On a rainy weekday in mid-April, Booker Gray, a case manager for the Center on Juvenile and Criminal Justice, stood in the reception area of a high school in the North Bay. He’d come to see a former client, a 17-year-old named John, who had been released the month before after two years locked up in San Francisco’s juvenile hall.

As a front-desk employee inspected Gray’s identification, a school counselor approached, wanting to discuss John’s new friends.

“They’re good kids,” the counselor said. “But they smoke pot.” 

“I’ll talk to him,” Gray said. “I’ll tell him that’s not gonna work.” 

As John’s case manager, Gray was one of several adults working with the Juvenile Probation Department to ensure that the teen followed the terms of his probation. Associating with weed smokers, Gray knew, could endanger John’s freedom.

“We gotta fine-tune some things,” Gray said later. “I don’t expect things to be perfect for John once he’s out.”

A few minutes after Gray’s arrival, he was joined by John, smiling widely, in a room near the school office. After sharing a hug, Gray asked after John’s kids — the teen already has a 1- and a 3-year-old. They then turned their attention to the pressing matter of purchasing John some new football cleats. Gray ordered a pair on Amazon as they spoke. 

Gray met John when the boy was 12. (John’s name, like those of the other juvenile offenders in this story, has been changed to protect his privacy and to allow his case manager to discuss his circumstances. Some details about the youth’s crimes have been omitted.) At the time, John was detained at juvenile hall for stealing a car and possessing a firearm. The boy was so polite at that first meeting that Gray wondered if he had been incarcerated mistakenly.

From then on, Gray texted, called, and visited John at least once a week. He brought food when John was hungry and gave him rides when he needed to get somewhere. 

“ He understood me,” John said. “He didn’t judge me. I could talk to him about anything. I could call him for anything.”

For a while, it seemed Gray’s work with John was paying off. Sacred Heart Cathedral Preparatory, a private high school in San Francisco, offered John a football scholarship. But the boy soon violated his probation, and the school rescinded its offer. 

Then, at 15, John was with a group of people when one of them shot someone. Although John hadn’t pulled the trigger, a judge found him culpable for attempted murder and sentenced him to two years in the “Secure Track” wing at Juvenile Hall, reserved for kids who have committed the most serious crimes. Gray didn’t give up on him, John remembers. “He stuck around the whole time.” 

After two years in juvie, John was released in March. A contingency of his release was an order to stay out of San Francisco except for court appearances. His mom, with whom John lives, moved out of the city to comply with the stay-away order. 

Two weeks after starting at his new school,  John seemed relieved to trade his precarious lifestyle in San Francisco for a stabler one in suburbia. “I don’t gotta play this tough role with people,” he said. “It’s just coming to school as a regular kid.”

After John’s release, Gray was no longer technically his case manager. But he continued to stay involved in John’s life. While catching up, Gray laughingly told John that his mom had forced him to stick around.

John rolled his eyes. “Because she thinks I’m going to get into some … ”

“Trouble,” both said simultaneously. 

“Look,” Gray said. “You ain’t have the best damn track record.”

Ten years ago, a child like John might’ve ended up in a de facto prison for youth run by the California Division of Juvenile Justice. DJJ, as it was known before shuttering in 2023, operated detention facilities across the state that were widely criticized for high levels of violence and gang activity.

Had John gone to a DJJ facility back then, “he could have been [in detention] for much longer,” said Sidney Hollar, a defense attorney who has worked exclusively with San Francisco’s young offenders for a decade. “And when he got out, he had learned from the best.”

But in 2020, Gov. Gavin Newsom signed legislation to unwind DJJ and devolve responsibility for serious youth offenders to counties. The rationale was that young offenders had a better chance of rehabilitation by staying closer to their homes and communities.

This sea change compounded a local effort to rethink juvenile justice. In 2019, the San Francisco Board of Supervisors voted to shut down juvenile hall, where a dwindling population meant that it cost $270,000 per year to jail a child. The effort to close the hall failed, largely because the mandate was never funded and because constructing an alternative would’ve cost hundreds of millions of dollars. But in the attempt to close juvie, a working group was created to design a better juvenile justice model for the city.

Katy Weinstein Miller, chief probation officer at the city’s Juvenile Probation Department and a former member of the 14-person working group, said that after two years of deliberation and public input, a plan was developed to get kids out of juvie as quickly as possible by pairing them with case managers working for local nonprofits. 

“ We tried to create a model that would ensure that every young person who was arrested and then going through San Francisco’s juvenile justice system got connected to a community organization as early as possible following arrest,” Miller said. 

The state and local efforts drastically changed how youth offenders are treated. Now, when a judge determines that a child who has committed a crime is ready to be released from custody, the Juvenile Probation Department refers the child to a case manager at the Center on Juvenile and Criminal Justice or a similar community organization. Along with a constellation of other adults, including parents, a probation officer, and defense attorneys, CJCJ case managers ensure that kids meet the terms of their probation, which might include completing high school to staying away from a particular neighborhood or group of friends.

These case managers are funded by a five-year $3.8 million block grant administered by the city’s Department of Children, Youth and Their Families. The grants fund case workers for minors and youth up to age 24 in the juvenile and adult justice systems.

In San Francisco, it’s not a novel idea to wrap a child who has committed serious crimes in multiple layers of adult support. CJCJ, Sunset Youth Services, and other social service organizations have worked with kids on probation for decades. Previously, the referral system was somewhat ad hoc; not every child who’d committed a crime would get a case manager. That changed following the effort to close juvie. 

These days, the Juvenile Probation Department handles cases for 300 to 350 children per month. Only around 30 of these children are incarcerated in juvenile hall. The rest are out in the world — trying to rebuild their lives while avoiding the risks that so often lead kids to trouble. 

To understand how youth offenders are faring in this new system, The Standard shadowed two CJCJ case workers over several days and watched as they met with — and sometimes had to chase down — their juvenile clients. Often, the children represented by CJCJ case workers do not have stable home lives with engaged parents. Their defense attorneys’ priority is winning their cases, not keeping them safe. Probation officers, even if they mean well, sit in a position of perpetual judgment. Having an adult whose sole responsibility is to support, feed, clothe, or sometimes just listen to these kids can make the difference between freedom and jail.

“ These case managers, they act as mentors,” Hollar said. “The value is you have the consistency of somebody in your life that really cares about you and really wants to succeed.”

According to a study of statewide carceral data commissioned by CJCJ, the youth crime rate in San Francisco dropped 73% between 2010 and 2022, compared with a 43% drop in youth crimes statewide over that period. This came at a time when San Francisco has incarcerated a lower percentage of youth offenders by relying more heavily on community organizations.

Hollar attributes these positive trends to CJCJ and other community partners working with the Juvenile Probation Department. “I think it makes a big difference,” Hollar said. “Not every county has these case managers — someone who can say, ‘Here’s the importance of going to school, and if you’re not going to school every day on time, you need to set your alarm, and you need to figure out a way to get there on time.’ And those kinds of things that we think are so obvious. But with some of our clients, they just never have learned all that.”

Juan, a 17-year-old on probation for assault, hadn’t been to class in a month because he didn’t feel safe at his previous school.

On his first day attending a new high school in San Francisco, his CJCJ case manager, Lucero Herrera, arrived at the school at 10:30 a.m.to (opens in new tab) check on him. She’d texted him that morning, offering to bring food, but he hadn’t responded. 

In the school’s office, an administrator told Herrera that Juan hadn’t shown up that day.

“Damn,” Herrera said. “Let me call Mom.” 

She stepped out of the office and into the hallway, decorated with flags representing dozens of colleges attended by alumni. On the phone, Juan’s mom said the boy had claimed Herrera was picking him up that morning, even though there was no such plan. Herrera and Juan’s mom both called the boy’s phone, but he didn’t answer.

Juan’s mom couldn’t leave her job prepping food at a restaurant, so Herrera offered to visit the family’s apartment and try to catch the boy at home.

En route, Herrera punched her hand and moaned in frustration. “Please be home!” she said to herself.

Juan was first arrested for assault at age 15. He’d been on juvenile probation since then; Herrera had taken over his case five months before. On the first day she was supposed to meet Juan at his high school, he cut class. The next day, Juan missed their meeting and was found drunk on Geneva Avenue. It wasn’t until the third day that Herrera finally met Juan in person.

“He was not trying to talk to me,” Herrera said. 

At the time, Juan and his little brother lived with their mother and her boyfriend in a single room at a homeless shelter. When his mother left for work at 5 a.m., Juan and his brother were forced to leave the shelter with her. She would drop them off on 24th and Mission streets, where a woman who sold tamales would watch Juan’s brother. Juan was left to his own devices.

“He was dealing with a lot of anger,” Herrera said. “ And he was like, ‘I need privacy. I need my own space. I can’t do this.’”

Given Juan’s criminal record and history of truancy, Herrera and the other adults in his  life had a difficult time convincing the San Francisco Unified School District to place him in a new high school. Herrera had tried to impress upon him the importance of attending the first day. “I had to stress that to him yesterday,” the case manager said. “ You have to engage in class, you have to show up every day. Or  they will kick you out.”

At the boy’s tenement building in the Tenderloin, no one answered when Herrera rang the apartment from the front gate. His mother remotely buzzed Herrera in. Once inside the building, Herrera first knocked, then pounded on the door to the apartment. Juan never answered. He wasn’t home. 

On the way back to her car, Herrera tapped out an email to Juan’s probation officer, saying the boy had not turned up for his first day of school, and she couldn’t find him. “I don’t like being a snitch,” she said, wincing, “but better to let them know, or else [he’ll] get in more trouble.” 

In her teenage years in the Mission in the mid-2000s, Herrera was a Norteño gang member. When she was 15, she stabbed someone and ended up in juvenile hall, then was transferred to a rehab facility for substance abuse, where she spent 17 months. Just before her scheduled release, she asked if she could prolong the program. 

“Cause I knew I wasn’t ready to go back home,” she said. “I was like, I think I’m gonna go back to doing the same shit.”

The request was denied. After her release from rehab, Herrera lasted six days on the streets before being locked up again, this time for attempted murder. Although she was 17, she was charged and convicted as an adult. She served a few months in county jail, was released, violated her parole, and was sent to state prison, where she spent four years. 

“ I tell young people, if I had a me helping me, I think I would have not gone to prison,” Herrera said. “I think my life would’ve been different.” 

After getting out of prison and being homeless on the streets of San Francisco for a couple of years, Herrera began volunteering with troubled youth. She had a knack for it, often using stories of her own experiences to connect with kids who’d committed crimes.

An hour after her visit to Juan’s apartment building, he called to say he had shown up to school shortly after she left. His story was verified by Juan’s probation officer, who tracked the boy’s location via an ankle monitor. But, to everyone’s shock and frustration, the school wasn’t equipped to take on a student who spoke only Spanish. So they’d sent him home. He’d have to transfer to another school.

After a morning spent trying to track down Juan, Herrera drove to the Bayview home of Amira, a 19-year-old former client who’d been arrested at 17 for theft and whose probation had ended four months before. Since then, Herrera had helped Amira find a job and get back on track to finish high school.

On that day, Herrera intended to take Amira out for a smoothie. But when Herrera texted that she was outside, the teen texted back that she was vomiting. It was morning sickness. 

Herrera gritted her teeth. “I’ve learned not to say ‘Congratulations,’” she said. “Because they might get an abortion.”

A few minutes later, Amira sat in Herrera’s passenger seat, bare feet pressed against the dashboard, looking queasy and in a foul mood. Amira cursed those in her life who’d warned her of the difficulty of being a single mom. 

“ I don’t really give a fuck about being a single mom,” she said. “ Bitches get married, and y’all still be single moms.”

Herrera asked her former client what she planned to do. “I think I’m anti-abortion,” Amira said. “ I’m not going to hell for killing no baby.”

Herrera offered to drive to Walgreens and purchase moisturizing masks and lavender to help Amira with the discomforts of pregnancy. She advised the 19-year-old to write a list of pros and cons to help her decide whether to keep the baby.

Amira ignored that suggestion but admitted that having a baby would be a challenge. “It’s hard enough I already have to deal with myself,” she said.

Amira was raised mostly by her grandmother, who smoked crack, sometimes leaving the girl and her sisters to fend for themselves. She experienced stretches of homelessness, sleeping on relatives’ couches. By her mid-teens, she was stealing from Sephora and reselling items on the street at 24th and Mission to support herself. After being arrested and placed on probation, she was paired with Herrera.

“I asked for a case manager because I needed somebody to talk to about my own life,” Amira said. As she described the impact Herrera had on her, the teen began to sob. “I don’t have a lot of people in my life that are role models. A lot of people in my life, they do drugs. [Herrera] helped me get back into school. She’s helped so many people. She might even stop people from killing theyself. Stuff that she would never even realize.”

Herrera eventually convinced Amira that after all the vomiting, a smoothie might make her feel better. The two drove to a juice shop near Dolores Park, where they each ordered a blue-and-yellow drink called “The Warrior.”  

Later, after dropping Amira at home, Herrera cried for a minute in her car. She was moved by what Amira had said about how Herrera had changed her life. 

She admitted that she worried about Amira’s future, and about whether she would go through with the pregnancy. But she was also relieved at where the 19-year-old had arrived: off probation, off the streets, back in school, and working. 

“ When someone catches a very serious case, I can’t judge. I gotta see people again for who they are,” Herrera said. She turned to etymology to explain further.  “‘Respect’ means ‘re’ — ‘repeat.’ And ‘spect’ means ‘to look at.’ Let’s repeat and see this person again. Over and over and over again.”