Chapter 2: Good People. Broken Systems.

What happens when everyone in a system is trying to do the right thing—and the system still produces the wrong result? Shortly after I became a juvenile court judge in 1999, a thirteen-year-old boy was brought into my courtroom from detention. His wrists were handcuffed. His ankles were chained. As I began explaining his constitutional rights, he raised his cuffed hands, began to cry, and called out: “I want to go home with Mommy.” I had to recess the hearing. Not because he lost his composure. Because I lost mine. What I learned afterward changed the course of my career. This child was a special education student whose individualized education plan specifically warned school personnel not to startle him because he might react reflexively. A substitute teacher, unaware of the warning, approached him from behind. He reacted. The incident became an arrest. The arrest became detention. And detention put a frightened thirteen-year-old child in chains before a judge. No one involved wanted that outcome. The teacher wasn’t a bad person. Neither was the police officer. The detention staff weren’t bad people. And yet the system had failed this child. Then the numbers revealed something even more troubling: children being swept into this system were not randomly distributed. Black children—especially Black boys—were being suspended, expelled, referred to police, and arrested at rates far exceeding their white classmates. That forced me to ask the question that would shape the rest of my career: Are we judging the character of the people—or the character of the system? In this episode of Conversations on Justice, I explore why good intentions are not evidence of good outcomes, how zero-tolerance policies transformed ordinary adolescent misconduct into criminal justice events, and why searching for individual villains can prevent us from seeing something far more consequential: a broken system capable of turning the good intentions of decent people into outcomes none of them ever wanted. I also share how that realization led us to stop asking simply what should happen to a child after entering my courtroom and start asking a much more important question: Why does this child need to be in my courtroom at all? That question eventually helped give birth to the School Justice Partnership. We returned routine discipline to educators, reserved law enforcement for genuine threats to public safety, created alternatives to arrest, and measured what happened. School arrests dropped dramatically. Court referrals fell. Graduation rates increased. And many of the children who benefited were Black children who had been disproportionately pulled into the old system. We didn’t replace the teachers. We didn’t replace the police officers. We didn’t replace the judges. We didn’t replace the children. We changed the system. And when we changed the system, the outcomes changed. That experience taught me a lesson I have carried throughout my career: Good people working inside broken systems can make broken decisions. Not because they’re bad people. Because that’s what broken systems do. This episode is ultimately not an indictment of the people who work within our institutions. It is a challenge to all of us who care about justice: When good people consistently produce outcomes nobody claims to want, perhaps we should stop asking “Who’s the bad person?” And start asking: “What’s broken?” Because compassion matters. Good intentions matter. But justice requires something more. Justice requires the courage to redesign the systems that defeat those good intentions. Get full access to Justice ReDesigned at steventeske.substack.com/subscribe