Well, though she is moreorless contemporary rather than historical, I'd have to say Rene Richards.
She had a lot on the line in her transition and transitioned more publicly than anybody I can think of ... even moreso than Christine Jorgenson. Renee was: New York City ophthalmologist and surgeon, Richard Raskind, strabismus surgical specialist when this was just a burgeoning specialty, a Yale graduate, a tennis professional and coach of the greatest woman tennis player ever (so far as I know), Martina Navratilova. All of this was in the mid-1970s when public mores and attitudes were WAY different than they are now.
Renee Richards never sought notoriety, fame or wealth. All she ever really wanted was a quiet and normal life. She could have and would have been wealthy. Transition cost her much indeed. She did it all under the microscope of the modern-day media. Too much! I admire the hell out of her!
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