By Andy Rose, CNN

(CNN) — A day after President Donald Trump’s second inauguration, the mayor of Portland, Oregon, knew that a “sanctuary city” like his was going to have a bumpy four years ahead.

“We must come together to live our city’s shared values of freedom from fear and sanctuary from federal overreach in the days ahead, no matter what our city may face,” Mayor Keith Wilson said in a letter to the city council on January 21.

In the past eight months, the city has reaffirmed that commitment by joining a lawsuit against the Trump administration and issuing a zoning violation notice for an Immigration and Customs Enforcement facility that has been at the center of almost constant protests throughout the summer.

Most of the protests outside the ICE facility, about 2 miles south of downtown, have been peaceful, but occasionally have ended in the deployment of tear gas and resulted in the facility being closed for several days in the summer.

President Donald Trump on Saturday followed through on his pledge to make the city a target of his next National Guard deployment, saying in a social media post he was directing Defense Secretary Pete Hegseth to “provide all necessary troops” to Portland, a city he described as “war ravaged,” to protect ICE facilities he claimed are “under siege” by Antifa and “other domestic terrorists.”

Trump has said, without evidence, that “paid terrorists” are wreaking havoc in Portland.

Last week, Trump refocused attention on Antifa – the loosely organized group of leftists and anarchists who are known for anonymity and destructive masked demonstrations – designating it as a “major terrorist organization.” The White House emphasized incidents in Portland, home to one of the oldest organizations in the United States to carry the Antifa moniker, in its statements about the designation.

Here is what we know about what is ahead for the city famous for loud protests and liberal politics as its standoff with federal immigration officials gets more tense.

Being a ‘proud’ sanctuary city could put federal funds in jeopardy

In spite of the president’s ire, Portland has doubled down on sanctuary city status, making it the first thing you see on its official website. Now the city council is moving toward an ordinance that would make it legally binding, prohibiting any Portland government organization from assisting in federal immigration enforcement, except for providing information that is already available to the general public.

The decision could be a costly one for Portland. The administration announced it would withhold a variety of federal grants – including FEMA funding, highway grants and airport improvements – from cities it classified as “sanctuary jurisdictions,” including some cities that don’t use that term. For Portland, that puts $350 million in jeopardy.

Portland joined 15 other local governments in a federal lawsuit against the Trump administration earlier this year, and a judge blocked the government from freezing those funds. But the administration is appealing, denying that they are cutting federal funding “in an indiscriminate or wholesale manner.”

Alongside Diversity, Equity and Inclusion policies, sanctuary cities have been the biggest direct targets of Trump’s second term, with three different executive orders specifically mentioning them and requiring the Department of Homeland Security to make a list of them.

In response, Louisville, Kentucky, dropped its policy refusing to hold immigration suspects in its local jail for ICE, with the mayor acknowledging that “millions of dollars in federal grants were at stake.”

From Portland, the message has been much different.

“As a proud sanctuary city in a sanctuary state,” Mayor Wilson said, “we are committed to protecting the rights and dignity of all who live here, working together to strengthen our community.”

Portland first called itself a sanctuary city nearly a decade ago with a nonbinding resolution saying the Portland Police Bureau “shall not cooperate with ICE except as expressly required by Federal Law.” This week, the city council discussed taking things further by making its sanctuary status permanent.

“I think that when we are facing such an extreme level of federal overreach … then we do have a responsibility to act boldly in ways that we haven’t had to act before,” said council member Angelita Morillo during a committee meeting Tuesday. “These are unprecedented times, and we have to do unprecedented things.”

None of the members of the public who testified at the meeting spoke against the proposal, which does not yet have a final vote scheduled.

ICE facility is the target of both protests and legal challenges

The story of protests against the ICE facility on Macadam Avenue is most starkly told through photos taken there over the past two years.

As the months wear on, you see an ordinary-looking tan brick and stucco building in an industrial area is gradually swallowed by increasing layers of fencing, its lower-level windows suddenly blocked by plywood, a concrete retaining wall covered in anti-ICE graffiti.

Protester Deidra Watts told the Associated Press earlier this month that she feels ICE’s actions against immigrants are cruel and require a loud response.

“In the face of that, there has to be people who will stand up and make it known that that’s not gonna fly, that that’s not something the people agree with,” Watts said.

In the summer, protesters blocking the processing facility caused it to be closed for several days, CNN affiliate KATU reported, something the Trump administration blamed on “anarchists and rioters.”

But the building has become a magnet for a wide variety of protesters, the Oregon Capital Chronicle reported, with daytime demonstrators mostly coming from religious organizations, quietly holding signs and monitoring the movement of migrants in and out of the building until the mantle is picked up by rowdier protesters at night.

While protesters have tried to shut down the building physically, the city government is trying to do it by other means.

So far this year, federal prosecutors have charged 27 people with federal charges for activity outside the facility, said Jessica Biggers, a spokesperson for the US Attorney for the District of Oregon. Most of the charges are for assaulting a federal law enforcement officer or failing to obey a lawful order, the district attorney’s office said in press releases.

Portland sent a notice to the building’s private owners last week, saying ICE has committed code violations by boarding up windows and keeping some detainees in the holding facility for longer than 12 hours.

“Federal records show that ICE violated its land use conditions of approval 25 times in 10 months,” the notice states.

The building used by ICE is owned by a family partnership whose beneficiaries are not listed publicly. An attorney for that partnership did not return requests for comment on the zoning violation notice.

Morillo, the council member, acknowledges it’s questionable whether the city could force the ICE facility to close, even if the legal violations aren’t addressed. And her proposal to add extra fees on buildings used for federal detention raised concerns from another council member.

“If we start to begin to cherry pick on who and how the federal government gets to rent places, that’s concerning to me,” said council member Loretta Smith.

The Trump administration says shutting down the processing facility, where undocumented migrants have to periodically check in with immigration officials, would actually make things harder on immigrants.

“If the city allows further separation of families by forcing ICE to operate processing elsewhere, that is on them,” ICE said in a statement to CNN affiliate KATU. “Lending no hand to ICE in the name of ‘sanctuary,’ means also lending haven for criminals that has proven to be a great risk to public safety and national security.”

Destructive protests of 5 years ago still on leaders’ minds

While city leaders have been largely supportive of the right to protest outside the ICE facility, they have also made it clear they do not want a repeat of the city’s most notorious demonstrations in 2020.

The murder of George Floyd in May of that year touched off protests – frequently violent – in major cities around the country, but the demonstrations in Portland continued for more than 100 consecutive nights.

Through that summer, a grim routine developed where peaceful marches would devolve into vandalism and threats against police officers. The Portland Police Bureau would declare a riot and order protesters to disperse, eventually responding physically against protesters. There were more than 6,000 uses of force by police during that period, according to city records.

In what turned out to be a foreshadowing of rhetoric that would get even hotter in his second term, Trump in July 2020 called Portland a “beehive of terrorists” and deployed the National Guard to protect federal buildings downtown.

Locally, the response was more complicated, with police frequently criticized for their use of force and tear gas. Eventually then-Mayor Ted Wheeler – who also served as the commissioner of police – banned the bureau’s use of CS gas, but a study later found so much gas had been deployed on a single night in June across 18 downtown blocks prior to the ban that it became a public health danger.

In 2022, the Biden administration’s Justice Department criticized the Portland Police Bureau, saying it didn’t do enough to review its procedures and see if its use of force was warranted.

Ultimately, most of the people arrested – including some accused of rioting – were released without charge after Multnomah County’s District Attorney’s Office announced in August 2020 it was declining to prosecute cases against protesters who did not use force, steal or damage property.

“If we leverage the full force of the criminal justice system on individuals who are peacefully protesting and demanding to be heard, we will cause irreparable harm to them individually and to our society,” former DA Mike Schmidt said at the time.

While hundreds of people who were arrested went free without charge during that turbulent year, prosecutors are now pointing to those past protests in a warning to people who hope to send a message about ICE.

“Let’s not kid ourselves,” Multnomah County District Attorney Nathan Vasquez said in June. “In the past, the voices of tens of thousands of peaceful protestors have been drowned out. Their message was hijacked by a small number of individuals with a message of vandalism, destruction and violence.”

And local officials have made it clear that, regardless of any concerns about more flare-ups in the tense standoff between ICE and protesters, they don’t want the Trump administration’s help.

“Like other mayors across the country, I have not asked for – and do not need – federal intervention,” Wilson said.

The-CNN-Wire
™ & © 2025 Cable News Network, Inc., a Warner Bros. Discovery Company. All rights reserved.

CNN’s Kit Maher contributed to this report.