A little more than four years ago, Sarah Iannarone, an unknown Portland State University bureaucrat, launched a long-shot bid for mayor, preaching the value of sustainability and smarter transportation and land-use policies.

She finished third, behind Ted Wheeler and former Multnomah County Commissioner Jules Bailey.

This year, Iannarone, 47, is back—and running a far more aggressive campaign, pounding Wheeler and the Portland Police Bureau on social media.

"Goddamn tired of watching reporters, medics, legal observers, peaceful protesters, and, yes, vandals getting targeted, arrested & assaulted by Portland Police," Iannarone tweeted July 2. "F*ck you, Ted Wheeler, seriously."

In this season of COVID-19, economic devastation and fire, it's protest that has come to define Portland in the eyes of the nation—and it's also come to define Iannarone's campaign.

Few have latched onto the energy of protest more than Iannarone, who has been on the front lines dozens of times, refers to herself as an "everyday anti-fascist," and has declared, "I am Antifa."

Iannarone—a neighborhood activist, policy wonk and longtime student of what makes cities succeed—hopes to defeat Wheeler, 58, who in turn hopes to become the city's first two-term mayor since the late Vera Katz.

Buoyed by his aggressive response to COVID-19, Wheeler nearly won reelection outright in the May primary, getting 49% of the vote. Iannarone finished second in a 19-candidate field with 24%.

But less than a week later, on May 25, Minneapolis police killed George Floyd. That changed everything.

After three straight months of protests, some civil rights leaders have asked Wheeler to resign because his police are too aggressive. At the same time, businesspeople have criticized him for not keeping downtown orderly.

The beneficiary of those conflicting views: Iannarone, whose chance of victory has risen as Wheeler's popularity has plummeted.

A recent poll showed two-thirds of voters disapprove of Wheeler's performance.

"This race is a toss-up," says Felisa Hagins, political director of Service Employees International Union Local 49, whose members endorsed Wheeler.

Mayor Ted Wheeler is taking heat from all sides, including the women seeking to unseat him. (Zane Fleming)
Mayor Ted Wheeler is taking heat from all sides, including the women seeking to unseat him. (Zane Fleming)

If Portlanders are fed up with Wheeler, Iannarone has a simple pitch for them: She hated Ted before it was cool. She's relentlessly opposed him for four years. And she offers Portland a clean break from the string of white men who have run the city since Katz left office 15 years ago.

"The city deserves better than Ted Wheeler," Iannarone says. "I have a real vision for Portland, and the reason I've pulled these policies together is because that's what I see as our pathway out of this mess."

Yet Iannarone is still unknown to many Portlanders. To oust Wheeler, voters will need to decide what they think of Iannarone. Are they exhausted enough after a string of mayors with conventional résumés that they're willing to bet on someone who spent her life outside the halls of power?

Here are seven things to know about her:

  1. Iannarone is an outsider without the typical résumé.

Katz served three terms as speaker of the Oregon House before becoming mayor in 1993. Her successor, Tom Potter, served as chief of the Portland Police Bureau (a job history that these days would make him unelectable). Sam Adams was Katz's chief of staff and a city commissioner before becoming mayor. Charlie Hales served two terms on the Portland City Council before he became mayor.

Wheeler's political résumé includes stints as Oregon state treasurer and Multnomah County chair.

Iannerone is seeking the top job in Portland having never served in any elected office or worked in city government.

She is instead an e-bike-riding mom from upstate New York who loves to sew, rummage through thrift stores, and stroll with her rescue mutt, Sir Francis Bacon. She pedals in the Naked Bike Ride. She has struggled financially, failing to pay state income taxes from 2010 to 2013. She didn't graduate from college until she was 32 and is still grinding away at her Ph.D.

“I am deeply rooted in the community, so I won’t need to be taught how to listen to the demands of the public or how to work through coalition to get things done,” Iannarone says. (Aaron Wessling)
“I am deeply rooted in the community, so I won’t need to be taught how to listen to the demands of the public or how to work through coalition to get things done,” Iannarone says. (Aaron Wessling)

Iannarone was born in Fulton, N.Y., a fading industrial town that was the birthplace of the Nestlé Crunch bar. Her father worked as a union electrician at Nestlé. (Iannarone won't eat Nestlé chocolate because of the company's environmental record.)

Iannarone bounced around during her early years: a bit of college in a culinary arts program in Providence, R.I., short stints in Charleston, S.C., and New Orleans, even a job as a private chef for the country singer Mel Tillis in Branson, Mo.

She married Nick Iannarone, a Philadelphia native, in Las Vegas in 1998. The couple moved to Portland, where they had their only child, a daughter, the following year. (The Iannarones divorced in 2019 after a long separation.)

While her daughter was a toddler, Iannarone returned to college at Portland State, graduating in 2005, the same year her husband opened the Arleta Library Cafe, which closed this year. She contributed the recipe for the cafe's signature sweet potato biscuits.

Iannarone says her life experience and work in the community are great training for City Hall. She notes that white men with strong political pedigrees have not done very well as Portland's mayors lately.

"They get a free pass when they fail," she says. "I have lived a life in three dimensions in this city —that's what makes me qualified to be the mayor right now."

2. An outsider has beaten an incumbent Portland mayor before.

It's been 36 years since a candidate with no previous political or executive experience beat an incumbent in a Portland mayor's race.

In that instance, Bud Clark, owner of the Goose Hollow Inn, stunned Mayor Frank Ivancie in the 1984 primary.

Ivancie was the last conservative mayor to run Portland: His strong support for the Portland Police Bureau defined him. Clark, by contrast, was a jovial publican with a world-class beard. He pulled pints of beer, punted a raft down the Willamette River, and ended his pronouncements with a loopy catchphrase: "Whoop! Whoop!" He was a living embodiment of Portland's values.

MAYOR PUBLICAN: Mayor Bud Clark saw high-profile police firings overturned by arbitrators.
MAYOR PUBLICAN: Mayor Bud Clark saw high-profile police firings overturned by arbitrators.

Chuck Duffy, a Clark aide, says the Goose's prominence and Clark's flamboyance gave him a higher profile than Iannarone enjoys.

"I don't think she has the cache Bud had," Duffy says.

But nobody in the political establishment thought Clark had a chance, either. The city had shifted left under Ivancie—he was just the last to notice.

Duffy and others say the same fate could await Wheeler if voter are sufficiently dissatisfied. "It would really come down to a sheer protest vote," Duffy says.

3. Iannarone may not have any political experience, but she has a lot of ideas.

In 2006, Iannarone began pursuing a Ph.D. in urban studies at PSU.

Adam Davis, a founder of DHM Research, who now heads the Oregon Values and Beliefs Center, advised Iannarone on research techniques for her graduate work. "She's smart and very passionate about issues," says Davis. "She can be laser-focused and she's a hard worker."

In 2008, she co-founded a new nonprofit at PSU called First Stop Portland.

First Stop provided tours of the city for foreign delegations curious about Portland's approaches to architecture, land use, sustainability, transit and other endeavors. The tours showcased Portland's leading thinkers and most innovative businesses.

"It was a terrific program for knowledge building, relationship building and business development," says Davis, who served on First Stop's advisory board.

Iannarone's boss at First Stop was Nancy Hales, wife of Portland's then-mayor, Charlie Hales.

Iannarone credits her time at PSU with giving her an immersion in smart cities and the kinds of policies that would fuel her first mayoral campaign.

Her top priority: ensuring Portland is carbon neutral by 2030.

"If you don't aim for things, you won't accomplish them," Iannarone says. "And even if you fall short, you've achieved more than you would have otherwise."

She has other plans, which include undoing the constitutional ban on real estate transfer taxes to finance new housing. She'd also expand the Portland Clean Energy Fund; take the city's money out of commercial banks to create a city-owned bank; and establish a municipal high-speed internet service.

“I am deeply rooted in the community, so I won’t need to be taught how to listen to the demands of the public or how to work through coalition to get things done,” Iannarone says. (Aaron Wessling)
“I am deeply rooted in the community, so I won’t need to be taught how to listen to the demands of the public or how to work through coalition to get things done,” Iannarone says. (Aaron Wessling)

Iannarone is comfortable discussing details as granular as how to create a renter bailout fund: She'd double the tax on AirBnb from 2% to 4%.

She wants to legalize all sex work and let anybody—not just citizens—vote in city elections. "While federal law prohibits non-citizens from voting in federal elections, states and cities are free to make their own decisions," her platform says.

If elected, Iannarone says, she'd draw an immediate contrast to Wheeler by granting Commissioner Jo Ann Hardesty's wish to command the Police Bureau and teaming up with Multnomah County District Attorney Mike Schmidt to investigate police violence during the protests. She'd figure out a way to keep right-wing extremists from fighting in Portland's streets.

Her campaign appeals to supporters such as Cameron Whitten, founder of the Black Resilience Fund. "Her vision is exactly the direction her city needs to go in," Whitten says. "She has a chance to help us heal and work on a policy that works for everyone."

Stephen Green, who is active in Portland's startup community, likes Iannarone's focus on small business. Green says she is a "master communicator."

"She meets people where they are and really listens," Green says. "Whether it's a person who has flown in from Japan and speaks a different language or a person who's houseless, she has a real ability to be present."

4. She can take credit for a signature accomplishment: the Arleta Triangle.

In 2005, Iannarone decided to help clean up her Southeast neighborhood, Mount Scott-Arleta, which is bounded on the north by Foster Road, the west by 60th Avenue, the east by 82nd Avenue, and the south by Duke Street.

She and other volunteers set out to revive a trash-strewn, triangle-shaped Portland Bureau of Transportation property at Southeast 72nd Avenue and Woodstock Boulevard.

Mark Lakeman, co-founder of the City Repair Project, which organizes such community undertakings, cautioned her against expecting cooperation from city officials.

"PBOT hadn't been able to be make that kind of project happen before, fixing a derelict space," Lakeman says. "But she was so well prepared and so persuasive she got PBOT to go along."

Arleta Triangle (Aaron Wessling)
Arleta Triangle (Aaron Wessling)

Iannarone and her allies raised money and created a community amenity, with seating areas, public art and native plants, now known as the Arleta Triangle. She often cites the project as evidence of her ability to bring disparate parties together to overcome challenges.

Iannarone's community focus won over her highest-profile backer, state Rep. Karin Power (D-Milwaukie), chair of the Oregon House Energy and Environment Committee.

In January 2018, when an ice storm gripped Portland, Iannarone helped set up an emergency warming center near Interstate 205 and Foster. Power responded to Iannarone's call for supplies, filling the back of her Prius at Costco.

"She puts in the work and she shows up," Power says. "That's the kind of thing that makes us all think, 'I should take the road a little less comfortable and do more.'"

5. Iannarone is less than transparent about her academic credentials.

Her characterization of her academic bona fides is a recurring issue. In the 2016 Voters' Pamphlet, Iannarone described her educational background as "PhDc"—the "c" standing for candidate.

In May 2020, she changed that description to "Ph.D. (ABD)"—which means "all but dissertation." She's repeated that phrasing in the November Voters' Pamphlet.

In other words, Iannarone purports to have earned a doctoral degree she's been working on since 2006, except for completing her thesis.

Under Oregon law, making a false statement in the Voters' Pamphlet is a felony.

"An example of a false statement under ORS 260.715(1) is stating the candidate has a college degree when the candidate does not," the elections manual says.

"She's absolutely violating the spirit of the law," says Jim Moore, a professor of political science at Pacific University (and a Ph.D.). "That 'c' or 'ABD' doesn't mean anything in academic nomenclature. She doesn't have the degree. It's that simple."

Iannarone defends the characterization. "It's actually a set of qualifications that I've accomplished," she says. "I am ABD and I have advanced a candidacy in a Ph.D. program. So that's actually accurate." (PSU professor Carl Abbott, Iannarone's Ph.D. adviser, declined to comment.)

Iannarone, in the pith helmet she wears to protests (top), has received money from 5,000 contributors. (Courtesy of Sarah for Mayor)
Iannarone, in the pith helmet she wears to protests (top), has received money from 5,000 contributors. (Courtesy of Sarah for Mayor)

6. Her communication is unfiltered.

Iannarone's Twitter account, @sarahforpdx, has 18,400 followers. That's a quarter of Wheeler's following, but Iannarone's posts are far more memorable.

Wheeler's posts have a Dudley Do-Right quality, which makes him an easy target for mockery and scorn. By contrast, Iannarone does the targeting. Throughout the year, she has used her social media presence to decry the city's police and its mayor.

"I'm publicly financed. Ted is bought and paid for," she tweeted Aug. 9. "I'm a progressive grounded in community. Ted is a neoliberal grounded in finance."

And on Sept. 4: "Wheeler has dug into refusing to address the true threats to our city: a rogue police force with sympathies for white nationalists."

Between 2016 and today, Iannarone traded in the pearls she wore in her first campaign for a gas mask. On dozens of nights over the past three months, she joined protesters outside the Mark O. Hatfield U.S. Courthouse.

In an Aug. 7 interview on KGW's Straight Talk, Iannarone repeatedly declined host Laural Porter's invitation to disavow property destruction at the nightly protests.

"Peaceful protests, in my opinion, might not necessarily be moving the conversation forward," she told Porter.

Iannarone says Porter didn't give her a chance to fully answer the question. The day after taping the show, she sent KGW a statement. "Criminal activity is illegal, and of course I don't condone it," she said in her follow-up. "What I'm focused on is ensuring police do not use violence and even lethal force against people who have done nothing wrong."

But John Horvick, a pollster at DHM Research, says he isn't sure Iannarone's public pronouncements resonate with most voters.

"I think the average voter in Portland would find her unappealing," Horvick says. "That voter not as liberal as Iannarone or her Twitter feed seems to think."

Iannarone acknowledges she's more outspoken than she was four years ago. She says there are two reasons for that.

First, she doesn't have to worry about offending contributors.

In 2016, she fell far short of her fundraising goals. Since then, she helped shaped the city's new public campaign finance program and is its biggest beneficiary, scoring $277,825 in city matching funds in the May primary. She is well on her way to maxing out for the general election.

Arleta Triangle (Aaron Wessling)
Arleta Triangle (Aaron Wessling)

Wheeler, who previously financed his campaign with big checks from real estate developers and business leaders, bet campaign finance limits approved by voters in 2018 would get stalled in court.

He got that wrong and his campaign has failed to generate donations. (Iannarone has raised $471,000 in 2020, nearly twice Wheeler's $258,000 total.)

The second big change: This time Iannarone is running against an incumbent with a track record instead of for an open seat.

"The last four years under Wheeler have made me a more vocal activist than even I would've liked to be," she says, "because I've had to fight against policies that I think would harm my community."

Observers who have worked with Iannarone say she has a temper. Two examples involve the Arleta Triangle.

Walt Nichols, a former chairman of the Mt. Scott-Arleta Neighborhood Association, clashed with Iannarone when he raised questions about the project's finances. "It's her way or no way and there's no middle ground," he says. "She is caustic and she takes things really personally when challenged."

Iannarone rejects that criticism: "Walt never volunteered, helped or wanted to be involved in any way except in telling us what to do and making demands of those of us doing the work," she says. "I have zero tolerance for lazy blowhards and, of course, pushed back."

Nichols notes that fallout from the project also led to another incident that demonstrates Iannarone's temper.

Iannarone and Brian Borrello, an artist on the Triangle project, sought restraining orders against each other in 2010. In court documents, Borrello accused Iannarone of spray-painting an image of "an ejaculating male penis with the words 'loose cannon' on my workplace door."

Iannarone and Borrello declined to comment on the allegation, but Lakeman of City Repair recalls the dispute. He says although Borrello is his friend, he can be a hothead.

"I've called him a dick myself," Lakeman says. "She just went a little further."

Arleta Triangle (Aaron Wessling)
Arleta Triangle (Aaron Wessling)

7. Despite Wheeler's unpopularity, Iannarone has struggled to win over key allies.

Iannarone is running to Wheeler's left. Yet she is not picking up some of the key endorsements she might have hoped to earn. Despite her aggressive climate plan, for instance, the Oregon League of Conservation Voters, the state's largest environmental group, recently endorsed Wheeler.

OLCV board chair Jules Bailey (who ran against her and Wheeler in 2016) says that's because Wheeler accomplished difficult tasks. He cites the residential infill project, which the City Council passed Aug. 12 after a five-year battle with neighborhood associations and other opponents.

"It's easy for somebody to stand up and say, 'I've got a plan,'" Bailey says. "It's another thing to stand up to powerful neighborhood and entrenched interests. Wheeler took a political risk in doing that."

On Sept. 14, the Next Up Action Fund, the voter engagement group formerly known as the Bus Project, endorsed write-in candidate Teressa Raiford for mayor. That was a repudiation of Iannarone, who got more than twice as many votes as Raiford in the primary. In a lengthy explanation of its decision, Next Up called Raiford "the fighter we need as Portland mayor to tackle the issues of police brutality, the climate crisis, houselessness, renter's rights, and equity pay for living wages." All things, of course, that Iannarone has pledged to do.

Teressa Raiford finished third in the May primary but is gaining traction as a write-in candidate. (Megan Nanna)
Teressa Raiford finished third in the May primary but is gaining traction as a write-in candidate. (Megan Nanna)

Two figures central to the past three months of racial justice debate also aren't convinced Iannarone is the answer.

State Sen. Lew Frederick (D-Portland) has led the push for police accountability measures in Salem. He's known Iannarone for nearly 20 years, much of that time as a fellow PSU grad student.

He endorses Wheeler. "She's a great person and has a lot of good ideas, but I think she'd be better in another role," Frederick says. "I may disagree with Ted on how he's handled police issues, but I still feel he has a better handle on how to manage the whole city."

The skeptic who could prove most costly to Iannarone is Jo Ann Hardesty, the city commissioner who holds considerable sway with the electorate—as she demonstrated by helping Dan Ryan defeat Loretta Smith in the Aug. 11 special election runoff for City Council.

Hardesty might seem the most sympathetic ear for Iannarone's criticism of the police and Wheeler's management of the bureau.

Iannarone even co-authored a March 12, 2019, op-ed in the Portland Tribune urging that the mayor put Hardesty in charge of the Police Bureau, an assignment she's pushed for ever since.

Hardesty endorsed Wheeler in the primary. She says she remains undecided whether she'll endorse him in November—yet she's not inclined to endorse Iannarone.

"She's a nice woman and she has some good ideas," Hardesty says. "But with the current crises, can Portland really afford another one-term mayor?"

WW intern Hank Sanders contributed reporting to this story.

Correction: This story incorrectly stated that Iannarone received the maximum allowable $304,000 in public campaign financing in the May primary. In fact, she received $277,825 from the program through the primary. Also, Nicholas Iannarone is a native of Philadelphia not Baltimore and the Arleta Library Cafe close in 2020, not 2018. WW regrets the errors.