In order to better understand the socialization and (re)production of privilege, most especially gendered privilege, within elite independent schools it is important to examine the masculine performances of its students enacted through bullying as well as the masculine environments in which these enactments are produced. This paper will begin explicating the messages received and the representations shaped by Rockport’s hegemonic masculine curriculum and the embodiment of these dynamics through research on bullying conducted with students and faculty at an elite, single-sex independent boys school, Rockport. The data revealed that bullying between boys at Rockport helped to discipline and reproduce hegemonic masculine boundaries; it was as much an expression of Rockport’s culture as it was a vehicle for policing and reproducing its culture. However, not only were the boys within Rockport gendered, the faculty and even the institution itself was gendered. In this way, it was systemic, both students and faculty acted within this institutional culture and held and managed expectations about their gender.