Kaitlin Sine Riordan had a normal childhood. Born the oldest of six children to conservative parents in Richmond, Va., she went on to become a successful student at the University of Richmond, where she joined an all-male fraternity and played on the male baseball team. This was possible because at the time, she was male.
Born John Riordan, she first experienced confusion regarding her gender identification around the age of five or six. Despite her father's best efforts to "make a man out of her," she never fully accepted her true self to be male, and instead internally identified as female. From there, she began a long journey to becoming transgender, which is chronicled in her autobiography, Bondage of Self.
Riordan has spoken to correctional staff at facilities such as Henrico County Sheriff's Office in Virginia about the importance of addressing transgender issues. Michael Wade, sheriff of Henrico County and vice president of the American Correctional Association, introduced Riordan at the Health Care Special Session and Luncheon on Saturday, expressing his gratitude to Riordan for telling her story. He said that having her speak to his staff "made people more open to asking questions they had never asked before because they were too afraid."
From a very early age, Riordan learned to suppress her feelings. "Quite frankly," she said, "I was in denial." In grade school, she would discretely try to research "what was wrong with her" at the school library. In 1965, the available research on the topic was very limited. Her confusion was a continuous distraction, causing her to struggle in school and turn to alcohol at the age of 13--a substance she struggles with to this day. "When I drank, I could be whoever I wanted to be, and I loved the way that felt," she said. Despite her budding struggles with addiction, she excelled in baseball, eventually culminating in invitations from the New York Mets and the Cincinnati Reds to try out for their teams. But she hid the letters, and never went to the tryouts. "I had a deep down intuition," she said. "I thought, 'What would happen if I really am that good, and someone finds out that I think I'm female?' My life would be ruined."
As she continued to "deny her innermost self," Riordan got married and had three children. Shortly after, she went to work for Phillip Morris USA, where she became very successful at the management level. At age 33, Riordan got divorced, determined to finally live the life...