Leslie Feinberg brought the complicated conversation about gender to the public when she published Stone Butch Blues in 1993. In addition to her communist beliefs and writings, Leslie dedicated her life to the protection of gender nonconforming and transgender people.
The Chevaliere D'Eon was a woman in 18th century France (historically known as Chevalier d'Eon) who, born as a man, was a soldier, a lawyer, and a spy for King Louis XV for many years before publicly declaring herself a woman, which was accepted as truth by the public. She acquired feminist works and did swordplay demonstrations in her heavy dresses. She lived as a woman for thirty three years in post-revolutionary France.
Christine Jorgensen was born George Jorgensen and the first American woman to undergo sex reassignment surgery. She went as far as Europe to receive confirmation from doctors there that her belief she was a woman was not a psychiatric disorder. She got it - and the surgery - and came back to the US a celebrity.