On a recent rainy morning, Chesa Boudin woke up sick. It had been a busy few weeks for the man who upended San Francisco’s political establishment by winning the race for district attorney in November. The 39-year-old attorney was on the kind of schedule that would threaten anyone’s immune system.

After nosing out Suzy Loftus in a close-fought race, Boudin was hounded by media requests, due in part to his remarkable life story.

Moreover, he had to mend fences with the mayor, the head of the police union and other high-ranking city officials who supported (sometimes vociferously) his opponent, Loftus, who in October had been appointed interim D.A. by Mayor London Breed, making her the “incumbent” in the race.

Boudin also had to start make staffing decisions for the D.A.’s office, which employs more than 200 people, and plot out the first 100 days of his four-year term after he is sworn in on Jan. 8.

Oh, he also got married soon after being elected, to Valerie Block, a brain researcher at the UCSF Weill Institute for Neurosciences.

“If the New Yorker called for a profile,” said Kelsey Russom, the manager of his transition team, “we’d have to say no.”

Still, Boudin, who is proudly Jewish, took time to speak with J. by phone in mid-December, apologizing for his weak voice. An ardent criminal justice reformer, he spoke about the challenges facing his city, including homelessness and drug use, about Jewish values and about a “commitment to human dignity” that he says has guided his professional life.

Boudin is no stranger to the national spotlight. In 2002, the New York Times profiled the young Yale undergraduate underneath the headline “From a Radical Background, a Rhodes Scholar Emerges.”

The radical tag, however, isn’t exactly his. It was Boudin’s parents, David Gilbert and Kathy Boudin, who were members of the militant, communist, anti-war group the Weather Underground in the 1970s — and who paid a heavy price for their involvement.

In 1981, when Boudin was just 14 months old, his parents participated in an attempted robbery of a Brink’s armored vehicle that led to a shootout near Nyack, New York. Three people died in the botched heist, including two police officers, and both his parents were sentenced to long prison terms.

The young Boudin, in turn, was adopted by Weather Underground leaders Bill Ayers and Bernardine Dohrn, who raised him in Chicago.

Kathy Boudin published academic papers while incarcerated, and after her release in 2003 she became an assistant professor at Columbia University. She is the co-director and co-founder of the school’s Center for Justice.

Gilbert remains incarcerated at Wende Correctional Facility in upstate New York, serving a 75-year sentence on three counts of felony murder.

Both Gilbert and Kathy Boudin are Jewish. He had a bar mitzvah as a youth in the Boston area, and though she had a “more secular” upbringing in New York City, her Jewish identity became stronger in prison.

“Many of the people she lived with in prison were religious,” Chesa Boudin said. “They drew on their faith to persevere in the face of lengthy sentences.”

Boudin recalled how a nun at the prison helped develop a center that facilitated visits between incarcerated mothers and their children. “If it weren’t for Sister Elaine and the Children’s Center, I would not have a meaningful relationship with my mother,” Boudin said.

Chesa Boudin went to the University of Chicago Lab School in Hyde Park, a day school populated by the children of university professors. His adoptive parents were, in fact, intellectuals — university professors themselves. He often has said his experience provides a stark contrast to the estimated one in seven U.S. adults who have had an immediate family member behind bars for at least a year.

“The experience of visiting a loved one behind bars is not unique,” he said. “What’s unique about my situation is because of the support, and second chances — obviously, the choices I made, and hard work, too — I’m in a very different situation than most people experiencing family incarceration.

“When you [take a kid’s] parents away at 14 months old [and] put them behind bars, you dramatically decrease the chances of that child ever becoming a Rhodes Scholar, or winning public office.”

Boudin said his upbringing was secular, but his family often celebrated Passover and Hanukkah with the family of his adoptive mother, Bernardine; her father, Bernard Dohrn, was Jewish. And “almost all” of his close friends at the Lab School were Jewish, he said, leading him to attend a bar or bat mitzvah “almost every weekend.”

“Judaism has been a constant theme in my life,” he said, mentioning ancestors who fled from the fringes of the Russian Empire because of anti-Semitism and poverty. “The fight for survival in the face of adversity has always been part of the tradition — to remember the real challenges that the Jewish people had to survive.

“People today find themselves in similar crises — refugees and people less fortunate than us, who are lost in the desert, so to speak.”

Boudin said Jewish values, broadly defined, are about a “commitment to human dignity rooted in the history of the Jewish people, and in the interpretation of the Torah.” He mentioned the story of Sodom and Gomorrah, when Abraham pleads with God to save a city of sinners, because, he paraphrased, “What if there are righteous people there?”

“It has absolutely informed the way I see the world,” he said.

Boudin is a public defender, not a prosecutor, who ran on a progressive platform backed by the likes of Sen. Bernie Sanders and the Black Lives Matter movement. He  was the only candidate who had never prosecuted a case.

We have to make it easier to get help than to get high.

His election reflected a growing frustration among voters with the U.S. criminal justice system, which locks up more people per capita than any other nation, and incarcerates African Americans at a rate 5.9 times greater than whites.

He’s part of a national trend of young, progressive candidates seeking, and sometimes winning, prosecutor offices, such as Larry Krasner (Philadelphia D.A.), Kim Foxx (state’s attorney for Cook County, Illinois) and Tiffany Cabán, who lost the Democratic primary for D.A. in Queen’s County, New York, but not before gaining national notoriety and the support of Sanders, Sen. Elizabeth Warren and Rep. Alexandria Ocasio-Cortez.

During his campaign, Boudin’s pledges included: tackling racial inequalities in the city’s criminal justice system, in which more than 40 percent of people arrested are black; ending a cash-bail system that he says unfairly penalizes the poor; and halting the prosecution of “quality of life” crimes which he says jam up the system and only “criminalize poverty and homelessness.”

While Boudin has become a champion for progressives, some people wonder whether his vision for San Francisco will help or hurt.

To many, San Francisco is beset by drug addiction, homelessness and high rates of property crime, as its economic inequality is among the worst of any city in the world.

In response to an ACLU questionnaire, Boudin said he would not prosecute crimes such as “public camping,” “offering or soliciting sex,” public urination or blocking a sidewalk — responses that raised eyebrows and garnered widespread media attention.

“It’s hard to believe that San Francisco’s leaders could make the city any worse,” Fox News’ Tucker Carlson said. “But this guy’s certainly going to try.”

Even the San Francisco Police Officers Association called him the “No. 1 choice of criminals and gang members” in some of the $400,000 worth of campaign ads against him. During the campaign, Boudin said he would do away with gang enhancements – which increase penalties for crimes committed by alleged gang members – and which he says are applied disproportionately to people of color.

“In the cases where we see serious conduct, we can already impose serious punishments,” he told the San Francisco Chronicle.

After the election, Boudin said he sat down for a cordial lunch with the chief of police and the sheriff. He also met with Mayor Breed, who was among the many influential supporters of Loftus (a list that also included Gov. Gavin Newsom, Senators Kamala Harris and Dianne Feinstein and the S.F. Democratic Party).

The common theme of those meetings?

“Everybody recognizes this city needs a district attorney’s office that’s functioning,” Boudin said. “From that perspective, they want to see me succeed. At the end of the day, we want the same things — a safer, fairer San Francisco.”

Speaking about highly visible drug use, homelessness and other problems in downtown San Francisco, Boudin said he “shares the frustration, shares the despair.”

“People who visit the city — who live in the city — see abject poverty, desperation, addiction and mental illness being untreated,” he said. “I share the need to address that problem.”

In San Francisco, it is not uncommon to see people using heroin or meth in the Tenderloin. In California, possession of drugs for personal use is a misdemeanor, but it often goes unprosecuted. Boudin said he does not think putting drug addicts in jail “is an effective use of resources,” nor is it an “effective response to drug addiction.”

“I think there is ample, empirical evidence that the war on drugs has not succeeded by any reasonable metric,” he said. “It has not decreased addiction [or] access to drugs, and it’s been costly — financially and socially.” A study released in September by the D.A.’s office showed nearly half of people convicted of crimes in San Francisco were arrested again within three years.

During his campaign, Boudin pledged to expand diversion programs for the mentally ill and drug-addicted to keep them out of the criminal justice system, which appears to many an inadequate response to problems of human despair. Of the four D.A. candidates, he was the only one who did not want more funding for the D.A.’s office.

If he can win support from the S.F. Board of Supervisors and other officials, he hopes to build a “centralized mental-health facility” run by health professionals, rather than law enforcement, and shut down county jail No. 4, which is said to be seismically unsafe, redirecting funds to mental health and drug treatment.

“Jails do nothing to treat the root cause of crime,” he wrote in a campaign platform description. “Rather, jails often victimize and destabilize an already vulnerable population, who are then released to the streets with no treatment plan or housing, often leading to more crime.”

In San Francisco, he said, “We have to make it easier to get help than to get high.”

Boudin told J. that on Passover he often visited his mother at her maximum-security prison. There weren’t many Jews inside, but there were enough to merit a seder led by a local rabbi. It was one of the only times, Boudin recalled, he was allowed to visit his mother outside of visiting hours.

He vividly remembers searching for the afikomen in the visiting room, an experience he called “profound.”

The relevance of the Exodus story to his life’s work is not lost on him, and after being elected, he gained even more understanding of that story.

“I see it as [being] about a search for redemption,” he said. “As a public defender, my focus was on saving people from prison. But as district attorney-elect, I take a broader view. It’s about public safety, redemption and healing.”