Possible Historical Trans Men
Since our understanding of gender hasn't always been the way it is now, the language that would describe a transgender person didn't exist. This means that a transgender person in the past couldn't self-idenitify as such, and their possible trans status becomes lost to history. These people are some of those cases where it is likely they could have been transgender men, but since we have no way of knowing if that is how they truly identified, we are left to speculate (Though most of the people here are considered trans men with almost certainty by scholars).
There are many cases of young females dressing and presenting as male in order to join the civil war. Some of them may have been women wanting to take action in the war, and others may have been transgender men.
Albert Cashier adopted a male identity before becoming a Union soldier, and kept that identity for the rest of their life. They were well-respected by their fellow soldiers in the Ninety-fifth Regiment. As they got older and their mental state deteriorated,, they were moved to Watertown State Hospital for the Insane, where they were made to wear women's clothes for the first time in 50 years. They died after tripping over their own skirt. Their gravestone reads "Albert D. J. Cashier, Co. G, 95 Ill. Inf." and was buried will full military honors.
Sarah Rosetta Wakeman enlisted in the Union Army under the name Lyons Wakeman at age 17. Their headstone reads “Lyons Wakeman” with full military honors.
Frances Louisa Clayton enlisted in the Union Army as Jack Williams. They were described as a “very tall, masculine looking woman bronzed by exposure” with an “erect and soldierly carriage”. They were said to out-drink any other soldier, as well as smoke, chew tobacco, curse, and gamble. They were described by fellow soldiers as an “accomplished horse-man” and a “capital swordsman."
Charley Darkey Parkhurst was a runaway as a youth and became stagecoach driver and rancher in California during the gold rush. They were also known as "One Eyed Charley. He may have been the first transgender man to vote in the US.
Harry Allen is mostly known from sensational coverage in the newspapers in the Pacific West in the early 1900s for prostitution and alcohol related crimes. Yeehaw