PORTLAND — A slender white man, helmeted and in black clothing, lit a torch and tried to ignite splintered shards of protective plywood tacked onto the front of the U.S. District Courthouse building.

“There is no such thing as a peaceful protest,” chanted one man standing nearby.

“No justice, no peace,” cried another.

From out of the crowd, a Black man stepped forward with a contrarian voice.

“When you are setting a fire, you mess with the (expletive) message,” he yelled. “How are you defending us when you are setting a (expletive) fire?”

His remarks, made around 1:30 a.m. Wednesday, touched off a stormy conversation in front of this federal building, that in July has become a target of unruly protests challenging federal policing policies under President Donald Trump, whose portrait was stamped on toilet paper wrapped around a pillar.

The protester’s question also resonates more broadly.

Plenty of Americans are angry over Trump’s policies that have included deploying federal Customs and Border Protection agents on tasks of domestic law enforcement, but many also are unsettled by the images of protesters emerging from the angry streets of downtown Portland.

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In Oregon’s largest city, other questions are asked with increasing urgency as tension escalates, including: How will this all end?

The protests began more than 50 days ago in response to the killing of George Floyd by Minneapolis police but now involves a faceoff with the Trump administration, whose Acting Secretary of Homeland Security, Chad Wolf, has declared federal law enforcement will continue to be on the streets in Portland to protect the courthouse.

On Tuesday evening and into the early morning hours of Wednesday, a series of intense skirmishes broke out between federal law enforcement and protesters. Some on the front lines of the protests were repeatedly trying to tear, pound away and ignite the plywood attached to the courthouse front.

Portland’s federal courthouse each evening hosts federal law enforcement who have used tear gas and other munitions to disperse protesters, some of whom have tried to damage the building. (Hal Bernton / The Seattle Times)

The U.S. District Courthouse here is a 16-story building named after the late Oregon Republican U.S. Sen. Mark Hatfield, and is a key venue where the American system of justice unfolds.

The federal judges whose offices are housed inside preside over cases that include protesters charged with criminal conduct. Other cases now pending seek to restrain the Trump administration. A case filed last week by Oregon Attorney General Ellen Rosenblum asks for an order restraining federal agents from using unmarked vans to allegedly “drive around downtown Portland, detain protesters … removing them from public without either arresting them or stating the basis for their arrest.”

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During a video federal court hearing Wednesday, David Morrell, an attorney for the U.S. government, called the motion “extraordinary” and based solely on “a few threadbare declarations” from witnesses and a Twitter video.

The media reports about detentions in July have helped to bring new energy to the Portland protests, and shift more of the focus from the Multnomah County Justice Center, where city police are based, to the federal courthouse just to the north.

This week, the Portland police — to a remarkable degree — have ceded the task of responding to federal law enforcement. Though generally out of sight, they are watching. In the early morning hours, they serve up a kind of postgame report that offers a chronology of some of the conduct of protesters.

A shift in tenor

On Tuesday evening, the crowd gathered by the county justice center and courthouse appeared to number more than 1,000. It included some of the new Portland protest celebrities such as those making up the Wall of Moms, whose bright yellow T-shirts stood out as they stood with arms linked.

State Sen. Lew Frederick, D-Portland, who grew up in Atlanta and as a youth attended civil rights protests, also was on hand. Frederick, who stayed until after midnight and witnessed some of the early volleys of tear gas and pepper balls, said he understands the motivations but does not condone the actions of those who smash windows, set fires and hammer away at the federal courthouse. He said that the nonviolent tactics of the Rev. Martin Luther King Jr., who was a friend of his family’s, could be an effective foil for law enforcement.

“They need to have anger and violence to respond to, and when you don’t give it to them, they are at a loss on how to respond,” Frederick said.

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Around 11 p.m., some people aided by hammers and crowbars began to kick and pound on the plywood protecting the courthouse’s glass doors, according to a Portland police report released Wednesday. Meanwhile, the much larger crowd was spread out in the parks and a blocked-off street.

The tenor of the protest soon changed.

By 11:15, federal agents had emerged from inside. They shot canisters of tear gas and rubber bullets and other less-lethal munitions, then retreated back inside.

The gas pushed protesters out of the park and to the west. They chanted, “Stay together, stay tight, we do this every night.’’

This cycle would repeat itself again and again, with increasing intensity deep into the early morning hours.

Through all this back and forth, there were casualties.

They included a man with an American flag who was struck in the eye by a piece of a projectile, a woman who was pulled out of a tent and appeared to have rib fractures and numerous people with serious respiratory reactions to tear gas, according to medics who tended to protesters and some of whom suffered injuries.

Daniel Kelly, a medic who has attended most of the Portland protests and said he served with the U.S. Army in Iraq, was hit by tear-gas canisters that caused massive bruising to his lower body.

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“I am clearly marked as a medic. And I had my hands up … but they hit me in one leg, then the other,” he said.

Kelly said that as more protesters wear protective masks to fend off tear gas, federal agents increasingly are turning to impact projectiles, and injuries are escalating. He said, earlier in the week, he responded to a man who suffered a compound fracture to his ankle that left the bone sticking out. And he worries what the days ahead will bring.

“That’s why I bring my Kevlar armor,” Kelly said.

Protests roll on

For both the protesters and the Trump administration, Portland is providing a treasure trove of images that both seek to use to expand support for their actions.

Trump tries to portray all protesters as anarchists, and flames make great video for campaign aids.

In the meantime, nightly video highlights from the protests are posted on social media, including by those – such as the Pacific Northwest Youth Liberation Front (YLF) – that do embrace anarchism.

A retweet from YLF points to a history of riots as helping, along with nonviolent protests, to spur political change in the United States. They make no apologies for their tactics, and, in tweets, urge critics to shut up.

But the protester who challenged the 1:30 a.m. Wednesday arson fire would not yield his opposition. He got into a lengthy discussion with another man who tried to calm him down. He stayed firm.

Eventually, the circle around the two men dispersed.

But no one, at least on that morning, picked up a torch to resume the attempt to set the courthouse plywood on fire.