By Quittner, Jeremy
The Advocate (The national gay & lesbian newsmagazine)
There is a particularly powerful American myth based on the literature of Ernest Hemingway. It revolves around the supermacho, hypermasculine, independent male who can act without internal conflict in the face of all the serious challenges thrown at him by nature and society.
Perhaps no one was more familiar with this myth than Gregory Hemingway, the youngest son of the world-renowned novelist. And yet by the time Gregory Hemingway died on October 1 at age 69 in Florida's Miami-Dade Women's Detention Center, his life had strayed wildly from his father's script for manhood. He had ventured into the uncharted and often complicated territory that many transgendered people face. At the same time, his death sheds some light on the struggle with family and friends, if not society as a whole, that all people who wish to express alternative gender identities can experience.
Described by friends and family as brilliant, muscular, athletic, and a sports fisherman, Hemingway was also an accomplished doctor, a writer, and the father of eight children by four different wives. Life had its ups and downs, especially since Hemingway suffered as an adult from manic-depressive illness and alcoholism, which caused him to have his physician's license revoked in the 1980s. But he hoped 1995 would mark a turning point in his life. He not only divorced his fourth wife but also underwent a sex change. Hemingway's oldest daughter, 49-year-old Lorian Hemingway, says that after the operation her father identified as a woman but answered to both Gregory and Gloria as well as to both masculine or feminine pronouns.
But the sex change didn't clear up everything for Gloria Hemingway, who died of heart failure in a private cell after being arrested for indecent exposure. Police found her wandering naked along a median strip in Key Biscayne, Fla., carrying a dress and high heels.
"[My father] was manic-depressive and was very open about that," says Lorian Hemingway. "It is almost a cliche to say, but those who are blessed with brilliance are cursed with the polar opposite. [My father] suffered the affliction of that disease."
Lorian says her father had always struggled with gender identity: "I talked to my mother about this, and she said that this was part of my father's psychological and physical composition from very early on."
And though she had only infrequent contact with her father after her parents divorced in 1958, Lorian recalls that during one phone call her father uncomfortably tried to broach the subject of wanting to have a sex change operation. …