Despite the growing body of feminist research investigating the relationship between sports initiatives and gender development goals, the literature to date has almost exclusively focused on female participation within sport for development programs. The purpose of this paper is to examine men’s behavior and provide novel insights into the perspectives and roles of men in sport for development work. This paper draws upon 11 months of ethnographic research undertaken between 2017 and 2018 in two organizations in São Paulo, Brazil, which use football as a tool to empower women. The findings reveal the diversity of roles men play in gender equality efforts and indicate issues men face, specifically the impact of ideas of manhood that hinder their ability to support broader social justice. The author ends the paper by outlining the necessity to explore masculinity and manhood in more depth to broaden the current understandings of the limitations and potential of sport for development initiatives to change the traditional model of male dominance and, consequently, have a more profound effect on gender equality.