Identity is a topic of growing interest, especially since it is now considered that it is not enough to know the traits and strategies of successful principals but also to analyze their professional identity. The work that is presented carries out a comparative analysis of the identity of two principals in disadvantaged contexts, one considered a successful principal and one less successful. Through the use of the grounded-theory methodology, the study show differences in the professional identity traits of the two principals and provides information to understand the complex world of the professional identity of principals in disadvantaged contexts.