Trump has had his sights on Portland, Oregon, for years. This is how we got here
By Celina Tebor, CNN
(CNN) — President Donald Trump has taken aim in his second term at some of the country’s largest Democratic-run cities – Chicago, Los Angeles, Washington, DC – sending in federal officers and, in some cases, the US military to aid immigration enforcement and root out what he calls rampant crime.
But one of his targets isn’t even among the country’s biggest 30 metro areas. Portland, Oregon – along the Willamette and Columbia rivers in a valley of Mount Hood – also fell short last year of the 30 largest US cities with the highest violent crime rates, according to the Real Time Crime Index – and its violent crime numbers have been dropping.
Though the president’s attacks on Portland have escalated in recent months – he’s described it as “war-ravaged” and tried to send in National Guard troops over state and local leaders’ objections – Trump has had his sights on the Pacific Northwest city stretching back to his first term, when protests erupted at the same Immigration and Customs Enforcement building now at the epicenter of demonstrations.
“This isn’t a peaceful protest that’s under control, like many on the left have claimed, it’s radical violence,” White House spokesperson Abigail Jackson told CNN on Wednesday, citing “rioters … charged for crimes including arson and assaulting police officers.”
“Earlier this month, Antifa militants brought a guillotine to the ICE facility in Portland,” she added. “President Trump is taking lawful action to protect federal law enforcement officers and address the out-of-control violence that local residents have complained about and Democrat leaders have failed to stop.”
Here’s how we got to this point:
Bubbling tensions nearly a decade old
Oregon hasn’t voted for a Republican for president since 1984, and Democrats have held a trifecta – controlling the governorship, plus the state Senate and House – for 12 straight years.
“Oregon is one of those states where, as soon as the polls close, it gets declared in favor of the Democratic candidate,” said Tung Yin, a professor at Portland’s Lewis & Clark Law School who studies national security law.
“We know that the president seems to care a lot about where he won votes and where he lost votes,” Yin told CNN. “And he seems to be out for some kind of payback for the places that he didn’t do well in.”
Long before Trump became president, Oregon’s largest city had a tradition of protest and the sort of progressive politics he abhors, from environmentalism to LGBTQ+ rights. The state in 1987 became the first in the country to declare itself a sanctuary for undocumented immigrants, and the Portland City Council declared its own sanctuary policy in 2017.
Portland also is said to be the home of one of the oldest cells of the decentralized, far-left “anti-fascist,” movement known as Antifa.
When Trump first won the White House in 2016, protests broke out in Democratic-led cities across the country, including Portland.
“Very unfair!” he responded on X.
By the summer of 2018, protesters’ ire had homed in on the White House policy of criminally prosecuting anyone who crossed the border illegally, which led to the separation of hundreds of children from their parents. Protesters in Portland set up outside an ICE building, calling their demonstration “Occupy ICE PDX.”
Trump soon was calling Portland out by name.
In a letter to state and local leaders, the president mentioned “repugnant hostility directed toward selfless ICE employees in Portland, Oregon,” from “anarchist protestors.” Similar protests also spun up in New York, Los Angeles, Detroit and other cities.
The following summer, Trump delivered a more direct warning: “Portland is being watched very closely,” he posted, adding he was weighing naming the amorphous Antifa an “ORGANIZATION OF TERROR.”
It was these demonstrations that “help set the stage for 2020,” said Chris Shortell, a political science professor at Portland State University. “And I think 2020 is a critical moment.”
How 2020 became a flashpoint
That was the year nationwide protests erupted over the killing of Black father George Floyd by a White police officer on a Minneapolis street. A bystander’s video of the officer’s knee on Floyd’s neck for more than 9 minutes as he repeated, “I can’t breathe,” prompted intense public outrage and refueled the Black Lives Matter movement.
As unrest flared in the nation’s capital, Trump quickly called up the National Guard. Elsewhere, he claimed local leaders had lost control, and in June 2020, he signed an executive order allowing the deployment of Department of Homeland Security officers to protect federal property.
In downtown Portland, thousands rallied for over 100 days. Mostly peaceful daytime protests at times devolved at night into rioting and arson. Police regularly deployed tear gas and rubber bullets as demonstrators shut down traffic on bridges and streets around the Multnomah County Justice Center and adjacent Mark O. Hatfield Federal Courthouse.
Trump wanted local leaders in Portland to ask him to call in troops, saying he would “bring in National Guard, end the problem immediately.”
“ASK!” he implored on X. Without a request for any assistance, Trump still sent in more than 700 officers from federal agencies – but did not deploy the National Guard.
The arrival of federal law enforcement raised tensions.
Federal agents beat and pepper-sprayed a veteran in Naval Academy gear and tear-gassed the mayor. A pro-Trump protester was shot and killed that August, and Trump gloated when federally deputized law enforcement officers shot his suspected killer.
“We sent in the US Marshals,” Trump said during a campaign rally in North Carolina, adding it “took 15 minutes (and) it was over.”
Local, state and federal Democratic leaders were quick to denounce the federal presence in Portland. Then-Mayor Ted Wheeler told Trump to “support us” or “stay the hell out of the way.” Then-Gov. Kate Brown called Trump’s actions “a blatant abuse of power.”
Oregon’s attorney general at the time sued the federal government, and two of its US House members joined a lawsuit against the Department of Homeland Security and other agencies, alleging federal agents violated their 10th Amendment rights.
2020 lives on in Trump’s 2025 mind
As Trump’s second term got underway, it was clear he hadn’t forgotten about Portland. When his Department of Education released its first list of five colleges it would probe over alleged antisemitism, Portland State – a large public school with a 91% acceptance rate – was among elite universities like Columbia and Northwestern.
After protests against Trump’s immigration policies revved up again this summer – including near the Portland ICE site at the center of 2018 actions – the president called out Portland as “war-ravaged” and followed through on his first-term promise to designate Antifa a terrorist organization.
And unlike in 2020, when he pressed local leaders to seek his military support to put down protests, Trump in late September – against locals’ wishes – simply announced the federalization of 200 members of the Oregon National Guard. A Trump-appointed federal judge has temporarily blocked such a troop deployment from anywhere to the city.
But even as Trump’s descriptions of Portland still recall – to “a point of obsession” – images of violent nighttime protests downtown in 2020, this year’s public shows of resistance at the west side ICE building are “so different,” Shortell said.
Since nightly protests began this June, 40 arrests were made through early Wednesday in the South Waterfront area, police said. That compares with over 500 people arrested during the 2020 protests.
On Monday night, journalists, protesters, Trump supporters and onlookers mingled within a single block of the ICE facility, a CNN crew witnessed. At that protest’s height, the crowd numbered 80 to 100 people, far fewer than the thousands who gathered nightly in 2020.
Given Trump’s continued characterization of Portland in line with the 2020 scenes, some local leaders and organizers suspect the federal government may be trying to agitate protesters, Shortell said.
“I think that there is some caution on the part of state and local leadership about making Oregon a target,” the Portland State professor said. “We know how easy it is to be a target, and we know that President Trump already views us as a target.”
CNN has reached out to the Department of Homeland Security about claims the president is targeting Portland.
Trump wants to “create the impression of chaos” at demonstrations outside Portland’s ICE facility to “justify more authoritarian power,” Sen. Jeff Merkley told CNN this week.
Now – five years after he introduced a bill to stop the Trump administration from deploying federal forces in Portland – Merkley has another message for his constituents:
“Don’t take the bait.”
The-CNN-Wire
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