Drawing on a critical discursive analysis of qualitative data gathered at a juvenile detention facility, this study explores how organizational actors live out paradoxes through enacting power relations. Based on our analysis, we elaborate a theoretical framework that conceptualizes (1) individual, role-based responses to paradox through which actors construct positions of control and resistance; (2) collective responses to paradox through which organizational members enact these power positions; and (3) the macro-level effects of such dynamics. Our findings demonstrate how micro-level power struggles keep paradoxical tensions in play. Furthermore, our study shows how, ironically, such struggles participate in the macro-level reproduction of the status quo.