Background/Context: Researchers have examined the challenges of staffing urban, under served classrooms primarily through large-scale data sets; policymakers have responded with strategies intended to recruit more or "better" teachers into the classroom through programs such as the popular Teach for America. Yet there is little qualitative evidence regarding the experiences of such teachers, which could enhance existing understandings of such challenges and current attempts to solve them. Purpose: This research examines the professional choices and trajectories of Teach for America participants over a twenty-year period, attending especially to individuals' perceptions of their urban teaching experiences, their beliefs, and their reasons for staying in or leaving the urban classroom, with the aim of better understanding the experiences of such teachers and the implications for staffing urban schools. Participants/Subjects: Research subjects included thirty participants from the inaugural cohort of Teach for America (1990-1992); this article focuses on the life stories of three such individuals. Research Design: This study draws on oral histories conducted with thirty individuals who participated in the first cohort (1990-1992) of Teach for America. It analyzes their stories within the context of scholarly literature on teachers and teacher policy, urban teaching, and the historical period of the late 1980s and early 1990s. Conclusions/Recommendations: This study suggests the nature of the contributions that nuanced, qualitative methodologies such as oral history can make. We found that, despite their initial differences from tradition-entry teachers, TFA participants' reasons for staying in or leaving the urban classroom looked very similar to those of observed among the population of urban teachers at large. Our data thus raises a question of focus: is attending to the conditions under which all urban teachers work perhaps just as important as attracting new or purportedly better candidates into urban teaching?