The purpose of this article is to examine the sport–celebrity relationship of singer–actress Jessica Simpson and Dallas Cowboys quarterback Tony Romo. This qualitative analysis of 100 magazine and 100 newspaper articles that coincided with the first publicized notion of the “Jessica [Simpson] Jinx” reveals the prevailing dominant ideologies of patriarchal structures, traditional gender roles, hegemonic masculinity, and deviance. This study uncovers typologies that mirror the archetypal sporting partnership, for example, Simpson’s feminine position as a “supporter” and her function as an “antagonist” (e.g., the femme fatale, Yoko Ono) and Romo’s position as a hegemonic male (the new-laddist, maverick sporting star) and victim. Through developing these themes, the researchers illustrate the concepts of villainization and victimization in the mass media, where Simpson was portrayed unfavorably. Romo, conversely, was portrayed favorably in the press, suggesting the need to maintain the patriarchal order while restraining female dominance.