It’s been almost a week since I returned to Portland, and the echoes of the past have been hard to ignore. This isn’t my first time here; it’s my third. Each time, I’ve left with more questions than answers, and this time feels no different. The city has a way of drawing you in with its promise of refuge, only to reveal a more complicated reality beneath the surface.
The old mantra, “Keep Portland Weird,” is nowhere to be found. Not on bumper stickers, not in graffiti, not in whispered conversations. The sentiment feels as extinct as the quirky culture it was supposed to represent. Portland isn’t asking to be weird anymore; it’s asking to be clean and safe, with the trademark symbol (™) hanging over it like a corporate watermark.
I get it. Clean and safe are easier to market than weirdness. They’re easier to regulate, to control, to sell. But the shift feels like a loss of identity—a city shedding its quirks to make room for profit margins and tidy narratives. Portland is no longer the scrappy underdog that embraced the marginalized and the unconventional. It’s a business now, and like any business, its goal is profit.
The Business of Belonging
Portland takes in over $15 billion a year in federal funding. It markets itself as a sanctuary for transplants and political refugees, people searching for a place where they can rebuild and belong. But once the money’s in hand, the city’s support feels like a bait-and-switch.
“Just get them out of the way and out of sight” might as well be the unofficial motto. It’s a sentiment echoed in cities across the country—Long Beach, Los Angeles, Las Vegas—but Portland does it with a veneer of progressivism that makes it sting even more. The city leans on “solutions” that are better than outright neglect but still fall short of addressing the root causes of systemic issues.
Fifteen years ago, the streets of Portland told a different story. The people living on the margins weren’t just surviving; many were thriving. There were communities within the chaos—people from all walks of life who managed to carve out spaces for themselves. I remember shoulder cats being a thing. Now, those thriving pockets have vanished, replaced by a narrower demographic: displaced youths battling substance abuse, forced into a cycle perpetuated by systemic failure.
In nearly a week, I’ve seen only one person over thirty sleeping on the streets—a holdout, a relic of an earlier Portland. The diversity of struggle has been replaced by a monoculture of despair. It’s hard not to wonder if the city’s efforts to address homelessness have created this unintended consequence: fewer people visible on the streets, but at the cost of erasing the individuality that once defined its unhoused population.
A City in Flux
When I left Portland over fifteen years ago, it was already grappling with its identity. Weirdness vs. practicality, individuality vs. conformity, art vs. commerce—it felt like a city constantly at war with itself.
Now, it seems the war is over, and commerce won. The city I came back to feels like a theme park of its former self, a polished facade hiding the same systemic cracks you’d find anywhere else. The creativity, the quirkiness, the sense of rebellion—it’s still there, but it’s been commodified, turned into something you buy instead of something you live.
But not everything has been erased. Oregon’s Ranked Choice Voting system still offers hope for better representation. It’s a step in the right direction, even if it’s not enough to solve the deeper issues. Representation matters, but so does action. Portland can’t keep marketing itself as a refuge while marginalizing the very people it claims to protect.
The Shadow of Weirdness
For all its struggles, Portland still casts a long shadow. The holdouts of a bygone era linger at the edges, whispering reminders of what the city once was. It’s a shadow and a dichotomy, a city trying to grow up while still haunted by its past.
This is Portland’s mid-life crisis. The city doesn’t have to pick between being weird and being clean and safe. It can be both, but only if it remembers the people who made it weird in the first place. The artists, the outcasts, the dreamers—they weren’t just accessories to the city’s identity; they were its soul.
I came back to Portland with hope, but what I’ve found is a city struggling to reconcile its contradictions. Maybe that’s fitting. Portland has always been a place of tension, a place where light and dark shift and blur.
The question isn’t whether Portland can figure itself out. The question is whether it wants to.
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