Boudin was there to visit an inmate: his father, David Gilbert.
When Boudin was in diapers, his parents dropped him off with a babysitter and never returned. Once operatives of the Weather Underground, a radical left-wing group most prominent in the 1970s, the duo acted as getaway drivers in an armed heist that left three men dead. Boudin’s mother served 22 years. His father will likely never be freed.
Decades visiting his parents behind prison walls piqued a passion for criminal justice. Still, for a man who has spent adulthood laboring in courtrooms opposing prosecutors, the 39-year-old public defender knew the news he had come to deliver that October morning in 2018 was likely to unnerve his imprisoned father.
“I’ve been thinking about a career change,” Boudin says he told his father, as they hugged and he gave him a cup of weak coffee and yogurt he had purchased from the penitentiary’s vending machines.
“What did you have in mind?” the 75-year-old asked, taking the seat catty-cornered to his son’s at the square table toward the back of the room.
George Gascón, San Francisco’s district attorney, had announced earlier that month that he would not seek reelection, paving the way for the city’s first race in more than a century with no incumbent. Boudin was seriously considering a bid for the open seat, joining the emerging wave of prosecutors promising sweeping reforms to upend a harsh, old-guard culture of law and order.
“Wow,” sighed Gilbert. But the more Boudin talked, the more his father understood.
“For most of my life, it was impossible to imagine that the district attorney’s office could be focused on undoing some of the damage done by overpolicing and mass incarceration,” Boudin explained later. “I think it’s up to people who care about the system and have been impacted by it to make sure this movement continues to build.”
Less than three months later, on Jan. 15, Boudin filed election paperwork to become the city’s top prosecutor.
A reform-minded shift
For decades, the race to become a district attorney was a referendum on which candidate could be the most tough on crime. Local prosecutors handle more than 90 percent of the criminal cases in the United States and have largely unbridled discretion deciding whether to pursue charges, how to set bail and propose the level of punishment.
Over the past several years, though, voters in conventionally red and blue states have selected progressive challengers over longtime incumbents, punctuating a growing consensus across the country that traditional approaches to criminal justice aren’t working.
As public confidence in the power of prosecutors to reshape the system evolves, reform-minded candidates, many with backgrounds in criminal defense, cropped up. Kim Foxx in Chicago and Rachael Rollins in Boston won their elections on promises of decarceration and police accountability. Larry Krasner, a one-time public defender and civil rights attorney, became Philadelphia’s district attorney in 2016, having never prosecuted a case.
Boudin, a candidate endorsed by all three, could be next.
In San Francisco, one of the counties voting in a new district attorney in November, Boudin joins three other candidates — former police commission president and counsel for the sheriff’s department Suzy Loftus, Alameda County Assistant District Attorney Nancy Tung and the state’s deputy attorney general, Leif Dautch — bidding to succeed Gascón, who had served for the past eight years.
A range of candidates
November’s race was set to be San Francisco’s first in over a century with an open seat.
After his parents were imprisoned, Boudin was raised in Chicago by adoptive parents, Weathermen Bernardine Dohrn and Bill Ayers, the group’s former leader. Ayers, now a retired University of Illinois at Chicago professor, wrote about bombings and life as a fugitive, and whether he associated with Barack Obama became an issue during the 2008 presidential campaign. Boudin went on to earn a bachelor’s and law degree from Yale and two master’s degrees from Oxford, where he was a Rhodes scholar.
Half of all Americans have a family member either currently or formerly incarcerated. Boudin believes what he felt and witnessed as the child of inmates made him a better public defender. He also thinks that the experience will make him a better prosecutor — whose power is one as an agent not just of punishment, but social justice.
When he entered the race, Boudin was the underdog. But after months of steadily increasing popularity, he has taken the lead in fundraising and prominent progressive endorsements — including one on Monday from Democratic presidential candidate Bernie Sanders.
In a city viewed as a liberal mecca beset by rising inequality, all four candidates align on overhauling the criminal justice system, ending mass incarceration and curbing police-involved shootings.
Of them, Boudin is the obvious “progressive prosecutor” choice and offers a more significant departure from the status quo, said Rory Little, a former prosecutor and defense attorney in San Francisco who is now a professor at the University of California, Hastings College of the Law and a nationally recognized expert in criminal law.
In the final weeks of a heated race, Boudin is viewed as a front-runner alongside Loftus, the contender regarded by many as “the establishment’s choice,” Little said.
And now, Loftus is also the incumbent.
Seventeen days before the election, Mayor London Breed swore in the 45-year-old lawyer as interim district attorney. Loftus’s appointment, announced hours after Gascón abruptly left office to run for district attorney in Los Angeles, incited widespread accusations that Breed threw the race and prejudiced voters in favor of the candidate she had endorsed.
A stark example
Despite San Francisco’s liberal reputation -- boasting legalized marijuana, declines to prosecute sex work and historically low rates of violent crime -- practitioners on the other side of the aisle see a picture patterned with aggressive and imbalanced policing.
“Some people will say San Francisco is a model and that we’ve solved the problem,” said Boudin, the only contender without prosecutorial experience. “Anyone who says that is out of touch with the communities that are impacted. There’s no other major city in the country as bad.”
San Francisco has the nation’s highest racial disparities in incarceration and the most extreme overrepresentation of people of color in its jails: African Americans make up 5 percent of the city’s population but more than 50 percent of those behind bars.
Approximately 17,000 people are booked into the city’s jail per year. Of them, 75 percent are drug-addicted, mentally ill or both, and more than half will be there for a week or less before leaving.
“We cannot have our jails serve as a revolving door,” Boudin said, underscoring the difference between an inherently violent individual and someone who is drug-addicted or homeless. If the root cause of a crime is addiction, illness or poverty, he continued, “We need to make sure they’re getting the kinds of services that are more cost effective, more humane and ultimately going to prevent crime from being committed down the road.”
At 36, Boudin was assigned to represent a young African American father charged with an auto theft. Based on the police report, he said the case appeared open and shut: the man was found sitting in the passenger seat of the stolen car and was positively identified in a lineup by an alleged eye-witness.
“I need to get out of jail right away,” Boudin’s client said during their first meeting. The man was desperate to get back to his family, but he could not afford bail, which was set in excess of $25,000, and so he offered to admit to a more-severe crime, of which he was not accused.
“He didn’t have enough faith in the justice system to think that innocence would set him free,” Boudin said. His experience growing up as a black man in San Francisco had taught him that pleading guilty, even to something he didn’t do, was the way to get out of jail.
(Boudin ultimately obtained surveillance footage, which revealed a woman — and not his client — had committed the crime. The judge dismissed the case.)
For someone who spent years of his youth inside his parents’ prison visiting rooms, one-off victories, though significant, were not enough. Boudin was frustrated by his limited ability to impact the system.
“When wealth determines criminal justice outcomes, it undermines the integrity of every conviction,” he said. Ending the cash-bail system, which discriminates against the poor, became a focus of Boudin’s work as a public defender and a core piece of his campaign platform.
After four years leading litigation efforts, a federal court ruling last month will force San Francisco to use a risk-based, rather than a wealth-based, approach.
Opposed by the establishment
Loftus is Boudin’s fiercest competition.
The 45-year-old attorney has spent her professional life as either a prosecutor or serving law enforcement agencies during San Francisco’s surge in police killings of unarmed civilians.
Lara Bazelon, director of the Criminal Juvenile Justice and Racial Justice Clinical Programs at the University of San Francisco School of Law told The Post that those who suggest that Loftus and Boudin are one and the same have missed the crux of what’s going on in this race.
“He’s truly progressive and Suzy Loftus is not,” said Bazelon, a former federal defender.
Loftus has criticized the city’s current handling of officer-involved shootings. “We have to fundamentally change it,” she said at a September debate.
During her tenure on the police commission — a period where officers opened fire at least 30 times, fatally striking 15 civilians, according to department data — Loftus boasted that more police officers were fired than ever before, though zero were because of a police-involved shooting. Instead, the police department gave medals of valor to several members of the force who were involved in civilian shootings, in some instances before the investigation had been completed.
Despite an earlier promise to remain neutral in the race, the police union spent $400,00 in television ads and sponsored a political action committee opposing Boudin, funding it with $50,000, according to campaign finance records filed in late October.
The city’s Deputy Sheriffs’ Association has also attacked Boudin, confirming his father’s fear: that his sins would be held against his son, who was 14 months old when the bank heist took place. In July, the association posted a video on its Facebook page entitled “Terrorist’s Son as SF District Attorney?” that detailed his parents’ offenses and cautioned against the candidate, calling Boudin a “communist radical of sorts.”
Undeterred by a ‘broken system'
Boudin spends a September morning at the entrance to the Glen Park transit station, handing out English, Spanish and Chinese fliers to morning commuters passing through.
Only a handful of people take the literature. Slightly more strike up a conversation.
One San Franciscan, self-identifying as a single-issue voter, wants to discuss “the city’s homelessness crisis.” Several people recognize Boudin from the Twitter feeds of writer and activist Shaun King or singer John Legend and stop to chat.
As a public defender, Boudin represents the people of San Francisco one client at a time. As San Francisco’s district attorney, he says he — and the attorneys he’d oversee — would represent “the People of San Francisco.”
“It shouldn’t just be luck of the draw who your lawyer is,” he says, smoothing the creases in his suit. Our criminal justice system should treat “The People” equally.
But years of prison visits led Boudin to believe the system is broken: Broken for victims, who have so little to show for billions of dollars spent on incarceration and punishment; broken for the families torn apart by crime and punishment; and broken for the taxpayers who foot the bill.
“It’s the least humane and least effective system imaginable,” he continued. “We have to imagine and envision the change we want to see. We should always fight for a more-just justice system.”
Editor’s note: The reporter is a former New York City prosecutor and has a parent who was formerly incarcerated.
Correction: An earlier version of this story misstated the university Bill Ayers taught at. It was the University of Illinois at Chicago. The story has been updated.