It isn’t uncommon for big business interests to throw cash at elections in hopes of moving the electorate—and not just at the federal level.
Amid growing wealth inequality and ongoing affordability crises, some Portland City Council candidates are also facing an onslaught of vicious election tactics from groups who appear motivated to take out progressive incumbents vying for a second term. In the weeks before the upcoming election, Portland’s moneyed opposition appears to have their sights set on District 4 Councilor Mitch Green, a democratic socialist who took office in January 2025.
One tactic they’re employing is billboard messaging. Earlier this month, a digital billboard sprung up, visible from a lot on Beaverton Hillsdale Highway—a pocket that is not incorporated into the city of Portland—saying Green did not pay his taxes. Another along Highway 30 in the northwest industrial district came late last week, referencing reports that he started a fire in his back yard while a burn ban was in place. Another, outside a convenience store in the District 3 Foster/Powell neighborhood appeared this week offering the same design as the previous tax ad.
These appear to be the first of many advertisements meant to damage Green’s campaign and tip the scales toward centrist candidates. Connected, well-funded interests are behind the campaign, but under 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 behind three committees associated with the campaign, according to state records. He runs a brand new political action committee (PAC) called Ditch Mitch, another called Go PDX, and another called Fix MultCo.
But it’s a bit unclear who is really running the ship. Asked about the committees in an interview Monday, 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.
Prosen told the Mercury he got involved in the campaign to unseat Green after Willamette Week reported in early August that Green had burned yard debris outside his home while local burn bans were in place. Green apologized then, and doubled down in an interview with the Mercury September 11.
“That was a profoundly stupid thing to do even if there was not a burn ban,” Green said. “Mea culpa. I did a bad thing. It was stupid.”
Prosen called the initial apology inadequate.
“Part of the reason I moved to Portland from California was because of wildfires,” Prosen said. “When I heard that he was lighting a brush fire in his backyard during a time when the Portland fire department indicated that it was no burn, that to me was pretty concerning.”
So, he got involved—but not alone. The main funders of the multiple committees Prosen said he “okayed” are the same institutions that have long held power in the city.
The billboards’ disclosures list United for Portland Action Fund as the campaign’s top funder. Jon Isaacs, the Portland Metro Chamber executive vice president of public affairs, is the PAC’s treasurer, and Doug Moore is its executive director. Isaacs declined to speak with the Mercury. Moore did not respond to multiple requests for comment. Metro Chamber spokesperson Monice Wong said she couldn’t speak for the PAC, because while they share an address, the two entities have a new firewall separating their activities.
But their goals are clear. Moore 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. Late last week, a billboard surfaced along St. Helens Road in Northwest Portland, paid for by the Ditch Mitch PAC. Portlanders first reported seeing a Ditch Mitch billboard on Beaverton Hillsdale Highway in early September, referencing an Oregonian headline from June 26 that claimed Green failed to pay a property tax bill.
“Politician Mitch Green voted to raise your taxes, didn’t pay his own taxes,” the billboard’s text reads in all capital letters. It also includes a link to the website ditchmitchgreen.com, which forwards to Green’s campaign website. (Prosen didn’t respond to the Mercury’s question asking why it forwards to that site.)
The assertion that Green hadn’t paid the tax was true, albeit briefly. Green paid the $7,328 bill in full, according to a receipt Green sent to the Mercury demonstrating he made the payment, effective June 29, just after being contacted by the Oregonian.
Green took responsibility for being late on his tax payment, saying the person who suffered the most was his wife, who has dealt with a stack of mail on his desk “for two years on a rolling basis.” He added that he thought the bill was already paid through an escrow account, and learned it had not been paid when the reporter contacted him.
“Everyday citizens? Not everyone pays their taxes on the day that they’re due,” Prosen said. “People are on payment plans. Some people forget to pay them. They get a notice in the mail. I think it’s a good thing that he paid them back right away. But I don’t think that it should be the public’s job to make sure that Mitch pays his taxes.”
That new billboard advertises a website of its own, which features a collection of the same images on anti-Green billboards.
Since taking office, DSA-affiliated councilors have faced pushback from entrenched political forces. Prosen too has been outspoken against DSA-affiliated candidates online, instead favoring candidates like Kellie Torres running in City Council District 3, and Washington’s 3rd Congressional District incumbent Marie Gluesenkamp Perez.
Prosen recently 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 for a reason.
“Guess who was not endorsed by this labor group?” Prosen said in the video. “The DSA. Oh, why is that? Because maybe they don’t support unions the way that they should.”
Prosen told the Mercury he doesn’t see DSA candidates as anti-labor, but said he noticed that some labor unions have not endorsed DSA candidates in this election.
“Anyone who follows the DSA knows that they are not anti-labor,” Prosen said. “I’m more of a results kind of person, and when I look at who supports labor, but then also who earns their endorsements, there’s an argument to be made for when you look at the endorsements from labor groups, there are a lot of labor groups that did not endorse the DSA [candidates.]”
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. NOLC’s top brass Laurie Wimmer, for instance, made inflammatory comments about DSA councilors earlier this year during a vote for Council president. As the Mercury reported, public records showed Wimmer saying she was “disgusted,” accusing progressive councilors of “race baiting,” and calling DSA the “MAGA of the left.”
As the election nears, wealthy local political activists and their allies are pulling out their checkbooks to defeat progressives who won City Hall offices through ranked-choice elections in 2024, two years after voters approved sweeping changes to how local government is structured.
Early last week, another billboard popped up soon after the Ditch Mitch billboard, endorsing Multnomah County chair candidate Julia Brim-Edwards in the county’s first ranked-choice election. It noted that the same PACs—Go PDX and United for Portland—were the top funders, with another PAC, Fix MultCo, listed as paying for the ad. Prosen declined to talk about why he supports Brim Edwards for chair.
The wealthy, organized opposition comes from a familiar, but largely opaque place. Isaacs, the United for Portland treasurer, also maintains a web of PACs that pass money back and forth to one another, including Portland Alliance PAC, Oregon Prosperity Action Fund, and Coalition for Portland’s Future. And their efforts aren’t happening in a vacuum. In late August, the Mercury reported on another group flying under the banner Go Portland Go, largely made up of connected, conservative interest groups like Partnership for Progress that use progressive language to oust progressive elected officials.
The efforts aren’t cheap, but they’re meant to hit a different audience than traditional ad buys or social media promotion, Prosen said.
“Everybody sees billboards,” Prosen said. “Not everyone is on social media, and not everyone likes to be connected to politics when they’re on social media. So, the idea of putting up billboards, I think it reaches more people where they are in their everyday lives.”
According to its public dashboard, Lamar—the advertising company that hosts the billboards—the Beaverton Hillsdale billboard costs $6,500 for a four-week run, although discounts are available for longer runs. Lamar says that billboard is seen an average of 73,000 times per week, largely from drivers headed into the city from the suburbs. In the northwest industrial area, the signs run $1,750 for four weeks, promising nearly 120,000 ad impressions per week. The Brim-Edwards sign hangs above the fine dining restaurant Le Pigeon, at a cost of $10,000 for four weeks, for 101,000 ad impressions per week. A Lamar representative did not respond to the Mercury’s multiple requests asking if the company granted any discount.
The billboards’ disclaimers may run afoul of state campaign disclosure laws. Political advertisements are legally required to include information about who paid for them. State law outlines strict guidelines for disclosure of who paid for communications in support of or in opposition to candidates.
While some of that information is included, Oregon law requires political action and petition committees to disclose both the full name of the committees and the PAC ID number as registered with the Secretary of State’s office. PACs are also required to file a Statement of Organization within three days of receiving a contribution or making an expenditure.
The Ditch Mitch billboard arrived on Beaverton Hillsdale Highway at least as early as September 7. But Go PDX, Fix MultCo, and Ditch Mitch all filed September 14—seven days after it first appeared, according to state records. The new website’s disclosure also fails to include the PAC ID registered with the state, though it does list the contributing parties.
Asked if Portlanders can expect more billboards, Prosen declined to comment. Asked if there were other PACs waiting to come online, Prosen hesitated.
“I’ll say no comment,” Prosen said.
