President Donald Trump has targeted some of the nation’s largest Democratic-run cities — Chicago, Los Angeles, Washington, D.C. — during his second term by sending federal officers and, in some cases, the U.S. military to help enforce immigration laws and stamp out what he calls rampant crime.
But one of its targets isn’t even among the nation’s 30 largest metropolitan areas. Portland, Oregon — located along the Willamette and Columbia rivers, in a valley of Mount Hood — also did not rank last year among the 30 largest U.S. cities with the highest violent crime rates, according to the Real Time Crime Index — and its violent crime numbers have declined.
Although the president’s attacks on Portland have intensified in recent months — he has described the city as “war-ravaged” and tried to send National Guard troops there over the objections of state and local leaders — Trump has had his sights set on the Pacific Northwest city since his first term, when protests broke out at the same Immigration and Customs Enforcement building that is now the epicenter of demonstrations.
“This is not a controlled peaceful protest, as many on the left have claimed, this is radical violence,” White House spokeswoman Abigail Jackson told CNN on Wednesday, citing “rioters… charged with crimes including arson and assaulting police officers.”
“Earlier this month, Antifa activists brought a guillotine to ICE headquarters in Portland,” she added. “President Trump is taking legal action to protect federal law enforcement officers and combat the out-of-control violence that local residents have complained about and Democratic leaders have failed to stop. »
Here’s how we got to this point:
Oregon hasn’t voted for a Republican for president since 1984, and Democrats have held a winning trio — controlling the governorship, as well as the state Senate and House of Representatives — for 12 straight years.
“Oregon is one of those states where, as soon as the polls close, they go for the Democratic candidate,” said Tung Yin, a professor at Lewis & Clark Law School in Portland who studies national security law.
“We know that the president seems to care a lot about where he gained votes and where he lost votes,” Yin told CNN. “And he seems to be seeking some sort of revenge for the places where he didn’t do well.”
Long before Trump became president, Oregon’s largest city had a tradition of protest and the kind of progressive politics he abhors, from environmentalism to LGBTQ+ rights. In 1987, the state became the first in the nation to declare itself a sanctuary for undocumented immigrants, and the Portland City Council declared its own sanctuary policy in 2017.
Portland is also reportedly home to 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 erupted in Democratic-led cities across the country, including Portland.
“Very unfair!” » he replied on X.
By the summer of 2018, protesters’ anger focused on the White House policy of criminally prosecuting anyone crossing the border illegally, which led to the separation of hundreds of children from their parents. Protesters in Portland set up in front of an ICE building, calling their protest “Occupy ICE PDX.”
Trump quickly called out Portland by name.
In a letter to state and local leaders, the president cited “the disgusting hostility directed against selfless ICE employees in Portland, Oregon” from “anarchist protesters.” Similar protests also took place in New York, Los Angeles, Detroit and other cities.
The following summer, Trump issued a more direct warning: “Portland is being watched very closely,” he posted, adding that he considered calling the amorphous Antifa an “ORGANIZATION OF TERROR.”
It was these protests that “helped set the stage for 2020,” said Chris Shortell, a political science professor at Portland State University. “And I think 2020 is a critical moment.”
It was the year nationwide protests erupted following the killing of black father George Floyd by a white police officer on a Minneapolis street. Bystander video showing the officer’s knee on Floyd’s neck for more than 9 minutes as he repeated, “I can’t breathe,” sparked intense public outrage and reignited the Black Lives Matter movement.
As unrest erupted in the nation’s capital, Trump quickly called in the National Guard. Elsewhere, he claimed that local leaders had lost control, and in June 2020 he signed an executive order authorizing the deployment of Department of Homeland Security agents to protect federal properties.
In downtown Portland, thousands gathered for more than 100 days. Daytime protests, mostly peaceful, sometimes turned into riots and arson at night. Police regularly deployed tear gas and rubber bullets as protesters blocked traffic on bridges and streets around the Multnomah County Justice Center and the adjacent Mark O. Hatfield Federal Courthouse.
Trump wanted local leaders in Portland to ask him to call in troops, saying he would “bring in the National Guard and end the problem immediately.”
“ASK!” he implored X. Without any request for help, Trump still sent more than 700 officers from federal agencies – but did not deploy the National Guard.
The arrival of federal law enforcement increased tensions.
Federal agents beat and pepper-sprayed a veteran in Naval Academy uniform and fired tear gas at the mayor. A pro-Trump protester was shot and killed last August, and Trump rejoiced when federal law enforcement officers shot and killed his suspected killer.
“We sent in the US Marshals,” Trump said at a campaign rally in North Carolina, adding that 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 away.” Then-Gov. Kate Brown called Trump’s actions a “gross abuse of power.”
Oregon’s attorney general at the time sued the federal government, and two of its members in the House of Representatives joined a lawsuit against the Department of Homeland Security and other agencies, alleging that federal agents had violated their rights under the 10th Amendment.
As Trump’s second term began, it was clear he hadn’t forgotten Portland. When its Department of Education released its first list of five colleges it would investigate for allegations of anti-Semitism, Portland State — a large public school with a 91 percent acceptance rate — was among elite universities like Columbia and Northwestern.
After protests against Trump’s immigration policies resumed this summer — including near the Portland ICE site, the center of the 2018 actions — the president called Portland “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 quell protests, Trump in late September — against the wishes of residents — simply announced the federalization of 200 members of the Oregon National Guard. A federal judge appointed by Trump temporarily blocked such deployment of troops anywhere in the city.
But even though Trump’s descriptions of Portland are still reminiscent — to the point of obsession — of images of violent nighttime protests downtown in 2020, this year’s public demonstrations of resistance at the ICE building on the West Side are “so different,” Shortell said.
Since nightly protests began last June, 40 arrests were made early Wednesday in the South Waterfront neighborhood, police said. This compares to the more than 500 people arrested during the 2020 protests.
On Monday evening, journalists, protesters, Trump supporters and spectators mingled within a single block of the ICE facility, a CNN crew witnessed. At the height of this demonstration, the crowd numbered between 80 and 100 people, far fewer than the thousands of people gathered each evening in 2020.
Given Trump’s continued characterization of Portland in line with 2020 scenes, some local leaders and organizers suspect the federal government is trying to agitate protesters, Shortell said.
“I think there is some caution on the part of state and local leaders 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 sees us as a target. »
CNN has contacted the Department of Homeland Security regarding claims that the president is targeting Portland.
Trump wants to “create a sense of chaos” during protests outside Portland’s ICE facility to “justify more authoritarian rule,” Sen. Jeff Merkley told CNN this week.
Now — five years after introducing a bill to block the Trump administration from deploying federal forces to Portland — Merkley has another message for his constituents:
“Don’t take the bait.”