PORTLAND — Mayor Ted Wheeler choked on tear gas late Wednesday as he stood at the gates assembled outside the federal courthouse in downtown Portland, where federal agents set off explosives and fired chemicals into a crowd of hundreds.

The Democratic mayor pressed a hand over his nose and mouth, already covered by a blue surgical mask, as a thick cloud of gas surged toward him. He had strapped on lab goggles to help protect his eyes, but still, the mayor said, his face burned and eyes watered.

“It’s hard to breathe — it’s a little harder to breathe than I thought,” Wheeler told The Washington Post while a man with a leaf blower turned the nozzle on the mayor to clear away any gas still hanging in the air. “This is abhorrent. This is beneath us.”

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As Wheeler stood at the fence, he was heckled and insulted. Some demonstrators called for his resignation. Others, who had been tear-gassed by the Portland Police Bureau over the past eight weeks, shouted questions at the mayor.

“How does that taste?”

“Does it burn?”

“How can you let your people get gassed out here every night?”

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Wheeler had come to the protest, he said, to stand with protesters in the face of what he has described as an “occupying force” — federal agents who were deployed by President Donald Trump to restore order to a city that the president has described as “worse than Afghanistan.”

For days, Wheeler, Oregon Democratic Gov. Kate Brown and other state and local officials have demanded that Trump withdraw the surge of federal officers from this Pacific Northwest city, where ongoing protests have continued nightly for more than 50 straight days. But little has changed.

Videos of federal officers pelting protesters with less-lethal impact munitions like rubber bullets and exploding pepper balls, shooting tear gas into city streets and launching stun grenades into crowds have captured millions of views on social media and incensed local lawmakers.

“The reason I am here tonight is to stand with you no matter what,” Wheeler had said earlier in the night to a roar of cheers from the steps of the Multnomah County Justice Center, where the county jail is located. “And if they launch the tear gas against you, they’re launching the tear gas against me!”

But many in the crowd didn’t believe him. They shook their heads and muttered words like “photo op.” One young man shouted, “You’re only saying that because CNN is here.”

For hours before Wheeler’s brush with chemical irritants, the mayor made a contentious and, at times, tense attempt to talk with protesters. On the wall of the justice center behind him, activists had displayed a list of demands. The last demand on the list, which included defunding the Portland Police Bureau by 50 percent and expelling federal forces from the city, was for Wheeler to resign.

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Wheeler tried to address Trump’s recent pronouncement that he would be sending a surge of federal forces to other Democrat-led American cities to help combat crime, starting with Chicago and Albuquerque, but the crowd shouted him down.

They wanted, instead, to talk about what, exactly, he was doing to get rid of the federal agents and asked about his dual role as mayor and chief of police. Some shared personal stories of run-ins with the police. Others demanded that he consider making sweeping systemic change to policing in Portland.

As he spoke, the constant thrum of the crowd was punctured with chants of “Quit your job!”

Amanda Lundbom, 36, attended the protest with her 16-year-old daughter. They stood off to the side as Wheeler took questions from the crowd. Lundbom has been going to Portland demonstrations since they began in late May, following the death George Floyd, a black man, in police custody in Minneapolis. She wanted to know what took the mayor so long to join them in the streets, calling for racial justice.

She was skeptical about the mayor’s commitment to stand on the front line of the protests, facing down federal officers in tactical gear.

“He has a whole army of Portland police officers who he could have out here keeping the citizens of this city safe while we are being brutalized by the feds,” she said. “Why don’t they stand with us? Protect us? He says he doesn’t want [the federal agents] here, but he’s not doing anything to stop them from hurting his people.”

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Wheeler wound his way through the crowd. When he began to veer away from the Mark O. Hatfield federal courthouse, protesters yelled, “You’re going the wrong way, Ted! Go to the front!”

Wheeler said he had never been tear-gassed before Wednesday night.

Just after 11 p.m., he got his first taste. A chest-pounding boom echoed through the square as dozens retreated from the fence. Some people who had come prepared with gas masks and leaf blowers moved toward the front.

Wheeler stood rooted to the spot in front of black-clad demonstrators carrying umbrellas and homemade shields.

The mayor’s protest appearance comes amid a competitive reelection bid in a city that hasn’t had a two-term mayor since 2005. Wheeler is being challenged from the left by Sarah Iannarone, who has made police accountability a primary issue of her campaign and has been tear-gassed at recent rallies against police violence.

Iannarone had publicly challenged Wheeler to show up to such a demonstration.

After he was hit with the gas, Wheeler said the experience made him rethink the city’s allowance that Portland police can use gas on protesters once a riot is declared. Under Oregon law, a riot can be any situation in which a person commits a crime while five or more other people engage “in tumultuous and violent conduct.”

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“I don’t think we should use these tools at all,” Wheeler said. “It makes me think long and hard about whether this is really a viable tool. I want to look at other options. This is not a good option.”

After nearly an hour, Wheeler had enough. A thick cloud of gas hung over the place where he stood as he and two security officers pushed through the crowd and away from the federal building.

Protesters marveled as he marched past. Many followed him, yelling as he went, urging him back toward the front of the line.

“I’ve been out here for more than 50 nights,” one man shouted. “Ask me how many times I’ve been gassed!”

An hour later, Portland police declared a riot outside the justice center, where Wheeler had stood just hours before, talking to his constituents.

Police told demonstrators to leave. If they refused, an officer announced, the department could tear-gas the crowd at will.