Purpose: The socialization literature has identified the importance of school administrator support in physical education teachers’ work experiences. The purpose of this study was to understand how principals’ own socialization influences their perspectives on and support for physical education. Methods: Data were collected through semistructured interviews with 29 school principals (14 males and 15 females) and 15 physical educators (11 males and four females) matched at the schools from which principals were recruited. Results: Qualitative data analysis resulted in four intersecting themes: (a) Administrators’ prior socialization and subjective theories frame support for physical education; (b) supportive principals are visible, engage with their teachers, and hold them accountable; (c) stress is exacerbated when principals and physical educators’ values and beliefs differ; and (d) school and policy constraints influence administrators’ vision and support for physical education. Discussion and Conclusion: Educational leadership programs should consider preparing principals to support the work of physical education teachers.