Background/Context: Although the study of elite schools has been quite popular in recent years, elite all-boys schools in the United States have largely remained outside the gaze of researchers. Purpose: Two stories are presented to identify possibilities for advancing gender justice in those schools. Methods: Drawing on interview data of participants at two schools, the stories presented reflect common practices and relations found in a larger study on the lessons that 127 recent alumni of elite all-boys schools across the United States learned through their experiences at these institutions. Findings/Results: The stories reveal the disturbing ways in which hegemonic masculinities are reproduced through practices of homophobia, heterosexism, and misogyny within elite all-boys schools that highlight the challenges of engaging in gender justice work. Conclusions/Recommendations: Three areas of practice for elite all-boys schools are proposed that are imperative in working toward gender justice: (1) school climate and environment; (2) leadership for and commitment to gender justice; and (3) teaching and learning.