PORTLAND, Ore. — As statues of Confederate generals, enslavers and other icons tumbled from their pedestals amid protests last month, President Trump issued an executive order meant to break the cascade. It enlisted the Department of Homeland Security, created in the wake of the Sept. 11 attacks to protect the country against external threats, to defend U.S. monuments and federal property against "anarchists and left-wing extremists" who he said are advancing "a fringe ideology."

The order signaled Trump’s eagerness to mobilize federal power against the societal upheaval that has coursed through America since George Floyd’s death. He sought to frame and create a culture war — right vs. left, right vs. wrong — and was taking a stand at the monuments that some view as historical homages and many others view as symbols of oppression.

But Trump’s June 26 declaration came too late. The momentum of the protests was fading in many U.S. cities, and confrontations between federal authorities and civilians were becoming less frequent. Then Trump found Portland, according to administration and campaign officials.

Still restive, the West Coast city with a long tradition of protest as a subculture of anarchism was staging peaceful mobilizations as well as smaller nightly clashes with authorities. Militant black-clad demonstrators were directing their anger at a large federal courthouse downtown.

Sinking in the polls over his handling of the coronavirus pandemic, Trump seized a chance to appear as a field general in a wider American cultural conflict over racial justice, police misconduct and the reexamination of American history and monuments. In Portland, he found a theater for his fight.

The Federal Protective Service officers responsible for guarding the courthouse were worn down and outnumbered, DHS officials say, and they sent teams of federal border and immigration officers to shore up their ranks in anticipation of larger protests on the July 4 holiday weekend.

“What is occurring in Portland in the early hours of every morning is not peaceful protesting,” acting DHS secretary Chad Wolf said this week. “These individuals are organized and they have one mission in mind: to burn down or cause extreme damage to the federal courthouse and to law enforcement officers.”

Trump has taken a keen interest in tactical operations against the protesters in recent weeks, according to White House and administration officials at the center of the response, who like others spoke on the condition of anonymity to discuss internal deliberations. When the fog of tear gas is thickest here in the wee hours of the morning, the president is sometimes up early on the other side of the country, calling Wolf for real-time updates from the front.

The scenes of militarized federal forces on the city’s streets have stunned many Americans and unnerved former Homeland Security officials, but they have not quieted the protests. In many ways, the agents and the barricades they have erected have re-energized the demonstrators and have converted the courthouse into a proxy for the Trump administration itself.

The fortified, battle-scarred building has resembled a beehive on recent nights, as protesters prod it with fireworks and other projectiles until a door swings open and federal agents burst forth with volleys of tear gas and stinging munitions. Then they retreat inside. The pattern repeats.

Trump’s campaign officials say that the president wants to amplify his law-and-order message to show he is a last bastion of safety for a reeling American public, and that U.S. cities ravaged by crime and unrest — which also happen to be heavily Democratic — are the right venue.

“Not only are the big-city mayors turning a blind eye, they are actively working against their own law enforcement and police forces who want to keep people safe,” Trump senior adviser Jason Miller said. “The first rule of government is to keep people safe. That’s what the president is doing.”

Trump announced a plan this week to deploy federal agents to Chicago, Albuquerque and other cities where violent crime has spiked, and he later told Fox News that he is ready to deploy 50,000 to 75,000 officers if welcomed by local authorities. While DHS and Justice Department officials have tried to emphasize their defensive operation in Portland is different, Trump calls it part of the same “chaos” he blames on “the radical left” amid their calls to defund police departments.

White House officials have been frustrated with news coverage depicting federal agents as aggressors, and on Friday, press secretary Kayleigh McEnany opened her briefing with a video montage of mayhem in Portland that segued into toppled statues and damaged monuments elsewhere. The footage was graphic, and Fox News cut away.

Trump has pushed for a Portland-style deployment in Chicago, one official said, but city officials made clear they prefer working with the FBI and other Justice Department agencies over DHS, whose reputation has suffered from its central role in Trump’s domestic policy agenda.

Three and a half years into his presidency, the standoff in Portland is also the culmination of Trump’s long-running battle against jurisdictions whose “sanctuary” polices have undermined his immigration agenda. The president’s use of highly trained Homeland Security agents in a domestic policing role was preceded by his willingness to employ a show of force along the Mexico border to stop migrant caravans.

In a meeting last week with advisers, Trump said that what has been happening in the nation’s largest cities is “ridiculous” and that “something has to be done about it,” according to a person who attended the meeting but was not authorized to publicly discuss the strategy session.

Stephen Miller, one of the president’s top aides, has regularly argued for more muscular action in U.S. cities, drafting talking points that say they are failing and that Trump will fix them.

“We will not let that courthouse be burned to the ground,” Miller said Thursday night on Tucker Carlson’s show, depicting the building as a kind of Trump citadel. “This is about the survival of this country, and we will not back down.”

Operation Diligent Valor

DHS officials have reported dozens of vandalism attempts and attacks on Portland federal buildings since May, and a timeline of those acts shows an escalation. Early graffiti rose to more serious recent incidents targeting the federal courthouse and the agents guarding it.

By the first week of July, protesters were trying to tear off the building’s plywood defenses, shooting fireworks at the structure and smashing glass. The officers defending the building have been attacked with rocks, bottles, ball bearings and balloons filled with paint and feces, according to DHS, and officials said three agents have sustained serious ocular injuries from lasers pointed at their eyes. Arson smoke merges with tear gas to produce scenes of bedlam.

The responsibility for guarding the building during protests usually falls to the FPS and the U.S. Marshals Service, but the agencies asked for reinforcements ahead of the July 4 holiday, fearing an uptick in vandalism and violence, according to Homeland Security and Justice Department officials.

Wolf called up the country’s most highly trained border and immigration agents, including units that typically focus on drug traffickers and powerful cartels.

Oregon Gov. Kate Brown (D), one of the administration’s fiercest critics, said she had no idea federal agents were being sent to her state to police protesters until photos of unidentified officers in tactical gear at the Portland federal courthouse began circulating on social media around July 4.

In the days that followed, the governor’s office began to look into what was going on in Portland, spokeswoman Liz Merah said, and discovered the Trump administration had increased the number of agents in Oregon’s largest city without letting anyone know.

“This is a democracy, not a dictatorship,” Brown said in a statement. “We cannot have secret police abducting people in unmarked vehicles. I can’t believe I have to say that to the President of the United States.”

Brown acknowledged that state authorities have declined to coordinate with federal officials and have only contacted DHS to ask them to stand down.

Portland Mayor Ted Wheeler (D) first heard about increased federal presence from officials in the Portland Police Bureau as the agency began its preparations to secure protests and events around July 4, spokeswoman Eileen Park said. Though Wheeler also serves as the city’s police commissioner, he said he was not consulted by Trump or Homeland Security officials before the federal government deployed agents to the city.

Despite Trump’s assertions that city officials were overwhelmed by nonstop protests, Wheeler has compared the presence of federal officers to gasoline being thrown onto an open flame.

“We had heard about it first when they were already here,” Wheeler said. “What we had been seeing on our streets was a de-escalation of the criminal activity, the violence, the vandalism that was being engaged in by a handful of people — we were seeing that tail off significantly.”

By mid-July, there were more than 100 officers from the FPS and other DHS agencies, including tactical teams from U.S. Customs and Border Protection and Immigration and Customs Enforcement, a deployment DHS dubbed Operation Diligent Valor.

There weren’t enough government vehicles for all the CBP agents in Portland, so officials decided to rent minivans, according to officials familiar with the effort. The rental vehicles soon appeared in cellphone videos that showed federal agents in military-style uniforms grabbing protesters off the streets using unmarked cars.

CBP also began using some of the detention cell space inside the courthouse — jail cells normally run by the Marshals Service — to detain and question suspects, according to officials familiar with the matter. At least 43 suspects have been arrested by federal agents in Portland so far, Wolf said this week.

Wolf speaks to the president several times a day, according to White House officials, one of whom said Trump is “deeply involved” in monitoring crime in U.S. cities and suggesting responses, particularly while watching news coverage of the protests.

Wolf also is at the White House several times a week, including a meeting this week with Chief of Staff Mark Meadows. Though Trump wanted more ardent DHS officials like Ken Cuccinelli and CBP acting chief Mark Morgan for the top job, Wolf has become one of Trump’s favorite Cabinet secretaries, according to senior officials. He has told aides he likes Wolf far more than his predecessors, who sometimes resisted the president’s expansive views of federal power.

One of the officials said the White House had long wanted to amplify strife in cities, encouraging DHS officials to talk about arrests of violent criminals in sanctuary cities and repeatedly urging ICE to disclose more details of raids than some in the agency were comfortable doing. “It was about getting viral online content,” one of the officials said.

U.S. Rep. Peter T. King, a New York Republican and Trump ally, said he understands why federal reinforcements are in many of the cities and argued that the “mayors are embarrassing themselves.”

“I understand why the feds are in there. Something has to be done,” King said, noting that he believes any action should only be in certain places. “You have to be careful how far you go and what you do.”

Federal agents have struggled to identify, isolate and arrest the protesters engaged in violence or graffiti, stymied at times by confusion about who in the crowd is who. Agents have had difficulty distinguishing individuals among dozens of people who are clad in all black and who are frequently wearing masks, law enforcement officials said. So at times they have grabbed an individual and taken them inside the courthouse for questioning before determining that they had no probable cause to charge them with any crime, the officials said.

The protests have swelled in size this week, mostly with peaceful demonstrators, including columns of parents known as the “Wall of Moms,” who lock arms to shield protesters, and “Leafblower Dads,” who use the landscaping tools to dissipate tear gas and blow it back at federal agents.

Captured on video

Two incidents captured on video have highlighted the ugly nature of the clashes, and what some protesters have said is the more forceful approach taken by deputy U.S. marshals. In the early hours of July 12, a protester holding what appeared to be a speaker across the street from the courthouse was struck in the head by a projectile fired from one of the people guarding the courthouse.

The man, Donavan La Bella, 26, has needed surgery for skull fractures, according to his family. Since the incident, the marshals have declined to say which agency fired on La Bella. On Friday, officials said they believe it was a deputy U.S. marshal, adding that they would not release the names of any of personnel involved in use-of-force incidents.

In a statement, the agency said its personnel guarding the courthouse “have shown incredible restraint under nightly threat by violent protesters while protecting lawful demonstrations.”

A week after La Bella was struck, 53-year-old Navy veteran Christopher David was beaten with a baton and pepper-sprayed by marshals outside the courthouse. David suffered broken bones in his hand, and marshals said the force was justified because he presented a threat to officers “by continuing to approach them and failing to comply with lawful commands to withdraw as they proceeded to reenter the courthouse.”

David has said he was trying to ask the federal agents why they were there. “Why are you not honoring your oath to the Constitution?” he yelled.

The agency also said it is not participating in Operation Diligent Valor, which is a DHS effort. “The US Marshals do not have the option of leaving Portland, as some have called for,” the agency said, noting that marshals’ duties include protecting the federal judiciary and courthouses.

On Thursday, the inspectors general at DHS and the Justice Department announced they would investigate how federal agents have used force, made arrests and conducted themselves in confrontations with protesters in Portland, Ore., and Washington, D.C.

Mac Smiff, 39, a Portland artist and editor in chief of a hip-hop magazine, said demonstrators have learned how to better prepare for the tear gas and munitions federal agents are using. Some have crafted homespun armor out of plastic. Others hold shields made from trash can lids, cut up plastic bins or plywood nailed behind a picture frame. They carry swim goggles, lab goggles, snowboarding goggles. Helmets, gas masks and half-face respirator masks abound.

“We’re out here trying to have a peaceful protest and I almost got hit in the face — just last night — with something that flew just inches from my face and hit a barrier. I’m not sure if it was a rubber bullet, a gas canister or what,” Smiff said, adding that he has gone online trying to buy a gas mask so he can take photographs of the protests. “We’re buying motorcycle armor so we can go out there. This is not Fallujah, this is Portland, Oregon, and it’s like war games out here.”

Wolf this week laid blame on the city and state officials who have asked him to pull federal agents out of Portland, and the breakdown in cooperation has left DHS even more dug in.

Wolf described the deployment as part of DHS’s legal mandate to protect federal property, rather than a response to the president’s June 26 executive order. Trump administration officials say the president has the authority to order such deployments without such an order.

“We still have a job to do. We will continue to protect that facility,” Wolf said. “What we know is if we left tomorrow, they would burn that building down. . . . We know they have tried.”

Relations between Oregon authorities and Trump officials turned more acrimonious after Wolf visited Portland last week. Spurned by city and state officials, he met with the police union and rejected calls to pull back DHS agents.

On Wednesday night, Wheeler, the mayor, joined protesters at a fence line outside the courthouse, but he was pelted with objects and heckled for the past use of tear gas against protesters by Portland police.

After some in the crowd shot fireworks at the building and attempted to light fires along the fence, federal agents unleashed tear gas. Wheeler was enveloped, and left the streets choking and gasping for air.

Dawsey, Barrett and Miroff reported from the Washington area.