I thought of her as Ohio, which is where she was from. She clerked at Movie Madness, back when Movie Madness was a nerve center, an essential resource, not a charity case. Also, back when the city was friendly—freakishly friendly, to a New Yorker like me—when you would take your time at the counter and chat with people, get their story. She had just shown up in town, she told me, had gotten on a bus and headed west, and by the time she got to Portland she was out of cash, so this is where she stopped. Found a couch to crash on, found a job, found a place, here she was. Hello, Portland.

This story is part of our 20th Anniversary Issue special section on Big Ideas for Changing Portland. Read more here.

Ohio stood for me, back then, for all the young people I’d meet around town. This was 2008, 2009. They always came from somewhere else: Montana, Alaska, Missouri, maybe small-town Oregon. They had fled the hopelessness at home, or the fundamentalism, had come to find their kind and do their thing. They were living four to a house near Division, or five to a house near Mississippi, working at a food truck or in a barber shop, playing in a band or drawing cartoons or just hanging out. And as I wandered the streets, it was them, these bohemian, working-class misfits, who seemed to me to give the neighborhoods their soul, their tone—their vibe.

And what a vibe. It was the reason I fell in love with the place at first sight, on a visit in 2004. A lot of visitors had that experience then, and the vibe was still going strong when, four years later, I came back for good. The sense was all around you, a cloud of good feeling, inventiveness, chill. I floated along the sidewalks, down Hawthorne, up Belmont. Thrift stores, herb shops, food carts, everyone bringing their dish to the picnic. Strangers smiling at you, serendipitous encounters all day long. 

The creativity: generous, abundant, not careerist and competitive like I was used to in New York. People created for each other, for their neighbors, for themselves, to make their environment more beautiful and interesting, to fill it with life. A goddess carved into a tree. Enameled insects peeking out of alleys by Alberta. A guy on Tabor building out a sculpture garden in his side yard one piece of scrap metal at a time. Cars decked out like mobile installations, miniature cities glued to their hoods. That painted intersection in Sunnyside, a blast of joy and color. 

The chill was ubiquitous. Actual Portland bumper sticker: “More relaxed than you, dude.” People idled in coffee shops in the middle of a weekday morning or sat outside sipping beer with lunch. Not long after I arrived, I was talking with a Portland native who’d returned here in his 30s. I was quizzing him about the place, trying to get my bearings. “What do people do here?” I said. He started laughing. “Everybody asks that,” he said. “No one knows.”

Last Thursday on Alberta, a street fair in my very own neighborhood, was, for me, the apotheosis of the vibe. It was like a monthly Portland Mardi Gras from May to September. The crowd was so thick you could barely move. Booths lined the street from NE 15th to 30th Avenues with people selling homemade crafts: earrings made from typewriter keys, insects made from knives and forks, silkscreens, tie-dye. Musicians stood on every corner—acoustic guitar players, jug bands, preteen violinists. A Native American drum circle set up in the middle of an intersection. Jugglers, tumblers, half-naked stilt walkers, aerialists, capoeiristas, dancers from Oregon Ballet Theatre. Cooking smells wafted over a crowd of the same kinds of people as the vendors and performers, a single community celebrating itself. The party went on until well after dark.

The finest thing about all this was that it was so unself-conscious. You didn’t feel like anyone was putting on an act: for the cameras, as it were, or the New York Times, or an imagined someone they were trying to impress or get in with. As opposed to, say, in Brooklyn, where status and success were the whole point. It was just who they were. It was why they were here. Which also made Portland unique, idiosyncratic. The city wasn’t trying to be like somewhere else, and it wasn’t trying to make anywhere else like it.  

The storm began in 2012, once the economy had finally recovered from the Great Recession. That is when housing prices started to climb again; that is when I saw the Portland building boom everywhere I turned. Condo cubes began to sprout on Division, Vancouver, Williams, Mississippi; taller buildings in the Pearl and the Central Eastside. Slabtown, an entire neighborhood, sprang up from scratch. Crossing the Fremont Bridge, I’d count the construction cranes: six, eight, 10 at a time. It felt like an inflection point arrived in 2015. I was away for the first four months of the year. Before I left, people talked about real estate a lot. By the time I came back, it was all they were talking about.

Not coincidentally, Portlandia was in its heyday. The New York Times was taking notice of the city, with glowing pieces in the travel and style and arts sections. Now Portland was a thing. Now the vibe was a commodity, a fucking brand. Now the new arrivals weren’t Ohios. They were Californias: tech bros and other young professionals—buff, basic—bringing their salaries, their lifestyles, their expectations. They didn’t want Portland, not really. They couldn’t have told you what it was. They came, they copied, they hired contractors to build tree houses and soaking tubs while they sat indoors and pecked at their laptops. The city, to a great extent, became a simulacrum of itself, a theme park that we might as well refer to as Portlandia. It became generic, imitative, superficial: something to buy, not be.

As I’ve walked around the city in recent years, the old creative energy and generosity have seemed to be missing, sapped. There are still plenty of creative people in Portland, of course, but many left during the pandemic, and no doubt many potential newcomers have been priced out. When money is tight, artists do not make things just to make them, things that might bring joy to those around them but will not put money in their pocket. 

During Last Thursday this past summer, the crowds were less than half of what they once had been. There were large gaps in the line of booths, which petered out around NE 26th. The crafts for sale were good, for sure, but not very DIY: more finished and professional, a few of them pretty high-end, some not crafts at all but mass-produced. The vendors all had business names and websites. There was a lot less music, most of it amplified; one breakdance crew, and a single forlorn hula-hooper. The event, which only runs from June to August now, shut down at 9. At the request of local restaurants, which didn’t want the competition, food sales were banned. The whole thing had a tourist feel, a pleasant evening’s recreation for suburban families and other respectable folks. I would say that people were looking around nostalgically for the old spirit, trying to raise the ghosts of Portland past, but they weren’t. They didn’t seem to know about the ghosts. We could have been anywhere.

I feel the chill fading, too, and also, what is maybe worst of all, the friendliness. Money—that is, living among people who are spending most of their waking hours in pursuit of it, in a culture that rewards it—squeezes people’s spirits. Strangers smiling at me on the street used to be a daily, even hourly occurrence. Now it’s rare. Portland is not a big small town anymore; it’s just another city. I read the following sentence on Eater earlier this year: “Eem feels like a place that treats every employee and customer with respect, a warm spot in a cold city.” A cold city! Are we in Portland or New York?

Can Portland “come back”? Obviously, the city has much larger and more pressing problems than a limp Last Thursday. The money tsunami, with its attendant climb in housing costs, led to an explosion of homelessness. Then came fentanyl. Then came COVID. Then came spikes in violent crime. Meanwhile, the schools continue to underperform. Those are the issues that need most urgently to be addressed.

But even if they were, I’m not sure that would resurrect the vibe. It may be that the only thing that would is continued decline. I know that sounds appalling. But I remember New York in the 1970s. The city was falling apart. It was also bursting with creative energy. The two conditions were connected. The city was cheap: cheap, cheap, cheap. By the end of the decade, it had lost a 10th of its population and more than half of its manufacturing jobs. The normies had fled to the suburbs, the factories had cleared out their lofts and moved to the South, and it sometimes seemed as if the only people left, in the Village and Chelsea and Soho, amid the rats and broken glass, were musicians and artists and junkies. But a lot of great art got produced. 

For Portland to become unique and genuinely interesting again, the money boil would need to be drained. Spaces would have to empty out; property values would have to plateau if not decline. Creative freedom can’t be planned or engineered. It can only be made room for. 

This may, in fact, already be occurring. After years of empty storefronts, in little pockets here and there, in the Lloyd Center, in downtown, landlords are offering new flexibility to creative types. We can never go back to the old, but perhaps we can combine the best of old and new—the independent, cooperative spirit, so deep in Portland’s DNA, and the recent infusion of people and wealth—to take us somewhere good. Now, when cities everywhere are ailing, we should remember that Portland has shown the way forward before. It can again. 

Critic William Deresiewicz, a former English professor at Yale University, is the author of The Death of the Artist and The End of Solitude. He lives in the Vernon neighborhood.