Peaceful protests on Friday afternoon and evening devolved into chaos in Oakland and San Jose, with tear gas and rubber bullets deployed, fires being set in the street and in commercial buildings, and several businesses looted. And in an incident that was simultaneous with the Oakland protests but not confirmed to be directly linked, two federal building security officers were shot in downtown Oakland, and one was killed.

The scenes of protest followed by some scenes of destruction and confrontations with law enforcement were echoed across the country Friday night, with protests in at least two dozen cities amounting to a a significant uprising against police brutality targeting people of color. The night of protest followed a similarly destructive one in Minneapolis on Thursday, which was the third night of protests there over the police killing of George Floyd.

And, it should be noted, Oakland has a significant recent history with peaceful political protests that are used by opportunistic anarchists to commit acts of vandalism in the later hours of the night — and according to many on the street Friday night, that is again what happened.

Protesters gathered outside City Hall in San Jose at 2 p.m. on Friday, and outside Oakland City Hall at 8 p.m., and in both cases, peaceful demonstrations became more unruly in the later evening hours. As the Chronicle reports, the Oakland demonstration began with a few hundred people and grew to around 5,000 in the streets of downtown and down Broadway/Auto Row, with some protesters marching onto the 880 freeway and blocking traffic at one point — much the way protesters in San Jose had done on 101 South on Friday afternoon.

One woman rode a horse to the march, telling the Chronicle, "Horses bring attention."

Later in the evening, a Walgreens at 14th and Broadway in Oakland was vandalized, broken into, and looted, and a fire was set inside the store; at least one car was set on fire; a Target store was looted via an "assembly line," per the Chronicle; a Lyft bicycle dock was pulled into the middle of the street and set ablaze; tear gas was deployed by the OPD; a large fire was started near the 19th Street BART station; fireworks were set off to cheers; and as KRON4 reports, a Mercedes-Benz dealership on Broadway was vandalized and set on fire. At one point, as seen in Twitter videos below, two men stole a small excavator, possibly from a construction site, and drove it down Broadway.

Oakland police made 22 arrests after detaining at least 60 people for looting. 13 Oakland police officers were reportedly injured after protesters threw objects at them.

"We have had demonstrations last night, and they started out peacefully and we stood with our community here in the city of Oakland to provide safe spaces and respectful spaces for our demonstrators," said Interim Oakland Police Chief Susan Manheimer in a video statement on Twitter. "What we saw later on in the evening turned violent and disruptive and we want to call on everyone who would come to Oakland and stand with us to respect the memory of George Floyd and the community to ensure that they are peaceful and respectful to the city of Oakland and especially our downtown businesses which have been suffering since the pandemic began."

She added, "We thank all the mutual aid and other agency partners that have helped us tonight, but as we have seen across the country, we saw damage and destruction here in the city. We will be back at it tomorrow, we stand with our community, and we want to ensure that everyone that comes to the city of Oakland is peaceful and respectful."

In what may or may not be able to be called a separate incident, given that it occurred just two blocks from where the protest began less than two hours earlier, a pair of security officers were shot around 9:45 p.m. by a gunman in a vehicle outside the Ronald V. Dellums Federal Building. As KPIX reports, the car pulled up and a suspect opened fire on the officers stationed outside the building at 12th and Clay streets in Oakland, injuring one of the officers and killing the other. Both reportedly worked as contractors for the Federal Protective Service of the Department of Homeland Security.

The Oakland Police Department said Friday night that it was "unknown" if the incident was related to the demonstrations a few blocks away. U.S. Marshals, Homeland Security and FBI agents are now leading the investigation into the shooting and murder.

In San Jose, at least one vehicle was reportedly destroyed on the street, and police also resorted to rubber bullets and tear gas to break up demonstrations, which according to the Chronicle had mostly dissipated by 9 p.m. A shooting also occurred in downtown San Jose as the protests wounds down involving Santa Clara County Sheriff deputies, and details surrounding that remain sketchy.

You can see more pictures from yesterday's protest-turned-riot in Oakland, below:

Previously: Second Protest Planned Friday Evening In Oakland Over George Floyd Death

Photo: Matt Charnock/SFist