Dispatch from Portland 2022: The Hipster's Lament

"It’s a cliche, but I always feel like saying, 'I’m not the one who changed.' Portland has taken an outrageous and bizarre turn and there is just no end in sight."

"I'm sorry to use you as a confession booth, generally speaking I don't share my thoughts about Portland with anyone," wrote Jake, whom I'd met briefly during an antifa/Proud Boys melee in Portland, Oregon in August 2020.

Jake, who works in advertising and asked that his real name not be used, reached out after seeing that I was back in the city, writing about the ramp-up in homelessness and how Oregon Ballot Measure 110, which made "personal non-commercial possession of a controlled substance no more than a Class E violation (max fine of $100 fine),” seemed to be a contributing factor.

“I am the quintessential Portland hipster,” Jake wrote, someone you’d expect to support measures that decriminalize drugs, keep people out of jail, and offer support to those living on the street. And yet the consequences of Measure 110, or what Jake saw as the consequences, had made him a realist.

“The ‘homeless’ guy who stole your catalytic converter generates more revenue than you do, dude,” he wrote, citing data that states an individual with a severe heroin addiction “can spend between $22,810 and $91,250 per year, on heroin, depending on its street price.”

“From the standard ‘social ecology’ paradigm of the average Portland liberal, the addiction habits of the ‘homeless’ population are an outrageous insult,” he continued. “No one is going to jail or prison for ‘addiction’; they are going to jail and prison for grand larceny, assault, destruction of property, burglary, etc. This reality needs to be taught and spelled out for most Portlanders.”

Jake found that his peers did not want this spelled out, or not yet. Also, that his views made him something of a pariah, as if the rise in crime (with the notable exception of drug/narcotic offenses, non-commercial possession no longer being a crime) and “those experiencing temporarily houselessness” (current Portland vernacular) were simply the cost of good intentions, and that it was up to Portlanders to “plumb the depths of our own prejudices” and become comfortable with people camping on their curb, pooping on their lawn, or shooting up next to them in the bar.

Such “quality of life” crimes have risen precipitously since I moved from Portland in 2019. Drive around the city for 20 minutes and you will pass hundreds of tents, in depressed areas and upscale ones, along freeway embankments, under bridges and across from grade schools. Particularly shocking to me were the blocks running perpendicular to downtown’s waterfront, which after dark on a recent Tuesday were completely lined with tents, a city within a city not in evidence a year ago. Had this been the scene in 2004, I would have wondered what was going on to make it so and given serious thought before moving to Portland. Friends I dined with that night, who relocated to the city in 2018, agreed. Also, they are looking to leave.

Jake said he, his wife and son are not leaving.

“It’s not looking pretty at this point but I’m still confident it will turn around,” he wrote. Also, about how his love for Portland is being tested, and why he has hope "the tide will turn." The following are his words, very lightly edited for clarity.

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I was/am the quintessential Portland hipster. I moved to Oregon in 1999 when rent was absurdly cheap. I had painting shows in cafes and galleries; worked in bars; my wife and I biked to the bluffs. Our idea of a great date was going to Powell’s for a few hours.

We bought a fantastic house on Portland's Eastside at the absolute perfect time. We did Airbnb for several years and loved welcoming people and making friends with many of our guests, we showed people around, told them about hidden gems, it was awesome. People were so excited to visit Portland and it was genuinely pleasant to share it with them. I got into advertising and worked directly with some top tier people. Portland was very kind to us. We took full advantage of that era. We loved the city and it felt like the city loved us.

It’s embarrassing to describe my background this way; I guess it’s a kind of disclaimer that I’m not some right-wing reactionary or heartless asshole. I’m still actually a registered Democrat but at this point I’ve literally been accused of being alt-right. It’s a cliche, but I always feel like saying, “I’m not the one who changed.” Portland has taken an outrageous and bizarre turn and there is just no end in sight.

I’ve gone through so many mixed emotions on this, from straight-up anger, to disappointment, sadness, disillusionment, embarrassment.

At this point I’ve basically stopped trying to get through to my friends and family who are committed to a “liberal” or “progressive” paradigm. Their delusions and refusal to take responsibility, to admit fault, to be humble in the face of obvious policy and ideological failures, has completely destroyed any charity or benefit of the doubt I once gave them. I see people like [district attorney] Mike Schmitt, [city council member] Jo Ann Hardesty, [pro-antifa failed mayoral candidate] Sarah Innarone and other prominent Portland public figures as extraordinarily dangerous people.

Interestingly, I do not have the scorn for [Mayor] Ted Wheeler that other Portlanders have. I see him more as a Richard II than a Claudius. Just a completely ineffectual, spineless, and cowardly man who never anticipated this. I feel sorry for him. He was attacked several times, intimidated, and menaced in his own home. People harassed him and insulted and openly mocked him relentlessly. I appreciate him because he didn’t pull an LBJ; he ran for re-election and stopped Sarah Innarone from taking the wheel.

The regular people of Portland, regardless of party affiliation or political leaning, have been watching the progressive policy disasters unfold, each one worse than the last. First, it’s the no-camping laws going unenforced, then it’s no traffic stops, then it’s defunding the Gun Violence Reduction Task Force, then it’s no enforcement of drug laws, then it’s open support for rioting during a pandemic. All of these issues are connected in the minds of regular Portlanders, and they are disgusted. I’ve had countless interactions and conversations with people who have nothing but contempt for the city leadership and the ideological framework it represents.

One of the many conclusions I’ve reached is that progressives, the academic left, the woke, whatever you want to call them, are abusive bullies. I’m ashamed to have been one.

I now identify as politically non-binary. The most visceral example of far-left bullie is, of course, antifa/BLM. Portland has fallen prey to this bullying from the highest level down.

The backlash is coming. There is a resentment under the surface that is palpable. There’s anger and a desire for revenge. I’ve seen evidence of people not only expressing the desire to “vote out” the prototypical liberal/progressive politicians, but people wanting vengeance against the common criminals that have become so ubiquitous in the city: drug addicted campers, smash-and-grab thieves, rioters, looters. Accurately or not, these people are conflated with progressive policies. If you read the comment sections on the Instagram page @wtfportland, you will see comment after comment lambasting progressives for their perceived support of lawlessness and criminality.

What will the backlash look like? I’m not sure. I don’t think there will be a tremendous amount of open violence (i.e., antifa/BLM-types getting jumped, or Charles Bronson-style vigilantism). But I do foresee actual disenfranchisement and open hostility towards anyone associated with the pre-election riots of 2020, which I view as the progressive’s “Woodstock years," a culmination of every adolescent, “Fuck you, Dad” fantasy they’ve ever had.

An unfortunate example of what I mean by actual disenfranchisement would be a working-class person who’s adopted far-left/NPR/”in defense of looting” views and is also saddled with large student loan debt, and the employers not even giving them a chance because of even a hint of support of antifa or BLM or far-left progressive issues.

Most employers will not openly admit to it, mainly for fear of litigation, but why would they hire someone who openly advocated for the smashing of windows and looting of businesses? From a practical and realistic standpoint, and however distasteful, if I owned a pizza parlor or a food cart or a shop, and I saw evidence for antifa/BLM/neo-Marxist sympathies, I’d just throw the application in the fucking garbage.

You can’t blame the business owners who’ve weathered this storm. Hostility and rancor seem perfectly reasonable responses at this point. And it will be the people at the bottom who will suffer.

My hope is that the negative emotion most Portlanders feel will eventually manifest itself as mockery and rejection and, eventually, lead to healing and forgiveness.

Another potentially good outcome would be for antifa/BLM types to feel a sense of shame and genuine embarrassment. Maybe in a few years people who rioted and spazzed out in pre-election 2020 riots will [feel some shame], and then they’ll get a pass for past bad behavior. That said, I won’t be surprised if a lot of [job] applications end up in the garbage. You can’t blame people for not wanting to invite a vampire into their house.

On the flip side, in many non-working-class professions in Portland, a politically correct ideology seems to be a prerequisite. I just don’t know how sustainable this dynamic can be in the long run. One of the weakest elements of far-left ideology is its apparent inability to course correct, as evidenced by the countless policy failures and total lack of self-examination or introspection. This creates discord and negative outcomes with serious consequences for citizens, consequences we experience every day.

I’ve seen firsthand how the far-left ideological framework is especially destructive and unsustainable in the creative fields. Comedy is obviously the most widely noticed creative genre that has suffered, but there are similar degradations in all the performing and visual arts. I’ve seen it firsthand.

It’s hard to articulate but this is perhaps the worst causality of this cultural revolution: Being betrayed and let down by people by colleagues and friends. I’m part of the creative community here. I have tremendous professional respect for many of these people. They were once hilarious, productive, intelligent, cool, stylish people, artists, musicians. They were awesome. Now, so many of them are just zombies; ideologically driven and anxiety-ridden and more miserable than ever.

A lot of people now disparage their accomplishments, “It was all based on gentrification, anyway.” That kind of thing. I think it’s just sad, watching previously amazing people fold and give up.

I remember reading a book about a follower of Sai Baba in India, a notoriously abusive cult leader/creep. The author talked about second-guessing himself and being forced to re-examine basic beliefs and assumptions, to the point where after only a few hours he would be completely exhausted. That’s what a contemporary Zoom meeting/struggle session is like. “Work” is rarely the topic at hand. Instead it's endless talk of the latest transgression in the office, a perceived slight, a national news story, or the current collective moral panic. So much wasted time.

Any reasonable solutions or incentives to get the situation with illegal campers, addicts, criminals under control will have to be coordinated, currently with the most unreasonable people. Jo Ann Hardesty and Mike Schmidt [whose office declined to prosecute 91% of those arrested during the 2020 protests] are fantastic examples of the brick wall that Portland is dealing with. Eric Garcetti in LA, Chesa Boudin in SF are similarly unreachable. They are ego-driven true believers. I don’t think they will ever offer concessions, apologies, amends, remorse, or show any humility. It’s just not in their nature. They need to get pushed out of the way.

I do think the tide will turn towards some level of rationality. But this will take several years and multiple election cycles. Until then, cities like San Francisco, Seattle, and my beloved Portland are going to continue to suffer.

This is part three of Dispatch from Portland: 2022. Click for part one and part two.

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