Throughout the book, Wilson portrays how structural systems of oppression inhibit personal development and community health. Wilson says that Maryland Governor Parris Glendening’s 1995 ban on parole for life prisoners both fueled and reflected the “super-predator panic of the 1990s,” which began “stacking young black bodies in prison cells” (123). Keith Showstack, Wilson’s lawyer, commends Wilson for his “incredible” record of self-improvement inside prison but also advises patience until the “political climate” is more favorable for his release (163). Meanwhile, Wilson takes a class in modern American history and learns methods by which “black poverty was planned” (171). He feels queasy inside courtrooms, which he describes as “the places America created to finish us off” (218). Even returning citizens, former inmates who have served their time and earned their freedom, stand little chance of success, for the justice system “is a vacuum, designed to suck money out of the pockets of the people struggling the most” (276).

Wilson develops an early distrust of the police, starting with his mother’s boyfriend. When police are called to Mom’s house during one violent incident, Wilson learns that “cops took the aggressive approach with a black man unless he was one of their own,” and things “always ended the same way: no report, no arrest, just a night away to sober up” (25).