By this time, with father's approval, Ray was passing as male. He was apparently a rival for the favors of a lady who used a large ear trumpet, but after the other man moved away, he ceased to call on the lady.
Joseph died in March 1894, and Ray continued the business. He lived in the back of the shop, and went fishing and hunting with other men from the town. The men would gather in his shop in the evenings to tell stories.
Dr Rowland tells what happened in 1911 when Ray was 62:
"As time passed, he became gray and looked quite old, complained of headaches, and often closed his shop at odd hours. Eventually, he began to wander about town at night and seemed disoriented. People who knew him and found him wandering would take him home. Finally, it became necessary to put him in the state hospital.The men of the town no longer gathered in Ray's shop to tell tales. Ray started to frequent the Christian Science Church, but still went to Dr Rowland when ill.
It is customary to strip each patient entering the hospital and give them a bath before they are given quarters. The hospital immediately discovered that Ray Leonard was a woman. After her secret was out Ray made a rapid recovery and came back to Lebanon to live the rest of her life.
The authorities made her wear dresses, but she confided to her friends that she wore pants below her dress because her legs got cold. ... Ray looked far more like a man to me than a woman. She would say, "Look at me, Dr. Rowland, do you think I have one feminine feature?" I had to admit that she certainly looked like a man. "
- "Woman Masquerades as Man 22 Years; Smokes But Never Votes". The Spokesman Review, Sep 29, 1911: 4. http://news.google.com/newspapers?id=BAJkAAAAIBAJ&sjid=q_MDAAAAIBAJ&pg=2996,5564653&dq=ray-leonard+oregon+-sugar&hl=en.
- Mary Canaga Rowland & F. A. Loomis. As Long As Life: The Memoirs of a Frontier Woman Doctor, Mary Canaga Rowland, 1873-1966. Seattle, Wash: Storm Peak Press, 1994: 107.
- Paula Martinac. "A Passing Woman". The Queerest Places, Feb 17, 2008. http://queerestplaces.wordpress.com/2009/02/17/a-passing-woman.
- Peter Boag. Re-Dressing America's Frontier Past. Berkeley: University of California Press, 2011: 211n100.
- "Ray Leonard, Oregon Pioneer and Passing Woman". History-Onyx 2: Wild Women West. http://users.wi.net/~maracon/lesson2.html.