Through the lens of women's tennis legend Serena Williams, this article examines the roles of masculinization and feminization as they relate to Black womanhood in sport. Over the course of much of her career, Williams was characterized as “aggressive,” someone who “bludgeoned her way” to success. But after the 2016 and 2017 announcements of her engagement and pregnancy, respectively, media characterizations shifted toward narratives traditionally aligned with femininity. Throughout, media discussion of Williams has been rooted in surveillance of her body, behavior, and closest relationships. Using feminist critical discourse analysis, this article argues that the noted shift in characterization was linked to Williams's strategic performance of docility and engagement with respectability politics, tied closely to her 2015 return to the Indian Wells Masters tennis tournament as well as her adoption of the traditionally feminized roles of wife and mother.