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 perspective of teacher career development (Burke, et al., 1987). Examining the careers of these urban physical education teachers allows critical lessons to be drawn from within and across these “mini-cases” of urban teachers across the career span. Participants included 9 secondary urban physical education teachers (4 F; 5M). Data were collected using (a) the Life Roles Rainbow (Super, 1990), (b) career information sentence stems, (c) in-depth interviews, (d) informal interviews, and (e) observations. Data analysis involved constant comparison with open, axial, process, and selective coding (Strauss & Corbin, 1998). Findings indicated that the organizational contexts of these veteran urban physical education teachers played the most salient role in shaping their beliefs and behaviors. While teachers reported similar organizational contextual factors across this group, individual responses to such factors differed greatly. These differences delineated these teachers into two distinct groups, Lifers and Troopers. Lifers and Troopers were compared based on their behaviors and beliefs related to three categories of organizational context: (a) general workplace conditions, (b) students, and (c) administration. First, Lifers described their workplace conditions with a sense of reality and empowerment, thriving on the daily variety of challenges within their workplaces. In contrast, the dynamic nature of urban schools seemed to deflate Troopers, draining their energies over the course of a school year. Second, Lifers described their students as resilient and energetic, appreciating students for these qualities and trying to build safe and effective learning environments for them. For Troopers, students’ energy and enthusiasm were perceived negatively as disruptions to the learning process, leading to an “I can’t do much here” teacher attitude. Finally, regardless of whether administrative support was viewed as positive or negative, Lifers found ways to address the situation to ensure physical education learning environments that facilitated learning for students. Troopers viewed administration as just another reason to be frustrated and felt little power to effect positive changes. Knowledge of workplace conditions’ specific effects on urban teachers’ career trajectories provides valuable information for initial preparation of novice teachers and for further professional development of veterans. Studying the lives and careers of longtime urban physical education teachers will help facilitate the design of professional development programs that meet the unique challenges faced by teachers in urban contexts.