The Most Memorable Campaign Ads Arriving in Portland Mailboxes—and Posted Along One Freeway

They are filled with dubious claims, tasteless comparisons, and outright howlers.

Crisp leaves, warm cider and a good cardigan: Autumn is defined by its rituals. One of them in Portland is trying to find your ballot amid a stack of campaign junk mail.

With Portlanders trapped in their homes, those political mailers take on new urgency. For some voters, these will be the only introduction they get to candidates and measures. But they are also filled with dubious claims, tasteless comparisons, and outright howlers.

Each election, we award prizes to the best, and worst, of what we found in our mailboxes.

Most Creative: Opponents of Measure 26-218, a $4 billion transportation tax crafted by Metro against business opposition, received plenty of funding from Nike, Intel and The Standard—and proceeded to play around with it in enjoyably absurd ways. One mailer was designed like a lottery scratch-off game and contained choose-your-own questions like "Do you know what Metro is?" and "Who killed Packy?" strongly implying that the regional government murdered a beloved elephant. (Metro runs the Oregon Zoo.) The massive mailer sent by the same campaign with photos of the Titanic, Godzilla and King Kong and the caption "Sometimes Bigger Isn't Better," a reference to the largest local tax increase ever proposed in Oregon, was elegant enough to frame.

Worst Prop: Mingus Mapps, a first-time candidate who wants to unseat Commissioner Chloe Eudaly and become the third Black man elected to Portland City Hall, sent out a picture of an empty chair. We get his implication: Eudaly's not leading. But given that Eudaly's chair is currently full and he's trying to introduce himself to voters, this was poorly done. Also, it reminded us of Clint Eastwood, in a bad way.

Most Compelling Art: Multnomah County Circuit Court candidate Rima Ghandour eschewed serious-looking lawyers and legal books, instead positioning herself in front of the George Floyd mural on the plywood covering the Apple Store in downtown Portland.

Most Untimely Endorsement: Ghandour's opponent, Adrian Brown, sent out a mailer with large photos of her endorsers, including NAACP of Portland president E.D. Mondainé. The same day it arrived in mailboxes, The Portland Mercury reported multiple allegations of sexual abuse levied against Mondainé by former parishioners of his church.

Meanest Reuse of a Tweet: United for Portland, the independent expenditure campaign supporting Mayor Ted Wheeler, ran a series of tweets by his opponent, Sarah Iannarone, on a mailer. Fair enough: Many of her tweets are revealing, some ill-considered. But one is totally out of context: a tweet from Sept. 3, 2018, in which Iannarone wrote, "Oh hell, no way I can support the Blazers this year." (She was referring to a partnership the team had with a rifle scope manufacturer.) Say what you will about Iannarone, her Blazermania is a consistent and real sentiment.

Best Branding: Dr. Lisa Reynolds' mailers in her bid for Oregon House District 33 feature colors and fonts similar to those of Dunkin' Donuts. At least one East Coast transplant in our newsroom wants a Boston cream-filled every time he opens his mailbox. Just what the doctor ordered!

Worst Combination of Photo and Caption: Iannarone sent out a mailer with the caption "What does Progress for Portland look like?" Aside from the erratic capitalization, the photo beneath it—showing a crowd of supporters who if anything look even whiter than the average Portland crowd—didn't capture the diversity the candidate touts as her vision for the city.

Most Shameless: OK, this one isn't a mailer, and it's been widely reported. But along Interstate 205 near Gladstone stands a billboard that describes Metro's proposed light rail expansion as a "virus train." It's the latest broadside against light rail from a political action committee run by GOP consultant Jim Pasero, who has been fearmongering in Clackamas County about trains bringing crime and "Portland creep" since at least 2012. This time, he's implying MAX will carry COVID-19 to the suburbs. Gross.

Willamette Week’s reporting has concrete impacts that change laws, force action from civic leaders, and drive compromised politicians from public office. Support WW's journalism today.