Chevalier d’Éon

Chevalier d’Éon, was a French diplomat, spy, freemason, and soldier who fought in the Seven Years’ War. He had androgynous physical characteristics and was a good mimic, a good feature to have as a spy. D’Éon appeared publicly as a man and pursued masculine occupations for 49 years.

As a spy, he successfully infiltrated the court of Empress Elizabeth of Russia by presenting as a woman. For 33 years, from 1777, d’Éon dressed as a woman, identifying as female, claiming to have been assigned female at birth, and demanded recognition by the government as such. The court agreed but it required that d’Éon dress appropriately in women’s clothing. He claimed to have been raised as a boy because his father could only inherit from his in-laws if he had a son.

Rumors circulated in London that d’Éon was actually a woman. A betting pool was started on the London Stock Exchange about d’Éon’s true sex. After a year without progress, the wager was abandoned. Once he retired he revealed to the public that he had been a woman the entire time.

Doctors who examined d’Éon’s body after death and discovered male organs in every respect perfectly formed. So essentially he was double crossdressing.