In a case that shows how Portland's political strife has spilled over into the city's outskirts, the Clackamas County Sheriff's Office has opened an investigation into Dixie Lea Bailey, a cigar store owner in Sandy and local "patriot" leader who's become aligned with Proud Boys activist Alan Swinney.
And even as Swinney battles well-publicized criminal charges in Multnomah County for pointing a pistol at protesters and firing paint balls at them, his ally, Bailey, has been wrapped up in a lower profile civil case in a Clackamas courthouse.
Bailey's case centers on a stalking petition accusing her of menacing and online harassment, including accusations that she pointed a gun at a liberal critic of hers. Bailey denies the allegations.
The two cases appear to have become somewhat intertwined. Swinney's lawyer is part of Bailey's defense, and court records show Swinney had been staying at Bailey's house in Rhododendron near the base of Mount Hood before being jailed on Sept. 30. Bailey has raised funds for Swinney's defense.
Last week, Swinney promised to stay with Bailey pending trial if let out of jail. But a judge denied his release after prosecutors cited social media posts by Swinney indicating he feels he is in a "civil war" and that "violence is the appropriate response to the protests occurring in Portland."
Bailey's situation is significant because, while clashes at Portland protests have drawn the public's attention, the stalking case sheds light on a more subtle form of political strife that's played out online and in the outskirts of Portland.
Bailey, who co-owns Mt. Hood Cigar Co. with her husband, is prone to social media posts with political commentary and images of herself firing guns. She has been a prominent leader in organizing conservative "Sandy Backs the Blue" demonstrations ostensibly meant to support the police. The demonstrations have been followed by similar "flag wave" actions in places like Estacada and Gresham.
Political targeting alleged
In court, Bailey blamed the stalking case on Milone, the restaurant owner who filed the stalking petition against her, arguing that Milone's online posts alerting people to Bailey's affiliation with Swinney were "just harassment and stalking."
Bailey's lawyer, Greg Oliveros, meanwhile, said she is being targeted because of her political beliefs and affiliation with Swinney — who reportedly wears a "Proud Boys" tattoo on his arm.
"Assuming that (Bailey) might be a member of the Proud Boys, (Milone's lawyer) hasn't proven that that (affiliation) has made her more dangerous," Oliveros said at a recent hearing. "There is an exhibit in this matter that shows (Bailey) with a machine gun, but that photograph doesn't suggest one way or the other that respondent is going to carry out and threaten a petitioner in any way."
Asked separately if Bailey is active with the Proud Boys, Oliveros told the Tribune, "I don't know that." He said Bailey had done nothing wrong.
Conflict started online
Court records show that Milone had been posting about Bailey and her affiliation with Swinney, even noting Bailey's home address.
Bailey testified that someone had been posting signs about her on her street, and a friend told her it might have been someone in a silver car – a silver car, Bailey told the judge, like the one she said she spotted in Milone's driveway on Aug. 25.
Milone said that Bailey showed up at Milone's house that day, pointed a gun at her and also took her picture with a cell phone, while saying "I got you, girl," and threatening to shoot her dogs.
Bailey, in court, denied pointing her gun at Milone or threatening her, saying she'd kept her pistol in its holster on her right hip during the encounter. What she held along with her phone was a cigar, she said. Her husband, who was driving, later testified that Bailey held only a phone, not a cigar.
What's not disputed is that Bailey immediately went home and posted Milone's photo and address on social media, calling Milone a "local antifa member," a "wicked witch," and accusing her of "doxxing" her — a term for posting private and identifying information about someone on the internet for the purpose of harassment — by sharing her home and business address.
"It is time to shed light on these Antifa (expletive)," Bailey wrote.
"Hey hey! Ho Ho! Joylenne has got to go!!" Bailey wrote in another post, misspelling Milone's first name.
Antifa is loosely defined term for leftwing protesters, which comes from "anti-fascist;" it also sometimes refers to anarchists who use aggressive or violent tactics at protests known as "black bloc."
Milone, in court, said that contrary to being an "antifa" member, she's never been to a protest in her entire life.
Bailey testified that she just happened to see the silver car, and that the visit to MIlone's house was not planned. In court, Milone's lawyer quesitoned that. Online, when a supporter told Bailey the visit to Milone she posted online about was legal, she responded, "I know. I spoke to the Clackamas County PD today before I made any plans."
Milone and a friend who stayed with her on the night of Aug. 25 claimed that Bailey later returned around midnight, driving by slowly while yelling, "I got you girl."
The friend testified that when she arrived at Milone's house after Bailey left the first time, she found Milone "visibly shaking" in fear.
Bailey, however, denied any subsequent in-person contact with Milone. The cigar store owner denied making threats and denied encouraging others to threaten Milone.
Regardless, after Bailey posted online about Milone, threatening language about her began appearing online, and fake negative reviews of her restaurant, too.
Milone, in hearings, complained that law enforcement hadn't done anything about her complaints, even failing to document all of her complaints about alleged harassment or menacing.
"They said it was free speech," she complained to a judge.
She also referred to a video circulating that purportedly shows Bailey using bear spray on a Black Lives Matter protester.
The Clackamas Sheriff's office as well as the Clackamas District Attorney's office declined to comment on the case, saying it's part of a pending criminal investigation.
The sheriff's office has been accused in recent weeks of being politically biased. A spokesman, Sgt. Marcus Mendoza, told the Portland Tribune that "Our office investigates claims of alleged crimes without regard to political affiliations. The case you are referring to is an ongoing investigation in which the Sheriff's Office took statements from those involved and completed reports. We then submitted the reports to the District Attorney's Office to review our investigatory report, determine whether a crime occurred, and file criminal charges as warranted. "
Court ruling expected
The civil stalking case has been making its way through Clackamas Circuit Court, and Judge Jeffrey S. Jones is expected to issue a ruling next month.
To some observers, Milone's experience, including the flag wave held near her business, shows the questionable side of the flag waves and "Back the Blue" demonstrations.
One video Bailey posted captures a person — apparently Bailey —telling Black Lives Matter counter-protesters, "when police are abolished, you're going to have to deal with us." The woman proceeds to say "You're mine. Just know that ... I know who you are. I've got your facebook. I've got your information. You're mine."
Another video posted by Bailey shows flag-wave attendees voicing conspiracy theories that have been promoted by groups like Q-Anon.
"Joe Biden's a pedo," the demonstrators shouted repeatedly at passing cars, referring to one such conspiracy theory.
Recently, the leadership of Sandy Backs the Blue have sought to distance the group from aggressive or divisive political messages.
Bailey is no longer part of that leadership. On Aug. 20, not long after the Sandy Post published an article about how Swinney and other Proud Boys had begun showing up at Sandy Backs the Blue events, Bailey posted a video saying she had formally relinquished her post heading Sandy Backs the Blue.
"There's some things that I want to do that can't necessarily be involved with Backs the Blue," she said.
Facebook posts by some of Bailey's supporters suggested they intended the flag waves as a way to punish business owners who had been vocal in their support of Black Lives Matter, or to recruit members into more aggressive "patriot" groups.
Following Bailey's posts about Milone, some of Bailey's allies began organizing a flag-waving outside Milone's restaurant, Koya's Kitchen, in Welches, planning to set it for dinner time, Facebook posts show — apparently to hurt her business and annoy customers. That particular flag-wave did not happen.
Some other business owners say they have faced similar campaigns. One of them, who'd vocally supported Black Lives Matter, showed up to testify in court, saying Bailey had harassed her and posted a photo of her own teenage daughter online.
After Bailey posted Milone's address on Facebook in late August, Swinney chimed in, urging people to attend a flag-wave in Milone's "little piece of America" and accusing her of "trying to ruin Trump supporters' lives."
He openly sought to use the action to recruit new members to his movement.
"Let's keep this growing," he wrote. "Help us build our numbers."
In a July post, he invited others to join him at a Sandy flag wave, saying "My plan is to hit these little towns and recruit, then we all go into Portland together."
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