This essay hypothesizes a transgeneric afterlife for Shakespeare’s steward Malvolio in Webster’s Duchess of Malfi. If Webster found material for his tragedy in the scapegoated household manager of Twelfth Night, Malvolio is transformed into two figures. Social-erotic fantasies foregrounded, Malvolio reappears as Antonio, the estate steward wooed by his aristocratic mistress. Sinister potential developed, he becomes Bosola, the brooding intelligencer delegated to manage Ferdinand’s malevolent desires. My hypothesis suggests that Webster was attuned to the social-historical liminality of the steward, that he used Malvolio’s erotically inflected relation to a female aristocrat to sharpen issues of historical transition and service. Webster’s tragedy enlarges the role of Malvolio and then strategically positions a strong aristocratic female character in relation to the two steward figures. The Duchess is doubly triangulated in the play, situated in a dramatic intersection between her two brothers and the two steward figures. Her clandestine marriage to Antonio challenges the feudal power that her brothers would preserve, and her insistence on unvarnished economic language in courting Antonio undermines aristocratic discourse and marks her commitment to an alternative social-erotic world, unbound by status or contract. Reading The Duchess of Malfi in light of Shakespeare’s Twelfth Night adds to the current reexamination of early modern service. In addition, the careful staging of the Duchess’s failure to achieve her desire because of the imposition of her brothers’ cruel desires, as managed by Bosola, provokes us to weigh radical potential against tragic inevitability.