Portland's Rapid Decline from Chic to Shabby

Once a symbol of progressive values, the city now struggles with homelessness, addiction, and crime.

Published on Feb. 7, 2026

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Portland, Oregon, once known for its chic and progressive image, has rapidly declined in recent years, with the city now grappling with a range of pervasive problems including homelessness, drug addiction, and crime. The city's struggles have become so pronounced that even progressive figures like author David Sedaris have taken notice, highlighting the city's stark transformation from a symbol of progressive values to a place defined by its social challenges.

Why it matters

Portland's rapid decline from a chic, progressive city to one struggling with significant social issues raises questions about the effectiveness of certain policies and the ability of even the most progressive cities to address complex urban challenges. As other major cities face similar problems, Portland's experience serves as a cautionary tale about the consequences of ineffective approaches to homelessness, addiction, and public safety.

The details

In a recent essay, author David Sedaris described his experience of encountering numerous homeless individuals and drug users during a walk in Portland, culminating in a dog bite incident. Sedaris was struck by the apparent lack of concern from locals, including a medical worker, about the state of the city. Portland's challenges, which also include rising crime rates, are not unique to the city, but its swift transformation from a symbol of progressive values to a place defined by these issues has made it a prominent example of urban decline.

  • In December, author David Sedaris wrote about his recent trip to Portland in a New Yorker essay.
  • Sedaris encountered numerous homeless individuals and drug users during a walk in the city.

The players

David Sedaris

A bestselling author and humorist who wrote about his experience in Portland in a New Yorker essay.

Portland, Oregon

A city that was once known for its chic and progressive image but has rapidly declined in recent years, now grappling with homelessness, drug addiction, and crime.

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What they’re saying

“I mean, how hard should it be to get a little sympathy when an unleashed dog bites you? What if I were a baby? I wondered. Would people side with me then? What if I were ninety or blind or Nelson Mandela? Why is everyone so afraid of saying that drug addicts shouldn't let their dogs bite people?”

— David Sedaris, Author (The New Yorker)

What’s next

As Portland continues to grapple with its social challenges, the city's leaders and residents will need to re-evaluate their approaches to addressing homelessness, addiction, and public safety in order to reverse the city's rapid decline.

The takeaway

Portland's transformation from a chic, progressive city to one struggling with significant social issues serves as a cautionary tale about the consequences of ineffective policies and the need for comprehensive, evidence-based solutions to address complex urban problems.