This article addresses teacher retention in a successful, new, small urban school. As a longitudinal study, it focuses on the intersections between individual teachers' expectations about teaching, contextual factors, and experiences at the school site and teachers' future career plans. The experiences and perspectives of three representative case study teachers indicated that even in a successful urban school, the match between contextual demands and teacher expectations and experiences led to different career decisions. (Contains 1 table and 2 footnotes.)