Trustee Perspective: Reentry Court: What I Learned About Second Chances From the Other Side of the Aisle

Philadelphia Bar Foundation - Trustee Perspective  

Written by Jacqueline Romero, Partner BakerHostetler

Reentry Court: What I Learned About Second Chances From the Other Side of the Aisle

When I became a federal prosecutor, I understood my role clearly: enforce the law, protect the public, and hold people accountable. What I did not fully appreciate—at least not until later—was how much accountability can also look like support, structure, and belief in someone’s ability to change.

I learned that lesson in Reentry Court.

During my time assigned to the Eastern District of Pennsylvania’s Supervision to Aid Reentry Program (“STAR”), I watched men and women who had served federal prison sentences stand before the same judicial system that once imprisoned them—this time not to be sentenced, but to be supported. These were individuals with felony convictions, long rap sheets, and real histories of harm. They were not blank slates. But they were also not who they had been at their worst moments.

Reentry Court exists for a simple but powerful reason: people coming home from prison face overwhelming odds. Housing. Employment. Addiction recovery. Mental health. Family repair. The stigma of a criminal record. The risk of reoffending is highest during the first months after release, precisely when support is most needed and often least available.

What I saw firsthand was a court stepping into that gap.

Reentry Court is demanding. Participants are not given a free pass. They are subject to frequent court appearances, strict supervision, drug testing, employment requirements, counseling, and treatment. Progress is tracked. Setbacks are addressed openly in court. And accountability is constant.

But so is encouragement.

I watched judges speak to participants with honesty and respect—praising progress, expressing disappointment when warranted, and never losing sight of the fact that the person standing at counsel table was more than the crime that brought them there. I watched probation officers go far beyond monitoring compliance, acting instead as problemsolvers and advocates. I watched volunteer mentors—many of whom had no obligation to be there—spend evenings and weekends helping participants navigate job interviews, study for the GED test, apply for college courses, rebuild routines, and stay grounded when old habits threatened to reemerge.

And I watched participants do the hardest work of all: changing their lives.

They found jobs—often entrylevel, sometimes humbling, always earned. They addressed addiction and trauma they had carried for years. They repaired relationships with children and partners who had every reason to doubt them. They learned to live with structure instead of chaos, patience instead of impulse, responsibility instead of blame.

Not everyone succeeded. Reentry is hard, and relapse—of one kind or another—is real. But even in moments of failure, the program responded not with indifference, but with course correction. Sanctions existed, but so did second chances within the second chance. As one judge assigned to the STAR program would frequently say, “Once you are in the reentry family, you are always in the reentry family.”

As a prosecutor, I had spent years arguing for sentences measured in months and years. In Reentry Court, I began to see time differently. Progress came in weeks of sobriety. In early mornings clocked at work. In moments spent with estranged children. In simply showing up—again and again—when it would have been easier to disappear or quit.

Critically, Reentry Court also made communities safer. When people leaving prison are supported, supervised, and invested in, recidivism drops. Families stabilize. Employers gain reliable workers. Communities acquire parents and role models. Cycles of incarceration are interrupted. This is not leniency; it is smart, evidencebased justice.

Reentry Awareness Month is a reminder that punishment alone does not end crime. What happens after incarceration matters just as much—if not more—than what happens during it. Courts like the Eastern District of Pennsylvania’s STAR Program recognize a truth that those of us in the system sometimes learn only by seeing it up close: people are capable of change when given structure, accountability, and meaningful support.

I entered Reentry Court as a prosecutor. I left with a deeper understanding of justice.

Justice is holding people responsible—and then giving them the tools to live responsibly. Justice is recognizing risk while fostering hope. Justice is a courtroom where success is measured not by sentence length, but by someone steadily piecing their life back together through hard work, discipline, and the support of a community that decided not to give up on them.

For the people I watched walk that path, Reentry Court was not a break. It was an opportunity—and one they had to earn every single day.

And for those of us privileged enough to witness it, it was a powerful reminder that accountability and compassion are not opposites. Sometimes, they are strongest together.

I invite you to join me on April 28 for a Justice Matters Forum program exploring the legal and systemic challenges of prisoner reentry and the lawyer’s role in advancing equitable outcomes, as part of the Philadelphia Bar Foundation’s public education series.