Gregory Hemingway

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Gregory Hancock Hemingway, medical practitioner: born Kansas City, Missouri 12 November 1931; four times married (eight children); died Miami, Florida 1 October 2001.

Ernest Hemingway was the literary embodiment of American machismo, so much so that he once crossed a Spanish street to punch an effeminate passer-by. It is ironic then, that his youngest son, Gregory, should have died, aged 69, in a women's prison cell, having been arrested naked five days previously on a Florida Key, with a dress and high heels in his hands.

Gregory Hancock Hemingway was born in Kansas City, Missouri, in 1931 to the writer and his second wife, Pauline, née Pfeiffer, a stylish, wealthy young Catholic from St Louis who was working for Paris Vogue when she met Hemingway and his first wife, Hadley, a love triangle the writer describes in A Moveable Feast (1964). His parents, who called him Gig, would go off on safari to Africa for months at a time; his mother admitted she had practically no maternal instinct, and as a result he formed "what psychiatrists call a 'dangerously' close relationship" with his father.

Growing up in the 1930s, he was aware of the contrasts between his parents' wealthy life in their Key West home, financed by royalties from The Sun Also Rises (1926) and A Farewell to Arms (1929) and Pauline's inheritance, and the effects of the Depression, whose casualties he met with his father in the famous Sloppy Joe's bar. But his parents were divorced in 1940, and his mother gained custody of him and his brother Patrick, although they spent each summer with their father in Bimini, Sun Valley or Havana.

Gregory Hemingway wrote rhapsodically of these holidays: meeting Ingrid Bergman, waking up hung over "from drinking what was left in the adults' glasses", feeding tame ducks and shooting wild ones; he was becoming a blurred copy of the strenuously masculine writer, whom he hero-worshipped and joined in quixotic escapades, such as searching for Nazi U-boats off the Florida coast. Ernest also taught him – in graphic detail – how to pleasure a woman. Gregory professed to have fallen in love with both Hemingway's third wife, Martha Gellhorn, and her replacement, Mary Welch, whom he taught to shoot, and felt "had a crush on me, too". When she announced her intention to sleep with "Gig", the expectant stepson lay awake, and she turned over and went to sleep.

Yet Gregory Hemingway became increasingly disenchanted with his father, who had become a snob, obsessed with "the Beautiful People"; drunkenness had "anaesthetised the pain which had accompanied the loss of his talent . . ." In response, his son seemed to falter, too. After attending Canterbury School in Connecticut, he dropped out of St John's College, Annapolis, and became a poorly paid aircraft mechanic, struggling to support his wife Jane and young daughter Lorian.

In 1951, aged 19, he was arrested in San Francisco "for taking a mind-stimulating drug before such things were fashionable". His mother informed Ernest Hemingway, but died the next day, leaving him "a small fortune". "I was suddenly a rich young man . . . But somehow it was wrong." He went to Cuba to see his father, who accused his son of having "killed" his mother with his drug charges. They never saw each other again.

Gregory was in his second year studying medicine at UCLA when Hemingway's near-death crash in Africa in 1954 prompted him to make peace with his father. Having wired congratulations when Hemingway won the Nobel Prize that October, in response he received a cheque for $5,000. He used it to travel to Kenya, where he spent three years as an apprentice professional hunter, shooting 18 elephants in one month, "God save my soul", but failed to get his licence due to his drinking. Back in the United States, his marriage broke up and he was drafted. "After an undistinguished career in the peacetime army, I went back to Africa to do more killing. Somehow it was therapeutic."

He had returned to finish medical school at the University of Miami when Ernest Hemingway told him of his belief that he was going blind and becoming impotent; "it was as if he had already given up living". "Tormented beyond endurance", estranged from his wayward son, fearful of blindness and impotence, Hemingway killed himself with a shotgun in 1961.

Part of Gregory's problems lay in the subsequent sense of responsibility he felt for his father's death. Later, when he met a reporter who broke down in tears over the memory of Hemingway's suicide, Gregory told him, "If you feel so strongly about it why don't you go out to Idaho and tend his grave?" The man hit him, and Gregory responded by breaking the reporter's nose, knocking out two of his front teeth, "and half of one of his ears was hanging loosely from the side of his head". Afterwards he felt no shame, only, "Damn, I might have been able to take Papa on the best day he ever had!"

In 1976 Gregory Hemingway published Papa: a personal memoir, an elegant, painful attempt to explain his relationship with his father. In his preface, he quoted from his father's Islands in the Stream (1970):

He was a boy born to be quite wicked who was being very good and he carried his wickedness around with him transmuted into a sort of teasing gaiety.

Norman Mailer's foreword remarked,

There is nothing slavish here . . . For once, you can read a book about Hemingway and not have to decide whether you like him or not.

Gregory sought to protect his father's reputation, and, together with his brothers, he challenged the tawdry "Hemingway Days" festival in Key West. In 1999, they founded Hemingway Ltd, registering the name as a trademark and "up-scale lifestyle accessory brand". (Their first endorsement was a range of shotguns.)

Like his father's, Gregory's later life was a troubled one. All his four marriages failed, leaving eight children; he underwent ECT, and lost his medical licence due to his drinking. In her 1998 memoir, Walk on Water, his daughter Lorian recalled how she had

fished with my father just once, before I knew he liked to dress in women's clothes . . . I never had a clue until my mother told me that he sometimes wore her girdle and painted his nails a bright, clean red.

His pursuit for identity had led him to question his own sexuality, recreating himself as Gloria Hemingway. Alcohol abuse accompanied his personal traumas; he was arrested on a charge of battery on a police officer in 1995, and on an aggravated assault charge in 1996.

On the day of his final arrest, Hemingway appeared to have been drunk, said the arresting officer, Nelia Real. He was placed in the women's jail, on the grounds that he had undergone a sex change. "He had no shoes and he had a dress and high heels in his hands," Real said. "I feel really bad that that happened. He was a very nice guy."

Philip Hoare