Matthew Omisore was 13 when he first got locked up for dealing drugs. By the time I met him, he was 16 – and serving his third sentence at a juvenile facility called the Rhode Island Training School. He and the other kids called it “The Ritz.” Matthew was a smart and funny kid. The guards liked him. They played chess with him. (Matthew usually won.)

The thing is…everybody at the Ritz knew that whenever Matthew was released, he was probably going to keep selling drugs.

I gave Matthew a tape recorder to document his life at the Ritz. He had already spent half his teenage years there. At the same time I also gave a recorder to Judge Jeremiah S. Jeremiah, a Rhode Island juvenile court judge.  His job was to decide if a kid like Matthew deserved a second chance. Or a third.

Two people from completely different worlds. But by the time I met them – they had come to know each other pretty well.

On this episode of the Radio Diaries Podcast, a story from two sides of the bench.

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Radio Diaries is part of Radiotopia from PRX, a collective of the best story-driven podcasts on the planet. This week’s episode is supported by Life on Record, a company that makes audio keepsakes, and Animoto, an online video builder.