The son of two left-wing radicals convicted for their roles as getaway drivers in an infamous 1981 armored-car robbery, he was raised in Chicago by adoptive parents Bill Ayers and Bernardine Dohrn, former leaders of the Weather Underground, a militant offshoot of the group Students for a Democratic Society.
During graduate school, Boudin headed to Venezuela to explore that nation’s revolutionary upheaval.
Now 39, Boudin — who worked for years in the public defender’s office in San Francisco and never prosecuted a case — is about to become San Francisco’s next district attorney.
Part of a wave of progressive prosecutors nationally that includes Cook County State’s Attorney Kim Foxx, Boudin says he’s determined to use the power of his new post to reform it. He’s calling for ending the cash bail system, addressing racial disparities and refocusing resources away from misdemeanors to corruption and corporate crime.
People who know him from when he was a lanky, gaptoothed kid hitting his stride at the University of Chicago’s Lab high school say his upbringing and experiences — including regularly traveling from Chicago to New York to visit his parents in prison — gives him unusual insight into the criminal justice system.
“I think growing up in the most notable and most intentionally integrated neighborhood in the city was a really important part of my childhood experience,” Boudin says. “In some ways, it’s things that have happened in Chicago since I left that have been inspirational in my decision to run. Big picture, I’ve been impacted by the criminal justice system my whole life.”
On Oct. 20, 1981, just two months after Boudin’s first birthday, his mother Kathy Boudin dropped him off at a babysitter’s house. Then, she and Boudin’s father David Gilbert took part in the robbery of a Brinks armored car to fund their revolutionary activities. The heist resulted in the killings of two police officers and a Brinks guard. Kathy Boudin, sentenced to 20 years to life, was paroled in 2003. Gilbert remains in a New York prison.
Dohrn and Ayers had come out of hiding only a year earlier, following their own involvement with the Weather Underground, a small group that led a campaign of politically motivated bombings in the 1970s.
Dohrn and Ayers met Gilbert and Kathy Boudin in the 1960s. The four were friends and members of Students for a Democratic Society — a national student activist group — and later of the Weather Underground.
Authorities didn’t pursue criminal charges against Ayers due to illegal surveillance tactics used by the FBI. Dohrn later got probation on charges in Illinois stemming from her activities in the Days of Rage demonstrations in Chicago in 1969 protesting the Vietnam War.
Ayers, now 75 and a retired University of Illinois at Chicago education professor, remembers hearing of the Brinks heist when he saw Gilbert on the front page of a newspaper. Dohrn, 77, a retired Northwestern University law professor, says they listened to news coverage on the radio that night.
The next day, they left their own two young children with friends to find Chesa, who was being cared for by Kathy Boudin’s parents, Leonard Boudin — a civil liberties lawyer whose clients included Daniel Ellsberg, Paul Robeson and Dr. Benjamin Spock — and Jean Roisman, a poet.
The decision to take Chesa into their home came in the following weeks, according to Dohrn and Ayers.
“We wondered: What if something happened to us?” Ayers says, noting that Chesa’s grandparents were in their 70s. “Parenting is a young person’s game.”
“We already knew we wanted a third child,” Dohrn says. “It turned out to be Chesa.”
Boudin’s early years after they moved to Chicago were often a struggle. He learned to read late and had temper tantrums “that would rage for hours and days,” Ayers says, resulting from the trauma of his parents being in prison.
Entering U. of C.’s lab school in first grade, Boudin was open about his parental situation, finding ways to let classmates know he had two parents in prison and lived with two other parents. As a kid, Boudin would regularly fly by himself to New York, where he’d stay with his grandparents ahead of trips to see his parents behind bars — experiences he would revisit in a college essay published by Salon.
“He would read poems his mother had written to him aloud in class,” says Catherine Chandler Deutsch, a longtime friend. “He was very open about all of it. It was a big part of who he was.”
His parents and friends credit therapists, teachers and the broader Hyde Park community with helping Boudin find himself and learn to deal with his anger.
“There were a lot of adults who worked with Chesa and gave him second chances,” Chandler Deutsch says.
By high school, Boudin was excelling. The U. of C. Lab School “gives you this freedom of what you want to learn and find out what you’re passionate about,” says Andy Rosenband, a high school friend. “The flexibility he was provided, I think, made a difference.”
Classmates remember Boudin as “exceedingly popular,” “charismatic” and “whip smart.”
“He could mesh with anyone,” says Brian Stal, a friend. “He had a lot of friends from all the different groups.”
Susan Shapiro, Boudin’s freshman history teacher, says school was a “safe place” for Boudin. She says his curiosity was encouraged and rewarded, and his competitive drive found an outlet.
“He wanted to learn, and he took what he was doing very seriously,” Shapiro says. “He knew this was an opportunity for him. And I think it mattered to him to show people that he was as serious as he was.”
After school, Boudin and his friends would often make their way to his home, where “the fridge was always stocked,” and there was a basketball court in the backyard and a pool table in the basement. They listened to R&B and rap. When his mother would call from prison, Boudin would pass the phone around to his friends so they could talk with her, too.
“It was very normal for me,” Chandler Deutsch says of the calls. “I think it was her way of being involved as a parent and knowing his friends.”
Bill Gerstein, a longtime Chicago educator and former owner of Mr. G’s Market in Hyde Park, gave Boudin his first job — bagging groceries. Gerstein says Boudin was mature and confident for a teenager. He credits Ayers and Dohrn for that.
“People in the Fox TV world probably think they were these radical, crazy parents, but they weren’t,” Gerstein says. “They were very involved, supportive.”
Boudin graduated from high school in three years and traveled to South America, where he would return often over the next 10 years to study and write. Despite news reports that he worked for Venezuelan President Hugo Chavez’s administration, Boudin says he never met him nor worked for the government. He says he did the translation work for a U.S. publisher, did research for his master’s degree and worked as a fixer for foreign journalists.
He headed to Yale University in the fall of 1999 and spent his junior year at the University of Chile. He was a Rhodes Scholar at Oxford University for graduate school and returned to Yale for law school, graduating in 2011.
Boudin clerked for Judge Margaret McKeown on the 9th Circuit Court of Appeals, based in San Francisco and, in 2012, became a Liman Fellow at the San Francisco public defender’s office. In 2015, he was hired there full-time after clerking for a federal judge for a year.
“I liked my job,” Boudin says. “I love the work public defenders do.”
Still, when he saw a chance to run for district attorney in 2019 — the first election for the office without an incumbent in the race in more than a century — he took it.
“When I looked around and realized the things that frustrated me in individual cases and systemically, I couldn’t change those as a public defender,” he says. “As district attorney, I’ll have the challenge and obligation to think systemwide how to fix those problems.”
In campaign ads, Boudin spoke of his background and his parents. More than half of Americans have had a family member behind bars, he says in one.
“My parents participated in a tragic and violent crime that had profound consequences on many of us, most significantly the three men killed and their families,” Boudin says. “None of our lives —those of us that are still alive — will ever be the same as they were or would have been but for the terrible events on that day.”
Boudin doesn’t think his parents should have been sentenced as if they’d pulled a trigger during the robbery. He calls the felony murder charges against them “draconian” and “antiquated,” noting that two years ago California “joined the majority of jurisdictions in the world in eliminating felony murder charges against accomplices who do not actually kill.”
He knows he’s been more fortunate than many kids whose parents are imprisoned.
“On one hand, I was in this unbelievably privileged private school that some of Chicago’s wealthiest families send their kids to,” he says. “And, on the other hand, I’m spending a weekend a month going through steel gates and metal detectors just to give my parents a hug.”
Boudin remembers a boy named Lorenzo, a few years older, he says he’d see when both were in the prison visiting room. Unlike Boudin, who was struggling in school, Lorenzo was getting straight As and was the star of his middle school basketball team.
“Why can’t you be more like Lorenzo?” Boudin says him mom Kathy Boudin would ask.
Lorenzo was black, an immigrant and being raised by his grandmother in a “rough part of Brooklyn.” After high school, Boudin got a letter from his dad saying he got a new neighbor in his cell block — Lorenzo.
“It couldn’t have been more of a stark contrast,” Boudin says.
He says he’s trying to find a “a better approach to crime and punishment than the one that we’ve blindly relied on without empirical evidence that it’s effective.”
Foxx, who ran in Cook County on a reform platform in 2016, endorsed Boudin last summer. They got together in December, when Boudin was in Chicago.
Foxx says Boudin’s election — which he won by fewer than 3,000 votes — and those of other prosecutors who campaigned as political progressives, show voters see value in their approach.
Boudin and Foxx both faced opposition from police unions. The San Francisco Police Officer’s Association called Boudin “the #1 choice of criminals and gang members” and spent $700,000 to campaign against him, the San Francisco Chronicle reported. The association did not respond to requests for comment.
Chicago’s main police union, noting Boudin’s local ties, wrote that his election “should send shivers throughout the country.”
“I have a really strong relationship with the chief of police,” Boudin says, “We don’t need to make each other’s job more challenging.”
He says prosecutors too often have used the number of convictions they get to prove their worth and that his measures of success include finding ways to reduce recidivism, engage crime victims through restorative justice practices and put fewer people in prison.
“If we can find better ways than jail or prison to address those first two issues — recidivism and victims rights and trauma — then I think we’re winning on all three,” says Boudin, who will be sworn into office on Wednesday. “The burden is on people like me to prove that the alternative is better.”