On the first weekend of my road trip, my friends Justin and Amna joined me. They are a couple and Justin, feeling that he had to sweeten the deal for Amna as a form of recompense for the inevitable bender that he and I would go on, had used an app to find a deal on a nice hotel for the weekend. The way the app worked was that you couldn't choose which specific hotel you wanted to go to. You could only choose an area and the app would use its algorithm to pick a hotel for you.

The algorithm chose a spot in downtown Portland called the Royal Sonesta, so I booked a room there as well for the first weekend, before I would move to an Airbnb to spend the rest of the week on my own.

When I arrived at the hotel, I found that it was just a few blocks away from one of the many skid rows of Portland. There’s a law in Portland that allows anyone to pitch a tent pretty much anywhere and not be removed by the cops, and so that’s what people do. There are tents everywhere, in poor areas and rich ones too, and they’re often clustered together in little blights.

It can be awkward to walk down the street in such an environment. Even in areas with expensive shops and restaurants, there were homeless people set up on sidewalks, many of them mentally ill in some visible way or just throwing a fit or something.

When I was in college, I read Edith Hamilton's Mythology and learned about an ancient Greek word that, I think, captures this feeling of awkwardness. The word is Aidos, which is the name of a God who personifies “the feeling a prosperous man should have in the presence of the unfortunate — not compassion, but a sense that the difference between him and those poor wretches is not deserved.”¹

After checking into the hotel and going out to explore with Justin and Amna, I began to notice something else about Portland. It was that almost everyone — or perhaps even everyone — had visible tattoos, piercings, gauged earrings, brightly colored hair, or some combination thereof. I saw a staggering number of face tattoos in Portland, so many that the idea seemed completely normalized within the local community. I had never seen anything like it and didn't know that such a place could even exist in America; it was a true city of punks.

A friend once told me joke about punks. It used to be, he said, that if you saw someone dressed as a punk, they wanted your wallet. But today they want to recite their poetry to you. I have found the observation of this little joke to be true. As intimidating as punks look, they are, far more often than not, the friendliest of strangers.

The Bifurcated City

On our second evening in Portland, Justin, Amna, and I had tacos at a small, casual restaurant on the East side of the Willamette River.

Portland, by the way, is bifurcated by the Willamette River, which cuts through the middle of city from North to South. The West side of the river is gray with a number of somewhat sinister looking skyscrapers and the East side is green with beautiful tree-lined roads and little houses. Here are two pictures I took that show this contrast.

The restaurant was on the green side of the river and we hadn't explored that area yet, so, after we finished our dinner, we walked around in the drizzling rain and eventually walked by a bar where we could hear music from the street. It was a Wilco cover band playing and I love Wilco, so we went inside. In the bar, there were wooden tables and chairs strewn about, each one of them in use, some standing area in the back, and a very short stage up front where the band was playing. The crowd was of mixed ages and there was a good portion of older, more mild looking punks — the kind with thick-rimmed glasses, neck tattoos, and nice looking sport coats or dresses, as opposed to leather jackets and ripped jeans.

I had never heard a Wilco cover band before and was surprised, in a way, that such a cover band existed, since Wilco isn't as popular as other bands, but their covers were great and I loved it, all the same.

We stood for a while and finally got a table towards the rear when some people left. Then Justin discovered that the bar in the back had a specialty in fine scotches, and so began our promised bender. He soon came back with two Lagavulins and, when the band took a break, we talked about how lucky we were in our lives and felt grateful.

After a few more drinks, we took an Uber back to the gray side of the river, near our hotel, and arrived at a punk rock bar that we had discovered the night before. The bartender there was the picture of a Portland punk: He was middle-aged, with long hair, an old leather jacket, and tattoos on his hands, and yet, when he talked, he was soft-spoken, articulate, and respectful — the opposite of what his appearance might first suggest. He poured some beer and shots for Justin and me and we watched the punk band there play for a while. Soon Amna, who wasn't drinking that night and who was by then probably tired of Justin and me and our presumably incoherent drunken talk, left to go back to the hotel.

I have always loved punk music. There is something cathartic about how loud and aggressive it is in person and it is surprisingly emotional to me. At the same time, there is an idealism among the punks, a certain ethos that makes many of them less judgmental than others. Justin and I were probably the most lame and clean-cut and square of all the people in the room, he and I being corporate slobs without any tattoos or piercings or anything, but I never felt unwelcome or judged or disrespected in the crowd of thrashing punks.

Justin and I went to one more place, a hip hop club, before getting separated, which often happens on a bender. Eventually I left the club and walked to Voodoo Doughnuts, a famous little chain there in Portland, and got a quantity of doughnuts that would only sound reasonable to a drunk person. I walked back to the hotel and was eating a doughnut in the lobby when Justin finally came in. We sat and ate doughnuts together in a satisfied torpor before finally going to bed.

On My Own

The next day, after checking out of the hotel and having breakfast together, Justin and Amna drove back home to Seattle and I checked into my Airbnb, which was in a lush area called Alberta on the green side of the river. After I finished unloading my car, I walked to a nearby strip to get groceries and it started to rain on my way back and I got pretty wet. Usually I would wear a raincoat for such an outing in the Pacific Northwest, but it turned out that I had forgotten my raincoat at the hip hop club the night before.

After drying myself off and settling into the little apartment, a spell of loneliness came over me. Apparently, the same thing happened to Steinbeck after he left familiar territory on his own American road trip. Here is what he says in his Travels:

A desolate loneliness settled on me — almost a frightening loneliness... I turned the gas mantle high, lit the kerosene lamp, and lighted two burners of my stove to drive the loneliness away. The rain drummed on the metal roof. Nothing in my stock of foods looked edible. The darkness fell and the trees moved closer. Over the rain drums I seemed to hear voices, as though a crowd of people muttered and mumbled offstage.²

It was only a moment, but the feeling was jarring. I was all on my own and my adventure had really begun.

To not have a raincoat in the Pacific Northwest is utterly insane, so I had to get my mine back. After dinner, I drove to the hip hop club but couldn't find parking nearby. There was a road called Burnside that I got stuck on that didn't allow me to make a left turn, which would have enabled me to get closer to the club, so I turned right and parked my car in the closest lot I could find.

That road Burnside, it turned out, was another dividing line of Portland. As soon as I made that right turn, I saw a profusion of tents on the sidewalks and people melting things on tinfoil with lighters.

When I was paying for parking at the machine in the little lot, a homeless-looking white guy came in from the street and walked around. There were just the two of us there in that parking lot and, as I was waiting for my credit card payment to process, he came awkwardly close to me, so close that he could have reached out and touched me. The guy was young looking, probably in his twenties, and was wearing all black — a black hoodie, backpack — the standard look.

I probably wasn't in any real danger, but the experience felt a bit scary. I assumed the man was a drug addict and that he was homeless, based on his puffy, scabbed skin and his tattered clothes. If the man were merely homeless, it wouldn't have been as scary, since, in that case, I would have still assumed that he was reasonable. But drug addicts are often not reasonable. We've all heard the stories or had the first hand experiences of dealing with addicts. They can be erratic, emotional, and one doesn't know what their limits are, what their current emotional state would enable them to do.

I walked out of the little parking lot and made my way to the club. When I got there, they said that I would have to come back later. Someone who works there had taken my raincoat home and would bring it back the following evening.

Walking back to the car, some other guy started following me. I couldn't tell if he was homeless, but he seemed to be hanging out with the other homeless people there. He was small and skinny and was coughing and spitting on the road, just one or two steps behind me. An old homeless man with a walker stopped him after I walked by and asked him for a lighter. By then I was about to turn into the parking lot. I got in my car and drove out of there.

Richard Rorty, Political Correctness, Masking, and Moralistic Sadism

The problem of homelessness in Portland is where I think one can see the breakdown of the modern Left and its current political strategy. My take is that the Left is applying a strategy that’s been successful before, but which isn’t fit to solve the problem of homelessness. Let me explain what I mean.

In his book Achieving Our Country, the philosopher Richard Rorty distinguishes between two social pathologies in American society and two corresponding Leftist political strategies intended to address them. The first pathology is what Rorty calls socially accepted sadism, which refers to the practice of publicly humiliating people who “bear an ineradicable stigma,” such as being gay or Black or transgendered or “other” in some relevant way.³ The second pathology is what he calls economic selfishness, which is the urge of the moneyed classes to protect their wealth and to restrict social mobility.

The strategy that developed to resist socially accepted sadism is known as political correctness. Political correctness aims to change America’s cultural norms by, in part, making it socially unacceptable to use racist, homophobic, and xenophobic epithets in everyday conversation. The widespread adoption of such politically correct attitudes, Rorty writes, “has made America a far more civilized society than it was thirty years ago.”⁴ And I agree with him. However, while this cultural strategy still has its merits today, I think that, in its application to the problem of homelessness, it is spurious.

Here’s an example of what I mean. On my first night in Portland, when Justin and Amna and I were out drinking, we met someone at a bar and talked briefly about homelessness in the city. One of the first things this person did was to correct our usage of the term “homeless.” The term we are supposed to use, he said, is “unhoused.” The idea motivating this small rebuke is that, by changing the way we talk about the problem of homelessness, the problem can be solved, or, at least, more easily be solved. This is the cultural strategy at work.

My objection is that this strategy doesn’t fit the problem. Here are two reasons why. First, the term “homeless” does not have the same negative connotations or intent as the racial, homophobic, or xenophobic epithets that the earlier movement aimed to make unacceptable. Making it unacceptable to use such epithets is an improvement, as Rorty recognized, but it is not clear that making it unacceptable to use a common word like “homeless,” which does not have any such negative connotations, is any improvement at all.

Second — and this is my main objection to this language focused strategy — is that, even if everyone were to change the way they talk about homelessness, this would still not fix the problem of homelessness itself. This is because homelessness is an irreducibly material problem. The problem of socially acceptable sadism, in contrast, can persist or be extinguished regardless of the distribution of wealth and economic opportunity within our society. The eradication of homelessness, on the other hand, requires changes in the distribution of wealth and opportunity. That is to say, it requires material changes. Its solution is not new language, therefore, but new laws that shift the distribution of economic opportunity in the appropriate way.

Still, many Leftists continue to believe passionately in the cultural-linguistic strategy. But I have come to suspect that there is something else lurking underneath this passion, at least in some cases. While the goal of the cultural strategy, as Rorty calls it, is to reduce sadism in American society, I think that it has given rise to a moralistic sadism of its own. There is a certain sadistic pleasure that many allow themselves in rebuking others for their apparent transgressions against America’s changing cultural and linguistic norms. It is the pleasure of believing in one’s moral superiority, and of believing, paradoxically, that one is morally justified in unleashing his or her own petty cruelty in shaming anyone who does not comply with these new standards.

I saw what seemed to be an instance of this moralistic sadism in the Still Requiring Masks signs posted in a few shops. While the reason for these signs was ostensibly to keep people safe from COVID-19, by the time I was in Portland, the vaccine had been generally available for over a year and Portland had one of the highest vaccination rates in the country.⁵ These facts led me to suspect that perhaps part of the reason why these signs were posted was to create opportunities for shopkeepers to partake in the sadistic pleasure of berating the unmasked for their apparent lack of care for the immunocompromised and to compliment themselves for their virtue.

This moralistic sadism, in my opinion, is an improvement over the outright bigotry and hatred that the original movement aimed to eliminate, but it is a considerable problem too. It is, it seems, yet another manifestation of the same all-too-human instinct to cruelty.

The Reformist Left, Karl Popper, and the Interpretation of History

If one follows me in my view that the cultural strategy is bound to be ineffectual in solving the problem of homelessness, then the question that naturally arises is: What, then, can be done?

There was a second Leftist strategy, according to Rorty, that would have been up to the task. This was the reformist Left, which developed to resist the urge to economic selfishness, the second of the two social pathologies that Rorty identifies. The reformist left, in contrast with the cultural left, was focused on political action. It was focused on changing or enacting specific policies and its achievements, while it existed, were substantial. They include the National Labor Relations Act of 1935, the Social Security Act of the same year, the Civil Rights Act of 1964, the Voting Rights Act of 1965, and the Medicare and Medicate Act of 1965.

All these legislative victories helped to reduce the concentration of wealth and power in American society and to distribute it more widely, thereby counteracting the urge to economic selfishness of the moneyed classes.

But what happened to the reformist Left? Why is there no salient movement today aiming to identify and enact the specific reforms that would solve the problem of homelessness?

The answer, according to Rorty, is that the reformist Left was derailed in the aftermath of the Vietnam war by a paralyzing pessimism that persists to this day. This pessimism is motivated by a reevaluation of American history that does not see the American story as anything to be proud of. It does not see it as a march toward ever greater democratic enfranchisement and freedom. On the contrary,

In this vision, the two-hundred-year history of the United States — indeed, the history of the European and American people since the Enlightenment — has been pervaded by hypocrisy and self-deception.⁶

This bleak vision of America's past, which Rorty saw come into ascendancy in the academy in the late sixties through the nineteen-nineties, has now entered the mainstream of American culture with artifacts like the New York Times' 1619 Project and bestselling books such as Robin DiAngelo's White Fragility, whose opening lines in the author's note say:

The United States was founded on the principle that all people are created equal. Yet the nation began with the attempted genocide of Indigenous people and the theft of their land. American wealth was built on the labor of kidnapped and enslaved Africans and their descendants. Women were denied the right to vote until 1920, and black women were denied access to that right until 1965.⁷

People who adopt such a view of American history, Rorty writes, “find pride in American citizenship impossible, and vigorous participation in electoral politics pointless. They associate American patriotism with an endorsement of atrocities...”⁸

Rorty's position, then, is that the adoption of such disenchanting views of American history sapped the necessary national pride and energy from the reformist Left and caused it to dissolve. “National pride is to countries what self-respect is to individuals,” he writes, “a necessary condition for self improvement.”⁹

I think that Rorty's analysis is right. Some degree of national pride is necessary to motivate the people to political action and it is hard to muster such pride in Leftist circles today because of an unyielding pessimism about what even is possible. But this pessimism need not persist. While the facts that the bleak view of American history emphasizes are undeniably true, it would be a mistake to believe that this pessimistic view of American history is incompatible with an optimistic one. Rather, as the philosopher Karl Popper writes in 1945, these two histories “may be complementary to each other, as would be two views of the same landscape seen from two different points.”¹⁰

Intuitively, there must be a way to tell the story of America that includes the stories of people like my grandfather, whom I talked about in my last post, and the many immigrants like him, together with the history of American slavery and the stories of Emmett Till and Trayvon Martin and George Floyd, in a way that does not take away from the good or the evil in either, and that captures the complex interrelations between the two.

If it is possible to tell such a story — and if it is possible to remind Leftists and Centrists alike that the American people are the people of the world and that, in the eyes of many, America remains the hope of the world — then the enervating pessimism of the Left need not frustrate political action. In principle, in democratic society, there is nothing preventing the problem of homelessness, or any other political problem, from being solved. In democratic society, the only thing blocking progress is ourselves.

While I had wanted to think more about these problems when I was in Portland, and while I had wanted to get out and explore the city more besides, I ended up spending the rest of my time there in my Airbnb writing code. The nature of my work is that there are some weeks where I need to work only a few hours a day, but then there are others where I have to work ten or twelve or fifteen hours a day to get something done, and my week in Portland was one of the busy ones.

On Monday night, I went out and finally got my raincoat back, but otherwise I only went out to get sandwiches for lunch and to have dinner at restaurants in the neighborhood, and that was about it.

By Friday, I had finished everything at work and, that evening, I loaded my car so that I could get an early start on Saturday. My plan was to drive six hours to Spokane and spend the night there and then to drive another six hours to my destination of Bozeman the following day.