People who were assigned the female sex at birth and lived as men throughout the 19th century often feared and avoided doctors. Doctors might ruin their lives by reporting them to the authorities for living in a gender that was different from their sex. Even after death, coroners who reported the sex of their subjects threw the lives of surviving family members and friends into a frenzy of chaos and speculation. James Allen and Abigail Naylor married in 1807, living together until Allen’s death in a workplace accident at a London shipyard in 1829. What can we learn from this dynamic past about current struggles for transgender rights and the future of gender?