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Portland City Council has voted against a proposal from Mayor Ted Wheeler that would have given him the power to designate a time and place for protests between groups with a history of violence.

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Commissioners Nick Fish, Chloe Eudaly and Amanda Fritz voted against the proposal.

Wheeler introduced the measure in response to what he characterized as escalating street violence. The right-wing groups Patriot Prayer and Proud Boys have repeatedly used the city as a staging ground for protests, provoking counter-protests and at times brawling violently with left-wing groups including Antifa.

Fish was widely seen as the swing vote. He said the vote was "a close call" and explained he was concerned the ordinance would set up a costly and divisive legal battle.

Civil rights groups, most notably the ACLU of Oregon, had lobbied against the ordinance and said it believed it left the city vulnerable to a lawsuit. The ACLU said the mayor's proposal infringed on the rights to freedom of speech and assembly and was likely unconstitutional.

Fish said he'd like the city to send a message to Patriot Prayer and Proud boys to "stay home," but that the ordinance wasn't the right approach.

"I’m not convinced that we’ve done everything we can with the tools already at our disposal," Fish noted, casting his no vote. "That includes arresting people who violate our laws."

Wheeler and Commissioner Dan Saltzman voted for the ordinance. They argued that the Portland Police Bureau needs more tools to prevent violence on the streets.

"We all fully respect everybody’s right to protest and exercise their rights to free speech, but there’s also a public safety factor," Saltzman said, arguing that it was reasonable for the mayor to try to separate groups that are antagonists.

"Patriot Prayer and Proud Boys, they’re playing us like a fiddle," Saltzman said. "They know they can come down to Portland because they know they can provoke the response."

Commissioners Eudaly and Fritz had made it known last week they would not support the ordinance.

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Last week, Eudaly publicly grilled Portland Police Bureau Chief Danielle Outlaw about her response to right-wing extremism and police use of force against protesters.

She noted that the bureau had provided new written answers to her questions, and struck a more conciliatory note before casting her no vote.

"The mayor and the police chief have good intentions with this ordinance," she said. "Even if they can't be as explicit as I can, know they want to stop right-wing extremists from disrupting our city and threatening our residents as much as I do," she said.

Business groups, including the Portland Business Alliance and Travel Portland were the most prominent advocates for the mayor's ordinance, arguing that the frequent violent clashes in the streets were hurting the city's reputation.

Eudaly urged local businesses to deny service to members of right-wing extremist groups — and urged Portland residents to boycott businesses that continue to work with the groups.

"They shouldn't be helping them peddle hate, raise money, print T-shirts, or publish websites," she said.

The vote represented a significant defeat for both the mayor and for Outlaw.

Outlaw sat quietly in the front row while the Council voted.

Wheeler quipped that anybody who could count could see the ordinance wasn't going to pass, but delivered a full-throated defense of it anyway.

"I thought this was a very reasonable preemptive tool to have in our toolkit," he said. "We are still interested in doing something more than the status quo, because the status quo is clearly not working for our community."

The mayor and the city attorney's office had, by all accounts, been working on the ordinance since August, when a protest in Portland attracted right-wing groups from across the country.

But Wheeler rolled it out suddenly in October, after a spate of national and right-wing media outlets slammed him for several incidents of protesters fighting with each other and bystanders.

He introduced the ordinance with little of the behind-the-scenes work at City Hall that characterizes most major policy developments. Wheeler informed his four colleagues on the Council of it just hours before a press conference announcing it.

Before casting his vote, Wheeler blamed the media for the ordinance's defeat.

"If you put an ordinance out there and there is any question about its legality, make sure your lawyers get to the media first, because once that frame is set it is very very hard to turn that frame around," he said.