At 8 pm on May 29, a throng of Portlanders started marching out of Peninsula Park and south along Martin Luther King Jr. Boulevard. For the next four days, civic leaders would plead with them to go home.

There's no telling when they will.

As in many other cities across the nation, Portlanders were protesting the death of George Floyd, a 46-year-old black man who died after Minneapolis police knelt on his neck, back and legs. And, as in other cities, the protests spiraled into riots and vandalism.

(Wesley Lapointe)
(Wesley Lapointe)

After two months of fear and isolation created by the COVID-19 pandemic, Floyd's killing felt like the breaching of a dam of frustration at the scores of other black Americans who have died at the hands of police.

Demonstrators demanded Portland police recite the names of the black citizens they have killed over the past 17 years: Quanice Hayes, Patrick Kimmons, Keaton Otis, Kendra James, Terrell Johnson, Andre Gladen. They chanted the familiar rallying cry "Hands Up, Don't Shoot!" and at times taunted the police with the jeer "All cops are bastards!"

(Wesley Lapointe)
(Wesley Lapointe)

Many were peaceful. But others set fires inside the Multnomah County Justice Center. Rioters looted shops—corporate giants and mom-and-pop storefronts. Teenagers ran up and down the escalators of an empty Target and cleaned out the Apple Store. On May 31, vandals tagged the federal courthouse until the building looked like an anguished Picasso.

Police, too, based on reporting on the ground by WW's reporters and photographers, ranged from permissive to militant. They allowed some protests to continue for hours. At other moments, they lobbed stun grenades and sprayed crowds seemingly indiscriminately with tear gas.

Such scenes are not new in Portland. This is: Black people are in charge of both the protests and the government response to them.

City Commissioner Jo Ann Hardesty asked to set the first curfew.

Pastor Roy Tate preached in the park before the initial march set out for the Justice Center.

State Rep. Janelle Bynum sat beside Gov. Kate Brown as she mobilized the Oregon National Guard.

And Lilith Sinclair is leading the marches that defy Hardesty's order to stay home.

(Aaron Wessling)
(Aaron Wessling)

These are not the largest protests Portland has witnessed, even in the past decade. (The 2011 Occupy marches drew 10,000 people.) They are not the longest. (Protesters of President Trump's election in 2016 blocked freeways for six consecutive nights.) They are not the most violent. (Proud Boys and antifascists beat each other bloody with batons and flag poles during scheduled brawls the past three summers.)

But the rioting that has followed each protest may have inflicted the most property damage in Portland history, at least in terms of storefronts shattered and looted.

And the chaos is part of a wave of similar protests and riots across the United States—creating the unsettling sense that American society teeters on the edge of collapse.

(Aaron Wessling)
(Aaron Wessling)

The destruction could be the result of cooped-up young people unloading frustration pent up over two months of quarantine. But it also seems to emerge from a place of despair, a recognition that black and brown people are dying at a greater rate from COVID-19 for the same reason they die at the hands of police: because white America has made them disposable.

A reporter asked one young Portlander, Jordan Simacre, whether he felt safe joining the protests.

"Being black in America, you're already born dead," he said. "Do I feel safe? No, not really. Part of that not feeling safe is why a lot of us are coming out and doing this reckless stuff, endangering our lives and protesting. We're already not safe. We're gonna make some noise with it."

(Wesley Lapointe)
(Wesley Lapointe)

For all Portlanders, the tension of this moment is that no one knows how much more destruction will be wrought in downtown Portland. But we also don't know what meaning will be assigned to it in the months and years to come.

Will this be the moment that brings about new accountability for police? Will the leaders who have been elected in Portland on platforms of police reform deliver on their high-minded promises to ensure that no more unarmed black men and women are killed by Portland cops?

Or will public sentiment turn against the demands of protesters? Will the president send in the military for a show of force—in Portland, or elsewhere?
What makes this moment so perilous and important is, we simply don't know how long it will last or what it will mean. So we asked four black leaders at the center of the struggle—Hardesty, Tate, Bynum and Sinclair—to say what they thought it meant.

In the following pages, you will find interviews with each of them, conducted in the midst of one of the most chaotic and raw periods this city has experienced. You'll also find vivid moments—captured in words and photos—from a city on the brink of history.

City Commissioner Jo Ann Hardesty

The person who asked to set a curfew across Portland last weekend was Jo Ann Hardesty—the first black woman elected to the City Council and a three-decade advocate for police reform.

With Mayor Ted Wheeler out of town May 29, Hardesty was acting mayor, giving her executive authority over the city. At around 11 on Friday night, she was preparing for bed at her East Portland home when she heard Portland Fire & Rescue—her bureau—sending fire engines downtown. She'd been up since 7 am and wouldn't sleep that night. She hitched a ride to the command station with Fire Chief Sara Boone, the first black woman to run the fire bureau.

Over the next three hours, Hardesty made the choice to, in her words, "close this down." At about 12:30 am, she called Wheeler: "I said to him, 'It looks like you and I talk,' because he and I made pretty much the same statement."

Setting a curfew was a remarkable decision by the former president of the NAACP of Portland, who spent 30 years watchdogging police and sometimes marching through the streets herself, bullhorn in hand. (She says she wasn't consulted on policing decisions this weekend and is waiting to review reports of arrests and police conduct before talking about what happened in the streets.) By June 1, after the curfew failed to persuade protesters to stay home over three nights that were by turns peaceful, tense and occasionally violent, she reversed herself and said the curfew should be lifted. But Wheeler, who had by then returned to town, kept it in place.

WW spoke to Hardesty about what this moment means to her. RACHEL MONAHAN.

What was your reaction Friday night to what you were seeing downtown?

Devastation, anger, sadness—all of those combined.

As I was looking at the people who were participating in the destruction, I didn't see any familiar faces. I came to a conclusion early on that these folks were not part of any peaceful protest concerned about the death and life of black people. It was clear to me that there were a group of folks that came just to be able to tear stuff up. And they were just having a grand old time.

A man fuels a fire on the desk inside the Justice Department. (Alex Wittwer)
A man fuels a fire on the desk inside the Justice Department. (Alex Wittwer)

At what point did you start to prepare for a curfew?

It was around 12:30 or quarter to 1, when we woke the city attorney up and asked her to start developing the document that would allow for a curfew. I'm sitting there and I'm watching all this chaos happening and I went, "Why aren't we just closing this down?"

I was walked through the process and said, "Let's do that." And the first response I got was, well, the mayor has to sign it. And my answer was, "I am the mayor. He's not here and let's do it." And within a half-hour we had it.

A police officer levels a firearm at a protestor as the crowd begins breaking into the building. (Alex Wittwer)
A police officer levels a firearm at a protestor as the crowd begins breaking into the building. (Alex Wittwer)

Why did you want a curfew?

We have never had the kind of destruction that we had on Friday night in Portland ever, even when Trump first got elected, which is why my firm belief is that the provocateurs were not from Portland, did not care about black lives.

[Also,] we have not lifted our stay-at-home order. So if we allow people to continue to gather in these high numbers when the county hasn't even been OK'd for opening yet, then we are putting people's health in danger. And that was at the top of my mind when I first recommended it. As you know, I am not a law-and-order kind of person. I'm not someone that thinks that police is the answer to every community problem. [But] we're nowhere near out of this pandemic yet. And I have the responsibility to keep people safe.

Maybe people saw it as a challenge because Mayor Wheeler said it. [Wheeler announced the curfew upon his return to Portland on May 30.] And anything Mayor Wheeler says about the police they can't trust. If he says it, then people want to go the opposite way. But my experience in working with him is, he's trying also to help make the Police Bureau a more just bureau.

[By June 1, Hardesty reversed her position on the curfew, and wanted it lifted. On June 2, Wheeler did.]

What changed your mind?

I made the initial call for curfew based on what I witnessed Friday evening and early Saturday morning, but we are seeing that it has had the opposite impact. I do not believe a continued curfew is the path to move forward.

(Aaron Wessling)
(Aaron Wessling)

Why did you support the governor calling in the Oregon National Guard?

We know the chances of officers making bad decisions when they're fatigued increase exponentially, and we're hearing loud and clear right now that already they are fatigued. Sometimes we make decisions that we never would have made if not for a crisis. While I am in no way supportive of the National Guard coming to police the streets, I do believe we need to find ways to provide relief for frontline officers, and in this instance, it means having unarmed National Guard officers support back-end functions for Portland Police.

What's the significance of this moment for police accountability? Is it different from past moments of protest?

I think we are in a moment that's radically different. I've participated in protests in Portland for well over 25 years. But it's been a cumulative pain and suffering that has been ignored for my lifetime around police and how they engage and interact with black people.

How many times can community members really trust a system that constantly exonerates police officers for a brutality against community members?

What we're seeing all across the country is, people have just come to the end of their rope. There is no faith that our system will ever work as it was intended, as it should be intended, for all people. It's never worked for black folks. And it's not working for black people today.

But let me be clear. I do not think what we're seeing around the country has been stoked specifically by black people's pain. I think we're seeing people taking advantage of black people's pain to create disruption and destroy communities.

(Mick Hangland-Skill)
(Mick Hangland-Skill)

And what are you hearing from black Portlanders right now?

Black Portland is all over the board right now, which is not surprising, since we're not monolithic, right?

Some people are just sad. I'm hearing that people want real action now.

Because even though this death of George Floyd did not happen in Portland, Oregon, I could name off Kendra James, I could name off Aaron Campbell, I can name off a whole host of folks who should have never lost their life.

I think every time a new police killing happens of a black person, all the other killings come back.

(Alex Wittwer)
(Alex Wittwer)

Do you have a message that you'd want to send to the citizens of Portland who are thinking about going out into the streets this week?

I would just beg them to please stay home.

We are on the cusp of really reforming our criminal justice system in the Portland metro area. There is hope here now because of the people we've elected.
It's not by accident I got elected. It's not by accident. [Latino Network executive director] Carmen [Rubio] got elected [to the City Council], and it's not by accident Mike Schmidt just demolished his competition [in the Multnomah County district attorney's race].

Mike Schmidt said exactly what I have been saying for 30 years and what other activists have been saying for decades, and guess what? The voters voted for him.
The mayor and I are already about to look at every single specialty unit within the Portland Police Bureau. By February, we're going to be presenting to the City Council all the units that should not exist.

And so that's why destruction of businesses and property and people is just so devastating, because we're just on the cusp of actually being able to do the kind of things I've been fighting for for 25 years in this community.

A mass die-in was held on Burnside Bridge at 7:12pm. A moment of silence was observed by the crowd for 8m46s, the time it took for George Floyd to die. (Alex Wittwer) 06012020
A mass die-in was held on Burnside Bridge at 7:12pm. A moment of silence was observed by the crowd for 8m46s, the time it took for George Floyd to die. (Alex Wittwer) 06012020

What else will you take away from this weekend?

Policing is what got us into this mess, and we have to acknowledge that policing is not what's going to get us out of this mess. We need to minimize as much as possible any use of force by people who are sworn to protect and serve. And when they step out of line, they should be fired.

I am a child of the civil rights movement. My parents promised me it was going to be better when I was an adult, and it's not. In fact, it's a lot worse. We have permission to be as racist and vile as possible.

I hope we come out of this insanity of 45's [President Trump's] administration as people who are more loving, more caring and really committed to making sure that we are living in an equitable society. That's my hope.

Pastor Tate was one of the first speakers at the vigil. (Alex Wittwer)
Pastor Tate was one of the first speakers at the vigil. (Alex Wittwer)

Pastor Roy Tate

Tate, 65, is a pastor at Portland's Christ Memorial Community Church on North Killingsworth Street. He has served as a religious leader of Portland's black community for nearly 40 years. Tate spoke at a vigil in North Portland's Peninsula Park on May 29 in honor of Floyd, where he described watching the events in Minneapolis and feeling as if it were "a knife in an already existing wound." Hours after he spoke, a crowd marched from the park into downtown, where rioters set fire inside the Multnomah County Justice Center. That development horrified him. TESS RISKI.

What is your perspective on the protests these past few days?

We have a right to protest. We have a right to speak. We're angry, we're upset, we're not happy with what the police officers did to George Floyd. This is another black man's life that was taken by the hands of police who are sworn to protect and to serve.

But we do not have a right to riot, to vandalize businesses and burn cars and do all of this type of behavior. This is not going to help the cause at all. If they think they're doing us a favor, well: You're not.

I'm saddened because I live in this city, I love this city. Portland is a beautiful city. And we do not want it destroyed.

What's the message that you want to send to the broader Portland community about police brutality?

If you want to be a police officer in this city, you've got to be willing to not be an individual who wants to take somebody's life unnecessarily. You've got to be willing to get yourself trained and get yourself in a position where you know how to handle a mentally ill person as well as a person of color. And I think that that's an issue that's been long going on—that many of these police officers are just not trained to be able to deal with that area.

(Aaron Wessling)
(Aaron Wessling)

What aspects of criminal justice reform do you think need to happen in Portland?

When they're making the arrest of a person of color, it always looks like it's a violent arrest. And when they arrest a white person, it's a different story. I've seen white persons with weapons not get killed, not get shot, or arrested. And I've seen black people with no weapons end up getting hurt or killed. There's definitely a problem somewhere that lies in the police department. I don't know if it's the training, the accountability. I think that some of these police officers, they need to be taken off the force.

Any final thoughts?

We really want to make it clear, coming from the black community, coming from the faith leaders, that violence is not something we want.

Rep. Janelle Bynum (D-East Portland, Happy Valley)
Rep. Janelle Bynum (D-East Portland, Happy Valley)

Rep. Janelle Bynum (D-Happy Valley)

Bynum serves a legislative district that includes East Portland neighborhoods where many black people moved when they were priced out of their longtime homes. She also campaigned for reelection in 2018 in suburbs where one resident thought a black woman walking door to door was suspicious enough to call the police. And she owns several McDonald's restaurants in Oregon City—the kind of small businesses targeted by looters that weekend. That's a lot of perspectives to weigh. Which may help explain why she appeared June 1 beside Gov. Kate Brown, who was performing a balancing act, too: decrying racist policing while calling in the Oregon National Guard to assist with handling Portland's protests. Bynum talked to WW about what white Portlanders need to learn. LATISHA JENSEN.

What's your reaction to what has happened in the streets of Portland over the past three nights?

Oppression and violence against black people was the original pandemic of the community. To have people come out and raise voices about that is reassuring. Humanity still exists.

You're the owner of several McDonald's restaurants. How do you react to seeing small businesses damaged and looted?

It angers me, because I can feel the faces of the people who put the heart and souls into their businesses. And to have them damaged, it really hurts. It's sad to think that you have to think about ways in which you have to protect your business from people who don't mean any good. What they were doing was not related to the death of George Floyd.

Protesters raise fists, take a knee, as they occupy Burnside bridge. (Alex Wittwer)
Protesters raise fists, take a knee, as they occupy Burnside bridge. (Alex Wittwer)

What are your thoughts on the governor deploying the National Guard?

I think the governor's values—she's not a tanks type of person, that's not who she is. She's keenly aware of the optics of the government cracking down on people and suppressing speech and the right to protest. The Portland police had reached a capacity issue and they need their officers to rest. Providing rest for them, I support.

What do white Portlanders not understand about what is happening right now? What do you wish they understood?

There are at least two sets of white Portlanders. Those who believe in their progressivism and that they could not possibly perpetrate any of this violence on the black community. And then there are those who believe that the violence that we speak of is a long time ago and they have no responsibly to the collective to help fix it. There may be a third group of people who are kind of in the middle and are trying to figure it out. I would put forth that this year, they're trying to figure it out.

(Mick Hangland-Skill)
(Mick Hangland-Skill)

How do you think people of color can encourage their white peers to learn and understand without exhausting themselves?

I've had no less than 10 conversations with white friends, and they pretty much said the same thing: "I don't know where to start or what to do." It reminded me of asking my 9-year-old son to clean his room. They can start by reading, engaging and talking to their children. It is not the work of black people to fix the mindsets of white people. That's not our job. That's too heavy and it's not fair.

Do you feel this weekend's protests will create outcomes different from previous ones?

Every one of my rural legislative colleagues, they're telling me what they saw was horrible and no one should be treated like that. That's really the first time I've heard them personalize the issue of racism.

I had a conversation with my oldest daughter's principal. Some months back, they had issued this directive to their students that, if they wanted to protest or kneel at their games, football players or basketball players needed to have a conversation with their coach and go through some convoluted procedure. That felt wrong. Talking with your coach first before kneeling amounted to asking white people for permission to feel and permission to say that our lives are not disposable. I followed up with him this weekend and had a conversation with him this morning. I think he finally understood. He finally had the lens to get it.

Lilith Sinclair 0531_Wesley Lapointe
Lilith Sinclair 0531_Wesley Lapointe

Lilith Sinclair

Sinclair, 25, is an activist who works with with the workers' rights group Portland Jobs With Justice. (That group is not directly connected to organizing the past week's protests.) Sinclair, who wishes to be referred to by the gender pronouns they and them, has been involved in activism for years, including volunteering at the Portland Occupy ICE Camp in 2018. Sinclair was an organizer of a march May 31 that drew thousands of demonstrators. During Sunday's rally, they led the group of over 1,000 demonstrators from Laurelhurst Park in Northeast Portland to downtown at the Justice Center. "We're not here for apologies," Sinclair said into a megaphone Sunday. "We're here to dismantle, defund and completely destroy the police." WW asked them about defying the pleas from city officials to stay off the streets. TESS RISKI.

What is a moment that you will remember most from the protests this weekend?

The flashes of moments where I got to connect with people. Every single black person that I locked eyes with, that was a moment of joy for me personally.

Local leaders have criticized protesters for destroying property. What is your response?

Both forms of protest—both the most militant and destructive, and the other [non-destructive] approach—are valid. I think that it's inappropriate for us to criticize the way that people grieve and heal from their trauma.

There's no way to easily sum up how intergenerational trauma is directly related to the uprisings, and the public grieving and the public anger and frustration, and the critical level of need that people are experiencing. It's nonsensical to tell a grieving community that you hear them and then ask for the literal military to stop them from publicly grieving.

For me, I cannot look at and will not look at these moments and these movements that are happening right now—we're living through history—as riots. Instead, what they actually are, are the uprisings that the U.S. and every other imperialist and capitalist, racist and oppressive system has seen across history. There only comes a certain level to which you can ask large and vast numbers of people to sacrifice their literal health, lives and sanity for the capitalist system that will not provide for them and will also exploit their labor for the protection of the continual padding of the pockets of the 1 percent.

(Aaron Wessling)
(Aaron Wessling)

What was your response to seeing Portland police officers kneel with protesters this weekend?

I think it's important to recognize that as soon as that photo opportunity apparently ended, they turned around and immediately started escalating the situation. Shaking hands with and taking pictures with the police will never be the answer.

Mayor Ted Wheeler called on the governor to deploy the Oregon National Guard to Portland. Did you think this was the right decision?

The response from Ted Wheeler is unsurprising. A lot of Democratic, or allegedly Democratic, privileged white leaders across the country are calling for the National Guard. They're telling residents that they are hearing us and our demands for justice and accountability and demilitarization requests, and then turning around and literally asking for the military. It is the most obviously hypocritical and self-damning thing that you could do, to tell that to a group of grieving people who have been experiencing generations of trauma that has gone unhealed. We have continuously not been able to politely request small changes to protect our literal lives.

Protestors surged out of Peninsula Park and made their way to MLK Boulevard. (Alex Wittwer)
Protestors surged out of Peninsula Park and made their way to MLK Boulevard. (Alex Wittwer)