Transition to adulthood is increasingly complex, extended, and challenging. Working-class Brown and Black young men face very difficult transitions, as they are overrepresented in the justice system, poverty, foster care, special education, and among victims of violence. What effects do these developments have on young people's places in free democratic society and on the contours and possibilities of youth citizenship? Specifically, how do incarcerated young men view the breadth and limits of democratic citizenship? This article analyzes voices of 25 incarcerated youth and those working with them--recorded through interviews, autobiography, and taped youth club meetings. Findings reveal that incarcerated young men experience expanding responsibilities, notably, criminal penalties; contracting rights and protections; and institutions and systems oriented to their expected failure. Voices presented critique the role of the democratic state (via the justice, educational, and other youth-serving systems) in protecting democracy for marginalized youth and other incumbent citizens. (Contains 3 notes.)