His victory marks a welcome shift from the “tough on crime” norms to bold positions that veer radically to the left

The local deputy sheriffs union shared a video declaring him the “son of terrorists”. The police union called him the “#1 choice of criminals and gang members”. But after five days of vote tabulations and a narrow 2,500-vote lead, Chesa Boudin is San Francisco’s next top cop.

The son of two leftwing Weather Underground radicals who served as the getaway drivers in a 1981 armored car heist that left two police officers and a guard dead, Boudin last week won the race for San Francisco district attorney, vowing to bring change to a city with a liberal reputation that it has not always earned.

Across the country, progressives ranging from presidential candidate Bernie Sanders to civil rights activist Shaun King celebrated Boudin’s victory as the latest in a growing groundswell for criminal justice reform.

In a way, his victory reflects the sort of world that progressive criminal justice activists across the nation have been trying to build over the past few years: one in which a person’s mistakes do not dictate the rest of their lives – nor the lives of their children.

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“Compassion,” Boudin told the Guardian. “That’s something we really need to return to the criminal justice system. For victims, for families of people impacted, for witnesses, for defendants and for their families, and frankly for people who work in the system. Compassion, for everybody whose life is touched by crime.”

For those fighting for criminal justice reform – to end mass incarceration, the criminalization of the poor, and the over-policing of black and brown people in a broken system that now counts more than 2.2 million people behind bars in the US – Boudin’s victory marked a welcome shift in the accepted “tough on crime” norms of politics and public safety. A candidate could win the position of top cop while veering radically left of the usual law-and-order script. A candidate could win taking bold positions: no longer charging gang enhancements, not prosecuting on minor quality of life crimes, creating a unit to look at past wrongful convictions, eliminating cash bail.

A candidate could win without playing it safe on public safety.

“I would talk about Chesa’s candidacy in the early days to people in the city, and they would say things like, ‘He’s incredibly smart, he’s incredibly charismatic, but he can’t win. He can’t win’,” said Lara Bazelon, a University of San Francisco law professor and Boudin supporter. “There’s this thought that there’s a fundamental ceiling on the movement and there are candidates that just can’t win. But that’s not true at all and this race proves it.”

Boudin embraced his rich backstory from the start of his campaign, speaking openly of his parents’ experience with incarceration in campaign ads and stump speeches as a nod to his understanding of the criminal justice system. His parents, Kathy Boudin and David Gilbert, were sent to prison when he was 14 months old, and for all his childhood, the only contact he had with them was behind bars. Gilbert remains in prison in upstate New York – Boudin was flying back from visiting him when he learned that he won the election – while Kathy Boudin was paroled in 2003 and works as an assistant professor at Columbia University.

Facebook Twitter Pinterest Kathy Boudin, a Weather Underground member, was sent to prison when her son, Chesa Boudin, was 14 months old. Photograph: HANDSCHUH/Associated Press

Boudin was raised in Chicago by Weather Underground founder Bill Ayers, and his wife, Bernardine Dohrn, another operative in the group. He went on to earn a bachelor’s degree from Yale University, two master’s degrees from Oxford University where he was a Rhodes scholar, and a law degree from Yale.

As district attorney, he’ll be top prosecutor, but he has never tried a case. His courtroom experience began on the other side of the aisle, at the public defender’s office, providing legal defense to those who could not afford it. His critics and opponents seized on his distinct resume, with some likening his candidacy to electing a fox to guard the henhouse.

Boudin rejects the premise. “I look at the work we do at the Hall of Justice, whether as a district attorney or a public defender or a judge or a sheriff’s deputy or juror, in big, broad terms and in trying to provide justice: None of us want to see the people who are arrested today come back into the system in a month or in a year,” Boudin said. “The challenge is finding ways to work collaboratively. We’re not always going to agree with what that’s going to look like, but I think there are going to be tremendous ways for us to do that.”

Facebook Twitter Pinterest Chesa Boudin, second from left, with his fiancée Valerie Block, stands with his parents, David Gilbert and Kathy Boudin, at the Wende Correctional Facility in Alden, New York. Photograph: Associated Press

Now the race is won, district attorney-elect Boudin will have the power to determine the kind of law enforcement that takes place in the city. By directing which cases his line prosecutors will and will not charge, Boudin ultimately decides the type of cases police officers pursue.

In San Francisco, the police union had long carried political clout and historically balked against any district attorney’s reform efforts. Former district attorney George Gascón – previously a San Francisco police chief – assembled a blue ribbon panel to look into systemic bias within the police force after racist and bigoted text messages between 14 police officers emerged in a federal corruption case (several more police officers were later implicated in another separate racist and bigoted texting scandal). The union, the San Francisco Police Officers Association (POA), responded by attacking Gascón on a statewide ballot initiative he co-authored that reduced some nonviolent felonies to misdemeanors – a ballot initiative that 80% of San Franciscans voted for and passed in November 2014.

In this election, the POA and other law enforcement groups spent $650,000 in polling and attack ads to defeat Boudin. But the days of the POA being untouchable appear to be over. At Boudin’s election night party, city lawmaker Sandra Lee Fewer, whose husband is a retired San Francisco police officer, led the crowd in a chant: “Fuck the POA! Fuck the POA! Fuck the POA!”

Mary Franklin Harvin (@EmEffHarvin) SF supervisors past and present are in the house. @SandraLeeFewer leads a “F*ck the POA” chant while @JaneKim, @MattHaneySF & others share the stage. #SFDA @KQEDnews pic.twitter.com/4kSe72n3qz

Fewer later released a statement saying she was sorry if the rank-and-file members of the police department perceived her actions as against them, but refused to apologize to the POA.

“The days of civility, and ‘we shouldn’t say these things about the POA’, that doesn’t fly in San Francisco anymore,” said Jason McDaniel, a political scientist at San Francisco State University.

But as district attorney, Boudin will have to find a way work with this police department – and perhaps, at times, this police union. “There’s a big difference between the POA leadership and the rank-and-file officers on the street, and I look forward to visiting every police station and listening to what police officers have to say,” Boudin said in an interview. “I’m open to working with the POA leadership too. I recognize there’s room to disagree and still work together. I know they don’t expect that our policies will make San Francisco safer, but I hope to persuade them over time that I’m right.”

﻿It’s Boudin’s detail-specific policies that give criminal justice activists hope for the direction of the movement. In a time when the term “progressive prosecutor” gets tossed around often – Boudin provided a template for what it truly meant to be a progressive prosecutor, Bazelon said.

“One of the things that Chesa was really successful in doing was explaining how much daylight was between him and the other three candidates,” she said. “What they tried to do was say, ‘We’re all about these reform ideas’. But he was going a step further every time. He ran on a platform of, ‘I’m going to establish an immigration unit in my office; I’m going to start a wrongful conviction unit and review excessive sentences; I’m going to offer restorative justice to any victim that wants it’. These are really bold proposals, and people really responded to that.”

Facebook Twitter Pinterest Boudin won San Francisco’s tightly contested district attorney race after campaigning to reform the criminal justice system. Photograph: Scott Strazzante/Associated Press

And the fact that he was successful, despite heavy opposition from law enforcement groups, signaled a change in the politics of public safety. It is becoming more widely accepted that the criminal justice system as it has existed in past years is broken in ways that disproportionately affect poor communities of color. No longer are voters as easily swayed by the fearmongering that the law enforcement groups deployed against Boudin, characterizing him as soft on crime.

“That tough-on-crime rhetoric did work once,” said John Crew, a former American Civil Liberties Union lawyer and local activist. “It’s why we have mass incarceration, it’s why we have such extreme racial disparities. But they tried to use it and it backfired so spectacularly, and I think it’s one of the reasons why Chesa Boudin got elected.”

Just this year, San Francisco agreed to pay Jamal Trulove $13.1m after a federal civil jury found that the police had coerced a witness into identifying him as the suspect. He was wrongfully convicted under the tenure of California senator and Democratic presidential candidate Kamala Harris’ as district attorney, and spent six years in prison. Trulove, an actor and activist, endorsed Boudin. Harris endorsed Boudin’s main opponent, who worked as a prosecutor under Harris.

Times have changed.

“As a district attorney, people often want to know what charges are you going to file, what punishment are you going to seek,” Boudin said. “But context is so important. That’s one of the things I’ve learned from my lifetime of visiting jails and prisons, and my work as a public defender. Often we only have a tiny window into what has happened in a particular case. You only see the video, or you only read the police report that is a couple witnesses’ version of events. You have to understand the big picture context. That’s the only way to prevent the people who did it from doing it again.”