Christine Jorgensen
Christine Jorgensen may be one of the first transpersons to decide to undergo gender reassignment surgery. She grew up in the Bronx and was drafted into the U.S. Army shortly after graduating from high school in 1945. She pursued getting a degree after her military service, attending several schools while working. During this period, she learned about reassignment surgery. She decided to venture to Europe to obtain special permission to undergo a series of operations, which started in 1952 according to Wikipedia.
It’s not clear if she had insurance before undergoing the treatments but we think it would have been best if she did. Her journey made the front page and she soon became an instant celebrity. She used her popularity to advocate for transgender rights and she quickly gained the respect of many because of her direct and polished wit.