The purpose of this study was to understand factors that influenced the career trajectories of veteran urban secondary physical education teachers. The careers of these teachers were studied from the theoretical perspectives of teacher efficacy and teacher career development. Participants included 9 secondary urban physical education teachers (4 females and 5 males). Data were collected using 7 qualitative methods. Data analysis involved constant comparison through the processes of open and axial coding followed by a cross-case comparison (Strauss & Corbin, 1998). Findings indicated that organizational contexts of these veteran urban physical education teachers played the most salient role in shaping their beliefs and behaviors. Although the organizational contextual factors reported were similar across this group of teachers, individual responses differed greatly. These differences delineated teachers into two groups of stayers: lifers and troupers. Knowledge of workplace conditions' specific effects on teachers' career trajectories provides valuable information for initial preparation of novice teachers and for further professional development.