Donald Trump and Portland got off on the wrong foot, to say the least.
The New York businessman’s upset victory over Democratic Sen. Hillary Clinton in 2016 sparked major unrest in Portland as soon as the broadcast networks announced the results.
Beginning on Nov. 8, 2016 thousands of Portlanders spilled out onto the streets, with police making more than 100 arrests over the following week. In retrospect, those nights of anger and shattered glass would seem like a brief prelude to the sustained protests of 2020.
Trump, now on his second term, has made good on a five-year-year old threat to federalize the Oregon National Guard and send its soldiers into the streets.
But while Portland has been a regular punching bag for the president — who often raised the specter of so-called civil disorder in the city as a campaign rallying cry — his rhetoric has escalated since then.
As recently as Tuesday, Trump told an assemblage of the nation’s top military officers that American cities should be used as “training grounds.” Here are the other salvos in a long-running war of words between the chief executive and the Rose City.
Here’s a timeline of President Trump’s comments about Portland
Aug. 20, 2018: Trump tangles with then-Portland Mayor Ted Wheeler over a long-simmering protest outside the U.S. Immigration and Customs Enforcement Office in South Portland.
At the time, Wheeler had explained that Portland police wouldn’t assist ICE agents in enforcing federal immigration law and had waited more than five weeks to clear a protest encampment. Sound familiar?
In a speech at the White House on immigration, Trump said the mayor’s decision left federal officers “to face an angry mob of violent people,” adding that the mayor’s actions were “shameful.”
June 20, 2020: Trump takes to the stage in Tulsa, Oklahoma for a campaign speech and references the recent toppling of historical statues in Portland, including one of George Washington in Northeast Portland.
“Two days ago leftist radicals ripped down a statue of George Washington,” Trump told the Tulsa crowd to a chorus of boos, “and wrapped it in an American flag and set the American flag on fire.”
July 29, 2020: As the George Floyd protests appear to be tapering down at the end of July, Trump announces that he’s surging Federal Protective Service agents to protect the Mark O. Hatfield federal courthouse, reinvigorating the demonstrations.
At a press gaggle before his departure on Marine One, Trump doubles down on his deployment of federal agents to Portland. “We’re not leaving [Portland] until they’ve secured their city,” he said. “If they don’t… we’re going to have to go in and clean it out.”
July 30, 2020: Trump tweets about Portland and the ongoing protests outside the federal courthouse, saying that “Homeland Security is not leaving Portland until local police complete cleanup of Anarchists and Agitators!”
Aug. 11, 2020: Trump again warns that Portland is the future of America, if the GOP doesn’t prevail at the ballot box: “They want every city in America to resemble Portland, in a form.”
Aug. 27, 2020: During a campaign speech at the Republican National Convention, Trump invokes the social justice protests roiling the city and claims his opponent, Democratic Sen. Joe Biden, and his allies will defund police departments across the nation, if elected.
“They will make every city look like Democrat-run Portland, Oregon,” Trump says.
Aug. 30, 2020: “Our great National Guard could solve these problems in less than 1 hour,” Trump tweets, responding to videos of protesters outside the Mark O. Hatfield federal courthouse.
Aug. 31, 2020: Trump blames a wave of violence in American cities on the “Biden party.”
He notes that, “In Portland alone, the federal government has already … arrested 100 rioters.”
(The Associated Press reported in October 2020 that 91 people faced federal charges, with the accusations including assault on a federal officer, civil disorder and destruction of federal property.)
Sept. 7, 2020: Trump makes another call-out during a press conference at the White House. “When you look around at Portland and you see what these Democrats are doing to our cities,” Trump says. “It’s very sad to look at it.”
Oct. 12, 2020: Trump tweets out in disgust after protesters vandalize statues of former Presidents Theodore Roosevelt and Abraham Lincoln. “The Radical Left fools in Portland don’t want any help from real Law Enforcement which we will provide instantaneously. Vote!” he writes in the first of five messages.
Sept. 17, 2023: The former president calls Portland a “burned down city” during a television interview.
June 27, 2024: While battling President Joe Biden on the debate stage, Trump refers to Portland as “ripped down.” “You ought to be ashamed of yourself,” Trump tells Biden, “when they ripped down Portland, when they ripped down many other cities.”
July 31, 2024: Trump namechecks Portland again while speaking before the National Association of Black Journalists in Chicago. He alludes to the city, and the punishment of its many protests, when asked if he’ll pardon those who stormed the U.S. Capitol on Jan. 6. “What’s going to happen to the people in Portland that destroyed that city?” Trump replied.
Sept. 5, 2025: Citing television news reports, Trump says he is weighing federal intervention in Portland: ”They’ve ruined that city.” For good measure, the president adds: “It’s like living in hell.
Sept. 19, 2025: Trump again lashes out against Portland, describing the city as “just people out of control and crazy. We’re going to stop that pretty soon.”
Sept. 25, 2025: Trump makes a third threat to send forces to Portland, calling the demonstrators “professional agitators and anarchists.”
Sept. 27, 2025: Most of Portland wakes up to Trump’s announcement that he will send “all necessary Troops” to “War-ravaged” Portland, citing the need to protect the ICE facility from “Antifa, and other domestic terrorists.”
Sept. 30, 2025: President Trump slammed Portland again during a speech before several hundred high-ranking military officers in Virginia. “This place is a nightmare,” he said.
Oct. 1, 2025: In a post on Truth Social, Trump claims that “conditions continue to deteriorate into lawless mayhem.” He says the federalized troops are “now in place.” It’s not clear if that claim is correct.
The Oregonian/OregonLive staffer Mark Graves contributed to this article.
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