U.S. District Judge Michael Simon has a weighty question in front of him: Has the city of Portland truly met all the requirements laid out in its six-year-old settlement agreement with the U.S. Department of Justice?

The federal government says yes. Last month, DOJ officials told the city they believed the Portland Police Bureau has met all the terms laid out in the 77-page settlement agreement, which was reached in 2014 after the DOJ found officers often used excessive force on people who were experiencing a mental health crisis. The document was intended to guide the needed changes within the bureau.

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But at Tuesday’s routine court conference on the agreement, Judge Simon said it’s not obvious to him the bureau has reached “substantial compliance,” a legal designation that would mean the settlement’s close to over. Once the city reaches the milestone, the clock starts on a year-long countdown in which the city has to prove it can maintain the changes.

“It appears to me there is a serious disagreement over whether or not the city is in substantial compliance,” said Simon, referencing testimony he’d received from local advocacy organizations.

But, the judge conceded, he was in legally strange and complex territory. While he had the power to determine the city was not in substantial compliance, he did not believe he had the authority to offer legal relief - without a motion from the Department of Justice. And since the federal government said it believes the city met all the requirements, that’s unlikely to happen.

As of Tuesday morning, it was unclear what the next steps would be. At the minimum, Simon said he’d like to hold another hearing in March.

Advocates’ pushback on the claim that the city was in compliance focused largely on one part of the settlement: the measure that stated the city must create an oversight board comprised of community members, which would ensure police were making – and keeping – the promised changes.

The city originally created the Community Advisory Oversight Board, but that collapsed in 2016. The city tried again two years later with the 13-member Portland Committee on Community-Engaged Policing, known as PCCEP. It was spearheaded by Mayor Ted Wheeler, who sat in the court for the first part of Tuesday’s hearing, but slipped out mid-morning.

At Tuesday’s conference, speakers testified to the judge that the committee was inefficient, disorganized, sparsely attended and “a barrier” to community engagement.

Juan Chavez, an attorney with the Oregon Justice Resource Center, pointed to the group's high attrition rate – 85%. He said the committee should be able to keep 50% of its membership for a full year to prove it was a legitimate committee.

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“PCCEP is not a seaworthy vessel as it stands to get us to wherever we need to go,” he told the judge. “If the people that are on this vessel are constantly bailing out water or jumping ship how is this vessel going to go anywhere?”

Dr. LeRoy Hanes, of the Albina Ministerial Alliance, agreed, noting he’d been a community organizer for 40 years.

“What PCCEP does is not community organizing,” he told the judge. “We need a 21st century community policing plan that is based upon the proposition that you can not arrest your way out of crime and you can not solve problems in the community without community trust.”

He pointed to a 2019 Oregonian poll that found 71% of community members said they don’t have a high level of trust with the Portland Police Bureau. That percentage was higher among Black, Asian, and Native American communities.

“There cannot be a confidence in the Police Bureau until this issue of mistrust began to be eradicated chip by chip,” he told the judge.

Philip Wolfe, who was the chair of the city’s original Community Advisory Oversight Board, said the committee that took its place had been boiled down to essentially “city people” with regular citizens who were distrustful that the body could accomplish what it promised. As a result, he said, PCCEP is “dysfunctional.”

“We can keep running PCCEP for PR purposes, we can have nice photos in The Oregonian,” Wolfe, who ran for city council two years ago as Portland's first deaf candidate, said through an interpreter. “But that’s the people that are there, and not the people who are scared to show up.”

Andrew Kalloch, a former ACLU attorney who now serves on the board, rebutted Wolfe’s characterization that the committee hasn’t been fully staffed due to deep dysfunction. Some members, he said, had moved from the area. Other youth members had gone off to college.

To address the concerns of those who bailed from the committee because they felt it wasn’t working, Kalloch said he wanted to focus “on process rather than product.” This meant ensuring that the committee’s volunteers know they may not always get the final results they’re after, they feel ‘respected’ by the process.

While debates on PCCEP’s merits took the lion’s share of the morning, others told the judge they believed the city shouldn’t be found in compliance for a simple reason, at the heart of the agreement: Portland Police officers still kill people experiencing mental illnesses.

"In 2019, the PPB killed five people - all people in mental health crisis," said Michael Hopcroft, a board member of the Mental Health Association of Portland. "At the same time, in NYC, with 10 times the population, NYC killed 10 people." He added that, according to the Washington Post's fatal shooting database, none of the people were in a mental health crisis.

The hearing will continue into Tuesday afternoon.