At least eleven people arrested at left-wing protests in Portland, Oregon, throughout 2025 faced prior charges for various crimes in the state — though none of them are currently in jail.
Familiar faces keep popping up in Multnomah County’s jails over Portland protests since January, including anti-deportation riots that prompted President Donald Trump to order the deployment of National Guard troops to the city, according to a Daily Caller News Foundation analysis of documents, local news coverage and law enforcement statements.
Between May and October, seven repeat arrestees were released without bail in their latest cases, while four more signed plea agreements or had their charges dropped, the DCNF found. The eleven new cases have led to charges such as theft, disorderly conduct, depredation of federal property, assault and attempted assault.
The repeat arrestees wound up in jail after previously facing charges ranging from disorderly conduct to rioting to possessing a firearm as a felon, records show. Police have arrested nearly 60 people at protests near the ICE facility since they began in June, according to the Portland Police Bureau (PPB).
All eleven repeat arrestees were charged this year over anti-ICE actions except for Hall, who was arrested with other protesters at a Portland State University speaking event for conservative activist Riley Gaines Barker, KATU reported. Authorities charged Hall with disorderly conduct and criminal mischief over the incident.
Protests are such a regular occurrence at the building that activists have sometimes set up a resting place at a nearby sidewalk with large white awnings, illegally blocking the sidewalk, a Portland police officer familiar with the situation told the DCNF.
“They have an enormous amount of supplies that get in there,” said the officer, who did not wish to be named for fear of reprisal. “Somebody’s funding them.”
Police have also observed a van driver pulling up to the encampment with items such as gas masks, helmets, baseball bats and sticks, the officer said. After city workers tell them to leave the sidewalk, they typically leave a mess of debris for them to clean, return to the same spot another day and put up the awnings again, the officer told the DCNF.
“What you have is a fishbowl of people that are either getting paid, or they’re so mentally deranged, that’s the dream,” the officer said.
Attorneys for Berry, Cox, Hall, Molina, McCarthy and Sidener did not respond to the DCNF’s requests for comment. A phone number and two email addresses for Winters’ lawyer would not take messages. Court records do not list attorneys for Oien, McFarland and Canfield.
McKenzie regrets breaking the law at Portland’s ICE facility during a June 15 protest, a defense attorney said in an Oct. 3 sentencing memo. Prosecutors said McKenzie joined other protesters to create a “shield wall” and obstruct federal agents from using the facility’s driveway. McKenzie pleaded guilty to failure to obey a lawful order, a misdemeanor, and was sentenced to one year of probation.
“[McKenzie] understands that the manner in which she expressed her dissatisfaction with specific government policies in this instance was a violation of the law, and she regrets her actions,” McKenzie’s attorney wrote about the June incident.
Authorities also arrested McKenzie in November 2023 for helping an anti-Israel mob ram a table through a glass door at Portland’s World Trade Center, the DOJ noted. McKenzie pleaded guilty to criminal mischief in local court for the attack and received six months of probation.
“Maintaining public safety during large-scale protests and demonstrations presents unique challenges,” a PPB spokesperson told the DCNF. “Officers often face rapidly changing situations and must distinguish between peaceful demonstrators and individuals engaging in criminal behavior. Despite this, PPB remains committed to protecting First Amendment rights while addressing unlawful conduct.”
Molina is charged federally with failure to obey a lawful order after entering the grounds of the local ICE facility on Aug. 21, the DOJ said. She also faces state-level assault, criminal mischief and trespassing charges from 2023, court documents show.
Obama-appointed federal magistrate Judge Youlee Yim You ordered Molina’s pretrial release on Aug. 22, but Molina was arrested less than two weeks later for allegedly violating that order, records show. Obama-appointed District Judge Stacie Beckerman ordered her second pretrial release in the case that day.
Molina has received multiple federal citations since 2021, including one in July at the local ICE facility for allegedly failing to comply with signs and directions, court documents show. The DOJ also charged her with destroying a security camera and other disruptive actions at Portland immigration facilities on seven different days between October 2020 and May 2021, according to court documents. She pleaded guilty in January 2022 to failing to obey a lawful order in two of the instances and was released from jail due to time served in custody.
The activist was convicted of disorderly conduct in 2019, records show. Three of her local cases are ongoing, while charges in the rest were dropped.
Molina, a self-described military veteran, said in an April radio interview that she attended pro-life protests with her parents as a child before she “went to college and learned some things,” after which she embraced leftist causes. She claimed to have been a victim of mistreatment by police and jail officials throughout her time in Portland’s justice system.
“There have been times that they have crossed the line into what is unlawful, not just unethical police behavior but unlawful behavior … I’m not even one of those people that just hate all of them,” she said. “I just don’t like being kidnapped.”
‘Where Are We Looting?’
While police do their best to gather evidence on arrestees, they are not responsible for the prosecutorial and judicial decisions that determine their fates, the PPB spokesperson told the DCNF.
“We continue to prioritize accountability by working closely with our partners in the criminal justice system to support strong cases,” the spokesperson said.
The office of Multnomah County District Attorney Nathan Vasquez, a former Republican turned independent, did not respond to the DCNF’s request for comment. Vasquez took office in January. (RELATED: Antifa Forcing Homeless Elderly Into Helping Anti-ICE Protesters, Police Say)
Trump has characterized Portland as a “war-ravaged” city due to the protests, state and city officials argued in a lawsuit challenging his looming National Guard deployment. Trump would not be the first to make such a move, as destructive leftist rioting in November 2020 prompted former Democratic Oregon Gov. Kate Brown to call in the guard.
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