The Downfall of America's Cities: Is Portland the Endgame?

Oct 06, 2026 11:15 AM
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The Downfall of America's Cities: Is Portland the Endgame?
Stormy Petrel, the dark harbinger. (Credit: Ward Clark via AI - Night Cafe Creator)
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Given that I am and will remain a denizen of a small rural community in Alaska, I am an odd one indeed to be writing about the state of America's urban areas. If you've been reading my work for more than the last few years, you know I grew up in a rural setting in Iowa, and today I am and will remain a happy rural dweller. I have little love for cities, despite having lived in them for four decades. I find them unpleasant; crowded, noisy, and, to be honest, they stink. I like the clean country air of the Susitna Valley, and if that means I have to put up with the occasional cow moose and her calf hanging around the property as happened this morning, that's fine.

So, why am I still worried about America's cities? Because our cities are the beating hearts of our nation. Much of the country's economic activity happens there. Urban areas host much of the country's industry and academia. What's more, our cities used to be the pride of the nation, but that's less the case now. Case in point: Portland, Oregon, once a haven, now a hellscape. And it's the fault of leftist politicians and leftist policies, which brings one to ask: Is Portland the left's endgame?

It may well be. A recent City Journal piece by Adam Lehodey paints an unpleasant picture of this once-pleasant city, now a haven of crime, homelessness, drug use, incompetent city officials, and oh, yes, the home base of the vicious little goblins of Antifa.

It’s 10:30 p.m. on West Burnside Avenue. Morbid figures drag themselves up and down the street. They have erected tents on sidewalks, where they smoke meth and fentanyl, obtained for as little as a dollar. Many hunch over, “nodding out” to preserve their high. Many are in wheelchairs. Portlanders step over them on their way to a night out at the handful of bars and clubs that remain open in the area.

Scenes like these epitomize the aftermath of pandemic-era drug decriminalization, police cuts, and progressive approaches to prosecution—policies that have left Oregon’s largest city with an under-resourced, understaffed police bureau struggling to enforce basic laws. The weirdness that once attracted so many to the Rose City has devolved into pervasive disorder and squalor, turning Portland into a case study in failed urban governance.

A failed urban area indeed, and one that people are fleeing, if they can; up to 40 percent of Portland's population are reported to have considered leaving, some for other cities and towns in the Pacific Northwest, some to other areas entirely, including cleaner, safer and more business-friendly places in Texas, Florida and other red states. And, honestly, who could blame them? The city's answer to every problem is to throw the taxpayer's money at it, and yet the homeless enclaves are growing, open-air drug use is increasing, and, yes, this is the home base of Antifa, who are openly hostile to any manner of business enterprise. 

And, when faced with a morning on the streets of Portland like this, who could blame them?

When the sun rises on West Burnside Avenue the following morning, the scene doesn’t look much better. A man lies with his genitals exposed. Another carries construction material down the street, swinging it at street signs as passersby cross to avoid him. Vagrants slumber on benches in well-to-do Laurelhurst Park. A woman rushes out of a CVS pharmacy, her jacket bulging with merchandise. An army of private security guards roams the streets, but the best they can do, one tells me, is “move along” anyone causing problems.

This, folks, is the leftist endgame. Do you want to know the direction our cities are headed under Democrat rule? Look at Portland. Do you want to know how our cities will collapse, into crime and despair? Look at Portland. Do you want to know how our major cities will die, how their residents will flee? Look at Portland. It's all happening right there, right now, every day.

It all started downhill long ago, but six years ago, Portland hit the TURBO button. In 2020, Oregon voters approved a measure to decriminalize user possession of drugs. As a result, drug use skyrocketed, as did the crimes, from aggravated assault to industrial-grade shoplifting, that went with that. Also in 2020, the city was caught up in the notorious "Summer of Love" riots, which caused billions in property damage — while the city of Portland slashed its police budget by $15 million. 

This started Portland on its downward slide, that it's still on today. 

There may be some small signs of hope. Mr. Lehodey continues:

But these feelings of hopelessness are not universal, because recent years have brought a pushback. In 2024, the Oregon legislature reversed drug decriminalization; in January 2025, tough-on-crime prosecutor Nathan Vasquez took over as Multnomah County district attorney. To bolster public safety fully, though, one key step remains: give police the power to enforce the law.

A measure that would have restored funding for the Portland Police Bureau failed to make it onto November’s ballot after entrenched progressive interests brought legal challenges against it, a city hall elections insider was caught following petition-gatherers, and signatures were disqualified at disproportionately high rates. Nevertheless, the fight for Portland continues.

Note that the political left can and will bitterly oppose any measure that might actually improve the city. Note that a measure, a ballot measure that would allow the people of Portland to have their own say in funding their local police department, was opposed by the city's establishment, leftists all. And note also that these people, like all leftists in these cities who continually make things worse, are almost universally sheltered, by wealth and/or private security details, from the damage their own policies have wrought. 

But it will take more than a ballot initiative. It will take Portland's voters to mandate a serious change of course, starting now, with the 2026 elections. Until that happens, any policy improvements will only be nibbling around the edges of Portland's problems.

Look to Portland, dear readers. Unless some major change of course is in the offing, and from looking at cities like New York and Seattle, that seems unlikely, this is the endgame for many of our major cities.

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