Is Chesa Boudin Radical Enough?

The son of Weathermen wants to be San Francisco’s next district attorney.

Chesa Boudin and his mother, Kathy Boudin, in the maximum security prison where she served her sentence for her involvement in the 1981 Brinks heist, which left three people dead.Ralf-Finn Hestoft/Corbis via Getty Images

Update, Nov. 9: Chesa Boudin declared victory on Saturday following a concession from Suzy Loftus, San Francisco’s interim district attorney.

“Look, I didn’t live through that time period,” Chesa Boudin says with a sigh. “I can’t imagine wanting to use violence as a tool for social change. I can’t imagine even thinking that would be an effective way for me to achieve political goals.”

Boudin, San Francisco’s deputy public defender and the Bernie Sanders–endorsed progressive candidate in the city’s DA election on Tuesday, can be forgiven for being a little annoyed. It’s an early July afternoon during a hectic campaign week, and the race is heating up in strange ways. The previous day, the San Francisco Deputy Sheriffs’ Association broadcast on Facebook just how little it thought of his candidacy by declaring him a “radical releaser.” The group also posted a video from the fringe, far-right John Birch Society that attacked him over his family’s background—Boudin being, in their words, the “son of terrorists” and “a communist radical of sorts” who may be funded by billionaire George Soros. “Share if you care,” wrote the DSA.

It was all so very 1969 of the sheriffs, summoning the Birchers to inveigh against the Weathermen. You half expected Wavy Gravy to show up in an attack ad. Boudin’s parents, Kathy Boudin and David Gilbert, were members of the militant left-wing Weather Underground, which began as a faction of Students for a Democratic Society and gained infamy in the late ’60s and the ’70s for a spate of political bombings—including at the Pentagon and the State Department headquarters—in protest of the Vietnam War. The group was four years dead when Boudin’s parents handed their 14-month-old to a babysitter and left to participate in one of America’s most notorious crimes, the 1981 Brinks heist, for which they acted as getaway drivers—Gilbert driving and Boudin sitting shotgun in a U-Haul truck that served as a switch vehicle. The perpetrators, led by members of the Black Liberation Army, got away with $1.6 million before a shootout ensued; three people were killed—two cops and a security guard.

Boudin’s parents were sentenced to long prison sentences for their roles in the crime. His father is still incarcerated; his mother was released in 2003 and is now the co-director of the Center for Justice at Columbia University, which works on mass incarceration issues. In their absence, Boudin was raised in Chicago by their close friends and fellow Weathermen Bill Ayers and Bernardine Dohrn, now a pair of retired academics who still haunt the fever dreams of right-wingers.

Today, Boudin, 39 years old, is vying to reform from within the sort of office his forebears quite literally tried to blow up. And as has happened throughout much of his adult life, he has had to parry attempts to conflate his parents’ actions with his own political leanings; 1969, it seems, is always being subpoenaed by his critics as evidence against him. A Slate article from 2002 all but lays his parents’ errors at his feet. The New York Times, in a blistering review of his 2009 book about his travels through Latin America, called him “the product of militant politics,” which was a good sight nicer than its assessment of his prose (“Please make it stop,” Dwight Garner wrote).

“I grew up knowing that my parents had used violence as a tool for social change, and that…it didn’t work by any metric, it hadn’t accomplished the political goals that they had, it had imposed a very heavy cost on the victims of the crimes and on me, and on them, our family,” Boudin says. “For me, it was an early and easy decision to reject violence as a tool for social change.”

His disavowal of his parents’ actions is well practiced, a politician’s answer, and he’s careful to untangle their methods from their goals: ending racism, inequality, the war in Vietnam, and the United States’ role in oppression at home and abroad. “I’m confident, I like to think, that had I lived through the ’60s and ’70s, I would have been organizing against the war in Vietnam as they were,” Boudin says. “I like to think that if I’d lived through the ’50s and ’60s I would have been doing whatever I could to be in solidarity with the civil rights movement. From that perspective, I think there’s a shared system of values, broadly defined. But when it comes to the tactics they used, it’s really hard for me to imagine.”

In the narrow context of the DA’s race, Boudin is the closest thing to a radical, if for no other reason than that his rivals—Suzy Loftus, Nancy Tung, and Leif Dautch—are all career prosecutors. David Alan Sklansky, author of the 2017 Progressive Prosecutor’s Handbook, places Boudin in the recent wave of progressive reformers who’ve run “on a platform that’s aimed at rebalancing the criminal justice system, insuring more scrutiny of police, taking new steps to avoid unjust and improper convictions, dialing back mass incarceration, and limiting the racial injustices and imbalances of the system.” He continues: “That’s a kind of DA that almost never won an election say 10, 15 years ago, and now is increasingly common. Boudin is in that mold if he wins.”

But outside the reactionary framework of prosecutorial politics, Boudin is no radical. The invocations of his family history have had the ironic effect of burnishing his institutionalist credentials. It was his mother, after all, who co-wrote something called The Bust Book, a handbook of legal advice for young leftists who get arrested, summarized by one Redbaiting congressman as “use the law to destroy the system.” Elsewhere, Kathy Boudin urged fellow radicals not to engage with the law on its terms. She wrote: “We need to attack the legal system of the United States—courts, grand juries, legislative committees, the ideology itself….” (This got the attention of the FBI.) Chesa Boudin, meanwhile, believes that with the right person installed in the DA’s office, “we can have a system that makes us proud.”

At a moment when Boudin is keeping the ’60s at arm’s length, the reform movement he wishes to join could use some of that old radical spirit. Sklansky notes that the new cohort of progressive prosecutors—including Larry Krasner in Philadelphia, the movement’s lodestar—has done little to devolve the power of the office, the key to bringing about real, lasting change. “All the progressive prosecutors I’m familiar with are using their powers to move the criminal justice system in the direction of more fairness, less harshness, more accountability for police, and less criminalization of poverty,” Sklansky says. “But I don’t think any of them have tried to reduce the powers of the prosecutor’s office. I think they’ve all made the calculation that using the power of the office to make these changes is the most effective way to affect the system.”

Boudin went to Oxford as a Rhodes Scholar and later attended Yale Law School. He spent a summer clerking on the South African Constitutional Court and learned about South Africa’s halting transition to “an imperfect, to be sure, but a racially inclusive, democratic society, and with it one of the most progressive constitutions in the world.” People like Albie Sachs, an activist who opposed apartheid and got his arm blown off by a bomb for his troubles, and Edwin Cameron, an anti-apartheid lawyer, became his models for social change—two white reformers who didn’t do war with the system but massaged it into something more equitable.

Boudin’s earliest memories, he likes to say in stump speeches, are of waiting in long lines full of Black and Brown women and children and going through prison gates to visit his parents. In his telling, his youth was shaped by these confrontations with the mass incarceration machine. He has witnessed how the criminal justice system tears apart communities and families, and exacts a brutal, asymmetric toll on communities of color.

All of which is why he has never prosecuted a case, and why, since 2012, he has actively worked against the prosecutor’s office as a public defender representing poor clients in criminal cases. It’s also why he’s chosen to run as the city’s top prosecutor. “If we are going to end mass incarceration—and we are, we are,” he said at a campaign event last June, “it starts with changing the people and the ideas that we put in the office of district attorney.”

While the right might call Boudin a socialist or a communist or a radical, his politics fall comfortably in line with the progressive wing of the Democratic party, and he’s racked up endorsements from grassroots progressive groups, Democratic city supervisors including Aaron Peskin and Hillary Ronen, and civil rights icons and activists like Angela Davis and Shaun King. His message is this: end cash bail; close juvenile hall and County Jail No. 4, the top floor of the seismically unsound Hall of Justice, where about 75 percent of those incarcerated suffer from mental health issues or substance abuse; stop the criminalization of homelessness and mental illness; prosecute “bad cops”; and rather than clog the court system with smaller, victimless crimes, focus resources and scheduling on prosecuting the most egregious ones. It’s a radical message only by the standards of the office. The conversation about criminal justice has shifted to such an extent that several of his opponents have laid claim to difference pieces of his platform.

“All of the four candidates in the district attorney race are, in one way or another, arguing for reducing incarceration,” The New York Times reported last May, seeing “little daylight” between Boudin and his main opponent, Suzy Loftus, but that’s not quite right. (The Bust Book writes that The New York Times, “although not useful for any other purposes,” makes for a useful weapon when “rolled up lengthwise and folded in half.”) Loftus is known as the establishment candidate, endorsed by the city’s major Democratic figures and organizations, including Mayor London Breed, Kamala Harris, Gavin Newsom, and the San Francisco Democratic Party. When George Gascón resigned as DA in October to explore a run for the same job in Los Angeles, it was Loftus, the assistant chief legal counsel in the sheriff’s department, whom Breed handpicked for the interim role—a brazen bit of political chicanery that has surely boosted Loftus’ electoral prospects. Loftus previously worked as a prosecutor in the city’s district attorney’s office before moving under Harris at the state Department of Justice. She then served as president of the San Francisco Police Commission during a scandal-ridden period of deadly police shootings. Of 15 fatal shootings during that era, 10 involved people of color. But she also ushered in a more reform-minded program, and as she often notes, she “oversaw the termination of more officers accused of serious misconduct than ever before.” According to police commission disciplinary reports, none was terminated for use of force incidents. And as Mission Local first reported last week, during Loftus’ tenure on the police commission, the SFPD coordinated with the FBI to gather information on civilians not suspected of criminal activity, directly violating local laws and infringing on First Amendment rights.

In a race in which nearly every candidate is claiming some flavor of reformer bona fides, Boudin’s background is unique in the field for having put those values into action. “Chesa’s lived the crusade for criminal justice reform since he was a child,” says Jim Stearns, a San Francisco political consultant working with Boudin’s campaign. “He’s the only candidate who chose not to be a prosecutor, and not to join this broken system.…He’s never charged money bail, he’s never cooperated with ICE.” (After Boudin stated at a debate in August that he would prosecute ICE agents, Tung, the law-enforcement candidate in the field, joked, “Chesa, if you were running for public defender, I would vote for you.”)

These distinctions are significant. In recent years, voters in cities across the nation—from St. Louis and Chicago to Brooklyn and Houston and well beyond—have sent tough-on-crime prosecutors packing in favor of unapologetic progressives who seek to end mass incarceration, money bail, and police brutality.

The best-known of the bunch is Krasner, a long-time civil rights attorney who’d made a career out of suing the police. Since becoming DA in Philadelphia, he has fired hard-line prosecutors and squared off against the city’s law-and-order culture. He endorsed Boudin early on. “A careful look at his career shows that he’s real about progressive reform, as opposed to being someone who knows what is fashionable to say in an election cycle,” says Krasner. “It’s incredibly important to look at the decisions that people have made, the sacrifices they have made, how effective they have been in pursuing actual progressive reform, before accepting the notion that a campaign is truly progressive.” And that’s vital, he says, because “as we’re seeing progressive candidates win around the country and saying the politically unsayable seems to be a successful strategy, well now everyone is saying it.”

“If you want someone who is going to do things differently, if you recognize, as all the candidates in the race do, that the system is broken, that we need fundamental changes, why would you expect to get those fundamental changes from people who have been part of the system their whole career?” Boudin asks rhetorically. “Why would you look to or trust people so deeply embedded in the status quo to have the imagination, the empathy, the ideas necessary to bring about that change?”

At an event he’d organized for Boudin, Shaun King, the co-founder of Real Justice PAC, who works to elect progressive prosecutors nationwide, spoke to a crowd of a few hundred about his belief in the need for a progressive prosecutor in a major city like San Francisco. “There is a part of me, I don’t mean it as a slight, that’s disappointed that San Francisco is not already there. What everybody in the room knows—and I’m not teaching you anything you don’t already know—is there is the hype of San Francisco and there is the reality of San Francisco. Most of the world thinks of this as the most liberal progressive city in America. What we’re saying is: We want the reality of San Francisco to match its hype.”

In San Francisco, more than 40 percent of all people arrested by police are Black, Boudin often notes, and the overwhelming majority—as many as 85 percent—of people booked into jail suffer from mental illness, substance abuse, or both. In recent years, local law enforcement has been embroiled in scandal for everything from officers shooting unarmed Black men to sending each other racist text messages.

David Latterman, a San Francisco-based political consultant who typically works with center-left candidates, says that Boudin is “not trying to mask who he is.” “A lot of hard-left candidates in San Francisco try to fake their way into being more centrist—seeming more reasonable. He’s not.…And so the question is, ‘Is that what the city wants?’” Noting the abundance of car break-ins and the perception that crime and homelessness and drugs are hurting the city’s reputation right now, Latterman says, “I don’t think the city’s in the mood for real leniency right now. They want the DA to actually be a DA, not a public defender, not a big ideologue.” While King calls San Francisco’s progressivism “hype,” Latterman calls it a “myth.”

Beyond that, there’s the entrenched political machinery that Boudin will have to contend with. Prior to the start of the campaign season, the only candidate with any name recognition was Loftus. And she runs in the right circles. “The thing about San Francisco that’s interesting is, this is a dues-paying city, especially in the political world,” Latterman says. “You show up out of nowhere and win? It doesn’t happen here.…Loftus, she’s a well-known figure and has been running for this office for a while, and has sort of always been seen as next up.”

But Boudin still has reason to be confident. In the last fundraising period, he outraised Loftus by more than $30,000, and has the highest number of individual donors in San Francisco—more than twice as many as Loftus. He has managed to tap into an active grassroots base of progressives in the city who view criminal justice reform as the only way forward. This, according to Larry Krasner, is how these kinds of campaigns are won. The progressive prosecutor movement “is really a grassroots movement, and I view progressive prosecutors as basically being technicians,” says Krasner. “The entire movement is the result of decades of those retributive policies and the cumulative effect of mass incarceration, after you’ve had a buildup and a buildup and a buildup.…The lived experience was the most persuasive thing you could ever have to make people hate those policies and hate mass incarceration.”

San Francisco’s University Club is a members-only social club resting at the peak of Nob Hill, the sort of place that drops $5 million on squash courts and hangs the heads of two African antelope on the wall of the main stairwell. “Get ready for a pretty conservative crowd,” Boudin texts me before a mid-September debate at the University Club. The dining room where the debate is held is all dark wood and big chandeliers, with panoramic views of the San Francisco skyline. This is not a natural setting for a progressive crusader to make his pitch. And while there is some dutiful talk of mass incarceration, the conversation returns over and over again to other, more personally pressing concerns. The swells here are worried about car break-ins and “the homeless problem,” not police accountability, restorative justice, and ending money bail, which, as Boudin tells this crowd of rich and powerful, “privileges the rich and the powerful.”

Rooms like this are where the ideals of progressive prosecution go to die. The Harvard Law Review and others refer to progressive prosecution as a “reformist reform”—a temporary technocratic fix to a fundamentally broken system—and the scene at the University Club goes some way toward explaining their pessimism. Boudin is asking to be put in charge of an institution built to serve the prerogatives of the people in here, the ones milling around the cheese table in their evening finery, talking about the unhoused as if they were a criminal class.

“The paradox of ‘progressive prosecution’ is that the criminal legal system is an oppressive institution,” the Harvard Law Review writes. “Attempting to make the ‘most powerful’ actor in such an institution more progressive seems to miss the point.” The solution, the authors argue, is not to give more power and resources to progressive DAs; it’s to make the office less powerful, for instance with legislation that permanently removes crimes from charging and sentencing menus. Use the law to destroy the system—Kathy Boudin’s Bust Book told us as much. Not all of 1969 needs to be kept at arm’s length.

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