Educators’ persistent disciplining of a small group of students positions them as “frequent flyers.” This identity prevents educators from developing an understanding that could enable them to reengage these students. Using the methodology of interpretive biography positioned within narrative inquiry and using a Gestalt-based analysis, this study presents the case narratives of three persistently disciplined students from one urban middle school in the southeast USA. Examining the central tensions of each case led to a richer and more comprehensive narrative of each student, reflecting his or her complex motivations and desires. Viewing students as the whole people reflected in these narratives rather than through the deficit-oriented lens that labels students as frequent flyers can shift educators’ practices to better support the learning of all students.