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This paper examines the lives and political careers of two of the most powerful women at the early modern Spanish Court: Catalina of Zúñiga, Countess of Lemos, and Juana of Velasco, Duchess of Gandía. These two noblewomen were distant relatives; their court careers followed a very similar path: both were appointed ladies-in-waiting during Philip II’s reign; both became widows while holding the title of Vicereines of Naples at the end of the sixteenth century; finally, both served as camarera mayor (mistress of the queen’s household) during Philip III’s and Philip IV’s reigns. Despite their parallel careers, they became political adversaries and heads of rival court factions: Catalina of Zúñiga defended the interests of her brother, the Duke of Lerma, while Juana of Velasco supported her sororal nephew-in-law, the Count-Duke of Olivares.