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 have been repeatedly appearing in Multnomah County’s jails over Portland protests since January, including during anti-deportation riots that prompted former President Donald Trump to order the deployment of National Guard troops to the city. This is according to an analysis by the Daily Caller News Foundation (DCNF), which reviewed 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.
These repeat arrestees ended up in jail after previously facing charges ranging from disorderly conduct to rioting and possessing a firearm as a felon, according to records. The Portland Police Bureau (PPB) reports that nearly 60 people have been arrested at protests near the ICE facility since protests began in June.
### Repeat Arrestees Named
Police arrested protesters Cory Oien, Samuel Berry, Tyler Cox, Eli McKenzie, Nathan McFarland, Emery Rose Hall, Julie Mikela Winters, Tracy Molina, Alistair Sidener, Darnell Andre Canfield, and Ian McCarthy between January and October in Portland — a city known for violent leftist or “Antifa” demonstrations.
Cox and Canfield’s latest cases were dropped in June and October because prosecutors did not proceed with formal complaints. McKenzie and Winters pleaded guilty to failing to obey a lawful order and intimidation of a federal officer, respectively, according to DCNF-reviewed documents.
Ten of the eleven protesters had prior arrests at other protests. Winters has pled not guilty to assault charges stemming from a dispute at the scene of a December traffic accident. McFarland, Sidener, and Molina also have violent charges pending against them.
Courts or prosecutors have dismissed violent charges against Hall, Oien, and Cox through the years.
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 that authorities charged Hall with disorderly conduct and criminal mischief over the incident.
### Protest Encampment and Police Observations
Protests occur so regularly at the ICE building that activists have sometimes set up a resting place on a nearby sidewalk with large white awnings, illegally blocking pedestrian access, a Portland police officer familiar with the situation told the DCNF.
“They have an enormous amount of supplies that get in there,” the officer said on condition of anonymity due to fear of reprisal. “Somebody’s funding them.”
Police have also observed a van driver pulling up to the encampment delivering items such as gas masks, helmets, baseball bats, and sticks.
City workers often tell protesters to leave the sidewalk, but they typically leave a mess of debris behind, then return another day to set up awnings again, the officer added.
“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 commented.
### Legal Representation and Responses
Attorneys for Berry, Cox, Hall, Molina, McCarthy, and Sidener did not respond to DCNF’s requests for comment. Attempts to reach Winters’ lawyer via phone and email were unsuccessful. Court records do not list attorneys for Oien, McFarland, and Canfield.
### Individual Cases and Sentencing
Eli McKenzie expressed regret for breaking the law during a June 15 protest at Portland’s ICE facility, according to a defense attorney’s sentencing memo dated October 3. Prosecutors said McKenzie joined other protesters to create a “shield wall” obstructing federal agents’ access to 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,” her attorney wrote.
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 Department of Justice noted she pleaded guilty to criminal mischief for the attack and received six months of probation.
### Challenges in Law Enforcement
“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.”
### Cases Against Tracy Molina
Molina faces federal charges for failure to obey a lawful order after entering the grounds of the local ICE facility on August 21, per DOJ information. She is also charged at the state level with assault, criminal mischief, and trespassing from 2023, according to court documents.
Obama-appointed federal magistrate Judge Youlee Yim You ordered Molina’s pretrial release on August 22, but she was arrested less than two weeks later for allegedly violating that order. Obama-appointed District Judge Stacie Beckerman then ordered her second pretrial release.
Molina has received multiple federal citations since 2021, including one in July at the ICE facility for allegedly failing to comply with signs and directions. The DOJ also charged her with destroying a security camera and causing other disruptions at Portland immigration facilities on seven different days between October 2020 and May 2021.
She pleaded guilty in January 2022 to failing to obey a lawful order in two of those instances and was released due to time served. Seven months later, Molina defaced the Portland ICE building with graffiti, pleading guilty later. U.S. District Judge Marco Hernandez sentenced her to one year probation and restitution for the vandalism but terminated probation early.
Before August 2025, Molina faced a dozen non-traffic criminal cases in local court involving charges like assaulting or interfering with law enforcement officers, disorderly conduct, criminal mischief, trespassing, resisting arrest, reckless endangerment, unlawful graffiti application, and attempting a class C felony. She was convicted of disorderly conduct in 2019. Three local cases remain ongoing; charges in the others were dropped.
Molina, a self-described military veteran, told a radio interview in April that she attended pro-life protests as a child with her parents before going to college and embracing leftist causes. She said she experienced 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.”
### Prosecutorial and Judicial Decisions
While police focus on gathering evidence on arrestees, they are not responsible for prosecutorial and judicial decisions that determine case outcomes, said the PPB spokesperson.
“We continue to prioritize accountability by working closely with our partners in the criminal justice system to support strong cases,” the spokesperson stated.
The office of Multnomah County District Attorney Nathan Vasquez, a former Republican turned independent who took office in January 2025, did not respond to DCNF’s request for comment.
### Political and Historical Context
Former President Trump characterized Portland as a “war-ravaged” city due to the protests. State and city officials argued against his planned National Guard deployment in a lawsuit. Trump would not be the first to take this step; destructive leftist rioting in November 2020 led former Democratic Oregon Governor Kate Brown to call in the Guard.
Oien, Berry, Cox, and Molina were arrested during Portland BLM protests in 2020. McFarland, a felon convicted in 2008 for delivering marijuana near a school, posted what appeared to be BLM protest footage from Salem on Instagram in May 2020 but faced no riot-related charges then.
“So whens the next protest and where are we looting?” McFarland posted on May 31, 2020.
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https://dailycaller.com/2025/10/28/meet-the-portland-leftists-who-keep-getting-caught-and-released/