PORTLAND, Ore. — Images broadcast worldwide of Portland Mayor Ted Wheeler getting tear-gassed alongside protesters made him an overnight standard-bearer for the growing movement against President Trump’s use of federal agents to tamp down violence in U.S. cities.

For many Portland residents, however, the moment felt ironic and hypocritical. Before federal agents arrived in the liberal city, local police repeatedly used tear gas on protesters, and Wheeler – who is also the police commissioner – is increasingly unpopular with those who feel he couldn’t, or wouldn’t, control officers. Before he was gassed this week, Wheeler fought to be heard over a hostile crowd screaming obscenities and then hecklers surrounded him as he left hours later with chemicals in his eyes.

The failure by the Democrat and sixth-generation Oregon resident to navigate this polarizing moment in his hometown reflects Portland’s simmering internal struggle over its identity. A city that prides itself on having one of the nation’s most progressive resumes is being challenged to move even further left by a growing anti-police constituency that’s elevating Black voices during America’s reckoning over racism. Those voices have long gone unheard in Portland, which is less than 6 percent Black.

“The national imagination of Portland – and even to some extent Portland’s imagination of itself – as a hotbed of progressivism and liberalism has never been matched by the political reality,” said Chris Shortell, a political science professor at Portland State University. “It’s not as liberal and progressive of a city as the national public holds it to be, and that’s particularly true on race.”

He calls it “the dark underbelly of Portland.”

“On the national level, you just see, ‘Hey, the mayor stepped out there and got tear-gassed!’ But that covers over the reality of the local political situation,” Shortell said.

In the weeks since George Floyd’s death by Minneapolis police, protests against racial injustice and police brutality have filled Portland’s streets. Days of peaceful marches that initially attracted up to 10,000 people devolved into smaller groups of demonstrators who set fires, vandalized buildings and smashed windows. Businesses and others have complained the city hasn’t been able to restore order.

But when Trump sent 114 federal agents to quell the unrest earlier this month, the city once more began to turn out in force against what Wheeler has called an “illegal occupation.” Crowds of several thousand demonstrators show up nightly outside the Mark O. Hatfield Federal Courthouse to square off with federal agents armed with tear gas, rubber bullets and stun grenades.

And while the city’s anger is channeled against Trump and his federal forces, beneath every protest lies tension about what Portland is, what it should be and how it will get there.

Federal officers advance on a group of demonstrators during a Black Lives Matter protest at the Mark O. Hatfield United States Courthouse Saturday in Portland, Ore. Marcio Jose Sanchez/Associated Press

It built its progressive reputation carefully over decades by breaking ground on issues like environmentalism, public transportation and urban planning. But on other progressive issues – racial politics and police reform key among them – Portland has fallen far short and to some, is proving slow to recognize that blind spot.

“We have this identity nationally as a city that is weird and progressive – you know, Portlandia,” said Gregory McKelvey, a Portland activist and police critic. “But we really earned this liberal reputation at a time where having a mayor that said, ‘Yeah, I think two gay people should be able to get married’ was seen as … radically progressive. The rest of the country has caught up with us and our elected officials are still at that level of progressive.”

The city’s overwhelming whiteness also informs the Black community’s impatience with reform. For years, Portland was an important base for neo-Nazi groups. Even now, right-wing groups like the Proud Boys and Patriot Prayer frequently hold rallies in the city.

“Portland in many respects is … where you could assume consensus existed because some voices simply weren’t heard, and that made it easier to govern and it made it easier to tell a story about what Portland is,” Shortell said of Black residents. “But now those groups have gained a voice.”

Some want to end all funding for police, others want to cut $50 million from their budget and still others want oversight reforms, such as an independent review board.

“Defunding the police is really a racial justice concern. It’s racial justice concern No. 1,” said Mac Smiff, a Black Portland resident who asked Wheeler pointed questions before the mayor was tear-gassed. “The only reason we’re doing graffiti and protesting is because you will not come to the table for what we ask for.”

Federal officers advance on demonstrators during a Black Lives Matter protest Friday at the Mark O. Hatfield United States Courthouse in Portland, Ore. Marcio Jose Sanchez/Associated Press

City Commissioner Jo Ann Hardesty, the first Black woman elected to that position, demanded last week that Wheeler cede control of police to her. He declined.

“The city needs stability and leadership right now,” Wheeler’s staff said in an emailed response to questions.

“The community called for the mayor to join and listen, and hear their frustrations with him, the police bureau, and the city,” the statement said of Wheeler attending Wednesday’s protest. “Despite knowing that he would be subject to anger and harassment, the mayor felt it was important to go and stay.”

The statement said the mayor was working to hold the Portland Police Bureau accountable and defended what it called the city’s “historic, unprecedented reform” of the agency.

That includes a vote last month to divert nearly $16 million from the police budget to programs that support people of color. It eliminates school resource officers, a high-profile gun violence reduction team and transit officers. The police chief, a white woman, also stepped down in favor of a Black man.

Wheeler is a “decent man” but he is also “a privileged white man who grew up among wealth and privilege,” Hardesty told The Associated Press. “And so I don’t know if he has what we need at this time. I can tell you that I have what we need to fundamentally change how policing happens in Portland – and I would be fearless about changing it.”

Hardesty wants to get a measure on the November ballot that would establish an independent police oversight system. She’s been fighting to reform the Police Bureau for three decades and blasted those who said she settled by accepting less than a $50 million cut from its budget – a sign of the divisions even among those seeking change.

“I suspect there’s a lot of progressive Portlanders who thought, ‘OK, they took $16 million out of the police budget, and that’s a really good step.’ And for the people who are really on the emotional edge of this issue, that’s not enough,” said Carl Abbott, a Portland State University professor emeritus of urban studies and planning.

“What does a good, well-meaning, progressive white protester do? They go out and march in the peaceful protests, they put Black Lives Matter signs in their windows and read books on how to be a better ally and then try to do it,” he said. “But none of those actions penetrate the culture of the police force, and that is the nub.”