PORTLAND, Ore. — After flooding the streets around the federal courthouse in Portland with tear gas during Friday’s early morning hours, dozens of federal officers in camouflage and tactical gear stood in formation around the front of the building.
Then, as one protester blared a soundtrack of “The Imperial March,” the officers started advancing. Through the acrid haze, they continued to fire flash grenades and welt-inducing marble-size balls filled with caustic chemicals. They moved down Main Street and continued up the hill, where one of the agents announced over a loudspeaker: “This is an unlawful assembly.”
By the time the security forces halted their advance, the federal courthouse they had been sent to protect was out of sight — two blocks behind them.
The aggressive incursion of federal officers into Portland has been stretching the legal limits of federal law enforcement, as agents with batons and riot gear range deep into the streets of a city whose leadership has made it clear they are not welcome.
“I think it’s absolutely improper,” Oregon’s attorney general, Ellen Rosenblum, said in an interview on Friday. “It’s absolutely beyond their authority.”
The state lost its bid on Friday for a restraining order against four federal agencies on the grounds that the state attorney general lacked standing, but several other challenges are still making their way through the courts.
Federal officers who arrived this month to help control protests over racial injustice and police violence have made dozens of arrests for federal crimes, including assaults on federal officers and failing to comply with law enforcement commands. More than 40 protesters have been arrested, and dozens now face federal criminal charges.
One protester standing on a city street outside the federal courthouse was shot in the head with a crowd-control munition, leaving a bloody scene and a serious facial injury that required surgery. In another incident, an officer was seen repeatedly using a baton to whack a Navy veteran who said he had come to speak to the agents. Videos taken by members of the public captured camouflaged personnel pulling protesters into unmarked vans.
The inspectors general of the Department of Justice and the Department of Homeland Security have opened investigations into the tactics.
During 57 consecutive nights of protests, demonstrators have squared off first with the Portland police and then with federal agents in what at times have been pitched battles, with protesters throwing water bottles or fireworks and agents responding with frequent volleys of tear gas. The arrival of the federal agents caused the protests to swell and focused the ire of protesters onto the Mark O. Hatfield U.S. Courthouse, across from a park shaded by mature trees.
What began as a movement for racial justice became a broader campaign to dislodge the federal forces from the city.
The federal agents from four agencies arrived after President Trump signed an executive order on June 26 ordering the protection of federal monuments and buildings.
Their presence quickly became a political rallying point.
Senator Ron Wyden of Oregon, a Democrat, compared the agents to an “occupying army.” Speaker Nancy Pelosi, Democrat of California, called them “storm troopers.”
Mr. Trump criticized the police protests around the country in cities “all run by liberal Democrats” and defended the move to send in federal agents, warning that with the continuing turbulence in the streets, “They were going to lose Portland.”
Chad F. Wolf, the acting secretary of homeland security, described the protesters squaring off with federal agents outside the federal courthouse in Portland as “anarchists and criminals.”
“We will continue to take the appropriate action to protect our facilities and our law enforcement officers,” Mr. Wolf said at a news briefing this past week. “If we left tomorrow they would burn that building down.”
There is broad agreement among legal scholars that the federal government has the right to protect its buildings. But how far that authority extends into a city — and which tactics may be employed — is less clear.
Robert Tsai, a professor at the Washington College of Law at American University, said the nation’s founders explicitly left local policing within the jurisdiction of local authorities.
He questioned whether the federal agents had the right to extend their operations blocks away from the buildings they are protecting.
“If the federal troops are starting to wander the streets, they appear to be crossing the line into general policing, which is outside their powers,” Professor Tsai said.
Homeland Security officials say they are operating under a federal statute that permits federal agents to venture outside the boundaries of the courthouse to “conduct investigations” into crimes against federal property or officers.
But patrolling the streets and detaining or tear-gassing protesters go beyond that legal authority, said David Lapan, the former spokesman for the agency when it was led by John Kelly, Mr. Trump’s first secretary of homeland security.
“That’s not an investigation,” Mr. Lapan said. “That’s just a show of force.”
John Malcolm, vice president for the Institute for Constitutional Government at the conservative Heritage Foundation, and a former deputy assistant attorney general during the George W. Bush administration, said federal agents have clear legal authority to pursue protesters who have damaged federal property.
“Once they have committed a crime the federal authorities have probable cause to go arrest them,” Mr. Malcolm said. “I don’t care how many blocks away they are from that property.”
While federal authorities are not intended to be riot police, he said, the federal government has the authority to send in troops in extreme situations in which there is a breakdown of authority and local officials are unable to effectively enforce local laws.
“But we are not there yet, and I pray that we don’t get there,” he said.
Outraged by the federal presence, government leaders in Portland have been looking for ways to push back against the deployment. The Portland Police Bureau ousted federal representatives from the city’s command post. Mayor Ted Wheeler, who himself was hit with tear gas fired by federal agents on Wednesday night, called the federal deployment an abuse of authority.
“My colleagues and I are looking at every possible legal option we have to get the feds out of here,” Mr. Wheeler said in an interview.
In the state’s legal challenge, Ms. Rosenblum argued that the operations of federal authorities, using unmarked vehicles to detain protesters, resembled abductions. The lawsuit called on the court to order the agents to stop arresting individuals without probable cause and to clearly identify themselves and their agency before detaining or arresting “any person off the streets in Oregon.”
But in his ruling on Friday, Judge Michael W. Mosman of the U.S. District Court in Portland said the state attorney general’s office did not have standing to bring the case because it had not shown that the issue was “an interest that is specific to the state itself.”
In an interview, Ms. Rosenblum said that having federal agents battling protesters in Portland was un-American because the country does not have a tradition of a national police force.
“The police should be ideally as local as possible,” she said. “It’s about trust, relationships and community building.”
She warned that all Americans need to be concerned about what is happening in Portland.
“It could be happening in your city next,” she said.
The inspector general of the Department of Homeland Security, Joseph V. Cuffari, told lawmakers in a letter that he planned to examine the authority the agency used to deploy agents to Portland.
Some of the protesters who originally focused their anger on the case of George Floyd, whose death in police custody in Minneapolis in May sparked demonstrations around the country, now have turned much of their attention to the presence of federal officers on Portland’s streets.
On Friday night, a crowd gathered outside a fence erected around the federal courthouse; some in the crowd lit fires, lobbed fireworks over the fence and attempted to pull it down with power tools. Federal agents entered the street to disperse the crowd at 2:30 a.m.
Most of the demonstrations during the evening, though, were peaceful. A group of military veterans lined up along the fence, joining a “Wall of Moms,” hundreds of mothers who have linked arms to challenge the presence of the federal agents, who had been there on previous nights. There was also a “Wall of Dads” carrying leaf blowers to combat the tear gas.
Jennifer Kristiansen, a family-law attorney, was one of many women who came out to the protests in recent days to join the “Wall of Moms.” In the early morning hours on Tuesday, she said, as agents were clearing protesters from in front of the courthouse, one of them reported to another that Ms. Kristiansen had struck him.
Ms. Kristiansen said that she had done no such thing and that one of the officers ended up assaulting her, groping her chest and backside during the arrest.
“This is not creeping authoritarianism,” Ms. Kristiansen said. “The authoritarianism is here.”
Zolan Kanno-Youngs contributed reporting from Washington.