Stevenson returns to the theme of mass incarceration—i.e. locking Americans in prison at historically unheard-of rates—throughout the memoir. He details the dramatic rise in the number of people imprisoned since he began his legal career in the early 1980s. He also explores how many people are imprisoned for nonviolent offenses, as well as children serving adult life sentences. Impoverished people and people of color are over-represented in prisons, and this imprisonment is profitable to the companies that build, own, and maintain prisons. Stevenson traces a historical line from this practice back to chattel slavery in the U.S. In part due to the Equal Justice Initiative's social justice work, by 2014, mass incarceration rates had stabilized.

Stevenson comments that by the late 1980s and early 1990s, fear and anger were sweeping the country and fueling mass incarceration. Criminologists stoked fears of black and brown children becoming “superpredators.” By 2000, the juvenile population increased while juvenile crime rates decreased, thereby proving the superpredator theory incorrect. But jurisdictions had already created laws to allow children to be tried as adults