Though Gresham Sykes identified several aspects of prisoner life in his classic text The Society of Captives, he failed to consider the role of race. In this chapter, we offer a critique of this oversight by exploring race from the time Sykes was writing to the present day. We show that race has been and continues to be an organizing principle within American society, including prison society and the free world to which exprisoners return. The consequences of discrimination and inequitable treatment have manifested in an intergenerational cycle of captivity, whereby Black, Latino, and Native Americans have been disproportionately subjected to punishment in the United States. Echoing Sykes's own call for reform, we argue that, to move towards an America that has equal treatment under the law and within society, regardless of race, thus breaking this cycle, criminological research must investigate how various individual, social, structural, environmental, and other contextual factors intersect within social phenomena. More importantly, criminological research must encourage social action to improve outcomes.