How candidates — and their donors — are navigating a first-of-its-kind election season in Portland

Editor’s note: Election Day is Tuesday, Nov. 5. Stay informed with OPB on the presidential race, key congressional battles and other local contests and ballot measures in Oregon and Southwest Washington at opb.org/elections.

When Portland City Council candidate Eric Zimmerman talks with voters who support his campaign, he’s often asked: “Which of your competitors should I also vote for?”

It’s an unusual question, but commonplace in Portland’s equally unusual campaign season, where voters will elect three councilors from an expansive pool of candidates to represent their district.

“It pays to be nice in this system instead of divisive,” said Zimmerman, the chief of staff for Multnomah County Commissioner Julia Brim-Edwards. Zimmerman is running in the city’s new District 4 on Portland’s west side. He’s joined forces with fellow District 4 candidate Olivia Clark, and both have been encouraging voters to vote for each other.

“It’s nice we’re able to have each other’s backs,” said Clark, who previously led TriMet’s public affairs office. “I really hope it helps.”

Candidates running for office in Portland this fall are navigating uncharted waters. It’s the city’s first election following new voter-approved changes to the city’s governance model and voting system. These tweaks have forced candidates to experiment with different campaign strategies with limited funds, a dynamic that has introduced its own campaign finance challenges.

No one is quite sure what approach will land candidates in City Hall, or how the atypical campaign season will set the tone for Portland’s new government body next year. With two weeks until Election Day, there’s little time to evaluate.

“We’re learning as we go,” said Zimmerman. “And I guess we’ll all see what happens soon.”

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From competitors to colleagues

Collaboration between candidates like Zimmerman and Clark is a byproduct of several changes approved by Portlanders in a 2022 ballot measure.

That measure established four new geographic districts, and grew the size of City Council to 12 — with three councilors representing each district. It also introduced ranked choice voting, where voters will use a single ballot to rank candidates in order of preference to elect three new councilors. This is called multi-winner ranked choice voting, and is used sparingly in the U.S — Portland would be the largest city to use it for city council races.

Under that system, voters’ choice for second, third and additional candidates may count just as much as who they rank first — meaning it could help to campaign alongside like-minded candidates to win a spot near the top of their supporters’ ranked ballot.

“You may be more likely to win if you make friends,” said Melody Valdini, a Portland State University political science professor who sat on the city committee that proposed the new district boundaries for Portland. Valdini has studied multi-winner ranked choice voting in Ireland, which has used the model since 1919. “This is what we’ve seen [in Ireland]. [Multi-winner] voting is always going to incentivize collaboration.”

Candidate Candace Avalos was on the charter commission that proposed the government changes approved by voters two years ago. Yet Avalos was skeptical of this collaborative approach when she began her campaign for East Portland’s District 1.

“I know, as somebody who has run [for office] before, that candidates can be messy,” said Avalos, who ran against now-City Commissioner Carmen Rubio in 2020. “I didn’t want to be associated with someone who might tarnish my reputation.”

That doubt eased once she started to get to know her competitors on the campaign trail with similar politics, like Steph Routh, an adjunct instructor at Portland State University‘s School of Urban Studies and Planning. Routh and Avalos have held joint house parties, handed out each other’s campaign fliers when they meet with voters, and regularly discuss endorsement and fundraising strategies.

“I know I can trust her to be in alignment with me on issues I care about,” said Avalos.

This collaborative strategy has all but erased negative campaign ads paid for by competitors in council races. While it feels good to stay positive on the campaign trail, Zimmerman said he believes it could be a disservice to voters.

“The lack of any negative campaigning may mean voters aren’t making fully informed decisions,” Zimmerman said. “Politics isn’t all sunshine and rainbows.”

Another downside of candidates’ friendly relationships? Potential campaign finance violations. In September, Willamette Week reported on emails showing that some city candidates were pledging to reciprocate campaign donations to reach a donor threshold to qualify for the city’s donation matching program. The secretary of state’s office is now investigating whether that quid pro quo agreement broke the law.

Candidates involved, including Zimmerman, say they were acting in the spirit of collaboration. Jake Weigler, a political consultant with Praxis Political with a long history in Portland elections, called it a risky example of “herd mentality.”

“It’s been great to see [candidates] all try and feed off of each other and learn from each other,” Weigler said. “It’s just sometimes, everyone’s trying to figure it out, but no one is saying, ‘Wait a minute, this isn’t appropriate.’”

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Struggling to stand out

Another side-effect of the new election format is voters are simply overwhelmed by the massive pool of candidates vying for their attention — on ballots, in hefty voter’s pamphlets, and in the sea of yard signs across Portland neighborhoods. A total of 118 people are running for office in Portland, with 19 people vying for mayor.

This large lineup is because the 2022 measure abolished primary races for city elections. That’s because historically low voter turnout for primaries meant that only a small percentage of the electorate was determining which candidates would advance to a general election. This change leaves voters facing a vast pool of candidates this November, the majority of which are new to political office. It’s up to candidates to catch voters’ eye.

“It makes it really hard for candidates to break out of the pack,” said Weigler. “It’s been challenging for candidates to develop a clear public persona or get broad name recognition.”

Clark, one of 30 candidates in District 4, said she is trying to meet as many voters as possible in person, through house visits and events — and then hope they spread the word.

“At house parties, I tell people to send emails to their friends to vote for me, and tell those friends to also email people,” Clark said. “It’s starting to sound kind of like a pyramid scheme.”

Both she and Avalos have also prioritized landing endorsements from a range of labor organizations, nonprofits, politicians, media outlets and other community leaders. Clark lists nearly 100 endorsements on her website, while Avalos notes just under 200.

“I knew endorsements were really a big part of the season,” Avalos said. “Voters are looking to groups and people they trust to tell them who they should support. It helps cut through the noise.”

The packed field has inspired new groups to form and offer endorsements, in hopes of swaying an overwhelmed electorate. The Portland Voter Guide PAC is one of those groups. Made up of a handful of progressive nonprofits that advocate for people of color, the committee formed earlier this month to fill a gap it noticed.

“We recognized that there was not a progressive, equity-centered political effort in the city of Portland this election that is vetting candidates,” said Jenny Lee, a spokesperson for the Portland Voter Guide PAC who also leads the nonprofit Communities of Color’s political advocacy arm. “So we aligned to essentially provide that service to voters and increase participation and civic engagement.”

The group has endorsed candidates in all four districts and the mayoral race, and has pointed out which labor unions share their endorsements. In just the past two weeks, the committee has raised nearly $200,000 in funds and mailed fliers listing their endorsements citywide to thousands of Portland households.

“We’re helping candidates communicate directly with voters, which has been harder for candidates to do this year,” Lee said. “They just don’t have the resources.”

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Penny-pinching to the polls

Money — specifically, the lack of it — has been a defining factor of Portland’s elections this year.

That’s due to unexpected limits to a program that provides public campaign dollars for city candidates. The city’s Small Donor Election program rewards candidates who pledge to accept only individual campaign donations under $350. The city matches the first $20 of all individual donations made to participating candidates 9-to-1, effectively turning a $20 donation into $180.

Nearly half of all candidates running for city office this year are participating in this program. The rest of the candidates must follow the city’s standard campaign finance rules, which cap individual donations at $579.

The Small Donor Election program caps its total public contributions to council candidates based on the number of individual contributions they collect. In the past, candidates who received donations from at least 250 Portlanders could receive up to $100,000 in matching funds, and those with more than 1,250 donations could collect $300,000 in matching city dollars.

But budget cuts approved by Portland City Council scaled these caps back by 60% this year, significantly altering candidates’ spending plans.

For Zimmerman, the budget cuts forced him to forgo hiring a campaign director, placing much of that work on himself.

For James Armstrong, a candidate in North Portland’s District 2 who owns an optometry business, it’s another reason to partner up with like-minded opponents in the race. Armstrong decided to pool money with fellow candidate Mike Marshall, co-founder of nonprofit Oregon Recovers, to buy campaign mailers that had Marshall’s information on one side and Armstrong’s on the other.

“Given our budgets, it will give us significantly more reach,” said Armstrong.

Armstrong has raised donations from just over 250 people, a benchmark that would have brought him $100,000 in city funds in previous elections. But this year, it’s only granted him $40,000, putting his total contributions at around $65,000.

According to Armstrong, it would cost him nearly his entire budget — $50,000 — to send three mailers out to 20,000 different households in his district. Now he can split the bill with Marshall, spending just half that.

“It pays to be creative,” Armstrong said. “And I think voters will appreciate that we’re supporting each other.”

These financial strains have felt even more restrictive in the mayoral race, in which candidates who previously could rake in up to $750,000 in matching funds can now only collect $100,000.

“There is no way that you can run a viable citywide campaign in a city the size of Portland with such little money,” said Dean Nielsen, founding partner of political consulting firm CN4 Partners.

Nielsen said that, for a presidential election year like this, Portland should anticipate that 80% of all registered voters cast a ballot. (That would be about 360,000 people, based on May 2024 voter registration numbers.) The cost for a mayoral candidate to reach that many voters — either through campaign mailers, advertising or events — would realistically be close to $1 million, Nielsen estimated.

This is why Nielsen left his post running City Commissioner Rene Gonzalez’s mayoral campaign in August. Gonzalez has just over $300,000 in his campaign coffers, including the $100,000 city funds, which Nielsen called “pennies.”

Nielsen chose to instead support Gonzalez through a campaign finance tool that has spiked in popularity this campaign season: an independent expenditure campaign.

This style of political committee is allowed to collect and spend money on ads to support or oppose candidates, as long as it’s not coordinating directly with a candidate. Crucially, unlike most candidate committees, there are no campaign limits to the size of donations independent expenditure campaigns can collect. These local campaigns are similar to the numerous deep-pocketed committees formed by special interest groups that have influenced national elections after a 2010 Supreme Court decision legalized their existence. This decision was underscored by the Oregon Supreme Court in 2020, which ruled that campaign limits to independent expenditures were unconstitutional.

It’s made them an invaluable and powerful resource in a crowded mayoral race, with nearly every top candidate being backed by an independent expenditure committee.

The pro-Gonzalez committee has raised nearly the same amount as Gonzalez did in his year of campaigning in just the past two months. Instead of being limited to donations of $350, the committee has collected some individual donations of $25,000.

Yet Nielsen is a reluctant adopter of the independent expenditure model. He argues it would be better for candidates to have direct control over how money is spent on their behalf.

“But once you start having financial limits, there’s no choice,” he said.

Nielsen said this wouldn’t be a problem if the city had decided to fully fund the campaign matching program this cycle. He noticed that, in previous Portland elections with a fully funded public funding program, like in 2020, there were no independent expenditure campaigns involved.

Independent expenditures aren’t limited to mayoral races. Doug Moore is the director of United for Portland, a political group backed by Portland business leaders, which has already spent upwards of $30,000 supporting preferred City Council candidates through an independent expenditure campaign.

Like Nielsen, Moore laments having to run campaigns without candidates’ involvement.

“I know that one of our city’s goals is to get big money out of politics, right?” Moore said. “But candidates do need to be able to carry their own message. And it’s just too expensive right now. Something’s got to change.”

The start of a new chapter

It remains to be seen how the bumpy path to Election Day will inform the incoming City Council’s operations.

“I think the City Council is going to have some real opinions about how this election felt and was conducted,” said Moore, pointing to their experience as “guinea pigs” in the new system.

From tinkering with the campaign finance program to the voter education process, he anticipates the new council and mayor proposing changes to swiftly set the stage for the next city election in 2026.

“They’re going to have to draw conclusions relatively quickly,” Moore said.

That will require the kind of collaboration candidates have demonstrated in their campaigns.

Valdini, the PSU professor, said that in places that have adopted the kind of ranked choice voting being used in the council races, the tone of collaboration observed on the campaign trail carries over into how elected candidates govern. But she can’t say the same for the race for mayor.

Portlanders will also be using ranked choice voting to elect the mayor, but unlike the council races, only one candidate will win. That doesn’t encourage friendly campaigning between competitors — and attack ads are more common. In a new City Hall where the relationship between councilors and the mayor will be critical, these polarizing campaign styles could cause trouble.

“Councilors will get into the office after being incentivized to work with each other, where mayors won’t,” Valdini said. “That could create an interesting dynamic.”

Valdini is eager to see how the first chapter of Portland’s new form of government plays out, after months of speculation from the public, academics, elected officials and political analysts. She understands why voters may feel wary and overwhelmed by the many new systems operating in tandem this election. But from her research, Valdini said she’s confident that Portland is heading in the right direction.

“It’s hard to have faith in government, I get it,” she said. “But this could be a great thing for Portland.”