Roger Ross Williams, the first black director to win an Academy Award, embarks on a deeply personal journey into the heart of the American prison system to try and understand how come so many of his childhood friends have ended up behind bars. He starts in his own hometown but soon finds himself navigating a maze of powerful institutions: police precincts, courtrooms, local jails, maximum security prisons and corporate empires. As he explores a massive and dysfunctional system, he encounters complicit politicians and prison profiteers, each with their own self-serving motivations to maintain the status quo, as well as prison administrators who recognise that most of their inmates should be free, yet are helpless to release them. His pursuit of an answer propels the film to examine the American society - from the free market ideals that America is founded upon to the savage ways in which the country has manifested those ideals.