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Jacob Macduff was shot and killed while apparently having a mental breakdown. Investigators say he had a knife.

PMG PHOTO: JAIME VALDEZ - Graffiti scrawled on the side of a vandalized insurance office in downtown Tigard last Thursday, Jan. 7, draws an explicit connection between police violence and riots.While Jan. 6, 2021, is a date that will be remembered for years to come in the United States, far from the halls of the U.S. Capitol, a local tragedy played out in an apartment complex parking lot in Tigard, Oregon.

That afternoon, his roommate and ex-girlfriend told The Times, Jacob Macduff's deteriorating mental health had taken a serious turn for the worst. Macduff lived with bipolar disorder and was known to experience manic episodes. While she had reached out to Tigard police before to express concern about Macduff's increasingly erratic behavior, Theresa Chapin said that on Jan. 6, it was a neighbor who called 9-1-1 for assistance as Macduff smashed his head over and over against a wall.

COURTESY PHOTO: THERESA CHAPIN - Jacob Macduff, right, takes a selfie with friend and roommate Theresa Chapin. Macduff was shot and killed in his truck outside his Tigard apartment on Jan. 6 after a neighbor concerned by his behavior called police.Five officers, including a negotiator, responded. Macduff had gone outside and gotten into his truck. The negotiator tried to coax Macduff to get out of his vehicle and talk to police, according to investigative records later released by the Washington County District Attorney's Office, but Macduff wasn't budging.

One of the officers, Gabriel Maldonado, broke the driver's side window with a spring-loaded tool. He later told investigators that saw Macduff had a knife, and he shouted at him to "drop it."

Maldonado said he fired multiple shots as Macduff rooted around between the seats, but that failed to stop him. The next shots he fired were fatal.

Three knives were later recovered from Macduff's truck, police said. It remains unclear what Macduff may have been reaching for.

Macduff had a criminal history and was known to Tigard police. While he never faced criminal charges in Oregon, according to court records, he was arrested in California in 2016 for allegedly punching a sheriff's deputy. Maldonado told investigators he was aware of that history and feared for his life during the encounter.

If you are struggling with your mental health or experiencing suicidal thoughts, help is available.

The District Attorney's Office investigated the shooting but soon handed the matter off to Attorney General Ellen Rosenblum for further review. The Tigard Police Department also placed Maldonado on "critical incident leave" until Feb. 23 and had him meet with a psychologist.

Maldonado resigned from the Tigard Police Department in April, taking a job with the Port of Portland Police Department. But the port soon fired Maldonado.

Oregon Public Broadcasting, Pamplin Media Group's news partner, reported that Maldonado had omitted information about the ongoing investigation in an email to the Port of Portland's human resources department and that a background investigator incorrectly reported back to the port that Maldonado had been cleared.PMG PHOTO: JAIME VALDEZ - Cynthia Cruz attends a rally for Jacob Macduff on Jan. 7 in Tigard. Peaceful at first, the demonstration quickly devolved into a riot after marchers reached City Hall and the police station and began smashing windows.

Chapin and Macduff's mother, Dr. Maria Macduff, were sharply critical of the Tigard Police Department's handling of the matter.

Maria Macduff said Tigard police had called her twice as they responded Jan. 6 to the apartment complex where her son lived.

The first time was to ask her permission to smash out the window of Macduff's truck, since they were aware it was registered in his mother's name. She agreed.

"I reminded them again that he had a mental illness and to be careful," she later told reporters.

The second time was to tell her he had been shot and killed.

Chapin was blunt in her judgment of how police handled the situation.

"They murdered him," Chapin told Pamplin Media Group.

The day after Macduff's death, dozens of protesters — many of them from outside Tigard — gathered on Southwest Main Street for a protest march against police violence, echoing those that rocked Portland repeatedly in 2020.

At first, the demonstration was peaceful. But when protesters reached Tigard City Hall, several began smashing windows and spraying graffiti on the sides of the building.

Tigard police had been observing passively, as Police Chief Kathy McAlpine later said. But when protesters began damaging the building, a column of officers equipped with riot gear emerged from where they had gathered as a contingency behind City Hall, dispersing the crowd. A riot was declared. Several downtown businesses were vandalized as well; one tag on an insurance office that also had its front door smashed read: "Stop killing people and we will stop rioting."

In September, a grand jury declined to indict Maldonado in connection with Macduff's shooting. Tigard police have mounted their own internal investigation.

McAlpine, who has often spoken of her focus on community policing and talked openly about her efforts to reform the Tigard Police Department's policies and procedures after George Floyd's murder in 2020, remains police chief in Tigard.

Read a letter to the Tigard community from Police Chief Kathy McAlpine written after the fatal shooting of Jacob Macduff and the declared riot in downtown Tigard.

McAlpine was a finalist last month to be hired as police chief in Tacoma, Washington, but city leaders instead chose a candidate from Texas.PMG PHOTO: JAIME VALDEZ - Police in riot gear form a line to protect Tigard City Hall on Jan. 7. Windows at City Hall and several downtown Tigard businesses were smashed by activists protesting police violence.

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