The retention of talented teachers continues to be a problem for many urban schools. This study is an effort to provide insight into the influence of life histories on the ability and decision of teachers to persist in the urban classroom. Through a series of interviews, the life histories of four veteran urban elementary teachers are recorded. Exploring early educational experiences, professional, personal, and familial relationships, and personal and educational beliefs as well as how they interpreted their own actions and decisions regarding being an “urban teacher” provided a rich understanding of their professional choices. This research provides accounts of the teachers’ unique life stories and explores how their histories helped shape their beliefs and understandings concerning education.