The purpose of this chapter is to explore subordinated masculinities, namely those of gay men participating in a softball team in Toronto, Canada, and to relate the research results to wider theoretical issues and debates. The chapter begins by presenting an overview of past research on gay men and sport, first focusing on key issues centred around the construction of masculinity. It then explores literature related to the role and politics of gay men participating in sport. The softball site under examination and how ethnographic research was carried out are described. Finally, the findings will be debated as to how they contribute to an understanding of the queer sociology of sport before offering ways forward to comprehend gay men participating in sport.