Female sports journalists work as tokens in gendered organizations where masculinity is integral to hierarchical logic and newswork processes. Through in-depth interviews, this longitudinal study explores how women in the industry manage their gendered and professional identities and make career decisions. Our findings suggest that although participants framed their decisions to stay or to leave in idealized terms, their choices were also guided by cultural and structural impediments acknowledged but accepted as natural and immutable. The women noted negative gender-related experiences, but most minimized them and saw their gender as an advantage. They also described their struggles to balance their work and social lives, the latter of which they saw as a necessary sacrifice to become ideal workers. We discuss these issues and suggest that sports media will fail to reach gender parity until these barriers are addressed; until then, the revolving door will keep turning.