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In Portland, a Prosecutor Must Decide: Which Protesters Should Go to Jail?

The sheriff, Mike Reese, warned Mr. Schmidt in an email that some protesters were bent on “starting fires, damaging property and assaulting police, community members,” adding, “They may feel even more emboldened if there is a public statement that appears to minimize their activities.” In response to one of the sheriff’s concerns, Mr. Schmidt said he revised the policy to greenlight prosecutions for rioting in cases where a defendant was accused of serious offenses.

The Oregon State Police also took a parting shot at Mr. Schmidt as troopers pulled back after a two-week deployment at the protests this month, saying they preferred to put resources in “counties where prosecution of criminal conduct is still a priority.” The governor, Kate Brown, a Democrat who endorsed Mr. Schmidt, made clear on Twitter that the State Police had always planned to withdraw after two weeks, and that they could be sent back if needed.

Since protests erupted around the country in the wake of Mr. Floyd’s killing in police custody, Mr. Trump has vowed to send federal agents to cities where he said liberal leaders were not doing an adequate job of keeping the peace. In Portland, federal officers who were sent in over the city’s objections engaged in almost nightly conflict with protesters at the downtown federal courthouse, with demonstrators lobbing firecrackers, water bottles and other objects at the agents, who often responded with tear gas and wide-ranging arrests.

Only the federal government’s agreement to a conditional pullback restored a measure of stability, though protesters then turned their attention back to the local police.

Portland’s feud with Mr. Trump is not necessarily over: On Wednesday, the White House chief of staff, Mark Meadows, said on Fox News that “it looks like we’re going to have to” send federal agents back to the city. Last week, federal officers, who had not entirely left town, clashed with protesters for the first time since July. The opening of the Republican National Convention this week gives Mr. Trump and his allies another opportunity to attack the city’s response to the demonstrations.

Mr. Schmidt began his journey to the district attorney’s office by teaching public high school in New Orleans, where all of his students were Black. The experience had a profound effect on him.

He remembers one student, a 14-year-old accused of possessing marijuana, who escaped punishment only because a camera captured on video an officer planting drugs. And he once asked students if they wanted to go to college. Few raised their hands, as others explained that, with the escalating gun violence in the city, they expected be dead by 22 or 23.

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