To say Stevie Fielding had a rough childhood would be an understatement. And for a brief time, director Steve James (HOOP DREAMS) was there to help as an “Advocate Big Brother.” In 1995, 10 years later, James returns to the rural Illinois town where Stevie and his family live to check in and discovers that life hasn't gotten much easier for them. Stevie has gone from being a troubled kid to a troubled adult, but now a prison sentence is looming. On top of the complexity of Stevie's life, James struggles to balance the roles of filmmaker and friend, when and how to cross lines, and is torn about how to help his "little brother" while finishing production of the film. The result is this potent award-winning personal documentary.