Friday night started at Revolution Hall in Southeast Portland where over 1,000 protesters sang "Happy Birthday" — the Stevie Wonder version — to Breonna Taylor, the 26-year-old Black woman who was killed by Louisville, Kentucky, police in a no-knock raid they executed on the wrong house. Taylor would have turned 27 on Friday. From there, the crowd marched west and crossed the Hawthorne Bridge.
Portlanders have taken to the streets each night for more than a week. Throughout these nightly protests, which started in response to the killing of George Floyd, a Black man who suffocated under the knee of a Minneapolis police officer, police have responded to the large groups of protesters with controversial tactics, including tear gas, flash grenades and a Long Range Acoustic Device, or LRAD.
Early in the evening, thousands gathered in Waterfront Park to hear from speakers, including city commissioner Jo Ann Hardesty.
“A revolution has started, do you hear me,” Hardesty said to uproarious cheers. “You’ve got policy makers shaking in their boots.”
While Hardesty was speaking at Waterfront Park a couple hundred protesters at the Justice Center confronted the police commissioner, Portland Mayor Ted Wheeler.
"I do not like the tear gas, I think it's ugly, it is not focused enough," Wheeler told a crowd of protesters, speaking through a bullhorn.
But after consecutive nights of enduring tear gas and other severe police tactics, protesters wanted action from the mayor to control the police.
The city is facing a federal class action lawsuit over the use of tear gas, and commissioners Jo Ann Hardesty and Chloe Eudaly have called for a ban on the gas, among other changes to the police.
"What are you going to do about it?" one protester shouted at the mayor.
"The city of Seattle late today banned the use of tear gas for 30 days except limited circumstances," Wheeler told the crowd over shouts of "We're not Seattle."
"We should do the same, tomorrow, my colleagues and I will be making an announcement..." Wheeler said through the bullhorn, as protesters shouted "Tonight! Tonight!" at him.
Wheeler also directed Portland police not to use sonic warning tones to control crowds.
That was around 7:30 p.m. Three hours later, some protesters started throwing water bottles, bananas, and bottles toward police while others tried to stop them.
"Who are you here for?" a young Black woman shouted at a white protester who had thrown something over the fence. "You're putting me in danger."
Meanwhile, the Portland Police continued to issue their warnings. "We continue to message to crowd in front of the Justice Center to stop tampering with the fence and to not throw projectiles at officers," the Portland Police said in a tweet. "We want this to be a peaceful demonstration."
A little after 11 p.m., the crowd became more agitated, with protesters continuing to throw water, fruit and bottles at police. The Portland Police Bureau said in a statement rocks and bricks had also been thrown.
"Many projectiles being thrown at officers from the crowd in front of the Justice Center," the police account tweeted at 10:58 p.m.
Police warnings of "criminal activity" in the crowd were met with boos and taunts from the demonstrators. Around the same time police called the protest an "unlawful assembly," a group of protesters knocked down the fence surrounding the Justice Center. As soon as that happened, police responded with violence, using tear gas, flash bangs and rubber bullets.
Appearing to adopt lessons learned from Hong Kong protesters, many people carried umbrellas to protect from tear gas and rubber bullets. Protesters also used orange cones and bowls to put out tear gas grenades. The crowd also stayed together and was slower to disperse in the face of police crowd control tactics.
Just before midnight, police issued a statement to reporters, calling on media to leave the area.
"To be clear ... this is an urgent message for media. It is unsafe, leave the area for your safety," public information officer Kristina Jones said in an email at 11:38 p.m.
Until well past midnight, police skirmished with protesters — using tear gas, flash grenades and other tactics. Protesters — still numbering several hundred — would disband from in front of the Justice Center, only to return a few minutes later.
The Portland Police Bureau said in a news release Saturday morning that its officers arrested 20 adults and one juvenile from Friday's demonstrations.
Rob Manning and Rebecca Ellis contributed to this story.