When someone using the legal name Mary East signed their will before John Salter, public notary of Poplar, England in 1779, they were declared a “spinster” – the legal designation for an unmarried woman. But none of these categories – spinster, woman, or unmarried – completely or even accurately described the person to whom they were assigned. The will revealed several things about the life and values of its author: a desire to reward dedicated employees and their families, concern for the poor of the community, respect for the local church and its minister, and a lack of relationship with relatives. But nothing in the will points to the life that inspired news coverage by dozens of publications throughout England and the North American colonies from 1766 to 1902. That life belonged to James Howe, who transformed themself into a man and husband at the age of sixteen in 1732. Howe lived as a man for over thirty years undetected, achieving wealth and the esteem of the local community of Poplar, England, as the owner of the popular White Horse Tavern in London’s East End (Figure 2.1).