As many as 500 demonstrators and 250 police from several Orange County cities were involved in seven hours of confrontations that ended around 2 a.m., Sgt. Bob Dunn said.
Most protesters were peaceful, but officers used pepper balls and beanbag rounds after some became violent. Police remained on tactical alert Wednesday morning.
The clashes followed a City Council meeting Tuesday in which city leaders voted to ask the U.S. attorney’s office to investigate weekend officer-involved shootings that killed two men and prompted a $50 million civil-rights lawsuit.
The council chambers were packed with people and about 100 protesters were unable to get inside, Dunn said.
They chanted and held a peaceful rally outside. But the crowd swelled and when some people pushed on the windows, police came out and pushed them back, Dunn said.
Demonstrators marched to police headquarters and back to City Hall, but violence didn’t erupt until around 6:30 p.m. when police detained a demonstrator who reportedly had a gun, Dunn said.
It turned out the man did not have a weapon, but some in the crowd began throwing rocks at officers, Dunn said.
While most protesters were peaceful, some appeared to be outsiders who “were prone to violence and wanted to incite” both the crowd and police, Dunn said.
Some demonstrators took over an intersection, and a splinter group walked to the scene of one police shooting and back, throwing rocks, vandalizing cars and throwing a Molotov cocktail that damaged a police car, Dunn said.
Throughout the night, knots of protesters spread through downtown, setting fires in trash cans and smashing windows of businesses, including a Starbucks, Dunn said. There also were reports that a T-shirt store was looted, he said.
A gas station was shut down after reports that some protesters were seen filling canisters with gas.
Police used pepper balls and beanbag rounds. Twenty adults and four minors were arrested, Dunn said.
About five people were hurt, including a police officer, two members of the media who were struck by rocks, and some protesters who may have been injured by police or during a fight between demonstrators, authorities said.
None of the injuries was believed to be life-threatening.
It was the fourth day of violence in the wake of two deadly officer-involved shootings.
The family of Manuel Diaz sued the city and the Police Department on Tuesday, claiming he was shot and killed Saturday while running away, lawyer James Rumm said. The family is seeking $50 million in damages.
The second shooting occurred Sunday when officers spotted a suspected gang member in a stolen sport utility vehicle. A brief pursuit ended when three people jumped from the vehicle and ran. Joel Mathew Acevedo, 21, fired at an officer and the officer shot and killed him, authorities said.
The back-to-back deaths took the tally of shootings by officers in this Orange County city to six so far this year, up from four a year before. Five of the incidents were fatal.
Police Chief John Welter said Diaz was shot after two officers approached three men who were acting suspiciously in an alley before running away. One officer chased Diaz to the front of an apartment complex.
The chief would not say what led the officer to shoot Diaz. But Welter said Diaz failed to heed orders to stop and threw something on the roof of the complex that contained what officers believe was heroin. Both officers were placed on paid leave pending an investigation.
Mayor Tom Tait said a description from court papers relayed to him by a reporter that Diaz had been shot in the leg and in the back of his head was “unsettling.”
Anaheim is a city of contrasts that ranges from upscale, hilltop homes to packed, gritty apartment complexes.
The city 25 miles southeast of Los Angeles is known as home to the Angels baseball team, and above all, to world-famous Disneyland.
As California’s Hispanic population has grown, so has the Anaheim’s, hitting nearly 53 percent in 2010, census figures show.
Residents’ concerns about the use of police force in the city aren’t new. Last month, Anaheim decided to look into hiring an independent investigator to review police shootings amid protests by relatives of those killed in officers’ gunfire.
Latino activists say that isn’t enough and they want federal officials to investigate the Saturday shooting.
Tait, who has called for state and federal investigations, said: “If the Latino community is saying there is a rift, then there is rift, and we need to address that.”
The police union issued a statement defending the officers involved in the shootings and said both men killed were gang members who had criminal records. The union also said that just before Diaz turned toward officers, he pulled an object from his waistband _ a place where gang members commonly hide guns.
The FBI is conducting a review to determine whether a civil rights investigation is warranted, agency spokeswoman Laura Eimiller said.
Associated Press video journalist Raquel Maria Dillon contributed to this report.