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“Did the surgeon’s knife make me a woman or a freak?” These words, emblazoned upon the movie poster for The Christine Jorgensen Story (1970), cut to the heart of cultural anxieties regarding “transgender” as a kind of “monstrosity.” However, transgender scholars have suggested embracing one’s status as a monster confers “dark power” via a reverse discourse (Stryker, 1994; Nordmarken, 2014). Often neglected by these scholars, though, are the ways that madness figures into imaginaries of transgender monstrosity, for instance in Jonathan Demme’s The Silence of the Lambs. Instead, the monsters elected for subversion are redeemed or rehabilitated by their humanistic virtues (i.e. Frankenstein’s monster from Mary Shelley’s Frankenstein, Stryker, 1994), even as the monsters most often conflated with “transgender” in public discourse are rendered inhuman via their presumptive “madness” (i.e. Buffalo Bill from The Silence of the Lambs, Norman Bates from Psycho). This paper interrogated contemporary understandings and applications of “madness” as the vehicle by which transgender “deviance” is untethered from human virtue (reason/logic), thereby becoming inhuman, or “monstrous,” in the first place. Drawing on several works of contemporary science fiction as inspiration (Ada Palmer’s Terra Ignota series, Martha Wells’ The Murderbot Diaries, and Isabel Fall’s I Sexually Identify as an Attack Helicopter), I argue that a more potent subversion would transmute imaginaries of mad, transgender monsters from being inhuman to becoming post-human, that is, explicitly critiquing liberal humanism, rather than electing for identification with humanist monsters unrelated to transgender representations in public discourse.