Women are vastly underrepresented in leadership positions in sport organizations both in the United States and internationally (Burton, 2015; Knoppers & Anthonissen, 2008; Whisenant, 2008). The realm of sport is perceived as a gendered space in which the concept of masculinity maintains dominance. This concept may have an influence on the decision making related to the hiring of new staff. When the owner of a men’s professional basketball team decided to hire a new head coach for the upcoming season, he found himself facing many different challenges. He believes that if knowledge, skills, and abilities are the parameters to evaluate a coach, then gender should not be an issue (Chelladurai, 2005). The focus in this case includes (a) organizational fit in hiring, (b) leadership and gender, (c) considerations of diversity, and (d) organizational culture and operations in hiring. This case exemplifies the need to understand that hiring decisions in large organizations are complex and involve a delicate balance of stakeholder interests.