Bill Winters was originally included in The Kids section in Before Gender. However, as I researched his adult years, I realized his wrestling career illustrates an even more interesting scenario in which his talents protected him from anti-trans prosecution.
Bill also went by Billie, Willie, and William. I decided to stick with Bill due to Willie Ray already having a chapter. I initially included a trans boy named William Freeman in the first draft of Before Gender, but decided to leave him out as another 1860s white trans boy with an accepting family (it is a similar story to that of Ray Leonard, although without as many details).
If I had to choose a favorite newspaper clipping used in Before Gender, it would be this 1909 exposé of trans people from the Midwest (St. Louis Post-Dispatch, April 18, 1909). It’s worth a read, see the full quality image here.
The St. Louis Post-Dispatch‘s front page biography of Bill offers a unique self-account of a trans man in 1909. (“Philosophy of Miss Winters”). The page is beautifully illustrated, albeit wildly exaggerated (camp?). You can see the full-quality image here.
World champion wrestler Cora Livingston (top, 1922) wrestled Bill in 1911. The wrestler on her neck is Jane Henry (via Getty).
Note that the St. Louis Post-Dispatch (Oct 12, 1911) uses the correct name but incorrect pronouns for Willie (Bill).
The Post-Dispatch compared Bill to another individual defying gender norms at the same time in St. Louis, Jim Davis (pictured).
Aside from the misgendering, I would love to see more cartoons of trans men in the papers (The Manhattan Mercury, Mar 3, 1909, page 3).
Some reporters appeared to understand Bill’s exploitation (The St. Louis Star and Times, Apr 22, 1911, page 7).
Without knowing the tone of the author, it’s difficult to tell if the article is a critique of patrol overreach or a celebration of police brutality. It features Bill’s trainer/handler/manager, William J. Schneider (St. Louis Post-Dispatch, Nov 17, 1909, page 4).