Ernest Hemingway’s Son Became A Transsexual Named Gloria

“About morals, I know only that what is moral is what you feel good after and what is immoral is what you feel bad after.” —Ernest Hemingway, Death in the Afternoon

In A Nutshell

American author Ernest Hemingway was among the most rugged men who ever lived. His manly exploits are legendary, but the rock-ribbed writer also came from a legacy of mental illness that transferred to his son, Gregory. Greg suffered from bipolar disorder, substance abuse issues, and gender dysphoria. In his sixties, he had a sex-change operation, becoming Gloria Hemingway.

The Whole Bushel

Pages could be filled with the many adventures of author Ernest Hemingway. Known for his minimalist style, he wrote of war, of hard-fisted men in the wilderness, the gravity of great violence. His own life was even more spectacular than anything in his novels, a sprawl of fishing, hunting, fighting, of guzzling liquor and courting doom at every turn. But beneath his brash demeanor, Hemingway wrestled with personal demons. His family was plagued by suicides and mental illness that some have ascribed to an inherited genetic condition called hemochromatosis, an inability to metabolize iron that leads to a host of destructive symptoms.

Unfortunately, this dark legacy would not die with Ernest. His granddaughter, model and actress Margaux Hemingway, famously overdosed in 1996, one day before the 35th anniversary of Ernest’s own suicide. But Ernest’s youngest son, Gregory, would have an even more bizarre life.

Gregory Hemingway grew up in his father’s foosteps, but early experimentation with drugs earned him the ire of his parents. After a nasty argument with his mother, Pauline, the stress of which killed her after exacerbating an undiagnosed health condition, Greg and Ernest became estranged from each other. In many ways, Greg’s life was as wild and tumultuous as his father’s. He spent drunken years in Africa shooting elephants before returning the United States to become a physician. He had eight children with four different women, but he too battled serious mental health problems, including bipolar disorder and alcoholism, and received electric schock treatment.

Gregory’s condition seemed to grow ever more strange as he aged. In his late fifties, his medical license was not renewed. He’d struggled for years with gender dysphoria, feeling himself to be a woman born in the body of a man. In 1995, while in his sixties, he had a sex-change operation, thereafter occasionally referring to himself as “Gloria.” Even then she struggled with her image, sometimes dressing as a woman and other times a man. She had one breast implant installed, then had it removed. In 2001, Gloria was arrested in Key Biscayne, Florida, for appearing drunk and naked in public. According to the police report, she was sitting on a curb attempting to put on thong underwear when they found her, and screamed when they tried to handcuff her. Five days later, she was found dead in her jail cell at the Miami-Dade Women’s Detention Center. The cause of death was labeled cardiovascular disease and high blood pressure.

Show Me The Proof

The Strange Saga of Gregory Hemingway
NY Times Obituary: Margaux Hemingway Is Dead; Model and Actress Was 41
The Telegraph: Gregory Hemingway