trying to survive as a mom. And so I know what it means to try to reach an outcome where everyone is happy even if along the way there were a few disagreements.

Is there anything you and Ted Wheeler agree on?

I think we both agree we need more affordable housing.

Do you think he secretly wants you to win?

I do not aspire to know what Ted Wheeler secretly wants about anything.