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A federal officer tries to disperse a protest in front of the Mark O. Hatfield U.S. Courthouse, in Portland, Ore., on July 21, 2020.Nathan Howard/Getty Images

Lawyers for Oregon argued Wednesday for a restraining order against federal agents deployed to quell protests in Portland, in a stand off that some legal experts have warned could lead to a constitutional crisis in an election year.

A federal judge heard the state’s and the U.S. government’s arguments in a lawsuit filed by Oregon Attorney-General Ellen Rosenblum, who accuses federal agents of arresting protesters without probable cause, whisking them away in unmarked cars and using excessive force to quell the unrest. Federal authorities have disputed those allegations.

The lawsuit is part of a growing pushback against the Trump administration’s use of federal agents in Portland and its plans to do the same in other cities that is deepening the country’s already considerable political divides. Democratic mayors of 15 cities condemned the use of the agents in a letter to the attorney-general.

The hearing Wednesday focused on the actions of more than 100 federal agents responding to protests outside the city’s Mark O. Hatfield Federal Courthouse, which has been a target for more than 50 nights of demonstrations against racial injustice after the killing of George Floyd at the hands of Minneapolis police.

The motion for a temporary restraining order asks U.S. District Court Judge Michael Mosman to command agents from the Department of Homeland Security, the U.S. Customs and Border Patrol, the Federal Protective Service and the U.S. Marshals Service to immediately stop detaining protesters without probable cause, to identify themselves and their agency before arresting anyone, and to explain why an arrest is taking place.

During the hearing – held by video conference because of the coronavirus pandemic – the state acknowledged that federal agents have the right to defend the courthouse but argued they had overstepped.

Ms. Rosenblum, the state attorney-general, said she was asking the court to “declare it not acceptable for federal officers to use unconstitutional, police state-type acts to detain citizens of Oregon without cause.”

David Morrell, a lawyer for the U.S. government, called the motion “extraordinary” and told the court it was based solely on “a few threadbare declarations” from witnesses and a Twitter video.

“The Hatfield courthouse did not damage itself,” he said, calling the protests “dangerous and volatile.”

It’s not clear when Justice Mosman will rule, but he challenged the state on whether it had the standing to ask for the restraining order. The judge noted that past legal decisions have required a state to establish a very high bar – “quasi-sovereign interest” – in order to successfully sue the U.S. government.

Lawyers for Oregon contended they had met that bar because the actions of the federal agents could erode Oregonians’ trust in all law enforcement, including state and city officers.

But Mr. Morrell, the U.S. government lawyer, disputed that, saying successful suits usually involved issues that affected many people, not “highly individual interests,” like the arrests.

The suit is one of several filed over law enforcement’s response to the Portland protests. On Thursday, a judge will hear arguments in a lawsuit filed by the American Civil Liberties Union on behalf of journalists and legal observers who say they were targeted and attacked by police while documenting demonstrations. A freelance photographer covering the protests for the Associated Press submitted an affidavit that he was beaten with batons, chemical irritants and hit with rubber bullets.

U.S. Judge Michael Simon previously ruled that journalists and legal observers are exempt from Portland police orders requiring protesters to disperse once an unlawful assembly has been declared. Federal lawyers say that journalists should have to leave when ordered.

Ahead of Wednesday’s hearing, a fence was raised around Portland’s federal courthouse, at which protesters and federal agents had clashed again overnight, according to police. Protesters repeatedly tried to break into the building and set fires around it, and the federal agents drove them back with tear gas and stun grenades, the police said.

Far from tamping down the unrest in Portland, the presence of federal agents has recently energized the nightly protests.

Mayor Ted Wheeler’s office said Wednesday that he would attend the protests later in the evening and there would be “some form of dialogue” with the demonstrators. Mr. Wheeler has been vocal in opposing the federal agents’ presence in Portland – but he has still come in for harsh criticism from many sides. Some, including fellow council members, have accused him of not reining in local police, who used tear gas before the federal agents arrived. Others, including business leaders, have condemned him for not bringing the situation under control.

As news of Mr. Wheeler’s planned appearance spread, one group that has been prominent in the protests, the Pacific Northwest Youth Liberation Front, told the mayor to stay away.

More broadly, the use of federal agents against the wishes of state and local officials – and the threat that it might be done elsewhere – was deepening the country’s already considerable political divides and potentially setting up a constitutional crisis months ahead of the presidential election. The standoff could escalate if U.S. President Donald Trump sends federal agents elsewhere, as he says he plans to do, including to Chicago.

The mayors of Chicago, Portland and other Democrat-led cities objected to such deployments and called them political in a letter to Attorney-General William Barr and Department of Homeland Security acting secretary Chad Wolf.

Federal authorities have defended their response, saying officials in Oregon had been unwilling to work with them to stop the vandalism against the U.S. courthouse and violence against federal officers.

Mr. Wolf told a news conference Tuesday that agents have been assaulted with lasers, bats, fireworks, bottles and other weapons. While he said federal agencies have made 43 arrests since July 4, he disputed that they were done by unidentified agents, noting that they have the word “police” on their uniforms.

Among the protesters this week was Maureen Healy, who joined a march Monday as demonstrators sang songs and chanted the names of Black lives lost.

Just after midnight, she saw a line of authorities wearing camouflage and dark outfits advance on the crowd. The crowd retreated, and Ms. Healy said she heard bangs, saw smoke and was struck by a projectile. She went to the hospital with a black eye, cut to her face and a possible concussion.

“I was protesting peacefully so why did federal troops shoot me in the head?” asked Ms. Healy, 52, who is the chair of the history department at Lewis & Clark College.

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