The purpose of this study was to examine the early career experiences of three physical education (PE) teachers who taught in urban charter schools. Using cultural relevance theory, three early career PE teachers were observed and interviewed for approximately six weeks each. Data were analyzed using constant comparison. Two major themes emerged from the data: the mechanisms of school support, and achieving "insider" versus "outsider" status during teachers' early careers. These findings highlight the challenges that early career PE teachers face in urban schools, and demonstrate how being a culturally relevant teacher can improve teaching in physical education.