Gregory Hemingway’s Tragic Life As The Transgender Child Of Ernest Hemingway

Published June 7, 2021
Updated June 10, 2021

Throughout his adult life, Gregory Hemingway struggled with gender dysphoria and tried to live as a woman — which irreparably damaged his relationship with his father.

Gregory Hemingway

Wikimedia CommonsGregory Hemingway, right, with his father and brother in Cuba in 1942.

The acclaimed novelist Ernest Hemingway once remarked that his youngest son, Gregory Hemingway, had “the biggest dark side in the family except me.”

The two men did indeed share many demons, including bipolar disorder and alcoholism, and they frequently clashed while Ernest was still alive. But while his father became famous for writing about macho male characters, Gregory Hemingway sometimes dressed in women’s clothing and at one point tried to go by Gloria Hemingway.

But reportedly, the father and son had more in common in this way, too, than either of them openly acknowledged.

Gregory Hemingway Explores His Gender Identity

Ernest And Gregory Hemingway

Wikimedia CommonsGregory Hemingway and his father, Ernest, with rifles in Cuba.

Gregory Hancock Hemingway was born on Nov. 12, 1931, in Kansas City, Missouri, to Ernest Hemingway and his second wife, Pauline, née Pfieffer.

As a boy, Hemingway was outwardly athletic — a quality that pleased his father.

But inside, Hemingway was drawn to classically feminine objects. When he was around 10 years old, he tried on his stepmother’s dress and nylons. His father caught him and went “berserk.”

Possibly, Ernest Hemingway’s reaction could be attributed to his persona as a writer, a man known for his masculine characters, and known for his own masculinity. But maybe Ernest Hemingway saw something in his son that he recognized in himself.

Recent biographies have revealed how Hemingway asked his wives to cut their hair short in order to match his, and his posthumous novel The Garden of Eden features a character who asks his wife to have anal sex with him.

Not that either of those facts truly proves that Ernest Hemingway may have questioned his gender identity or sexuality, but shortly after he caught his son in women’s clothing, he told him, “You and I come from a very strange tribe.”

The Death That Finally Destroyed The Hemingways

Pauline And Ernest Hemingway

Wikimedia CommonsErnest Hemingway and his second wife, Gregory’s mother, Pauline.

Gregory Hemingway continued to face opposition as he explored his gender identity. At age 19 in 1951, he was arrested at a Los Angeles movie theater, which his father later chalked up to “taking a mind-stimulating drug before such things were fashionable.” In reality, he’d been caught trying to use a women’s bathroom.

His mother Pauline bailed him out, but when she called her now ex-husband to tell him what had happened, Ernest Hemingway exploded. For over an hour, he harangued Pauline and blamed her for their son’s behavior.

Unbeknownst to anyone in the family, however, was that Pauline had an adrenal gland tumor. The stress of the call caused her adrenaline to spike, and she died suddenly that night.

Ernest immediately turned the blame onto his son, telling him: “You killed your mother with that stunt in L.A.”

In the subsequent years, Gregory Hemingway struggled with guilt and depression, dropped out of school, and fled to Africa where, in very Ernest Hemingway-like fashion, he drank heavily and shot elephants.

He never saw his father again.

But over the years, Hemingway and his father would exchange a number of bitter letters to each other. Hemingway called his father a “gin-soaked, abusive monster,” and Ernest accused him of stealing a pair of nylons from one of his wives.

In 1959, Hemingway was accepted to medical school in Miami. He promptly investigated his mother’s death and found that she’d suffered from adrenal cancer and came to the conclusion that the stress of her last phone call likely killed her. Hemingway thus wrote to his father: “It wasn’t me who killed her, you bastard, you did.”

Following the letter, Ernest became increasingly depressed. In 1961, he died by suicide — and his son blamed himself for the death of yet another parent.

Gregory Hemingway’s Final Years As Gloria

Gloria Hemingway

Sven Creutzmann/Mambo photo/Getty ImagesThe police picture taken of Gloria Hemingway in 2001. She died days later.

Gregory Hemingway’s final decades were troubled. His four marriages ended in divorce, and because he drank heavily, he lost his medical license.

He continued to try to live as a woman, and in 1995, Hemingway underwent sex reassignment surgery. According to his daughter, after the surgery, Hemingway mostly identified as a woman but answered to both Gregory and Gloria, as well as to both masculine and feminine pronouns.

“I’ve spent hundreds of thousands of dollars trying not to be a transvestite,” Hemingway told the Washington Post in 1987.

At the end of September 2001, Hemingway was arrested in Miami for indecent exposure. Police found her impaired and naked on Key Biscayne while holding a pair of high heels. Because Hemingway had female genitalia, she was sent to the Women’s Detention Center — but she would never come out.

Five days later, Gloria Hemingway was found dead in her jail cell of natural causes. She was 69 years old.

“What I really wanted to be was a Hemingway hero,” Gloria Hemingway wrote in her 1976 book Papa: A Personal Memoir.

But maybe she was. In Hemingway’s posthumous book, Islands in the Stream, the famous writer depicts a relationship between a father and a son:

“[The son] had a dark side to him that nobody except [the father] could ever understand. Neither of them thought about this except that they recognized it in each other and knew it was bad and the man respected it and understood the boy’s having it.”

After reading about the life and death of Gregory Hemingway, check out these 21 Ernest Hemingway quotes. Or, learn about Lili Elbe, a tragic transgender pioneer.

Kaleena Fraga
A staff writer for All That’s Interesting, Kaleena Fraga has also had her work featured in The Washington Post and Gastro Obscura, and she published a book on the Seattle food scene for the Eat Like A Local series. She graduated from Oberlin College, where she earned a double degree in American History and French.