In recent decades, no major American city can match the sharp ups and downs of Portland, Oregon. From a poor but pretty backwater burg of white gearheads and provincials in the 1980s, Portland underwent an exceedingly unlikely – and quite radical – transformation to become one of the country’s most distinctive and culturally vibrant urban renaissance stories in the 2000s (the New York Times memorably declared Portland “cool and refreshingly unneurotic” in 2007).

But then, in the 2010s, the self-described “weird” and fun city, experiencing a rapid influx of young and educated newcomers drawn by post-Portlandia “where young people go to retire” hype, experienced what writer and journalist (and former Portland resident) Nancy Rommelmann has dubbed “Portlandization.” As the decade wore on, she wrote, Portland became increasingly enamored with ostentatious displays of performative virtue signaling and the militant policing of increasingly narrow and rigid progressive orthodoxies. Then that all exploded into the seemingly endless – and endlessly destructive – protests that roiled the city in 2020, which combined with a failed experiment in the decriminalization of hard drugs to bring the city to its knees, and from which Portland still has yet to fully recover.

So we asked Nancy Rommelmann, who has written extensively about Portland’s travails for Reason and Tablet and on her Make More Pie Substack page (she also co-hosts the popular Smoke ‘Em if You Got ‘Em podcast), to join us on BCB to unpack what went so wrong with Portland’s fairy tale rise and why, and where the city stands today (Rommelmann left Portland in 2019 but visits frequently and continues to write about the city).

In our conversation, we trace Portland’s evolution first into a creative, affordable, rising city and then into a symbol of blue-city political and governance struggles. We discuss Portland’s food and cultural boom in the 2000s, the growth of ideological conflict and “outrage culture,” debates around #MeToo and due process, the 2020 protests and attendant unrest, the impact of Oregon’s drug decriminalization experiment, and broader tensions within progressive urban politics.

While Nancy is largely critical of Portland’s recent trajectory, she also acknowledges the legitimate social grievances that have animated the city, and she sharply critiques right-wing and Trump administration efforts to distort and politically capitalize on Portland’s much more benign recent ICE protests, and she ends our conversation with cautious hope that Portland will fully recover.

“I get accused of being like a real naysayer about Portland, and I do have bad things to say about Portland, but I do wish good things for the city, because it's a beautiful city,” Nancy tells us. “The food is can be great, you can grow anything, and why would I not want it to fly again?”

Our editor is Quinn Waller.

OUTSIDE SOURCES:

Nancy Rommelmann, "Portlandization: It Can Happen to a Place Near You," Tablet Magazine, July 11, 2019.

Nancy Rommelmann, "The Dream of the '90s Died in Portland," Reason, March 22, 2021.

Nancy Rommelmann, "Drugs 1 - Oregon 0," Make More Pie, Feb. 29. 2024.

Nancy Rommelmann, "Trump's Troops Return to a City That Moved On: Dispatch from Portland," Reason, Oct. 6. 2025.

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