Four years and what seems like a lifetime ago, Multnomah County District Attorney Mike Schmidt was elected with a staggering 77% of the vote, as part of a national movement of reform-minded prosecutors with a new approach to criminal justice.

Schmidt’s landslide victory came while the COVID-19 pandemic still felt novel. And while the region’s housing crisis was in full swing, sidewalks filled with tents and people openly using drugs weren’t as ubiquitous.

Schmidt’s victory was before massive racial justice protests began and centered Portland in the crosshairs of the 2020 presidential election. It also came before Oregon’s fentanyl crisis and the passage of Ballot Measure 110, which decriminalized small amounts of hard drugs, and before Portland saw record gun violence and homicides.

Now, Schmidt is facing a tough reelection bid, as some county residents argue he failed in his central duty to keep the public safe, and even contributed to the county’s downfall. So vulnerable is Schmidt’s position, that he’s drawn a challenger from within his own office.

Nathan Vasquez, a longtime prosecutor in Multnomah County, touts support from the region’s business community and law enforcement unions. To many of them, he represents everything Schmidt isn’t: a tough-on-crime prosecutor who they say can clean up the county.

Related: OPB Ballot Guide | 2024

To some voters, the May election is a referendum on state and local policies, many of which are out of Schmidt’s control, while others see a backlash to the national movement as a whole.

“The pushback is that the American public doesn’t have a huge amount of patience,” said Laurie Levenson, a former federal prosecutor who teaches at Loyola Law School in Los Angeles. “So if reforms don’t work quickly, they’re going to be rejected.”

But the tone of the race and the attention it’s attracted may say more about Oregon and the political climate of the state’s most-populous county than the candidates’ ability to do the job, according to former prosecutors, elected officials and local political strategists.

“It’s a lot of people from different sides of our community focusing their energies and their value systems and overlaying it on the DA’s race,” said Bobbin Singh, executive director of the Oregon Justice Resource Center, a civil rights nonprofit that advocates for people behind bars in Oregon. “It’s a proxy fight.”

The candidates

Schmidt and Vasquez are locked in a race that has descended into personal attacks and resembles a polarized political contest, despite the district attorney’s office being nonpartisan.

Schmidt, a Democrat, spent six years as a prosecutor in the Multnomah County district attorney’s office before he pivoted to policy work in Salem. In 2015, Schmidt was hired to lead the Oregon Criminal Justice Commission, a state agency that advises lawmakers on criminal justice legislation and policy.

In 2020, Schmidt ran for district attorney and pitched himself as a progressive prosecutor, tapping into a national movement that elevated reform-minded candidates who vowed to enact policies to reduce mass incarceration. Schmidt promised to eliminate cash bail, focus on prosecuting violent offenses over low-level crimes, and reduce the long-term effects of the criminal justice system by clearing away old criminal charges — which he’s largely accomplished.

And he said his work is not finished.

“Like any job, there’s a steep learning curve. And this job is probably one of, if not the, toughest law enforcement role in the state of Oregon,” Schmidt told OPB’s “Think Out Loud” in April. “You need the community to be behind you to help you build these initiatives.”

Vasquez has worked as a Multnomah County prosecutor since 2001. A longtime Republican, he registered as a member of the Independent Party in 2017. In interviews, Vasquez attributed this switch to his “disgust” with the rise of Donald Trump. As a senior deputy district attorney, he manages a team of a dozen prosecutors. Vasquez has focused on violent crime and several high-profile felony cases, including prosecuting a man convicted of shooting at a group of women, killing one, in a Northeast Portland park in 2022.

He argues Schmidt has made the county less safe.

“If we just kind of look over the four years, he set the bar incredibly low,” Vasquez said, referring to the spike in violent crime during the pandemic, also during an interview with “Think Out Loud” in April.

Related: Multnomah County DA Mike Schmidt makes case for reelection

An ‘avatar’ election

A poll commissioned by the Portland Metro Chamber found that 69% of Multnomah County voters who were surveyed in December said the city is on the wrong track, pointing to concerns with crime, homelessness and the cost of living.

“People are seeing this election as an avatar for crime and public safety in their community, and it’s a chance for them to express their feelings about that,” said John Horvick, senior vice president of Portland-based DHM Research, which conducted the poll.

Horvick believes Schmidt may have an advantage due to the expected low voter turnout in a primary election — a dynamic that Horvick says historically energizes more Democrats and fewer non-affiliated voters.

Doug Moore is the executive director of United for Portland, a nonpartisan political organization formed to recruit and support candidates in Portland-area races. United for Portland is not endorsing a candidate in the race, but Moore has personally donated to Schmidt’s campaign. He agreed that the district attorney’s race feels more like a referendum on all local elected officials that voters have lost faith in, than on Schmidt himself.

“We elected very progressive leaders,” Moore said. “Voters are now saying that they aren’t getting things done to better our community. So that opens up the door to less progressive, more conservative candidates to say, ‘Here’s a solution.’ What voters crave is a solution.”

For example, in 2022, Portland City Commissioner Jo Ann Hardesty, a staunch progressive who sailed into office on a police reform, lost her reelection campaign to Rene Gonzalez, a Democrat who has since positioned himself as the council’s most conservative member in decades.

Related: Challenger Nathan Vasquez makes case for why he should be Multnomah County’s top prosecutor

A challenging 4 years

Months into the COVID-19 pandemic, with a consequential presidential election on the horizon, the majority of Multnomah County voters chose Schmidt to replace District Attorney Rod Underhill, who was leaving office.

Six days after that election, a Minneapolis police officer murdered George Floyd. Weeks later, as nightly protests concentrated in downtown Portland, Underhill announced his early retirement, thrusting Schmidt into office six months earlier than anticipated.

Related: Multnomah County District Attorney Rod Underhill announces retirement

Deborah Kafoury, who was the chair of the Multnomah County Board of Commissioners at the time, said Schmidt was handed “a shit sandwich” with this move.

“For a first-time elected official, it was definitely challenging,” Kafoury said. “It’s important to talk about the time and the place that we were in when he took office.”

Schmidt came in hot: A week after starting the job, he held a press conference where he announced he would only prosecute racial justice protesters who were arrested for property damage, theft, or the use or threat of force against another person. To some, this signaled Schmidt’s commitment to civil rights at a moment of unrest. To others, like law enforcement unions and property owners in downtown Portland, this was the county’s top prosecutor encouraging members of the public to break the law.

In total, Schmidt’s office rejected 895 protest-related cases between June 2020 and June 2022, accounting for 82% of all protest arrests, according to district attorney’s office data.

Vasquez says the policy was wrong.

“His first act was to 100% destroy the relationship with Portland police,” Vasquez said in a March debate hosted by the Portland Metro Chamber. “He told them loud and clear he didn’t value them with his protest policy. He told them loud and clear they were second-class. And they left in droves, sadly.”

“Mr. Vasquez forgets that he was on the stage next to me announcing that protest policy,” Schmidt shot back during that debate. “He doesn’t want to remind you of that. He didn’t bring up those objections then. But now, he has revisionist history.”

And indeed, Vasquez was there on Aug. 11, 2020, where he thanked Schmidt for his “thoughtful, in-depth conversations and considerations” of the policy. Schmidt appointed Vasquez to oversee the protest cases.

This divisive moment appeared to set the tone for the rest of Schmidt’s term in office, cementing a rocky relationship with law enforcement that defined his tenure.

Months later, Oregon voters decriminalized small amounts of drugs through Measure 110, coinciding with an influx of cheap and deadly fentanyl on Portland’s streets. Schmidt backed Measure 110. It passed in Multnomah County with 74% of the vote. Schmidt adopted the new law early, weeks before it went into effect.

A massive shortage of public defenders in Multnomah County forced the courts to dismiss hundreds of criminal cases, making it difficult to hold potentially dangerous offenders accountable. And the number of officers in the Portland Police Bureau plummeted in 2021, due to retirements and burnout. That hampered response times and lowered arrest rates, which gave the public the impression law enforcement didn’t care.

Some officers used Schmidt to explain the bureau’s shortfalls, to the point that then-Chief Chuck Lovell had to issue a bureau-wide memo urging officers to stop telling Portlanders that they could not fight crime because of Schmidt’s prosecutorial constraints.

Despite these hurdles, Schmidt still attempted to bolster public safety through new programs, such as forming a team of prosecutors solely focused on violent crime and establishing a commission of experts tasked with reducing gun violence. He also created several task forces between police and prosecutors to zero in on car and retail theft, which skyrocketed during the pandemic. In a policy shift, Schmidt went to the Legislature earlier this year to successfully lobby for changes to Ballot Measure 110, namely criminalizing drugs once more.

But this work did little to change the minds of skeptics.

It was also muted by a simmering issue in his own office that boiled over in the past year.

Several female prosecutors on the team of roughly 90 attorneys raised concerns about Schmidt’s management of the office, citing sexism. The Oregon Bureau of Labor and Industries found last year “substantial evidence” Schmidt’s office discriminated based on employees’ gender and sex. BOLI stated that Schmidt’s office, which includes a staff of about 200, promoted more men than women into leadership positions during the first 18 months of his tenure.

But Schmidt said last year that he disagreed with BOLI’s findings and that his office had promoted 31 men and 31 women since he was elected. Multnomah County also hired an outside law firm to conduct an investigation. The investigation corroborated Schmidt’s assertion.

Schmidt has faced other critiques. An internal survey of staff showed discontent among women and people of color in the office.

When Vasquez announced his campaign last year, he criticized Schmidt’s decision to not prosecute some low-level crimes and called for greater collaboration with law enforcement to prosecute all offenses. He also called for changes to Measure 110, the drug decriminalization bill, placing responsibility for its passage on Schmidt, who endorsed the law.

“This is a shining example of Mike Schmidt’s failed policies,” Vasquez said at the March Metro Chamber debate. “In 2020, he was the mouthpiece for this.”

Schmidt acknowledges the policy was wrong for not connecting people to treatment swiftly enough.

“I pivoted on this issue,” he said during an April debate hosted by the City Club of Portland. “That’s what leadership is. You take in new information and you go forward with what you think is the best plan to move the country forward.”

Battle lines drawn

Vasquez has secured endorsements from six local law enforcement unions, including the Portland Police Association and the Multnomah County Deputy Sheriffs Association. In a joint statement, the unions wrote that “our public safety system clearly needs new energy and direction,” and that Vasquez has a record leading with “a fair but firm hand.”

Josh Zwick is the president of Multnomah County Deputy Sheriffs Association, which represents 135 deputies and sergeants. He said the union supports Vasquez because they’ve seen his work ethic up close.

“He really cares,” said Zwick, who has personally worked a case with Vasquez. “He cares about communities and about working with the police. He knows how to bridge that gap.”

Zwick, who has worked for the sheriff’s office for 20 years, said that he’s never met Schmidt.

More recently, the Portland Metro Chamber, a local business lobbying group, praised Schmidt for working closely with their organization to craft policies that “have directly led to a decline in crime.” Yet, the chamber chose to endorse Vasquez — and hand over a $2,500 check — saying he is “broadly respected by the legal and public safety community.”

“Our members believe that the Multnomah County DA’s office needs a reset under an experienced prosecutor who can improve morale in the DA’s office and unify our public safety agencies,” the group wrote in a statement to OPB.

Related: Multnomah County announces new gun-violence efforts, including mobile mental health team

Vasquez has the backing of his colleagues, too: The union representing Multnomah County prosecutors — of which Vasquez is a member, and Schmidt is not — voted to endorse him and contributed $5,000 to his campaign.

Others have shown their interest in Vasquez with big money. He’s collected just over $1 million since entering the race, including thousands from Nike co-founder Phil Knight, real estate mogul Jordan Schnitzer, Columbia Sportswear CEO Tim Boyle, and developer Greg Goodman. These are many of the same contributors to the short-lived campaign to repeal Measure 110, which was put on pause after the Legislature passed changes. They’re also some of the same people who say they’ve given to People for Portland, a campaign that’s paid to erect giant anti-Schmidt billboards in downtown Portland over the past year.

These billboards suggest Schmidt isn’t doing enough to tackle public safety problems such as drug use and homelessness. They also chastise Schmidt for leaving jail beds empty.

But at least on that point, Vasquez may not be all that different from Schmidt.

“I don’t think that filling up our jails is what will make our streets safer,” he said in a statement to OPB.

Schmidt, in comparison, has raised just over $800,000. While he’s still trailing his opponent, Schmidt’s collected nearly $500,000 more than he raised in his 2020 run. Some of his top donations have come from the Drug Policy Alliance, the New York organization that backed Measure 110, and the Safety and Justice PAC, a committee that advocates for criminal justice reform-minded candidates and policies, such as Measure 110.

The forces behind these donations tell a clear story.

“This race is a backlash against Measure 110,” said Felisa Hagins, political director at the Service Employees International Union Local 49. SEIU is not endorsing a candidate in the district attorney’s race.

Related: Multnomah County DA plans to drop significant number of protester charges

Hagins, who personally supports Schmidt’s reelection, said she’s equally frustrated with seeing public drug use and a growing homelessness crisis, but that replacing the top prosecutor won’t change that. Giving Schmidt time to carry out his vision will, she said.

“It takes a long while to make change in an entrenched system,” Hagins said. “And law enforcement is the most entrenched system I’ve seen.”

Despite the thorny challenges of the past four years, Schmidt’s supporters say he’s lived up to his campaign promises. Racial justice groups and social service providers have rallied around Schmidt, pointing to his work establishing diversion programs that keep vulnerable people out of jail and expungement clinics that help people erase low-level offenses from their record.

He’s earned the endorsements of some of Oregon’s top Democrats — including Attorney General Ellen Rosenblum, former Gov. Kate Brown and Multnomah County Chair Jessica Vega Pederson.

For some of Schmidt’s backers, their support is complicated.

Tera Hurst is the executive director of the Health Justice Resource Alliance, an organization established to help the state carry out Measure 110. Hurst said she was “heartbroken” when Schmidt backed House Bill 4002, the legislation that reintroduced criminal penalties to people caught with small amounts of illicit drugs. But Hurst understood why he did it.

“I don’t think it was the right thing to do, but I also recognize that being an elected leader, especially in a position like that, you do need to step up to what your constituents and community are asking you to do,” Hurst said.

Related: Oregon governor signs bill criminalizing drug possession

Schmidt still has Hurst’s endorsement. She believes Schmidt is more interested in helping drug users get into treatment and avoid jail than Vasquez would be. Hurst, who has spent much of her career working for elected officials, also believes the race reflects the “pendulum swing” of local — and national — politics away from progressive ideas in recent years

“Just four years ago, we were in such a different mental, compassionate space, and now we’re back to the criminalization of poverty,” Hurst said. “There’s a lot of people who get harmed by that pendulum. It’s dangerous.”

Reform prosecutors weigh in

This spring’s election for Multnomah County district attorney is being watched nationally as an indicator of the health of the progressive prosecutor movement.

The movement, which grew during the Trump administration, centers prosecutors who want to overhaul the criminal justice system and create alternatives to incarceration.

Philadelphia District Attorney Larry Krasner rode this wave into office in 2017. Just like Schmidt, Krasner faced intense scrutiny for enacting a reform-minded agenda early in his tenure.

“What’s happening in Portland is broadly similar to what’s happening all over the country, which is that a pandemic happened, crime went very high, now crime is dropping like a rock,” Krasner said. “We do need to get to a point where this country is less incarcerated, and safer.”

Krasner won reelection in 2021, he said, by running on his record.

Others have struggled.

In 2022, San Francisco District Attorney Chesa Boudin, a reform prosecutor, was recalled by voters before the end of his first term. But Boudin said his experience offers few lessons for the fate of the national progressive prosecutor movement. He argues that his recall election — in which he wasn’t pitted against an opponent — is not at all like the race for Multnomah County district attorney.

“A recall in San Francisco is a terrible proxy for any normal, general head-to-head election,” Boudin said.

Levenson, the Loyola law professor, said some of the biggest pushback reform prosecutors face comes from within their own office, where career prosecutors have a certain way of doing things. Big changes rolled out without buy-in can sink a term.

But Levenson said she’s not surprised that reform prosecutors get elected.

“In fact, they got elected by quite a margin in some areas because people are searching for a change — a better way to do things,” she said. “We have not really solved our issues about crime and criminal justice, so new ideas are welcome.”

And in many ways that’s the dynamic voters are grappling with in Multnomah County.

Kafoury, the former county chair, said there are clearly people in Schmidt’s office who don’t like what he’s doing. She said that the office has changed little since the early 1980s, at times putting Schmidt’s agenda at odds with the status quo.

“That office has operated in that same way since and has not taken on new innovative programs, or tried things that sometimes challenge what people have been taught and told,” Kafoury said. “Change is really hard.”

For his part, Vasquez says that he is progressive prosecutor.

“Do I consider myself to be the same type of progressive prosecutor as the current elected in Multnomah County? I don’t,” Vasquez told OPB’s “Think Out Loud.” “I see myself as someone who looks to bring very practical solutions to helping individuals out of the criminal justice system and to serving victims.”

But Schmidt said Vasquez is just saying what he needs to say to get elected in a progressive community.

“The idea that he’s a progressive prosecutor is laughable,” Schmidt said during a Portland City Club debate. “I’m telling you, he would not be accepted in those circles because he’s not one. But this is Multnomah County and he knows what he has to say so I guess that’s what he’s got going for him.”

Whoever wins and whatever direction county voters decide to take their public safety system, the bitter and personal tone of this campaign is a harbinger of the challenging months to come this election year.