In 1995, Director Steve James (Hoop Dream) returned to rural Southern Illinois to reconnect with Stevie Fielding, a troubled young boy he had been an Advocate Big Brother to ten years earlier. He began a film to discover the forces that had shaped Stevie's entire life. Part way through the filming, Stevie is arrested and charged with a serious crime that tears his family apart. What was to be a modest profile turns into an intimate four and a half year chronicle of Stevie, his broken family, the criminal justice system and the filmmaker himself, as they all struggle with what Stevie has done and who he has become.