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Why Does Trump Keeping Insulting Portland?

Posted on October 1, 2025

Rachel Monahan

a look at downtown, Mt. Hood in the background

Another view of Portland. (Rachel Monahan / City Cast Portland)

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According to the president, Portland is a “nightmare” and a “war zone” that looks “like World World II” and “is burning down.” And that’s just Trump’s descriptions from yesterday.

As he makes the case for deploying the National Guard to Portland, the president is using a string of absurd exaggerations — or outright lies.

Reality Check

Trump has, at best, a touch-and-go relationship with the truth. Gov. Tina Kotek and the Oregonian newspaper are among those pointing out that if Trump isn’t wholesale making this up, he’s watching old news clips from Portland's 2020 protests. (On Sept. 5, FOX News aired clips from 2020 in a story about the current ICE protests, according to the state and city’s lawsuit to block the deployment.)

And, of course, each time the President has painted a ridiculous image of our city — over many years now — he’s been greeted with mockery: “Portland? The place with therapy llamas at the airport?” posted one user on Threads.

I've felt so much fear and worry and concern in our community, but also so much joy and doubling down on what is delightful about our city.John Notarianni , City Cast Portland

But What’s at Stake?

“Our nation’s founders recognized that military rule — particularly by a remote authority indifferent to local needs — was incompatible with liberty and democracy,” the state and city’s lawsuit states.

The 10th Amendment of the Constitution defers powers to the states not explicitly given to the federal government — which includes policing. Federal law, specifically the Posse Comitatus Act, forbids the military from engaging in law enforcement operations in the U.S. But there are exceptions — like in the event of an insurrection.

river with big pink in background, Portland, Oregon

Portland in sunnier times. (Rachel Monahan / City Cast Portland)

In the past, local leaders thought there was a reason to get the National Guard's assistance. During the 2020 protests, Oregon’s then-Gov. Kate Brown called them to Portland. What’s unprecedented today is that Portland police say they don’t need the help. And the Oregon National Guard has never in its history been called into service over the objections of the state’s governor.

On Friday, we may find out what the courts think, when a federal judge is scheduled to hear Oregon’s case to block the deployment. (The troops aren’t likely to arrive till next week.)

[At] a protest in front of the South Portland ICE facility, all they were doing was the Cha-Cha Slide by DJ Casper. I gotta say, the only thing those kids were at war with was rhythm.Claudia Meza , City Cast Portland

Alarmingly, the President of the United States continues to make a broad case for the use of military troops in America — to fight “the enemy within,” he said yesterday at a meeting of generals and admirals.

“It seems that the [cities] that are run by the radical left Democrats, what they’ve done to San Francisco, Chicago, New York, Los Angeles, they’re very unsafe places,” he said. “We’re going to straighten them out one by one….That’s a war too.”

“We should use some of these dangerous cities as training grounds for our military,” Trump also said.

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