As our nation struggles with issues of equality and justice, it’s relevant to examine the legacy of race and ethnicity in Hawaiʻi. Katherine Irwin and Karen Umemoto shed light on challenges teens living in Hawaiʻi’s inner cities and rural areas face in our justice system. What sort of obstacles do they encounter with law enforcement, the courts, and correctional services? Where is our justice system succeeding? Based on nine years of ethnographic research, the authors highlight how legacies of injustice endure, prompting teens to fight for dignity and the chance to thrive in America, a nation that the youth describe as inherently “jacked up”—rigged—and “unjust.” While the story begins with the youth battling multiple contingencies, it ends on a hopeful note with many of the teens overcoming numerous hardships, often with the guidance of steadfast, caring adults.