Hemingway's son Gloria: when Ernest Hemingway's son died in prison, the world learned he had been a troubled man who found the strength to live his life as he saw best--as a woman. (Culture).

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. "`What if your father became your mother?' he said, and I will never forget that," she says. "I think that is what he wanted to be--he would have preferred to be my mother rather than my father."

Still, Hemingway's struggle is something some of her closest friends would rather not acknowledge. "He was an active, muscular, heterosexual guy, and he was a magnificent father," says Donald Junkins, a retired professor at the University of Massachusetts at Amherst and a scholar of Ernest Hemingway's work. Junkins had been a close friend of Gregory Hemingway's since 1990 and was the best man at Hemingway's fourth wedding. "The other life, it's one I don't want to talk about much. Gregory was troubled in his later years," Junkins says.

Such reactions on the part of friends and family can contribute to depression and feelings of rejection, says Vanessa Edwards Foster, spokeswoman for the Houston-based National Transgender Advocacy Coalition. "We are sad to hear the manner in which she died, and the fact is that a number of transsexuals struggle with depression and family issues," she says. "Growing up the son of Ernest Hemingway was not exactly the easiest thing, and this was something that she fought over the years."

Foster says many transgendered people are angered by what they see as the lurid way the media has covered Hemingway's death. "There is an automatic presumption that transgenders are like sideshow freaks, or automatically we are criminals or presumed to be something less than savory," she says. "It is degrading and dehumanizing to the community."

Lorian Hemingway sympathizes with transgendered people's sentiments. "I would say the exact opposite is true and that you would find far gentler people in the transsexual community--and the gentleness and the peace that comes from realizing who you are and allowing yourself to be who you are," she says.

That tranquility is something she hopes her father found toward the end of his life. "I am proud of him for going through with it. I wish I could have said that to him, and I hope it brought him some peace in the years he had left," she says, adding, "My husband and I were talking about it, and if there was anything good about those last hours, it was that he was in the women's cell, where he would have chosen to be."

Quittner also writes for Business Week.