This is one of the many articles in the Mercury’s 2026 Halloween Issue. Find a print copy here, subscribe to get a copy mailed to you here, and if you’re feeling generous and want to keep these types of articles coming, support us here.—eds.
In 2024, two years after voters approved sweeping changes to how Portland’s government is structured, Portlanders voted in six progressive city councilors—four of them Democratic Socialists of America (DSA) members. Now, as three of those four are vying for reelection, wealthy local political activists and their allies have been pulling out their checkbooks to prevent them from winning a second term.
Recent Mercury reporting provides voters with context around what moneyed interests are doing to prevent progressives from gaining office. Here’s what to watch out for.
Billboards
Connected, well-funded interests are spending tens of thousands of dollars on a billboard campaign, using a new web of monikers ostensibly run by grassroots activists.
Local political activist Kyle Prosen—also known as the drag queen comedian Poly Poptart—is listed as the treasurer for three political action committees (PACs) associated with the campaign, according to state records: DitchMitch, goPDX, and fix multCo.
But it’s unclear who is actually running the ship. Asked about the committees in an interview September 21, Prosen wasn’t particularly familiar with the details.
“I’ve been briefed on things, but I don’t always remember everything on the top of my head,” Prosen said.
That’s because well-funded interests appear to be using an old playbook. United for Portland Action Fund, a Portland Metro Chamber-aligned PAC, is the campaign’s top funder. The PAC’s executive director told Willamette Week earlier this year that the Metro Chamber’s aim for this election was to “stop DSA from taking over the council.”
With DSA in its crosshairs, the shots fired come in the form of billboards. “Politician Mitch Green voted to raise your taxes, didn’t pay his own taxes,” at least one billboard’s text reads in all capital letters. Another says Green started a fire in his backyard while a burn ban was in place.
That Green, a democratic socialist, hadn’t paid the tax was true, albeit briefly. Green paid the $7,328 bill in full, just after being contacted by the Oregonian. He said he thought the bill was already paid through an escrow account, and learned it had not been paid when the reporter contacted him. As to the burn ban, Green took responsibility, saying it “was a profoundly stupid thing to do even if there was not a burn ban. Mea culpa. I did a bad thing. It was stupid.”
Questions have arisen as to the legality of the billboard campaign. On October 5, Seth Woolley, a software engineer and elections watchdog, filed a 182-page complaint outlining 16 separate counts of potential campaign finance violations. The complaint alleges that United for Portland established goPDX, DitchMitch, and fix multCo for the purpose of concealing original funding sources for the election-related billboard campaign.
“The three new entities added names and disclosure layers, while retaining the same administrators and using the same advertising vendor,” the complaint says. “Complainant alleges that obscuring the original sources was the principal purpose of this structure.”
Woolley’s complaint also alleges that the committees began the campaign prior to registering with the state, and knowingly reported false dates and incomplete information required for independent expenditures. Violating the state elections laws outlined in the complaint may carry civil penalties for untimely reporting, while violations like obscuring the original sources of the funds could be charged as a Class C felony. That can carry up to $125,000 fine and up to five years in prison.
Painting DSA as “Anti-Labor”
In early September, Prosen posted a social media video of himself walking alongside District 4 incumbent candidate Eric Zimmerman at a private Labor Day picnic hosted by the Northwest Oregon Labor Council (NOLC)—a statewide coalition of labor unions—saying DSA candidates were not invited “because maybe they don’t support unions the way that they should.”
Prosen told the Mercury he noticed some labor unions have not endorsed DSA candidates in this election. There may be a reason for that. Similar to the frantic responses from Republicans and moderate Democrats over the rise of DSA candidates like Mayor Zohran Mamdani in New York, and dozens of recent primary wins across the United States and in Oregon, hostile rhetoric has echoed in local politics, including in labor leadership circles.
Earlier this year, the Mercury reported on public records showing that NOLC’s top brass Laurie Wimmer used inflammatory comments about DSA councilors, saying she was “disgusted,” accusing progressive councilors of “race baiting,” and calling DSA the “MAGA of the left.”
But aside from Wimmer’s preferred unions, local progressive candidates’ campaign websites show strong labor support from rank-and-file union members and unions—collectively, AFSCME, LiUNA, North Coast States Carpenters Union, Portland Association of Teachers, Protec17, PSU-AAUP, SEIU, Portland Tenants United, UFCW, AFT-Oregon, Teamsters, PCC-FFAP, and more.
Progressive language, conservative money
“We’re on a mission to make Portland the model of progressive governance—again,” reads the website for Go Portland Go, which registered as a PAC in April.
But despite using the term “progressive” all over its website, blasted in social media ads, and calling itself a “grassroots coalition,” the effort is largely backed by Portland’s moneyed political actors. Many of them have bankrolled fights against progressive policy for years.
The main funder of Go Portland Go is Partnership for Progress, a nonprofit political advocacy group founded in 2025. Partnership for Progress has strongly pushed against policies brought by progressive councilors, advocated for homeless camp sweeps, spoken out against the Preschool For All tax on high-income earners, and advocated for increased funding for police—including the failed Portland Enhanced Community Safety ballot initiative that would have used money from the Portland Clean Energy Fund to hire more sworn officers.
Partnership for Progress donated $32,000 to Go Portland Go in June, according to state records. The organizations also share some leadership; Partnership for Progress co-leader Vadim Mozyrsky, who founded Partnership for Progress along with current City Council District 4 candidate Eli Arnold and past city council candidate Bob Weinstein, also sits on the steering committee for Go Portland Go. Partnership for Progress is also listed as a coalition member on Go Portland Go’s website.
Over the past year, Partnership for Progress’s newsletters have featured satirical, AI-generated images that spin narratives of Portland in decline. They largely blame the four DSA members—District 3 incumbent candidates Angelita Morillo and Tiffany Koyama Lane, District 2 Councilor Sameer Kanal, and Green, the District 4 incumbent—for what they perceive as the poor state of the city.
Go Portland Go’s second-highest donor is local billionaire and Columbia Sportswear CEO Tim Boyle, who donated $25,000 in June, the latest in his consistent donations to conservative causes. Boyle recently donated $100,000 to the aforementioned failed Portland Enhanced Community Safety ballot initiative. In 2023, he gave $150,000 to a group lobbying to dismantle Measure 110, the state law that decriminalized possession of controlled substances and began to build a network of statewide treatment centers for people with substance use disorders. Boyle also donated $125,000 to Betsy Johnson, the conservative independent candidate for governor, in 2021.
Tied with Boyle for second-largest donor is out-of-state contributor Jeff Swickard, CEO of Swickard Auto Group, which operates dealerships up and down the West Coast and Hawaii. He also owns Big Pink and other downtown high rises.
A number of local businesses signed on as “coalition members” for Go Portland Go, expressing their support publicly on the PAC’s website. Many of those were restaurants, including Le Pigeon and Canard, whose co-owner Andy Fortgang clashed with progressive councilors earlier this year over the foie gras ban successfully passed by progressive Councilor Green.
In an interview with the Mercury, Fortgang cited safety concerns as a major reason for supporting Go Portland Go.
“We stopped using [our outdoor] space because there were just too many instances of our employees or our guests being yelled at, attacked, bothered by people on the street,” he said.
Go Portland Go’s website says it’s “not generally” against the DSA, saying the title means a lot of different things to different people. However, Go Portland Go’s candidate endorsement criteria would effectively prevent DSA-aligned candidates from earning endorsement: “1. Prioritize local issues over national. 2. Fund public safety. Yes, including the police. 3. Support businesses. Small, medium, AND large. 4. Make Portland more affordable. Reduce red tape, fees, and taxes. 5. Collaborate, compromise, and solve real problems.”
Indeed, Go Portland Go did not endorse any DSA-affiliated candidates, but it has endorsed centrist Kellie Torres and frequent swing voter Steve Novick in District 3, as well as three centrists in District 4: Eli Arnold, Eric Zimmerman, and Olivia Clark.
Police Tweets
In mid-September, local political forces piled onto Green and DSA-affiliated incumbent candidates after the Oregonian published a story first dug up by a local right-wing blogger highlighting a series of Green’s tweets criticizing the police and calling for police abolition in 2020.
Portland Police Association President Aaron Schmautz called for Green to resign, Portland Police Bureau Chief Bob Day potentially illegally mixed official duties with electioneering, and District 4 Councilors Olivia Clark and Eric Zimmerman pounced on the opportunity to join in on intimidating Green and progressive candidates into silence.
That compelled the Mercury’s editorial team to publish a rare editorial opinion piece, “Knee-Jerk Reactions to Councilor Green’s Tweets Are Hypocritical and Dangerous,” on September 17. There, we outlined a number of issues with the claims, and presented some context regarding Portland’s history of racialized and politicized police violence.
Now, Mayor Wilson has pulled the other progressive councilors’ views on police into the spotlight—claims which seemingly focus less on nuance and more on the politics of fear. In an interview with KGW in late September, Mayor Wilson said he “can’t in good conscience endorse anyone who advocates for the abolishment of our police.” He added that Koyama Lane, Morillo, and Green had all signed onto the DSA national platform and committed to abolishing the police in a questionnaire, which was not true of all three candidates. The DSA national platform does call for eventual police abolition, but within the context of supporting community needs, demilitarizing police departments, and disempowering police unions.
Koyama Lane posted a video on social media in response to Wilson’s comments on KGW. “He’s using classic political scare tactics, trying to make Portlanders think that I want all policing and prisons to disappear tomorrow,” she said. “…We need a public safety system where we send the right responder to the right situation, where police officers are no longer forced to act as social workers doing jobs that honestly they never signed up for. Real public safety means freeing up our police for actual emergencies. Real public safety means demilitarizing local police forces. Real public safety means fully funding the community programs that prevent crime before it even starts, and it also means that elected officials stop trying to scare voters. Let’s focus on real solutions.”
It wasn’t the first time Koyama Lane addressed Wilson’s remarks. In a September 25 Microsoft Teams message obtained by the Mercury, Koyama Lane asked Wilson why he was distorting her views and leaving out critical context. In response, Wilson directed Koyama Lane to the right-wing blogger’s original post, which weaponizes anti-Semitism, calls Oregon House of Representatives candidate Tammy Carpenter an “ugly person,” accuses democratic socialist candidates of welcoming terrorists in their “big tent,” and “working with monsters.”
“You are distorting the truth, and I’m very upset,” Koyama Lane wrote back.
This November, it’s up to Portlanders to decide whether or not it’s acceptable to distort the truth in the city’s elections. Moneyed interests are hoping Portlanders won’t notice the sleight of hand.
