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The Prison-to-School Pipeline

Two out of three students released from incarceration never return to school. Meet five people fighting to change that.

October 10, 2016

Tim Kennedy

Tim Kennedy

In the generation since tough juvenile sentencing laws peaked in the 1990s, educators and advocates have fought to dismantle the school-to-prison pipeline. They’ve developed alternatives to zero-tolerance disciplinary practices.

They’ve lobbied for and won changes to local policy. They’ve rallied the support of the federal Justice Department and even President Obama himself.

Yet dismantling the pipeline is not enough to help the nearly 100,000 youth already in the juvenile justice system’s custody, or the hundreds of thousands more who have served time and been released. Roughly two-thirds of students released from the system never return to school. What chance do they have?

Doing the Work

These five alumni—lawyers, educators, analysts—are working to improve the part of the pipeline that receives less attention: the one leading from incarceration back to the classroom. And from there—with some work—to a brighter future. 

CHRISTINA GRANT is assistant superintendent of Philadelphia's alternative schools and has placed a big bet on the power of career and technical education to improve life prospects for incarcerated youth. Will it pay off?

EMILY FOX is drafting an updated Juvenile Justice Local Action Plan for the San Francisco Department of Children, Youth, and Their Families. 

GEDÁ JONES HERBERT teaches students about the law and how to navigate it, even in a system that often seems set up against them.

RACHEL BRADY is working to ensure incarcerated students with disabilities are receiving the same accommodations they would receive at school if they weren’t in custody. 

RAHEIM SMITH is a special education teacher in Brooklyn serving adolescents awaiting trial and those already sentenced to detention.

GETTING INVOLVED is easier when you know where to start. Find resources and tips for working in the juvenile justice field.

Christina Grant Meron Menghistab

Christina Grant

(N.Y. '03)

On a sweltering day in August, Christina Grant (N.Y. ’03) arrived for a meeting at the Philadelphia Juvenile Justice Services Center (PJJSC), a secure juvenile detention center that also houses a school for detainees. The PJJSC is one of two schools in the city for students in custody, and one of about 25 under Grant’s leadership as the School District of Philadelphia’s assistant superintendent for alternative schools (known as the Opportunity Network).

Entering the center, she knew the routine. She greeted the guards. Sent her bag through an X-ray machine. Walked through a first security door leading into a restricted area. The door shut behind her and she waited for the click. “You know this secure door process messes me up,” she said. She hit the buzzer to be let through the final door.

On the other side, she met with a group of her principals. About an hour later, during a tour of the facility, they entered a spare, brightly lit room. A half-dozen student detainees in identical navy blue jumpsuits sat waiting. Grant didn’t ask, but knew that most of the students were in detention for felony-type offenses like robbery or selling illegal drugs. She had brought them together with the principals to discuss the curriculum revamp of their school that’s been months in the works: a new, state-of-the-art career and technical education program (CTE) designed to give students in the prison pipeline a new pathway out.

Some students seemed intimidated by the meeting set-up, others slightly skeptical as they heard about the career education that awaited them. So what did they think, Grant wanted to know. Would it be a good use of their time?

One of the younger, quieter students offered that he’d like to learn about graphic design again. That was his favorite class at his old high school; it’s what brought him to school—when he went, he said. The oldest student in the room, at age 20, liked the idea of using his time in detention to learn skills that could make him real money down the line. He said financial troubles—shouldering a relative’s cancer bills—were what drove him out of school in the first place.

At one point, Grant ended up talking with a wiry 17-year-old detainee who calmly alluded to his difficult childhood. As a condition of his upcoming release, he told her, he’d be required to attend therapy offered by the state. But he wasn’t optimistic it would help, he said, given the traumas he’d lived through.

Grant wasn’t having it. Her voice rose, though not in anger. Her Long Island accent came out. No one, she told the student, knows how to process pain without help. She said when her father died several years earlier, she couldn’t handle it without therapy. “It was all that kept me from losing my mind.”

He listened. He nodded.

Deana Ramsey (left), principal at the Philadelphia Juvenile Justice Services Center, says the new career and technical education courses at her school are distinguished by their focus on innovative, economically useful skills. Meron Menghistab

Grant’s dad was a mechanic. Their family was solidly middle class, though she was a first-generation college graduate. Before coming to Philadelphia in 2015 through Teach For America’s School Systems Leaders Fellowship, Grant spent years working for and with charter schools, most recently as a superintendent based in New York City with the Great Oaks Foundation. It’s where she learned to write grants and developed the attention to every detail to make sure the money made the most impact.

Grant considers expanding and strengthening the help available to students in the alternative schools she supervises her most important charge. That could mean changing the academic options, like introducing the new CTE classes in the two detention center schools, but it could also mean getting students therapy, tutoring, financial advice, or legal guidance.

The work of getting them back on track is hard, she says, but “it’s not rocket science.” High-quality resources and better support equal improved outcomes for system-involved students.

This year, Grant’s second as assistant superintendent, her theory of change is being put to its first major test. In April, Philadelphia was one of four districts in the country awarded a Juvenile Justice Reentry Education Program grant from the U.S. Department of Education, created to support top-drawer technical education, plus wraparound and re-entry services, in juvenile justice facilities.

In short, Grant and her team got their two detention schools almost $1 million over three years to get kids out of detention and help keep them out. The money will fund five new CTE courses at both the Juvenile Justice Services Center School and Pennypack House School (for students charged as adults). The goal is to help 825 students in the first three years escape the prison pipeline and start over as young adults with an edge up on a stable career.

Wood shop, this isn’t. The two offerings that are launching this year—Introduction to Telecommunications and Technology and Network Cabling-Copper Based Systems—teach skills such as laying fiber-optic cable that, with a 40-hour credential and some practice, could translate to a $50,000-a-year job at a telecommunications company like Verizon, Grant says. For the Opportunity Network’s students, half of whom identify as homeless at least part of the year, that kind of career ladder is life changing.

The CTE money is creating opportunities that couldn’t have existed otherwise—something Grant has understood since early on in her role, when she realized the district’s budget wouldn’t be enough to cover all the wraparound services and supports her students needed. She says her first thought was, “All right, we’ve got to write some grants,” and got to work.

“This is not CTE for CTE’s sake—putting children somewhere breaking rocks,” says William R. Hite Jr., Philadelphia’s superintendent, who has championed Grant’s work from the beginning and says he is astounded by the speed and extent of her progress. For technical education to be relevant, he says, it must create “skills and abilities that children can then transfer to real opportunities, whether those are in college or in the work world.”

Both Hite and Grant are keenly aware that for decades, disadvantaged students, especially students of color, were often tracked into vocational classes instead of completing college-prep curricula. Because of that history, skepticism of CTE runs deep among educators who fear second-class standards for students in poverty or in alternative schools that are stigmatized as holding grounds. For many, to-and-through college remains the only acceptable goal.

Grant and the Opportunity Network’s leaders anticipated that concern when they wrote their grant application. As a result, their CTE students will leave detention with personalized transition plans that include a path to post-secondary education. Students who complete their diplomas while in detention will be able to proceed directly to coursework at the Community College of Philadelphia, thanks to a new partnership. Students who are still working toward their diplomas will be allowed to enroll in any Philadelphia school offering CTE programming; they won’t be restricted to their home schools. Either way, there will be avenues for them to continue developing the skills they’ve learned while in detention.

“It’s almost like we’re giving students a prescription,” says Wanda Y. Jenkins, who’s acting as project manager for the awarded grant. “Say you’re in the hospital and you get discharged: You’re given instructions on how to take care of yourself. We’re doing that here.”

And once students leave detention, they won’t be on their own: The grant calls for case management support for each student, in addition to the contributions of probation officers, social workers, and transition liaisons.

“My urgency doesn’t come from, ‘All kids can learn and we must make sure they go to college’—which is great and true. My urgency comes from, ‘If we don’t get it right for these children they will end up in prison.’ It’s concrete.”

Christina Grant

Philadelphia Assistant Superintendent

Grant knows this pathway from prison to school via tech training is unproven. (The CTE grant came loaded with conditions and benchmarks the schools must meet, so by spring, there will be preliminary data on the program’s impact.)

Grant worries about whether she’s allocated enough resources to fully support the programming—she’s already rearranged her alternative education budget once to fund more central office support—or if she’s overestimated student interest and persistence in the new job-oriented courses.

But she worries more about not trying. According to a 2009 report by the Sentencing Project, at least two-thirds of school-aged youth released from custody don’t end up back in school.

That’s one of the reasons she keeps returning to the Juvenile Justice Services Center and why she keeps engaging the residents with such candor—debating the importance of therapy, for example.

During the meeting at the detention center, Grant asked the older student—the one who left school to help pay a family member’s medical bills—how long he had been in the system, and where. He described a circuitous path in and out of schools, neighborhoods, jails, and detention centers. Grant hung on his every word.

He’s nearing completion of his diploma and should be able to polish off his last few credits while in custody, he said. But he’s been warned that processing and transferring credits from so many different places will be a paperwork nightmare.

Grant tells the Juvenile Justice Services Center’s principal to ensure the student has her contact information before he’s released. She promises she’ll do everything she can to help.

“It changes you, as a person, to see children in prison,” Grant says. She values the resourcefulness she learned in her previous jobs with charter networks, but her perspective has shifted this past year as she’s set out to prove that the prison pipeline can be broken.

“My urgency doesn’t come from, ‘All kids can learn and we must make sure they go to college’—which is great and true. My urgency comes from, ‘If we don’t get it right for these children they will end up in prison.’ It’s concrete.”

Emily Fox Talia Herman

Emily Fox 

(New Jersey ’08)

“If one more person tells me to build a rec center, I’m going to punch myself in the face,” says Emily Fox, laughing but not completely joking. Fox has spent much of this year buried in spreadsheets and interview notes in her office at the San Francisco Department of Children, Youth, and Their Families, where she’s drafting an updated Juvenile Justice Local Action Plan for the city. If it’s approved, it will provide strategies for cooperation between more than 40 nonprofits and public agencies that interact daily with system-involved youth. For kids facing arrest, it could mean that instead of long stays in detention, they’d be placed in alternative to detention programs and set up with counseling and mentors.

It’s not that rec centers are bad; it’s just that they’re an adult’s default idea for what teenagers would want to do, says Fox, who spent several years doing reform work with the New Jersey Juvenile Justice Commission before moving home to the Bay Area in 2015. So in addition to countless consultations with representatives from places like the District Attorney’s Office and the San Francisco Unified School District, she’s held focus groups with students in Juvenile Hall. Kids want mentors, stability when they transition out of custody, and programs to keep them out of the system in the first place, she says.

In April, the plan is scheduled to be finalized by the city’s Juvenile Justice Coordinating Council. And resources have never been more abundant, Fox says. San Francisco has fewer school-aged children today than it did in 1990 but a lot more wealth—money that could be used to staff more counselors at school wellness centers or to help ensure quality housing for low-income families. “At this very second, we have the leadership and the wherewithal and the money, seriously, to do this,” she says. “If in this moment, in San Francisco of all places, we can’t do it? I’m afraid of what that means.”

Gedá Jones Herbert Kristin Little

GeDá Jones Herbert

(Greater Nashville ’09)

One way to help students stay out of detention is to teach them about the law and how to navigate it, even in a system that often seems set up against them.

GeDá Jones Herbert, a graduate of the University of Michigan Law School, is site manager of the Law Program at the Bay Area nonprofit Fresh Lifelines for Youth (FLY), a 12-week legal education course for at-risk and system-involved adolescents. She recruits, trains, and supports volunteers, including Teach For America alumni, who lead Law Program classes at schools and community sites across Santa Clara County. She also teaches two classes per week. (Her favorite lesson is a mock trial, where students are able to imagine themselves as lawyers, judges, and jurors—as opposed to defendants.)

FLY’s Law Program is not a “scared straight” approach, says Jones Herbert, whose first legal education came from her mother, a criminal defense attorney. The program equips students with coping skills and de-escalation strategies, delivered by positive adult role models in a safe and supportive environment. It develops their empathy for the justice system’s many actors. Students don’t just gain an understanding of how, for example, gun and gang laws dramatically affect sentencing in California; they consider, through role plays and discussions, why different people might support or condemn those laws. After participating in the program, more than 80 percent of students report they are less likely to break the law and have more confidence to deal with negative peer pressure.

“We see ourselves as guides,” Jones Herbert says. “We’re here to provide knowledge, to educate our youth on what the laws are, what their rights are, what choices they have in a situation.”

Rachel Brady Sally Ryan

Rachel Brady

(Chi–NWI ’07)

Incarcerated students with disabilities are legally entitled to the same accommodations they would receive at school if they weren’t in custody. But Rachel Brady knows that “legally entitled” doesn’t always mean “actually happening.”

Brady is an attorney at Equip for Equality, which advocates for disability rights in Illinois. And she’s a perpetual thorn in the side of the Illinois Department of Juvenile Justice (IDJJ). Through the public defender’s office, the Juvenile Probation Department, and other sources, she learns about students who are in custody (or transitioning out) and also have individualized education programs (IEPs). Brady knows how often those IEPs are overlooked or never received by detention centers, so she represents these students to ensure their IEPs are up to date and implemented. When they aren’t, she sues the IDJJ School District to comply. When it’s too late for services to be provided while students are in detention, she sues the district to provide compensatory services: six months of tutoring, say, paid for by the IDJJ district.

Brady stresses that the IDJJ is in the middle of profound, positive structural reform, thanks to a 2012 settlement with the ACLU that mandated change. But structural reform moves too slowly for her clients, many of whom have moved from school to school and could benefit hugely from a consistent, high-quality educational program while they’re in detention. “I struggle, because these kids have so many factors working against them that a good IEP isn’t going to fix everything,” Brady says. “But part of my hope is that I’m at least inching the department toward change.”

Recently, one of Brady’s clients cut off his electronic monitoring bracelet and fled, the day after Brady got him set up with a new IEP. “When he’s back, I’m going to represent him,” she says. “And they’re going to implement his IEP.”

Raheim Smith Tamara Porras

Raheim Smith

(N.Y. ’13)

Raheim Smith is a special education teacher at Passages Academy – Belmont, a Brooklyn school serving adolescents awaiting trial and those already sentenced to detention. He has a pretty straightforward message: Developmentally, kids need unconditional love and support. “They need someone to let them know that they care about them,” he says. “Not care about them because you want to see them succeed, but care about them because you care about them.”

Our juvenile justice system, and much of traditional education, offers the opposite, he says. Study and you’ll get good grades. Behave and you’ll get parole. Instead of unconditional support, kids face conditions at every turn. “We quit on them too quickly,” Smith says, which “floods the system” with kids who need significant but, on the whole, moderate interventions and makes it harder for exceptionally troubled students to get the support they need.

Change a few variables in his own life and he could have ended up like his students, he says. Smith spent much of his Long Island adolescence homeless or on the brink of it. He enlisted in the army almost immediately after graduation. Eighteen years later, he brings a mixture of military stoicism and outsized compassion to his classroom, where he’s taught just about every subject but art at least once since 2013. Of course students need consistent, high-quality instruction, he says. But they also need someone to love them when they fail and fail again. “If that’s what we’re providing in the system—consistency and care, real care—these students will start to turn around.”

Youth in Custody: The Numbers

24% were not enrolled in school when they entered custody

26% repeated a grade in the year prior to entering custody

30% of youth in custody have been diagnosed with a learning disability

48% are below grade level

53% skipped class in the past year

57% were suspended in the past year

Most “longer-term” students—students who were enrolled in a school in detention for 90 days or more—make little academic progress while in custody.

47% earned at least one high school course credit at a juvenile justice school

25% enrolled in a local school district upon release

9% (of longer-term students between ages 16 and 21) earned a GED or high school diploma

2% enrolled in postsecondary education upon release

Ultimately, 66 percent of youth released from custody do not return to school, according to the Federal Interagency Reentry Council.


Getting Involved

  • Some state juvenile justice departments, including Illinois and Texas, offer volunteering opportunities for community members who wish to get involved. Search online for your state’s juvenile justice department to learn more.
  • Even in states without centralized volunteering services, individual detention centers often work with their own networks of volunteers. The best way to find out if your local facility has any need for volunteers is to call and ask.
  • The Center for Juvenile Justice Reform at Georgetown University offers a variety of certificate programs for organization and system leaders interested in studying “policies, programs and practices that improve outcomes for youth at risk.”
  • To learn more about the Bay Area’s Fresh Lifelines for Youth program, or to become a volunteer, visit its website:

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