Ernest Hemingway’s transgender son

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/Gloria/Vanessa Hemingway

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?

~ ~ ~ ~ ~ ~ ~ ~ ~

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.

One reviewer wrote, “Eloquent and thought-provoking, the author of this book does an incredible job weaving us through the tapestry of his journey with gender dysphoria. A Rollercoaster Through A Hurricane is written as beautifully as any novel I’ve ever read. Greg allows us to witness his most personal secrets and stories as he shares the truth of his becoming whole. Using humor and heartfelt honesty, we are taken inside the life of a person, who on so many levels, is a relatable guy! Greg writes as though he is your friend, sharing his truth with unwavering grace and gumption, he holds nothing back. As I read each chapter, the words flowed like water and I found myself unable to stop reading!”

In light of learning about Greg Hemingway, and with the new Burns/Novick documentary on Ernest, perhaps a new subtitle for my book is appropriate: “The Son Almost Rises”?  (cough, cough)

~ ~ ~ ~ ~ ~ ~ ~ ~

I am more than sad that our world has fallen to where it has with so many things—I recently heard a man with PTSD say, no, he has post-traumatic stress, but it is not a disorder, because if the D is on the PTS it means something is wrong with him, and he is not his PTS (as folks say, “I am not my cancer”)—and that it has extended to we who have issues with our gender identity.

I have always preferred the term “gender identity disorder” to “gender dysphoria.” Indeed, I experienced issues with my gender identity for my entire life, and my issues profoundly disordered some of life’s most important things, but I did not suffer dysphoria—which means “ill feelings,” when a person gets to where he can no longer live with himself, even hates himself—until 2013.

I had a disorder, perhaps not a disease as Valerie Hemingway termed it, but definitely a malady, a dis-ease, a physical condition which, undoubtedly, began in the womb when my endocrine system was disrupted.

Disrupted. That word, alone, speaks to disorder. Things not being right. Something that’s wrong.

I understand our current sensibilities regarding these matters. I’ve lived through them with two therapists and a host of doctors. It is hard enough living this duality, we don’t need professionals assessing us with, “Wow, are you ever screwed up.” So, thank you, professionals, for coming a long way on our behalf.

Even so, we do a disservice to those who have gender issues—who have any issue—if we don’t call it exactly what it is. I identify with Greg Hemingway so much more than his first name and his gender identity issues. His wife, Valerie’s, assessment nailed me right in my heart:

  • Lacking critical early help.
  • Trying to find a cure.
  • Striving for solace.
  • Seeking a retreat from the unbearable responsibilities of who he was/who I am.

41% of people who have gender identity issues, who attempt to kill themselves, do not succumb strictly from outward pressures. The internal pressure is worse than a plugged up pressure cooker ready to burst its lid. Even if I had no outward pressures, I believe I still would have wanted to remain male. Indeed, as content as I am today living as a female, even having had surgery on my vocal cords and now highly anticipating my own sex reassignment, I can say that my preference would be to be a male.

That’s what my DNA is. That’s what I was supposed to be, male in both body and mind, sex and gender, outward identity and inward. That is who I would be if not for a disordering of my hormones.

I speak for no one else but me. I have gotten to know enough transgender folks to know that their internal struggles were or are just as serious as mine, but they get to tell their own story, and label their situation as they prefer.

I am thankful that it was not until 2013 that I finally crashed. I have no imagination large enough to picture myself in the 1970s, when I hit adulthood, finding it impossible to live in my male skin. Or in the 1980s. Or 1990s. It was hard enough going public in the 2010s, it is unfathomable what my experience would have been decades earlier.

We are making progress. We have a long way to go. As we move forward, I pray no one ever lose sight of this most important thing about we who have suffered gender identity issues.

It. Is. Terrible.

Greg Hemingway was prone to heavy drinking and publicly acting out. He was arrested for an improper public display while presenting as a woman. Before he would make it to court, he died of an ailment with which he had suffered for years, hypertension, coupled with heart disease. Surely, his physical situation, if not due to, was exacerbated by his internal struggles.

He didn’t kill himself, but I find that his inability to have peace, because he lived in a world which would not allow him to have peace, killed him.

If and when we, who find that our gender and sex do not match up in the black and white way of male and female, finally tell you, family and friends and coworkers, please immediately know that we have been suffering the deepest of pain. You can alleviate the worst of it with a compassionate heart, and a reaction like this: “I am so sorry, but I am so glad you were able to tell me. I don’t know much about this, so I will want you to explain things so that I can grasp as much as I can. I will be here for you, however you need me.”


7 thoughts on “Ernest Hemingway’s transgender son

  1. i didnt know any of this. i do know some history of ernest hemingway. i do the same thing, ya know. i go to theninternet all the time during movies or documentaries and look up information. it is one time i am so thankful for the internet. that and it is how i became friends with teo kids down the road

    …however you need me. that is good stuff.

    good morning gina joy!!


  2. I believe the picture shown at the beginning of the article is of Ernest Hemingway’s first son, Jack.

    The second picture is, correctly, a picture of Gregory/Vanessa.


  3. read this on Michael Savages site: Doc Hemingway as a physician in Jordan ,MT was very competent , and saved my Grandfathers life once. Putting his personal short comings aside, I felt I must point this out.


    1. W~ I’m really glad you posted this. It’s great to hear Doc Hemingway was a good physician. It’s so easy to lose sight of recognizing one’s positive attributes when discussing what troubles/d them.


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