Gloria Hemingway: Shadows of a Famous Legacy

The acclaimed novelist Ernest Hemingway once remarked that his youngest child, Gloria Hemingway, had “the biggest dark side in the family except me.” The two Hemingways indeed shared many demons, including bipolar disorder and alcoholism, and they frequently clashed while Ernest was still alive. While Ernest Hemingway became famous for writing about macho male characters, Gloria Hemingway pursued a life as a woman, changing her birth name from “Gregory” to “Gloria.” Interestingly, the two Hemingways had more in common in this way than either of them openly acknowledged.

Exploring Gender Identity

Early Years: Gregory to Gloria

Gloria Hemingway and her father, Ernest, holding 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 Pfeiffer. As a child, Gregory, who later became Gloria, was outwardly athletic, a quality that pleased his father. However, inside, Gregory was drawn to classically feminine objects. At around 10 years old, he tried on his stepmother’s dress and nylons. His father caught him and went “berserk.”

Ernest Hemingway’s Reaction

Ernest Hemingway’s reaction could be attributed to his persona as a writer known for his masculine characters and his own masculinity. But maybe Ernest saw something in his child that he recognized in himself. Recent biographies have revealed how Hemingway asked his wives to cut their hair short to match his and how his posthumous novel, “The Garden of Eden,” features a character who asks his wife to engage in non-traditional sexual activities. These facts hint at Hemingway possibly questioning his gender identity or sexuality. Shortly after catching Gregory in women’s clothing, he told his child, “You and I come from a very strange tribe.”

The Death That Shattered the Hemingways

A Tragic Incident

Gloria Hemingway continued to face opposition while exploring her gender identity. At age 19 in 1951, she was arrested at a Los Angeles movie theater, which her father later chalked up to “taking a mind-stimulating drug before such things were fashionable.” In reality, she’d been caught trying to use a woman’s bathroom. Her mother Pauline bailed her out, but when Pauline called her now ex-husband to tell him what had happened, Ernest exploded. For over an hour, he harangued Pauline and blamed her for Gloria’s behavior.

Pauline’s Sudden Death

Ernest Hemingway and his second wife, Pauline, who is Gloria’s mother.

Unbeknownst to anyone in the family, 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 Gloria, telling her, “You killed your mother with that stunt in L.A.”

Struggles and Estrangement

Guilt and Depression

In the subsequent years, Gloria struggled with guilt and depression, dropped out of school, and fled to Africa, where, in very Ernest Hemingway-like fashion, she drank heavily and shot elephants. She never saw her father again. Over the years, Gloria and her father would exchange a number of bitter letters. Gloria called her father a “gin-soaked, abusive monster,” and Ernest accused her of stealing a pair of nylons from one of his wives.

Medical School and a Harsh Revelation

In 1959, Gloria was accepted to medical school in Miami. She promptly investigated her mother’s death and found that Pauline had suffered from adrenal cancer. She concluded that the stress of her last phone call likely killed her mother. Gloria wrote to her 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 daughter blamed herself for the death of yet another parent.

Gloria Hemingway’s Tumultuous Final Years

Struggles with Identity and Addiction

Gloria’s final decades were troubled. Her four marriages ended in divorce, and because she drank heavily, she lost her medical license. She continued to try to live as a woman, and in 1995, she underwent sex reassignment surgery. According to her daughter, after the surgery, Gloria mostly identified as a woman but answered to both Gregory and Gloria, as well as to both masculine and feminine pronouns.

Arrest and Tragic End

At the end of September 2001, Gloria was arrested in Miami for indecent exposure. Police found her impaired and naked on Key Biscayne while holding a pair of high heels. Because she had female genitalia, she was sent to the Women’s Detention Center — but she would never come out. Five days later, Gloria was found dead in her jail cell of natural causes. She was 69 years old.

Legacy and Reflection

A Hemingway Hero

“What I really wanted to be was a Hemingway hero,” Gloria wrote in her 1976 book “Papa: A Personal Memoir.” In her struggle against a repressive father, Gloria dared to live the life that felt most genuine to her, a feat that perhaps even her father understood in some way. In Ernest Hemingway’s posthumous book, “Islands in the Stream,” the famous writer depicts a relationship between a father and a son that perhaps mirrors his own with Gloria: “[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.”


Gloria Hemingway’s life was a tumultuous journey marked by a struggle for identity and acceptance. Her story reflects the complexities of familial relationships and the pursuit of personal authenticity against societal expectations. While her life was fraught with challenges, Gloria’s courage to live as her true self stands as a poignant testament to the human spirit.

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