Back in 2020, Portland, Oregon became somewhat notorious for ongoing skirmishes between federal authorities and local police against self-declared Antifa. These anti-fascists mostly turned out to be white elite kids with little else to do and who, curiously, behaved a lot like brownshirt fascists. This was all part of the race panic of 2020, and it seems most of the country has moved on from that. But, I had recent occasion to visit Portland, Oregon and wondered: does Portland still deserve its reputation as one of America’s wokest cities?
To be fair, what follows is hardly a rigorous study. It’s my observations mainly from the neighborhood my Airbnb happened to be in. For reference, it was east of the river near an area Google maps seemed to call Eliot. It consisted of older homes, very YIMBY (some of the dwellings I was pretty sure were shelters for the homeless or chronically mentally ill, both of whom were in plentiful supply) with a hipstery vibe.

Also, for reference, I’m from Orlando, where things like Black Matter Lives signs are a curiosity from the past. Orlando does have its hipster neighborhoods, but I can’t remember seeing a ton of progressive paraphernalia even in those neighborhoods1. By contrast, such things were everywhere in this little posh Portland neighborhood.
To set the scene, on my first morning there, as I was emerging for a walk, I happened to spot a college-age woman with a backpack who seemed to be aimlessly checking a box near a lamp pole. She proceeded to walk a few steps, ripped some petals from a beautiful rose bush growing near the sidewalk and sprinkled these down the inside front of her shirt. This incident was very much par for the course for Portland.
It happened to be the weekend of the “No Kings” protests. I actually think this was, finally, a movement with excellent branding from the left after a string of remarkable failures over the past 10 years. Instead of shrieking about fascism, which seems increasingly unhinged, this protest movement succintly addressed Trump’s idiosyncratic authoritarian leanings, and referenced our own patriotic past throwing off the shackles of monarchy. I hope this isn’t a one-off and reflects a true change in the progressive movement, one I could get behind. Of course, the protests were advertised on chalk pavement notes:
I’ve got no real issue with that. People have the right to protest (I’m too lazy), and this one I can get behind. If only it had been left at that.
But…like going in a time warp, Black Lives Matters posters abounded. Again, to be clear, people have every right to post these on their private property. It just did feel remarkably insular for so many folks to not realize that most of the race panic of 2020 proved to be untrue, and BLM the organization mainly used it to grift, lining their own pockets and buying manions. Note, I tried to take these pictures, in most cases, so as not to make the house or address identifyable.
Other progressive causes, including the “River to the Sea” Palestinian slogans were in evidence. Note: I think there are very smart defenses of the Palestinian cause (Zaid Jilani has been among the best on this score), but I felt that these seemed more like group membership signalling rather than strategic efforts to convince fence-sitters.
To add to the progressive vibe, community gardens were popular in this area. My impression of them was that the average community garden would likely be capable of feeding, say, half a person. I’m not sure what the real point of them is, although if people want to get together and garden, that’s obviously fine.
The neighborhood also seemed obsessed with Halloween, which I entirely support. Note that I visited in June, although a Portland June does feel like a particularly chilly Orlando Halloween, so maybe it works. I loved it, but this also made clear this neighborhood had no HOA.
Back to the failure to exit 2020. Even the “In this house we believe…” signs were still around.
Keep in mind that, aside from the one BEWARE house, all the posters I photographed are from a single, fairly short street.
I found it interesting that along one wall, someone had painted a mural dedicated to black citizens. Compared to other murals in the city, this one seemed to invoke more a sunrise in the heartlands of Kansas than anything having to do with black Americans (yes, I’m saying it’s dull). I’m not sure what black Americans are supposed to be “still here” after…
Potential taggers were warned that tagging (which was common in Portland) this mural would be “racist”.
Surprisingly, the taggers seemed to comply. I suspect in most circumstances, taggers would be the sort to feel egged on to confront a morally scolding movement that veers toward social conformity and authoritarianism. But in Portland even the taggers are cowed by “racism” accusations.
Despite, all this, apparently Portland still has a big racism problem. Indeed, they’ve got a support line in the event you are subjected to racism (not if you’re white though, you’re out of luck).
And of course, this neighborhood was no big fan of Donald Trump. I’d be curious how anyone daring to fly a MAGA flag would do (there were exactly 0 posters or flags of any right-wing belief anywhere in the neighborhood).
Ok, so I’m having a bit of fun with this. Again, it’s important to emphasize that one neighborhood doesn’t represent an entire city. Traveling through other parts of Porland, I’d say such ostentatious displays of wokeness were less common, though still periodically in evidence. By contrast, I saw nothing at all from the political right. That’s hardly a scientific survey, just my impression.
And I do need to put this in an important context: I generally really liked Portland. It’s a beautiful city with lots of interesting things to do. And the woke neighbhorhood really just amused me. I didn’t find it offensive or anything, though my bar for getting offended is pretty high.
Overall, I think people have the right to group together with others with shared beliefs. So long as they don’t try to foist their nutty beliefs on the rest of us, that’s fine. That was the problem with 2020…some insane ideologies and pseudoscientific panics started to eek out into actual policy, enforced by rigid social censorship and shaming. That predictably ended in disaster. So long as it’s confined to flag-waving in one neighborhood or city, it’s just kind of funny.
But would I guess that Portland remains one of America’s wokest cities? Probably so.
To be frank, one is more likely to see Trump stuff, which is silly in the opposite direction.