An organizer of a massive protest in Portland addresses the crowd of hundreds in front of the city's police station on Monday.

PORTLAND, Maine — Hundreds of protesters converged outside the police station and some were later pushed back by police in the street on Monday night in the largest and most charged rally yet in Maine prompted by the death of George Floyd and other police killings.

The rally began peacefully but devolved into the night and early morning near the police station on Franklin Street, where police pushed back a crowd and later stood opposite them. At times, they deployed pepper spray with some getting close to their line and others hurling water bottles from afar. Many protesters shouted down those who threw bottles, at one point forming a protective wall in front of police.

Police arrested 23 people, according to a city spokesperson, after events escalated around 9:30 p.m. A man steered a semi-tractor-trailer truck through Middle Street, parting the crowd and antagonizing protesters. He was charged with reckless conduct with a deadly weapon, a felony, while 22 others were charged with failure to disperse. All have met bail and were released Tuesday morning.

It was the biggest similar Maine protest since at least 2016. Perhaps more than 1,000 people first gathered at the Portland police station on Middle Street just after 7 p.m. and proceeded to different locations. Organizers said the police took down a memorial erected in honor of Floyd, prompting the third rally in Portland since Friday.

After laying in the street to stage a massive “die-in” in front of the station, protesters erected the memorial again and moved on to City Hall. The protest moved back toward the station and held there for half-hour as state and local police gathered beyond a barricade at the top of the stairs.

Organizers appeared ready to disperse the crowd for the evening, stating into a megaphone that it was time to head home and see if their memorial stays in place the next day, when the large unmarked cargo truck appeared, its driver attempting to slowly drive it through the crowd.

Nobody was injured, but some protesters interpreted it as a hostile act. The truck stopped and the driver, a black man, was led away by police. It was not clear if he was among the people arrested on Tuesday, but his truck remained among the crowd.

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That broke down as officers with batons and protective shields fired pepper spray into the crowd. One fired a projectile believed to be a rubber bullet, which ricocheted off a pole and did not appear to hit anyone. Past midnight, more than 150 officers were on the scene, locked in a tense staredown with at least as many there to rally.

“The protest organizer called out over the megaphone that it was a peaceful protest and anyone throwing anything needs to go home because they aren’t a part of this,” said Denali Fleurant, a 23-year-old white man who was pepper sprayed by police during the standoff.

At the outset of the protest, Portland police Lt. Robert Doherty said he had “never seen anything like this” in more than 30 years on the force and approached protesters to wish them a safe night.

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City police were joined by Maine State Police, the Cumberland County Sheriff’s Office and South Portland police. At one point, some state troopers with batons, helmets and face shields complied with demands to “take a knee” while guarding a police vehicle on Congress Street.

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Some downtown stores were damaged after the rally. Glass doors and windows were smashed in the Urban Outfitters store on Middle Street. It appeared that people had entered the store and knocked clothing racks over. A photojournalist for CBS affiliate WGME reported that one of the station’s cameras was stolen.

Protest organizers have called for a meeting with Police Chief Frank Clark, who told the Portland Press Herald he had reached out on Monday to activists who organized marches in Portland on Friday and on Sunday. Their response has not been disclosed.

The marches occurred along with protests in dozens of cities across the nation since Floyd, a black man, died on May 25 after a white Minneapolis police officer pinned him by the neck with a knee for several minutes. The officer was charged with murder and Floyd’s family ordered an autopsy finding he died of asphyxia.

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Maine cities and towns such as Bangor, Belfast and Rockland also have seen protests. Demonstrators marched through downtown Portland Friday and a large group met at the police station Sunday and demanded to speak with Clark, who did not appear.

BDN writer Nick Sambides Jr. and WGME contributed to this report.

Michael Shepherd

Michael Shepherd

Michael Shepherd joined the Bangor Daily News in 2015 after three years as a reporter at the Kennebec Journal. A Hallowell native who now lives in Augusta, he graduated from the University of Maine in...