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What San Francisco DA Chesa Boudin learned from his terrorist mom

Chesa Boudin was just 14 months old when his terrorist mom and dad went to prison. The experience left a lasting mark on the boy, who grew up to become the controversial, left-leaning district attorney of San Francisco, now facing a recall election over his soft-on-crime policies.

Chesa’s mother, Kathy Boudin, who was released in 2003, died earlier this month of cancer at 78. Though she remade her life working as an adjunct professor at Columbia University’s School of Social Work, she will always be remembered for her role in one of the most violent armed robberies of the 1980s.

As the daughter of affluent Manhattan attorney Leonard Boudin, who represented controversial clients such as Fidel Castro, radical politics were hard-wired into Kathy’s genes. After attending the Little Red Schoolhouse in downtown Manhattan — a training ground for liberal thinkers — she majored in Russian Studies at Bryn Mawr College. While her classmates celebrated graduation, she was behind the Iron Curtain studying at the University of Leningrad. The previous winter, she spent time with Russian peasants on a farm.

“The opinion at Bryn Mawr was that Kathy was more interested in social justice than most of us,” a former dorm-mate, who didn’t want to be named, told The Post. “Maids and porters there were all black and it was not a place of equality. Kathy wanted to do something about it.”

Susan Braudy, who wrote “Family Circle: The Boudins and the Aristocracy of the Left” and also attended Bryn Mawr with Boudin, said, “The first thing Kathy did of note was organize the maids and porters who were getting paid very little at Bryn Mawr. She was a leftwing troublemaker on campus, threatening long-held traditions.”

Weather Underground member Kathy Boudin was convicted on felony murder and robbery charges after a 1981 Brink’s truck heist that left a guard dead.
AP

At a 1968 protest in Chicago’s Bryant Park, she met fellow radical, David Gilbert, a pioneer of the Weathermen, a radical offshoot of the Students for a Democratic Society. Later, she and Gilbert would become lovers, and conceive Chesa, their only child.

In 1969, Kathy was at a loose end and considering grad school — though she applied to Yale School of Law, she was not accepted, her former dorm-mate said — and she also joined the Weathermen, which later became known as the Weather Underground. At the time, the FBI characterized Kathy as “a kind of beacon for anti-war activities,” according to Braudy’s book. But, in her family of leftist influencers, this would have been considered a badge of honor.

David J. Gilbert, Kathy’s husband and the father of her son, Chesa, was also convicted.
AP

“It was almost a competition with her father,” Braudy told The Post. “She was competitive and angry and wanted to do the most leftwing thing, which would make her the most virtuous by leftwing standards. Her good friends were very radical.”

In October 1969, Kathy and other members of the Weathermen ran through Chicago’s pricey Gold Coast neighborhood, smashing windows in parked cars, homes and luxury businesses during a weekend-long demonstration dubbed Days of Rage. Kathy was among 284 people arrested and released on bail.

Undaunted, on March 6, 1970, Kathy found herself at an elegant Greenwich Village townhouse owned by the father of her friend and fellow radical Cathlyn Wilkerson, along with other members of the Weathermen. Her former Bryn Mawr classmate Diana Oughton and Queens native Terry Robbins were there, attempting to build a nail bomb, which they planned to unleash on a dance at Fort Dix military base in NJ. But Robbins crossed two of the wrong wires and the bomb detonated prematurely, killing himself and Oughton in the process.

Actor Dustin Hoffman lived next door to the West Village townhouse that blew up while members of the Weather Underground were constructing a bomb. Kathy was in the house and was the only survivor; afterward, she disappeared for years.
AP

Kathy survived, and her clothing was blown off, as she ran naked onto 11th Street and disappeared for 11 years.

By then, her parents were no longer impressed by their daughter’s leftist bona fides, Braudy said. “They worried about her,” said Braudy. “I worked for Ms. magazine and Kathy’s mother wrote a story about not knowing where her daughter was — but she knew. Kathy’s parents mostly knew where she was.”

On the lam — with a series of aliases, no shortage of LSD trips and missions for the cause including helping spring Timothy Leary from prison – Kathy worked for catering companies and even became a paralegal under the phony name of Ann Harriet Applebaum. But she also brazenly participated in a documentary called “Underground” with her real name on the credits.

Chesa, seen here with his dad during a prison visit, was adopted by other Weather Underground members while his parents were jailed.
AP

Meanwhile, she deepened her relationship with Gilbert, a lapsed Explorer Scout who graduated from Columbia University in 1966, picking him “to father a child with her,” Braudy said. A friend of Braudy’s once spotted the young couple in Central Park, “beating each other up” to toughen themselves for what they saw as the impending revolution, she added.

By 1981, Kathy and Gilbert’s son, Chesa, was 14-months-old, and the couple were “squabbling new parents, living separately in New York, keeping their revolutionary dreams alive by helping … rob banks,” writes Bryan Burrough in “Days of Rage: America’s Radical Underground, the FBI, and the Forgotten Age of Revolutionary Violence.”

On October 20, Kathy left Chesa with a babysitter in upper Manhattan while she and Gilbert drove a U-Haul to a former Korvettes department store near the Tappan Zee Bridge to take part in a robbery. Minutes away, three Brink’s security guards were carting bags of cash from a Chemical Bank to an armored vehicle.

Kathy, seen here with Chesa several years ago, was paroled in 2003.
Corbis via Getty Images

Laying in wait in a separate van were five members of the ultra-violent Black Liberation Army, an offshoot of the Black Panthers. When the guards came into view, four masked men emerged from the van with guns blazing. Six bags of cash were stolen. One guard was murdered, another practically had his arm blown off, and the Brink’s driver was knocked out by shattered windshield glass.

The thieves loaded sacks containing $1.6 million into the van and took off for Korvettes. Once there, they started moving the money intothe U-Haul, as Kathy and Gilbert sat in the front. Meanwhile, a college student spotted the armed revolutionaries and their blood-splattered bags of money and called police.

As Gilbert drove the U-Haul with the five armed robbers in the rear and Kathy in the passenger seat toward the New York State Thruway, roadblocks had been set up.

Nyack, NY, officer Waverly Brown was one of two policemen killed by members of the Black Liberation Army as Kathy and Gilbert were helping them flee after the Brink’s robbery.

Police pulled them over, and Kathy hopped out with her arms raised, before taking off, scampering up the side of the highway. When an off-duty officer caught up with Kathy and wrestled her to the ground, she shouted, “Don’t shoot me. He shot them. I didn’t.”

Meanwhile, cops were trying to open the rear door of the U-Haul when the five men charged out in a blaze of gunfire. Two officers were killed, some of the robbers got away in a carjacked vehicle, and it took five years before everyone involved was apprehended.

“The police were not expecting that,” said Ron Jacobs, author of “The Way the Wind Blew: A History of the Weather Underground,” referring to the armed attack. “But I think this was a contingency plan for the robbers. They had done several of these hold-ups before. They called them ‘expropriations.’ They had made a decision to wage war against the United States and ambushed police officers with no qualms.”

Kathy Boudin at Columbia University
Columbia University

Kathy and Gilbert were among four whoimmediately wound up in custody. In his book “Love and Struggle: My Life in SDS, the Weather Underground, and Beyond,” Gilbert wrote that he was punched in the face and groin at the police station. “Given the nature of what went on, I am surprised they made it to jail,” Jacobs told The Post. “I’m surprised they didn’t wind up getting shot down after the cops were killed in cold blood.”

The collateral damage in all of this was Chesa.

After Kathy pled guilty to first-degree robbery and second-degree murder in 1984, she was sentenced to 20 years to life in prison. Gilbert, found guilty of robbery and murder, was sentenced to 75 years to life. Custody of Chesa was given to Bill Ayers, an education theorist, and Bernadine Dohrn, a law professor, who were also both members of the Weather Underground.

According to Jacobs, Ayers and Dohrn did their best to shield the young boy. “They kept Chesa out of the limelight in the hope that he could have an impact on the future and also so that he would have a better chance of living a normal life.”

Chesa Boudin was elected San Francisco’s District Attorney in 2019.
AP

They also played down the crimes his parents committed.

“When I was little, they would try to describe the robbery using Robin Hood as an analogy,” Chesa told New York magazine. “They would emphasize that they weren’t trying to keep the money for themselves. They were trying to take money from a bank, which had a lot, and give it to communities that didn’t have any and that nobody was supposed to get hurt. But people did get hurt, and they were being punished as a result.”

While visits to his parents were frequent, they were not always peaceful. One trip to see Kathy ended with Chesa climbing a tree on the prison grounds. “He screamed, ‘I hate you. I hate you.’ He didn’t want to leave and he hated her because she deserted him,” Braudy said. “Kathy was very self-absorbed and did not take it seriously. You wonder why they both went to the robbery. In terms of Chesa, one of them should have stayed behind.”

Chesa (pictured with his father) has said that his parents’ incarceration has inspired his liberal policies.
Corbis via Getty Images

Chesa later wrote about enjoying the rare opportunity to spend a weekend with his dad in a trailer on prison grounds in New York State. But it ended badly. “I had a temper tantrum,” he wrote. “The joy of every prison visit was punctuated by the grim realization that I was going to have to leave, and that my dad would not be coming with me.”

In September 1983, Gilbert and Kathy were married by a prison chaplain. But eventually they divorced, while still serving time, and Kathy took up with a woman she met behind bars.

“She was competitive and angry and wanted to do the most leftwing thing, which would make her the most virtuous by leftwing standards.”

Susan Braudy, author of “Family Circle: The Boudins and the Aristocracy of the Left,” about the college-aged Kathy Boudin

Despite his fractured upbringing, Chesa flourished as a student, attending Yale as an undergrad, and winning a Rhodes scholarship to Oxford in 2002.

One year later, Kathy was released from prison, going on to co-found Columbia’s Center for Justice, focusing on the consequences of incarceration. (Gilbert’s sentence was commuted last year by Gov. Andrew Cuomo. His lawyer did not return a call for comment.)

Patrol officer Edwin O’Grady (right) was also killed in the Brink’s escape.

Chesa, meanwhile, graduated from Yale Law School and set his sights on a career in social justice. Now 41 and married with a baby of his own, he was elected San Francisco District Attorney in 2019, successfully battling a $650,000 campaign from pro-police entities to stymie his bid. He was endorsed by notorious revolutionary Angela Davis, who once had a place on the FBI’s most wanted list. “In San Francisco, [her endorsement] helped him more than it hurt him,” Jacobs said.

Today, some believe Chesa is carrying on his family’s tradition of radical politics but from the inside. He has minimized cash bail and is the first San Francisco DA to level homicide charges against a police officer, for the 2017 killing of an unarmed black man. He’s also charged three other police officers for beating suspects. Tony Montoya, the head of the San Francisco police officers’ union accused Chesa of publicizing the charges in an “almost celebratory” manner.

Meanwhile, murders in the Golden City are on the rise: 56 in 2021 compared to 48 in 2020 and 41 in 2019.

The scene of the Brink’s robbery in Nanuet, NY.
AP

Now, even in a city as progressive as San Francisco, the tide is finally turning against Chesa Boudin. The DA will officially be forced into a recall election on June 7 during California’s statewide primary, amid open criticism of his policies. Brooke Jenkins, one of about 50 prosecutors who left the DA’s office after Chesa was elected, said his extreme policies had made it difficult “to hold some of our most dangerous offenders accountable and, many times, to do what we need to protect the public.”

But that hasn’t stopped Chesa from pursuing his revolutionary ideas, especially the ones closest to his heart. Soon after his 2020 election, he launched a program helping parents facing certain low-level charges to attend classes and receive therapy instead of a jail sentence.

Faced with allegations that he is favoring lawbreaking parents like his own, his response was unapologetic: “You point me to a place in the criminal justice system where the quality of justice is not arbitrary.”