On a dreary May morning in San Francisco, as people hustled to work along choked streets and highways, a young woman in an orange jumpsuit stood before a judge in the city’s Hall of Justice and awaited the court’s ruling. Arrested on charges of drug-related theft, she was about to find out whether she would be forced to spend more time behind bars, or whether she might be transferred out of the city’s jail to seek rehabilitation services for addiction. Chesa Boudin, a 38-year-old public defender in a pinstripe suit, was by her side. He had been working for weeks to secure her release.

“This is someone who has suffered tremendous amounts of trauma and is doing relatively low-level crimes directly related to her history of trauma and her addiction,” Boudin later told me of his client, who is trans and Latinx and had already spent at least three weeks in jail. “And she wants treatment.”

The judge, a thin white man in black robes, didn’t take long to come to a decision in the case. “Keeping you in county jail,” the judge told the defendant, “isn’t therapeutic for you.” He asked her if she would be willing to stay in a women’s treatment center in the city and then, when she consented, the judge signed a release order. It was Boudin’s first court appearance of the day, and he had managed to secure a small, if imperfect, victory for his client. She would be freed from county jail within a week.

For Boudin, whose life has been shaped by intimate personal experience with this country’s prison system, such victories are important, but they are not nearly enough. As a child, Boudin traveled to and from correctional facilities to visit his parents, two former members of the militant left-wing group the Weather Underground who were incarcerated when he was just a toddler. In these prisons, he saw the gears of the mass-incarceration machine up close: the way they ripped families apart, fractured communities, and exacted a relentless, unequal toll on people of color. As he got older, going to law school, he wrote, came to seem “almost inevitable.”

“My role models,” he explained, “were lawyers dedicated to social justice and extending the benefits of the rule of law to traditionally excluded communities.”

But the rule of law is not so easily extended, even by dedicated attorneys, even in San Francisco. Despite its reputation as a liberal redoubt, San Francisco remains a city where justice often looks a lot like injustice—where, Boudin points out, as many as 85 percent of people booked into jail are suffering from some combination of substance abuse problems and mental illness, and more than 40 percent of all people arrested by the police are black. It is also a city where law enforcement has been embroiled in a string of terrible scandals in recent years, including one in which officers were caught sending each other racist and homophobic text messages.

And so, despite never having prosecuted a case in his life, despite spending the last five years working against the prosecutor’s office, Boudin is doing what most public defenders would have found unfathomable just a few years ago. He is running to become the city’s next district attorney. And, as he takes the lead in fundraising tallies and prominent progressive endorsements, he seems to be enjoying significant momentum.

“When we happen to have the first open DA race in a century,” he says, “it is too critical a moment to just stand by and watch and allow candidates who are essentially committed to the status quo to be the only candidates and the only options for San Francisco voters.”

For decades, liberals and leftists have largely spurned district attorney races across the country, and the consequences have been devastating, Boudin believes. “For almost my entire life, true progressives who were committed to ending mass incarceration viewed the district attorney’s office as a kind of a forbidden political space, and the result was that we didn’t contest power in what is arguably the single most important and powerful position within the criminal justice apparatus,” Boudin tells me.

That was a “huge strategic mistake,” he says. “It was one that in many ways was motivated by principle, but folks on the left basically abandoned district attorneys’ races in the thousands of DA offices across the country to candidates who were competing with each other to be tougher on crime.”

Now, however, thanks to the rise of Black Lives Matter movement and years of work on the part of criminal justice reformers, the political landscape is starting to shift. A new electoral movement has emerged to place opponents of mass incarceration in DA’s offices across the nation and thus radically alter the role that prosecutors play in American life.

This new “decarceral” prosecutor movement, as it is sometimes known, scored a major early victory in 2016, when longtime civil rights attorney Larry Krasner ran a winning grassroots campaign to become Philadelphia’s new DA. Since taking office, Krasner has sought to deliver on his campaign promises to reduce mass incarceration in the city by challenging its entrenched law and order culture. He has fired hard-line prosecutors in his office, effectively decriminalized marijuana, and reduced low-level and nonviolent crime prosecutions. And he has dramatically scaled back the use of money bail.

This process of shifting the system from within has not always been smooth, or easy. Krasner has bumped into stiff resistance from the courts and from the Pennsylvania state government, which have sought to stymie his reform efforts. In July, the state legislature passed a bill, targeted specifically at the Philadelphia DA’s office, that undermined Krasner’s prosecutorial power.

Still, such challenges have not deterred others, and the decarceral movement has established a foothold in a handful of counties, both expected and unexpected. In Massachusetts, two lawyers, Rachel Rollins and Andrea Harrington, won their elections in Suffolk and Berkshire counties in 2018 running on platforms that aim to end “tough on crime” policies in their communities. In St. Louis County, meanwhile, progressive prosecutor Wesley Bell has cracked down on the use of money bail and the prosecution of nonviolent offenses. Just this summer, public defender Tiffany Cabán, a working-class queer Latina from Queens, came within 55 votes of defeating the Democratic machine’s chosen candidate to become the borough’s next DA.

Now, Boudin wants to be the movement’s torchbearer in Northern California.

“I see San Francisco as a critical front line in this national movement,” says Boudin, of his decision to jump into the race. “I see San Francisco as a city that has the potential for tremendous leadership in many areas, because of its wealth and its technology and its diversity and its history and its progressive values.”

There has not been an open race for the San Francisco DA’s office for more than a century. Most prosecutors who have taken over the office have either been appointed by the mayor after an incumbent stepped down, or won an insurgent race against an incumbent, as Kamala Harris did when she beat prosecutor Terence Hallinan in 2003. But now, the current DA George Gascón has decided to retire and there is a four-person election to replace him.

While Gascón was a progressive, pursuing reforms that saw the creation and expansion of collaborative courts that work with defendants to offer alternatives to jail time, Boudin believes there is ample room to improve the way the city prosecutes (or declines to prosecute) crimes.

Among other goals, Boudin wants to beef up units that investigate predatory landlords, corporate environmental crimes, and political corruption. He wants to stop the office from asking for money bail, in most cases. He wants to push the local criminal justice system to continue to build up and better fund the city’s collaborative courts, such as drug court and young adult court. And Boudin, who is fluent in Spanish, wants to hire more staffers who speak languages other than English to better provide services to San Francisco’s linguistically diverse population.

“We are now at a critical moment,” he says. “We may look back in 10 years and say, well, Larry Krasner for example, was the apex of this movement. Or we may look back and say that [people like Krasner] were the beginning of a sea change, and I think that’s still a question mark. It is up to us to determine.”

Boudin joined the race to succeed Gascón after spending a lifetime straddling what he calls “two worlds.” He is a white man with a Yale Law degree and two master’s degrees from Oxford, which he earned during a Rhodes scholarship. He has held two federal clerkships and a longtime position in one of the most prestigious public defender’s offices in the nation. His grandfather, Leonard Boudin, was a prominent civil rights attorney who represented famous activists like Paul Robeson and Daniel Ellsberg. On the morning The Nation accompanied him to court, he chatted amicably with the judge and prosecutors across the aisle, perfectly at ease with his legal colleagues.

But Boudin is also the son of parents who have spent decades in prison. His earliest memories, he often tells people at his campaign events, are “going into prisons and being searched by guards.”

Boudin was 14 months old when his parents, Kathy Boudin and David Gilbert, were arrested for their role as getaway drivers in the 1981 Brink’s robbery in which two police officers and a security guard were killed. His mother was sentenced to 20 years to life in prison and his father was sentenced to 75 years to life.

After his parents’ imprisonment, Bill Ayers and Bernardine Dohrn, also former members of the Weather Underground, took a toddler-age Boudin into their home in Chicago. He spent the rest of his youth taking trips to New York to visit his imprisoned parents.

“I picture him sitting on my lap when we had a phone on the wall in the kitchen and he would sit on my lap and talk to Kathy from prison,” says Dohrn, of Boudin’s early years. “And he would hang up and ask me, ‘When are they going to get out?’ And I started making up this story that they will get out when you are grown up.”

Dohrn’s story turned out to be partly true. After he graduated from college, Boudin’s mother Kathy was released from prison after 22 years behind bars. She is now the codirector of the Center for Justice at Columbia University, where she works as a research scientist studying mass incarceration and its consequences. His father is still imprisoned in New York, and Boudin regularly visits him on weekends, buying groceries and heading into the prison for a few days at a time.

Boudin believes his long and intimate exposure to the American prison system sets him apart from most other members of the bar. “I have not literally but figuratively been shackled to this world of mass incarceration,” he tells me, “to this system of mostly black and brown prisoners; to the indignities and humiliation of getting searched every time you want to see your parents.”

“And that is a reality that is actually shared with a majority of Americans,” he adds, noting that more than half of all Americans have an immediate family member who is currently or formerly incarcerated. “I think it has made it easier for me to connect with my clients as a public defender.”

During his time in the public defender’s office, where he is still working today, Boudin helped create an immigration unit that works to prevent undocumented immigrants from being handed over to federal immigration authorities. He helped launch a bail unit that labors to prevent defendants from being saddled with money bail and forced into pretrial detention. And he helped lead a protracted litigation campaign to whittle away at the legality of money bail in California.

Whether Boudin and the broader decarceral prosecutor movement can have similar success in reforming this country’s DAs offices is still an open question. Even Boudin’s own family, with its history of militant left activism, has doubts.

“Traditionally, prosecutors are in bed with the police and the police bring them their cases and instead of doing a serious screening of the cases the prosecutors put police officers on the stand and they lie and that has been an easy path to obtain convictions,” says Dohrn, Boudin’s adoptive mother and a former clinical associate professor of law at Northwestern University. “I have seen it in my work with the juvenile system, but it is even more apparent in the adult system.”

“You are hearing me question whether things can be different or not,” she adds, “but if anyone can convince me it is certainly someone like Chesa.”

As the race to succeed Gascón unfolds, Boudin is relying on his personal history, his litigation record, and his daily work with criminal defendants to distinguish himself from a field of three other candidates who want to be San Francisco’s next DA, almost all of whom have sought to portray themselves as progressives on matters of criminal justice reform. Boudin’s most formidable opponent in the race—indeed, the person to beat—is Suzy Loftus, an establishment-backed prosecutor who is currently legal counsel at the San Francisco Sheriff’s Department. Loftus, a former president of the city’s police commission, also worked in the San Francisco DA’s office and the California attorney general’s office under Kamala Harris. Harris has endorsed Loftus. Senator Dianne Feinstein, and many other prominent Democrats leaders in the state, including Governor Gavin Newsom, have endorsed her as well.

Loftus, with her years of prosecutorial experience, is running on a platform that her spokesperson, Debbie Mesloh, describes as “very progressive” and includes “a commitment to a reduction of mass incarceration, ending cash bail, and looking at financial justice within the system.” As evidence, she points to Loftus’s endorsements by multiple criminal justice reform advocates as well as her proposal to establish a new civil rights unit within the DA’s office.

Some critics, however, say Loftus’s record indicates that she may not be as progressive as she contends.

“I think Suzy Loftus in the context of the San Francisco DA race is essentially the Joe Biden candidate, representing the more moderate…approach,” said John Crew, a longtime criminal justice reform activist with the ACLU and a vocal critic of the San Francisco Police Department. “Is [her approach] bad, awful, going in the wrong direction? No. But we are in a moment where we need drastic changes, and I think her record on the police commission in particular shows insufficient urgency and insufficient passion.”

Crew particularly questions Loftus’s commitment to take on San Francisco’s police union, which he describes as a “bad cop lobby” that is to criminal justice reform what the NRA is to gun control. He points to what he describes as Loftus’s tendency to “duck” on controversial issues around police accountability, as when she refused to endorse a 2016 bill in the state legislature that sought to make records of police misconduct in the state more transparent.

“I personally asked her to take a position on it and she never came out in support of that bill,” says Crew, noting that the police union was ardently opposed to the legislation.

Loftus, in response, says that she has stood up to the police union in the past, particularly when she led the city’s police commission and helped set a policy that set new limits on law enforcement’s ability to use lethal force.

“Under my leadership on the police commission, San Francisco police officers began wearing body cameras for first time. We reformed the use of force policy for the first time in 20 years. I am the only person in this race who the Police Officers Association has attacked with television and radio ads,” she says, adding that she “took away the ability of officers to shoot at moving vehicles and took away their ability to use carotid restraint.”

“The policies instituted under my leadership have resulted in a 30 percent reduction in the use of force,” she says.

Boudin, for his part, has made it clear in his policy platform and in public statements that he is ready and willing to take on bad cops as soon as he steps into office. If he wins in November, he says he will make investigations into police misconduct a priority by funneling more resources to attorneys who specialize in such work.

“The minority of officers who violate the law with impunity do tremendous damage to public safety, to community trust, and the integrity of the criminal justice system,” he says. “I’m committed to liberating our communities, and all honest police, from the bad officers who have been allowed to take over the Police Officers Association.”

Such statements have not endeared Boudin to law enforcement, and in early July, the San Francisco Deputy Sheriffs’ Association went on the offensive, posting a video on its Facebook page that attacked him over his family background and called him a “radical releaser.” “Terrorist’s Son as SF District Attorney?” the video shouted in big block letters, before describing Boudin as a “communist radical of sorts.”

It is unclear whether Boudin’s insurgent campaign will win in the end. There have been no polls of voters yet. But recent fundraising numbers are promising for Boudin. His campaign has significantly out-raised Loftus this calendar year. According to the latest campaign filings, Boudin has gathered a little more than $505,000 from over 2,500 donors since January. Loftus has raised a little more than $343,000 in the same time period. Boudin credits the strong fundraising to “grassroots organizing and a social media presence that is growing exponentially.”

Meanwhile, Boudin’s campaign continues to galvanize a progressive base that has long sat out DA races, garnering the support of a range of prominent progressive groups and individuals in California and beyond, including Larry Krasner, Shaun King’s Real Justice PAC, Our Revolution, the San Francisco Tenants Union, the Latino Democratic Club, the Harvey Milk Democratic Club, five members of the city’s Board of Supervisors, and Tiffany Cabán. Indeed, Cabán traveled from Queens to San Francisco in late August to campaign for Boudin. She backs him, she says, because “we need more people nationally in this fight. We need to be building a powerful coalition of not just progressive, but decarceral, prosecutors, and San Francisco can play a huge huge part in that.”

Still, as Cabán’s own narrow loss in Queens suggests, even the most progressive communities are tough battlegrounds for candidates who want to radically roll back the law-and-order culture at the heart of America’s criminal justice system. Even buzzy left-wing candidates with lots of campaign cash can struggle against the establishment forces that have dominated DA’s offices for decades.

Back in the Hall of Justice on that May morning, Boudin hustles in and out of an adjacent holding cell to talk to clients and try to win them the best outcomes in a rigged system. Dozens of men and women, many of them black and Latino, all wearing orange jumpsuits, shuffle through the drug court. Some are diverted to rehabilitation programs, but most are sent back to jail. It is a relentless torrent of people struggling with addiction, mental illness, or both, languishing behind bars in one of America’s most progressive cities, often because they cannot pay bail.

Boudin spends part of the day with them, counseling and comforting and fighting for them. And then, when he finishes his work, he hits the campaign trail, trying to convince voters that another justice system is possible.