More than 1,000 demonstrators protesting police violence against people of color once again flooded Portland’s streets on Tuesday night, marching to different areas of the Old Port and the Eastern Prom for the fourth time in five days to express their outrage over the death of a Minnesota man in police custody.

Unlike Monday’s protest, which was marred by arrests, burglary and vandalism, Tuesday’s demonstration was mostly peaceful with the highlight coming after Portland Police Chief Frank Clark and Portland City Manager Jon Jennings took a knee in solidarity with protesters on the steps of the police station.

The protest started with about 300 people in Monument Square on Congress Street, where an organizer mentioned the previous night’s protests when violence and vandalism flared – resulting in the arrests of 23 people – and asked participants to avoid a similar situation Tuesday night.

The woman, identified only as Mary, urged people to be peaceful, saying, “Yesterday was beautiful, but it didn’t end well, let’s do this right” referring to the arrests and vandalism that marred Monday’s protest.

The procession of demonstrators then walked to the Portland Police Station on Middle Street where they were met by Clark and Jennings.

After one speaker told the crowd that police officers needed to be trained to be more understanding and compassionate toward people of color, the crowd, which had swelled to about 500 people marched to the Eastern Prom where they staged a die-in, lying on their stomachs with their hands behind their backs while chanting, “I can’t breathe.” Those were the words George Floyd uttered as a former Minneapolis police officer pressed his knee into Floyd’s neck  until he lost consciousness and stopped breathing.

Protestors chant “I can’t breathe” as they lie down in a mass die-in on the Eastern Prom in Portland during Tuesday’s protest. Gregory Rec/Staff Photographer

The dramatic demonstration on the Eastern Prom lasted for about 9 minutes, roughly the same amount of time that former Minneapolis police officer Derek Chauvin pressed down on Floyd’s neck with his knee while three other officers looked on.

The situation in Portland Tuesday night became tense at times, with anti-protesters carrying American flags and one white man shouting expletives at a group of black men.

Police wearing riot gear assembled at Pearl and Middle streets after a group of seven men dressed in orange hunting vests and carrying American flags began to agitate protesters. The men carried signs that said they supported police.

Maine State Police and members of the Cumberland County Sheriff’s Office – the squads were dressed in riot gear – then marched down Pearl Street and stood nearby as a Portland police officer talked to the men. The group left peacefully and were not seen again.

People fill Monument Square in Portland during the protest Tuesday evening. Gregory Rec/Staff Photographer

An officer was spotted on the rooftop of the Hampton Inn, leading to postings on social media about the possibility of a police sniper, a scenario dismissed by Portland Police spokesman Lt. Robert Martin.

He was not certain how law enforcement resources were deployed Tuesday night, but said the officer was most likely an observer positioned to gain a better vantage point. Martin added that people shouldn’t jump to conclusions that the officer was carrying a weapon, saying he could have been using some type of observation device.

By the time the demonstrators reached the Eastern Prom, the size of the crowd had grown to about 1,000 people. The protesters marched from the Eastern Prom down Congress Street to Congress Square, where organizers thanked everyone for what appeared to have been a largely peaceful demonstration. At around 8:45 p.m., organizers using a bullhorn urged everyone to “go home safe.”

But at 10:15 p.m. a group of about 100 protesters reformed outside the police station and began setting off fireworks as police in riot gear lined up across Franklin Arterial and fired rubber bullets at protesters who threw bottles.

An officer is positioned on the top of the Hampton Inn in Portland as hundreds come together in the streets Tuesday night to protest violence by police against people of color. Derek Davis/Staff Photographer

Just before 11:30 police asked people to disperse and began advancing their line down Franklin Arterial, making a few arrests as they went.

The outburst of violence mirrored events on Monday night, when over 1,000 protesters amassed outside the police station and engaged in a confrontation with police that moved around the downtown area and lasted until nearly 2 a.m. Officers from 15 other police departments joined Portland police and stood shoulder-to-shoulder carrying wooden batons and plastic riot shields.

Everyone arrested during the demonstration posted bail by Tuesday morning, said Martin, the police spokesman. All but one person was charged with failure to disperse, a misdemeanor. One man, the driver of a tractor-trailer that entered the protest area near the intersection of Middle Street and Franklin Arterial, was charged with reckless conduct with dangerous weapon, a Class C felony.

Throughout Monday night, there was a push and pull between organizers who sought to keep the demonstrations peaceful, and people who threw water bottles and other objects at the police, destroyed property and defaced businesses. At one point, some police knelt with protesters, drawing cheers from the crowd. Others talked with protesters from the police line, but most officers remained silent or did not react or engage.

Police vehicles lead a large group of protestors along Congress Street as the group returns to Congress Square Park after marching to the Eastern Prom on Tuesday evening. Gregory Rec/Staff Photographer

Protest organizers finally got a meeting with Chief Frank Clark on Tuesday after two days of trying.

Hamdia Ahmed and Abdul Ali, who organized a protest on Friday and are planning a demonstration Wednesday outside the Portland police station, met via Zoom with Clark, Westbrook Police Chief Janine Roberts, and city and state leaders to discuss issues of race and policing, and the broad, overarching issue of police treatment of black and brown people across the country, Clark said. The problems are systemic, Ahmed said, according to Clark, and she did not single out the Portland department.

“We did a lot of listening,” Clark said. “They articulated that they wanted to be heard. They wanted us to hear them. We vowed to continue the conversations.”

Another organizer who planned the protest that became violent Monday has been communicating with city officials, as well.

Protests have roiled the nation since the death of Floyd, 46, on May 25. Chauvin, the former officer, has been charged with murder in the death and the three officers who were with him were fired but have not been charged.

A man is arrested behind a line of police in riot gear along Franklin Street in Portland on Tuesday night. Gregory Rec/Staff Photographer

After days of demonstrations, protesters undeterred by curfews coursed back into the nation’s streets Tuesday, hours after President Trump pressed governors to put down the violence set off by Floyd’s death and demanded that New York call up the National Guard to stop the “lowlifes and losers.”

As more demonstrations began taking shape around the country, and cities including Washington prepared for another possible round of scattered violence after dark, the president amplified his hard-line calls of a day earlier, in which he threatened to send in the military to restore order if governors didn’t do it.

Clark had released a statement Tuesday afternoon in which he expressed disgust at Floyd’s killing, but said a small segment of the demonstrators were determined to cause trouble, leading to the harsher response by officers.

“Our goal remains providing a safe environment for those wishing to peacefully express their views and First Amendment rights,” Clark said in the statement. “We are fortunate that no one was seriously injured and that most of the property damage was minimal. Unfortunately, a committed smaller segment of this group ended up making this event anything other than a peaceful and lawful protest. They took the opportunity to commit acts of violence, damage public and private property and place my officers and the public at risk. We will not stand for such criminal behavior.”

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