Explanation: The Roman Emperor Elagabalus had a gender identity whose exact composition is hotly debated by modern historians. Notably, they preferred being referred to as a woman, and offered up to half of the Empire for a surgeon who could successfully transmute their genitalia from male to female.

While they were not a good Emperor, one imagines struggling with gender identity issues while a teenager tossed into ultimate autocratic control of the most powerful Empire in the world was an aggravating factor. Perhaps HRT could have softened some of those stressor-induced bad choices…