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President Trump is trying to destroy mail-in voting, but nothing can exterminate campaign mailers. Long after we have all been killed by self-aware spell-checking robots, the mailrooms of our empty apartment complexes will be overflowing with glossy flyers featuring political candidates surrounded by adoring children.
Tina Kotek and Christine Drazan are duking it out on TV, and World Series games are interrupted by warnings from across the Columbia River about something called a “John Braun.” But the battle for control of Portland City Hall and Multnomah County headquarters? That’s fought in mailboxes. Local campaign finance limits mean most local candidates can’t afford television advertising—and the most the Portland Metro Chamber will spring for is a couple of attack billboards. (We kind of hope Mitch Green’s giant head continues to keep watch over the Crystal Ballroom after the election is over.)
So mailers are where the house-to-house fighting happens. Which means it’s where the more inspired and ridiculous concepts get trotted out. Each election, we at WW bestow our Mailer Awards to the standouts.
We ask WW staff across all departments to bring in mailers they’ve received from candidates running for local, state and federal office. Then we gather in one of our conference rooms, sort through the dozens of mailers and bestow upon them accolades. It’s a lot like our endorsements, but much less important. Think of a high school yearbook’s senior superlatives, but 30% meaner and 90% funnier. Or at least we think so. —Garrett Andrews, Sophie Peel and Rachel Saslow
Most firefighters: Kellie Torres
Every public safety–focused candidate loves to pose with firefighters. The more mustaches, the better. (Yes, we know there are women firefighters.) Kellie Torres, who’s running to unseat one of the two Democratic Socialists of America members representing District 3 on the City Council, takes the top prize with 11 firefighters posing with her in a photo. Honorable mention: Julia Brim-Edwards—whose desired job as Multnomah County chair has little if anything to do with Portland Fire & Rescue—managed to corral three mustaches into one frame.
Best guilt by association: MultCo for All
Julia Brim-Edwards, according to a mailer sent by progressive political action committee MultCo for All, “received maximum contributions from the co-host of a Trump fundraiser.” That’s an impressively limber stretch to frame Brim-Edwards as a Republican in disguise. (Wouldn’t it have been simpler to mention that she used to be a Republican political strategist and worked for former U.S. Sen. Bob Packwood?) Anyway, the PAC behind the mailer is backing Shannon Singleton in the race for Multnomah County chair, and the Trump party-thrower in question is timber heir Peter Stott, who gave Brim-Edwards $603 in February.
Most frequent references to résumé: Tiffany Koyama Lane
Did you know City Councilor Tiffany Koyama Lane was a teacher? You will after reading her mailer, in which “Teacher Tiffany” mentions this work experience as many times as possible. She’s actually been working full time as a city councilor for the past two years, but still often refers to herself as “Teacher Tiffany.” She does so again in her reelection campaign. In one of her mailers, which features ample children both in classrooms and in the wild, the word “teacher” appears 11 times. After all, who can dislike a teacher? No one.
Best unattributed quote: Eli Arnold
City Council candidate Eli Arnold, a bike cop with the Portland Police Bureau, ran unsuccessfully two years ago to represent District 4 on the 12-member council. He’s back again, and this time he’s trying to swap the image of an officer with that of an affable, down-to-earth renaissance man intent on making transit fareless across the city. That policy is a known goal of the Democratic Socialists of America, a group to which Arnold decidedly does NOT belong. But we bestow this accolade not for varied interests but for an unattributed quote on one of Arnold’s mailers. Beside a photo of Arnold astride an e-bike, his mailer proclaims, “He became a police officer and ‘community dad at large.” We wonder who awarded him this title. Was it his wife or some kind of independent panel? Such a nebulous term requires you to interpret it yourself—and maybe that’s the point: Arnold is whoever you want him to be. Certainly not just a cop.
Most twisted metaphor: Christine Drazan
Christine Drazan, Republican nominee for Oregon governor, is feeling the squeeze on her mailer featuring a photo of one hand juicing an orange, another clutching an empty, battered leather wallet. “Thanks to the status quo in Salem…We’re squeezing a lot more than oranges these days,” it reads. Were we squeezing a lot of oranges before? Citrus fruits did not ask to be dragged into our state politics; leave OJ alone.
Best guest appearance by a white man you might remember
Babies: They represent all that’s good in the world. Freshness. Hope for tomorrow. Infinite possibilities. But apologies to private citizen Earl Blumenauer—who represented Oregon in Washington, D.C., as congressman for 28 years before retiring in 2025—he now projects none of these. In his endorsement of Portland City Councilor Steve Novick, Blumenauer, 78, perhaps appeals to nostalgia for a simpler time of bow ties and bike pins.
Best stunt baby
Now here’s what we’re talking about. Kellie Torres employs the time-honored political ploy of putting a darling baby front and center. Though Torres possesses the politically unfortunate combo of deep establishment ties (she’s a longtime City Hall staffer) and no legislative record (she’s never held office), the tyke is indeed a positive association for the nonheartless among us.
Best Trump-adjacent slogan
Is this horseshoe theory? Portland City Councilor Angelita Morillo, the city’s best-known democratic socialist, has lately employed a stock political phrase that’s also a favorite of President Donald Trump’s. In fact, he’s emblazoned the phrase “Promises Made, Promises Kept” across rally banners, T-shirts and White House websites. And not just in Trump 2.0; he used the phrase often in his first term in the White House as well. In 2018, Trump even accused former New York City Mayor Bill De Blasio of plagiarizing “his” expression. Turns out, the rather common turn of phrase has been used by politicians at least as far back as Hubert Humphrey in 1968.
Most unbridled confidence
In case you hadn’t heard, doctor-lawyer-former County Commissioner Sharon Meieran, who’s running for Multnomah County chair, has a plan. And if you don’t allow her to use that plan, well, you’re essentially saying it’s fine to let homeless people die on the streets. The view from Meieran’s mailer is bleak: the worst untreated mental illness and highest homeless death rate in the country. What’s more, the county is wasting money and only one candidate has a plan that would do anything about it. The savior complex is hard to miss. “Multnomah County is broken,” the mailer plainly states. “Sharon Meieran will fix it.”
Best menu: Mitch Green
Not only does Portland City Council District 4 candidate Mitch Green use a campaign logo that bears an uncanny resemblance to a Miller beer ad—white type on red background; diagonal upward slope of the script—he includes a hot dog illustration with “Mitch” written in mustard. That’s not just a cute graphic: For close followers of Portland city politics, it harks back to Green’s 2025 initiative to legalize sidewalk hot dog vendors. (The ordinance has not yet gone to a full council vote.)
Best reason to bust out your reading glasses: Julia Brim-Edwards
We get it! Multnomah County chair candidate Julia Brim-Edwards has gotten a shit-ton of endorsements. She lists more than a hundred of them on the front of a mailer, in tiny, dizzying type—starting with former Oregon Govs. Ted Kulongoski and Barbara Roberts and continuing on through a who’s who of individual Portlanders (spotted: yoga teachers, lawyers, Cleveland High’s longtime journalism teacher, a Menashe). If those aren’t enough evidence, curious voters are directed to her website for the entire list. We’re good.
Least convincing photoshop: Tina Kotek
Kotek’s mailer says, “When Donald Trump comes for Oregon…Christine Drazan stands with him.” The accompanying picture is a poorly photoshopped presentation of her Republican challenger Christine Drazan standing next to President Donald Trump. The fail starts with bad photo choices: They’re low resolution, have strange filters on them that make them gray, and indecipherable backgrounds (best guess is a warehouse?). Plus, the politicians are the wrong size compared alongside each other. At least we know it’s not AI.
