This essay hypothesizes a transgeneric afterlife for Shakespeare's steward Malvolio in Webster's Duchess of Malfi. Socioerotic 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. Attuned to the historical liminality of the steward, the essay argues that Webster used Malvolio's erotically inflected relation to a female aristocrat to sharpen issues of historical transition and service. His tragedy enlarges Malvolio's role and strategically triangulates a strong aristocratic female character in relation to the two stewards. The duchess's 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 socioerotic 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.