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In 1857, New York’s premier literary magazine, the Knickerbocker, published an anonymously-written short story, “The Man Who Thought Himself a Woman.” It was surprising that the author depicted what we would call today a transgender identity in a way that implicitly accepted the protagonist’s self-assessment. Though we know that men and women exhibited cross-gender dress and behavior, we have very little documentation – fictional or otherwise – about the attitude of others toward such people or about their own self-understanding. Could this fictional account shed some light on the mid-century view of those who wished to live as the other gender? Despite the singularity of the tale, its presence illuminates a complex and unexpected understanding of transgender identity (at the risk of using an anachronistic label) in mid-nineteenth-century America. I argue that the description and plight of Japhet Colbones, the main character, highlights themes of deceit and secrecy characteristic of earlier portrayals of atypical gender presentation, foretells the labeling of deviant pathology that was just around the corner at the turn of the century, and even portends today’s emphasis on self-determination at any cost. My essay offers a close reading of the story, accompanied here with its reprinting.