Democrats Beware: A Progressive DA Fights for His Job — in Hipster Portland

PORTLAND, Oregon — The “Keep Portland Weird!” t-shirts are on sale and it’s still common to encounter employees wearing N-95 masks. Yet that’s not what greets visitors at the iconic Powell’s Books downtown here.

The first image is of the private security guard staged just past the entrance.

With its ubiquitous hipster coffee and IPAs, enduring live-and-let-live ethos and a politics so deep blue that the homeless guy outside the Whole Foods in the Pearl District solicited patrons to buy him a beer by bearing a “Fuck Trump” cardboard sign, Portland is hardly ripe for a Republican takeover.

But on Tuesday, the voters of Multnomah County, the surrounding jurisdiction and a county that has not voted Republican for president since 1960, could replace their incumbent district attorney, Mike Schmidt, with a man who was in the GOP until after Donald Trump became president.

“What I hear when I’m knocking on doors, is ‘Hey, I consider myself very liberal but this is out of step — we’re not getting served well,’” said Nathan Vasquez, a longtime prosecutor in the county office and now unaffiliated voter who’s challenging his boss, adding: “People definitely want public safety. It doesn’t mean people are wholly abandoning the idea of criminal justice reform. They just want it delivered in a pragmatic, practical way.”

Should Vasquez prevail, it would represent more than the rejection of a progressive prosecutor. It would be the culmination of simmering local frustration with crime, homelessness and drug abuse and a resounding correction to the shift left on criminal justice that took place here and in so many cities in 2020.

It should also get the attention of Democratic lawmakers everywhere. They’ve mostly found success by elevating abortion and MAGA, the party’s best one-two since Dobbs, but their vulnerabilities on quality-of-life issues remain and could prove particularly acute with the broader presidential electorate this fall.

While San Francisco’s recall of San Francisco District Attorney Chesa Boudin momentarily drew national attention two years ago, the prosecutor battles have raged on, overshadowed by the presidential race but offering a more revealing measure of how curdled many voters have become post-pandemic.

In Chicago, home to the second-largest DA’s office in the country, the progressive Kim Foxx did not run again and was replaced in March by a former judge who pledged to prosecute retail theft as a felony and said Foxx did “not believe in accountability.” And in Los Angeles, George Gascon, who’s called himself the “godfather of progressive prosecutors,” is facing a challenge this November from a former Republican, who’s decrying “a culture of lawlessness” and sounds a lot like a subscriber to the broken windows theory of law enforcement.

“It may start with smash-and-grab car theft but it then escalates into violent crimes,” Nathan Hochman, the challenger in Los Angeles, told me. Hochman, now an independent, said he’s up by double-digits in his polling for one straightforward reason: “Angelenos feel less safe today than when Gascon came to office.”

In Portland, the backlash has arrived.

Schmidt is on the ropes. His defeat would represent a full circle moment from 2020, when Portland exploded and Trump officials delighted in the images of Proud Boys and Antifa squaring off.

A former assistant DA and legislative aide, the then-38-year-old Schmidt claimed 77 percent of the vote that year, and in that summer of demonstrations and riots said he wouldn’t prosecute protestors charged with crimes like disorderly conduct or interference with a police officer.

Yet the DA race here is hardly the first sign Portland voters want a shift back to the center.

In 2022, Jo Ann Hardesty, a progressive activist and voice for police accountability, lost her city council seat after a single term at the hands of a moderate political novice from the business community, Rene Gonzalez, who’s now running for mayor this fall.

Then, last month, came the culmination of a revolt against the ballot measure passed in, yes, 2020, that decriminalized hard drugs such as heroin.

The implementation of the referendum was “malpractice,” Rep. Earl Blumenauer (D-Ore.) told me.

“We have one of the worst records in the country for addiction and Measure 110 was predicated on getting people those services and we didn’t do it,” said Blumenauer.

Faced with voter fury over open-air drug dealing and usage along with spiraling deaths, Oregon’s Democratic governor and legislature approved a bill to recriminalize possession of even small amounts of such drugs.

In a state that saw a surge in opioid overdoses in 2023 — 628 in the first six months of the year, compared to 280 in all of 2019 — the repeal represented an admission of a failed policy change.

A few weeks after Gov. Tina Kotek signed the recriminalization, The Oregonian went into the field with a poll and found 78 percent of voters in metro Portland believe homelessness is a “very serious problem” and over 60 percent said local governments should be allowed to fine or arrest anyone who refuses to leave public spaces.

“All of my lefty neighbors who want to do right thing are like, fuck it, this is not working,” Dwight Holton, a Democrat and former U.S. attorney here, told me.

Jeff Mapes, who has covered Oregon politics since the 1980s, said: “I’ve never seen anything like it, the extent of how upset people are.”

One prominent Oregon Democrat, speaking not for attribution, said Schmidt is effectively the “fall guy” for fed-up Portlanders eager to register a no-confidence vote on … somebody.

And in a city where displaying a MAGA sign would amount to a hate crime — especially without a trigger warning — the DA race is one of the few ballot lines where Democrats can vote guilt-free for change. It’s not a mayoral election, let alone a statewide or federal contest.

A Republican hasn’t been elected Oregon governor since 1982, the GOP’s second-longest losing streak in the country after next-door Washington, in no small part because of the Democratic vote trove Multnomah County reliably delivers. In 2022, when Kotek won by less than four points statewide, she took 73 percent of the county’s votes. According to Kerry Tymchuk, who runs the Oregon Historical Society, no Republican has carried Multnomah since former Senator Bob Packwood’s 1986 reelection.

But those are just statistics. It’s hard to overstate Portland’s capacity for tolerance. It has long been a refuge for those from other parts of the country and the world seeking a fresh start and non-judgmental community. That includes the governor and her wife.

This tradition has also meant a stream of homeless people.

“Portland always had a lot of transients — back to the hobos riding the rails,” said Mapes, who recalled the well-worn path to Baloney Joes, a homeless shelter by Burnside Bridge.

But the camps, the drugs, the robberies — it finally has reached a breaking point. And Schmidt is in part the target, Blumenauer explained, because he’s the first major local figure up for reelection.

“It has galvanized a lot of crankiness and people are right to be cranky,” said the congressman.

Blumenauer has represented Portland since his election to the state house in 1972 and defends Schmidt, saying the DA has “governed in a thoughtful way” since taking over amid a time of crisis. But the congressman, the picture of Portlandia quirk with his bow ties and bicycle lapel pins, concedes voters here are “not getting the performance they expected from their government, I agree.”

The private security guards — always a sign of insufficient or ineffective policing — are not just at Powell’s. They’re at Nordstroms and inside that Whole Foods. And the CVS across from the Whole Foods doesn’t have a single aisle without at least one locked enclosure to prevent theft.

Just last week, Willamette Week reported the county signed a five-year, $40 million contract earlier this year with a California-based firm for armed and unarmed security at libraries, homeless shelters and county offices.

“People are risking their catalytic converter to come downtown for dinner,” Betsy Johnson, a salty, Democrat-turned-independent former state senator told me. “And now some of the rich people in the southwest and northwest hills [of Portland] have seen the chaos in downtown and they’re wondering: when do we have to get a guard for our community?”

Vasquez points to the declining size of police and a plunge in prosecutions since 2020 under Schmidt.

“Prior to him coming into office, we ranged somewhere between 12,000 to 20,000 cases a year,” said the challenger. “Under him, post-Covid, we were under 6,000.”

There is, though, a deeper anger that’s easy to detect, especially among mainstream Democrats who resent the city becoming a soundstage for Fox News snuff clips of urban excess and blame it on outside progressive groups.

“The white left decided anarchists were better than cops,” said Holton, faulting “folks outside Portland treating us as a lab for policy experiments and what were clearly failed experiments.”

That includes groups such as the Drug Policy Alliance, a New York-based organization that helped bankroll the ballot measure decriminalizing hard drugs and is now a major funder of Schmidt.

Not that he minds the race being nationalized.

The district attorney is trying to fend off his challenger now the same way other local Democratic candidates, including successful candidates for mayor in Chicago and Los Angeles, did running against candidates to their right: by embracing their party label and painting the opposition as Trumpy or at least MAGA-adjacent.

Schmidt’s allies have sent direct mail accusing Vasquez of pursuing policies deployed by “disgraced Trump ally Rudy Giuliani” and said he’s controlled by “MAGA & NRA puppet masters.” (Vasquez called himself a “moderate centrist” and said he’d vote for Biden but expressed dismay that he and Trump “are our two best options.)

Schmidt’s signs and advertising makes sure to identify him as a Democrat even though the DA race is technically non-partisan.

Closer to home, Schmidt has linked Vasquez to Johnson, the former state senator who ran as an independent for governor in 2022, because they share a similar funding base from Oregon’s centrist business community.

“I’m in half of his ads,” Johnson exclaimed, “you’d think I was fucking Darth Vader’s sister.” (As a candidate for governor, Johnson called Portland “the city of roaches,” a play on its preferred nickname, “the city of roses.”)

Schmidt’s right in the sense that there are moderates and Republicans conspiring against him. Dan Lavey, a longtime GOP strategist and Oregon power player, helped organize “People for Portland,” a group that’s hounded the DA with ads and billboards decrying Portland’s “Schmidt Show.”

“In a one-party city and state it’s pragmatic Democrats vs. progressive Democrats fighting it out,” Lavey told me. “I call it therapy vs. discipline.”

That’s the DA’s challenge. His problem isn’t Republicans and the business community money crowd — it’s Portland’s Democratic voters.

Ben Johansen contributed to this report.