Everybody had a different set of experiences based partly on who their father or mother was.

For example, if you are the child of esteemed parents, then people look at you as an esteemed kid as well, and it is certainly different from how they think of an average child from an average family.

Children of the prosperous and famous are most likely presumed to be raised in an atmosphere that sets them up for success. Suppose the mother is an accomplished doctor, attorney, engineer.

While the father is an equally respected scientist, it is expected that their children too will do well in life given the family cultures and financial resources.

It isn’t easy to compete with a successful parent, a story that George Hemingway experienced first-hand.

For almost his entire adult years, the former physician was living under the shadow of the legendary father, Ernest Hemingway.

At 69, Gregory was found dead in an unlikely place: the Miami-Dade’s Women’s Detention Center. His father once said that Gregory had the most prominent dark side in the family except for himself.


10 /10 Naked Pedestrian

On September 25, 2001, a park ranger at Key Biscayne, Florida, reported a naked pedestrian. An officer responded to the report and made the arrest.

According to the arresting officer, the person was drunk or otherwise impaired but very lovely. Jail officials classified the person as a woman and therefore confined her in the women’s section of the jail.

This person was none other than Dr. Gregory Hemingway, the youngest son of the late writer Ernest Hemingway.

A spokesman for Dr. Hemingway later said that his employer was believed to have undergone sex reassignment surgery.

9 /10 Found Dead

On October 1, the day Dr. Hemingway was due to appear in court for a hearing about the charges of indecent exposure and resisting arrest, he was found dead in his cell.

A spokesman for the Miami-Dade Police announced, referring to the autopsy report, that the cause of death was ruled cardiovascular disease and hypertension.

Dr. Hemingway was born in Kansas City, Missouri, and spent his childhood in Key West, Florida.

Like his father, the son eventually developed a heavy-drinking habit and battled with depression. Much of it was triggered by the intention to live up to his father’s reputation.

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8 /10 Killing Elephants

The elder Hemingway, son of a musician mother and physician father, received the Nobel Prize in Literature and Pulitzer Prize for fiction.

He was one of the most accomplished writers in America and almost as famous for his macho adventurous lifestyle.

In an interview with the Washington Post in 1987, Dr. Hemingway talked about the pressures of keeping up with the expectation of being his father’s son.

In one such attempt to do so, the young Hemingway once went to Africa in a safari and killed 18 elephants in a month.

7 /10 Gregory, Also Known As Gloria

In between the deep desires to live up to the father’s reputation, Dr. Hemingway also had another well-hidden compulsion to go out in public dressed as a woman.

He admitted to having spent most of his adult life struggling against the compulsion, a fight he often lost. When arrested in Key Biscayne on September 25, the affidavit listed Gloria as an alias.

He was then living in Coconut Grove, Miami. Few know for sure whether this was the “dark side” his father spoke of in 1941 when the son was only 10-year-old.

6 /10 Nervous Breakdowns

Dr. Hemingway said his father was aware of the cross-dressing habit. The pressure of being a male Hemingway and this particular compulsion put him in a contradictory state.

On one side, he had a seemingly unrestrained desire to put on a woman’s clothes, while on the other, there was the impulse to be at least nearly as masculine as the father.

However, the former predisposition he tried to subdue by spending hundreds of thousands of dollars for therapy. Some of the treatments led to a mental breakdown, causing him to drift without purpose.


5 /10 Strained Father-Son Relationship

A book about his father titled “Papa: A Personal Memoir” by Dr. Gregory Hemingway was published in 1976.

Growing up, Dr. Hemingway admired his father very much, and probably until his death, but he also described the increasingly strained relationship in a somewhat concise manner in later years.

One of the major starting points was the death of his mother, Pauline Pfeiffer, in October 1951.

She died just a few hours after a heated phone call with his father (they had divorced by this time) over Gregory’s use of the mind-stimulating drug. The elder Hemingway blamed his youngest child.

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4 /10 Ruptured Artery

It later came to light that Pauline Pfeiffer suffered from a rare adrenal gland disorder.

The heated conversation with her ex-husband triggered a massive surge of adrenaline, hence increased blood pressure, which eventually caused a ruptured artery.

When Dr. Hemingway learned about his mother’s illness and cause of death, he detested his father.

More than two decades after his mother’s passing, he claimed to have understood the circumstances surrounding the finger-pointing.

In his book “Hemingway: A Biography” American literary critic Jeffrey Meyers wrote that Gregory had a troubled childhood.

3 /10 Industrial Physician

When young Gregory reached his early 20s, he was living on his mother’s inheritance. At this stage of life, he took a journey to Africa to become an apprentice hunter.

He retained the job for about three years, although he never received a professional license due to his uncontrollable drinking habit.

As the idea of being a hunter is out of the question, he attended medical school at the University of Miami.

In the early 1970s, he practiced medicine and worked in New York City as an industrial physician. He described the job as dull but necessary.

2 /10 Memoir For Money

Finding himself in need of money, Dr. Hemingway wrote the memoir. He wanted just enough to leave Manhattan and start a new life.

The memoir was more like a short account of his relationship with his father rather than a detailed biography of a legendary writer from the son’s perspective.

Dr. Hemingway wrote in the memoir that young Ernest was neither a professional celebrity nor a bully; instead, he remembered the father as gentle and kind.

An admission that he became a physician after putting aside the inclination to be a Hemingway hero also was in the book.

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1 /10 Son Of A Great Man

The death of Gregory Hemingway marked the end of a troubled, tormented series of lifelong struggles, which included depression, alcohol, mental breakdowns, failed attempts as a hunter, and being a transvestite.

He also lost his license as a physician due to his drinking habit; he had not practiced medicine for years at his death.

Scott Donaldson, the president of Hemingway Society, said that Gregory had a difficult life, for it was not easy for him to be the son of a great man.

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