Portland Mayor Ted Wheeler stood Wednesday among the front lines of protests outside the federal courthouse, where he and hundreds of other people were tear gassed repeatedly by federal officers.

Demonstrators have converged every night for eight weeks in downtown Portland to call for systemic reforms to the police bureau Wheeler oversees. The mayor’s appearance on Day 56 attracted attention and jeers from the crowd of more than 2,000 people.

Wheeler pledged to stand beside protesters subjected to consistent force by federal law enforcement who have made the Portland protests a national storyline.

The mayor told people he was raising alarms across the nation to warn other cities about what could unfold in their towns.

Wheeler and a team of city security guards spent nearly three hours at the demonstrations, including about an hour in front of the courthouse. Federal officers released gas on the crowd after some people threw things, walked inside a new perimeter fence and aimed fireworks toward the building.

Wearing a disposable mask and plastic goggles, Wheeler stayed at the fence through multiple rounds of tear gas. Organizers of the demonstrations had encouraged Wheeler to bear witness to federal force.

“The reason I am here tonight is to stand with you,” Wheeler told the crowd. “If they’re launching the tear gas against you, they’re launching the tear gas against me.”

Wheeler is the city police commissioner. The Portland Police Bureau has also regularly used tear gas on protesters, although that has waned in the face of scrutiny and a wave of lawsuits against the city.

Yet on early Thursday morning, Portland police warned people they might use tear gas to break up the crowd after declaring it a riot. Wheeler had left in a cloud of tear gas less than an hour earlier.

The police bureau’s repeated warnings came on the same day the Portland City Council issued an immediate ban for all Portland police employees to stop cooperating with federal law enforcement.

By 2:30 a.m., Portland police had not responded in force like they had warned. But the hours-long confrontation between demonstrators and federal officers continued to periodically flare up outside the federal courthouse. The addition of a fence surrounding kept the crowd — and the federal response — contained almost entirely to the building. Officers repeatedly emerged to set off gas or shoot non-lethal projectiles toward protesters.

Protesters greeted Wheeler’s arrival at the start of the night by chanting his name preceded by an expletive. The crowd often shouted to drown out what he was saying. He first stood in a throng of protesters near the Justice Center, next to the federal courthouse on Southwest Third Avenue.

Some protesters asked Wheeler questions, and the conversation was captured in part by TV crew microphones. Wheeler said he does not like the use of non-lethal projectiles or gas on crowds, because they are often deployed in an indiscriminate way. He said he has directed the use of such devices to be targeted to specific incidents. He did not make clear when he issued that directive; and police force in response to the protests has sometimes extended to bystanders.

Throughout the night, both Wheeler and the crowd focused on the recent escalating force by federal police. The mayor said protesters were taking the best possible step in response to the action: “Be here, be heard, be unified and be clear … We want them to leave.”

Around 10 p.m., Wheeler made his way to the steps of the Justice Center, where Black Lives Matter organizers were leading a rally and invited him to address the crowd. When one organizer asked Wheeler why he had not showed up every day, he said he had. He went on to list actions by City Council in recent weeks.

As he spoke, someone used a projector to display demands of him onto the side of the building. The demands included forcing federal officials out, freeing any jailed protesters, significantly slashing the police budget and, ultimately, resigning.

Wheeler left the stage after about 20 minutes and talked with people in the crowd.

Focus started to shift to the federal courthouse after 10:30 p.m. Officials had built a new fence bolted to steel bars that blocked people from collecting directly next to the courthouse entrance.

Some people set off fireworks toward the building and threw debris over the fence. A small fire ignited near the edge of the fence.

As the situation escalated, young Black Portlanders continued to lead the rally at the Justice Center. One person reminded the crowd about the peaceful aim of the protest. But within minutes, a speaker told parent groups who had gathered to leave to avoid confrontation with federal officers.

Most people stayed, including Wheeler. Wheeler talked to several people in the crowd by the Justice Center, including Micah Fletcher, the man who was stabbed in a 2017 MAX train attack that left two other men dead.

The federal courthouse continued to draw more attention. After some people started shaking it, the Federal Protective Service used a loudspeaker to tell the crowd not to tamper with the fence.

Around 11 p.m., a few people found a way into the fence and wandered near the courthouse entrance. Federal officers ordered those people to leave.

Wheeler navigated to the front of the fence, surrounded by reporters and at least five security guards wearing earpieces.

Federal officers emerged from the courthouse around the same time the mayor arrived. Agents appeared to detain some people, including one person who had been roller skating in the area blocked by fences.

Some officers set off tear gas and other devices to break up the crowd. Many people stayed or returned soon after. Wheeler put on goggles and remained at the fence, flanked by guards.

By 11:25 p.m., the debris fire continued to burn on the sidewalk. Portland police said on Twitter that fireworks or a similar type of device had ignited the flames.

Federal officers emerged again around 11:40 p.m. and set off devices, including some that emitted gas, smoke or sound, to break up the crowd. The situation calmed down for a few minutes, then federal officers reemerged after warning people to leave federal property.

Wheeler and his security guards left after federal officers set off more tear gas. Some people followed Wheeler back toward the Portland Building on Southwest Fifth Avenue. He retreated inside the city office with guards.

By midnight, several hundred people returned to the courthouse. Some people again set off fireworks. Other people ran into the fenced-off area to throw debris or embers toward the building. Federal officers again released a cloud of tear gas around 12:20 a.m.

Portland police soon after declared a riot at the Justice Center next door and ordered people to leave the area. It was the first audible action by police in recent nights of protesting.

Police warned the crowd that if they did not leave, they would be subject to tear gas and other types of force.

An Oregonian/OregonLive journalist who spent several hours outside the Justice Center did not see anything happen that prompted a riot declaration centered on that building. The crowd’s attention was fixed on the courthouse.

Portland police repeated the riot warning at least 10 times. But as of 3 a.m., police had not arrived in force.

The order to leave did not prompt demonstrators to go.

Police issued a statement around 2:45 a.m. that explained they had labeled the gathering a riot because it had “created a grave risk of public alarm.” Police said that some people had also damaged fire hydrants overnight, causing them to spew water into the street.

Police said they did not arrest any one over the course of the night.

Federal officers appeared to detain at least two people.

By 12:50 a.m., hundreds of people remained near the courthouse, where a few small fires burned on the pavement in front. Federal officers walked toward the crowd and shot projectiles at people while setting off tear gas.

The tense face off continued past 3 a.m. Federal officers often emerged to try to break up the crowd, and protesters stayed. Some people stood near the fence, while others milled about nearby streets. Two people waved American flags, and one person carried a city of Portland flag.

Earlier in Wednesday evening, Wheeler issued a statement on Twitter about the use of force on protesters by federal agents.

The mayor said he had heard “concerns within the community” that federal officers may be approved to use lethal force on protesters. He said Oregon’s top federal official, U.S. Attorney for Oregon Billy Williams, “assures me that the federal government has no plans to use live ammunition on Portlanders tonight, and that such an order would be unlawful.”

Still, Wheeler urged people to stay safe downtown.

The mayor’s note of caution arrived hours after President Donald Trump announced a “surge” of federal law enforcement into U.S. cities to respond to “radical” groups, as federal officers have in Portland for several consecutive nights.

Ryan Nguyen, Dave Killen and Beth Nakamura of The Oregonian/OregonLive contributed to this report.

— Shane Dixon Kavanaugh;

— Noelle Crombie;

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