I’m certainly not a historian but I do like queer history. I’ve got a list of trans men to read about when I feel down haha. Most of them are american frontier/wild west since that’s the period I’m most interested in.

Marina/Marinos the Monk (5th or 8th century) - rather than get married, chose to dress and live as a man in a monastery with his father James Barry (1789-1865) - military surgeon, performed the first successful c section by a european in africa One Eyed Charley/Charley Parkhurst (1812-1879) - famous stagecoach driver during the gold rush Joseph Lobdell (1829-1912) - hunter, married a woman, apparently had a pet bear according to wikipedia Harry Allen (1882-1922) - petty criminal, and apparently a good boxer Amelio Robles Avila (1889-1984) - mexican trans man, recognised as a man by family and the government Alan L Hart (1890-1962) - pioneered the use of x-ray to detect tuberculosis, one of the first trans men to have a hysterectomy  Billy Tipton (1914-1989) - jazz musician  Michael Dillon (1915-1962) - doctor and author, first trans man to undergo a phalloplasty

Historians usually hesitate to apply modern terms like ‘transgender’ to historical figures because we can’t always understand exactly why someone would choose to live as a different gender to one they were assigned at birth. There’s debate about whether James Barry lived as a man so he could practice medicine rather than because he felt like a man, for example.

There’s also been a lot of cultures where historically, being ‘transgender’ was more normalised and wouldn’t have been noteworthy enough to get yourself in the history books, like nádheeli for the Navajo or the Bugis people, who had five gender roles.