Ernest Hemingway’s transgender son

Eilers Pizza Blog:

I happened upon this quite by accident. When I watch documentaries and biographical movies, I like to get on the Internet and learn more. Reading the Wikipedia page of Ernest, I clicked on the links to his children, and learned that his youngest of three children had a long struggle with his gender identity.

Gregory Hemingway on Wikipedia

Gregory Hemingway never lived full time as Gloria or Vanessa, his two chosen names, but after contemplating sex reassignment surgery (SRS) in the early 1970s, he finally had it in 1995. He was married five times, to four women, with whom he fathered eight children. He was a medical doctor in family practice. And, by his late teens, he and his famous father were estranged.

One has to wonder whether, if he were born two generations later, his gender identity issues would not have been such that wife Valerie wrote, “All his life, Greg fought a losing battle against this crippling illness. He lacked critical early help because his parents were unable or unwilling to accept his condition nor could he come to terms with it himself for a long time, taking up the study of medicine in the hope that he would find a cure, or at least a solace. Failing that, he developed an alternate persona, a character into which he could retreat from the unbearable responsibilities of being, among other things, his father’s son, and of never ever measuring up to what was expected of him, or to what he expected of himself.”

How many issues might one plumb from this assessment?

The phrase that resonates with me is “this crippling illness.” Nowadays, no one speaks in such terms about gender dysphoria. Indeed, a few years ago it was officially changed to gender dysphoria from gender identity disorder, so that it would not be classified as a disorder, and certainly not as an illness.

Because, as everyone knows, there’s nothing wrong with people who have the body of one sex and the brain of the other.


Remove the outward pressures—family who might reject you, making your way socially and professionally, and how one is viewed and treated by the rest of the world—and the internal pressures remain:

  • Who am I?
  • Who am I supposed to be?
  • Should my body win the day, or should my mind?
  • How does one find the right answers to these monumental questions?

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April 2021: I wrote this piece (which concludes below this interlude) in 2017, when I thought I’d be living the rest of my life as a trans woman named Gina.  To my shock, in 2018 I stopped experiencing myself as female.  When this persisted, I returned to living as a male and Greg.  In 2019, I published my memoir.

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