G. Hemingway, 69; Youngest Son of Famous Novelist

Gregory Hemingway, the youngest son of novelist Ernest Hemingway and a former physician who underwent a late-in-life sex-change operation, died Monday in a private cell in the Miami-Dade Women’s Detention Center in Florida. Hemingway was 69.

Miami-Dade police said an autopsy revealed that Hemingway, who suffered hypertension and cardiovascular disease, died of natural causes.

A spokeswoman for the Miami-Dade County Corrections and Rehabilitation Department said medical staff confirmed that Hemingway had undergone a sex-change operation and was classified as a female when booked into the women’s detention center.

Hemingway was arrested on Key Biscayne, an island community near Miami, last week. Responding to a park ranger’s report of a naked pedestrian, police charged Hemingway with indecent exposure and resisting arrest without violence.

Police said Hemingway, found holding a dress and high heels, appeared to be drunk or otherwise impaired during the arrest.

Hemingway’s death marked the end of a tormented life, one that included, alcohol, depression, nervous breakdowns, electroshock treatments and a desire to wear women’s clothes.

“He had a difficult life. It’s not easy to be the son of a great man,” Scott Donaldson, president of the Hemingway Society, told Reuters.

Born in Kansas City, Mo., the son of the novelist and his second wife, Pauline Pfeiffer, Gregory Hemingway spent much of his early years in Key West, Fla.

In the 1976 best-selling book “Papa: A Personal Memoir,” Hemingway portrayed his father as a loving childhood companion who taught him to be a champion wing shot and displayed his courage by rescuing his young son from sharks.

Growing up with “Papa,” there were fishing trips off the island of Bimini and hunting and skiing trips to Utah.

“In his youth,” Hemingway wrote, “my father was not a bully, a sick bore, or a professional celebrity. . . . The man I remembered was kind, gentle, elemental in his vastness, tormented beyond endurance.”

But Hemingway clearly had mixed feelings about his father, with whom he had an increasingly strained relationship in later years.

In his book, Hemingway said his father blamed him for his mother’s death in 1951. Pfeiffer died hours after a heated long-distance phone call with her ex-husband in Cuba over Gregory’s use of a mind-stimulating drug while visiting the West Coast.

His mother, Hemingway wrote, was soon shouting into the phone and sobbing uncontrollably. “I’d seen papa’s ability for destroying people with words.”

Years later he learned that his mother had a rare adrenal gland disorder and that the emotionally charged phone call had likely produced an abnormally high surge of adrenaline that caused her blood pressure to rise to the point of rupturing an artery.

“After that episode with mother [on the phone], I simply wanted to kill him,” Gregory told a reporter more than two decades later. “I hated his guts for years. But I came to understand him.”

Despite the earlier good times with his father, Jeffrey Meyers writes in “Hemingway: A Biography” that Gregory Hemingway had a troubled childhood. In 1941, Ernest Hemingway told Pfeiffer that their 10-year-old son had “the biggest dark side in the family except me.”

In his early 20s, Gregory Hemingway followed his father’s footsteps by going on safari to Africa, where he shot 18 elephants in one month. Living on an inheritance from his mother, he worked three years as an apprentice hunter. But his uncontrollable drinking, he wrote, prevented him from obtaining a professional hunter’s license.

In his memoir, Hemingway said he became a physician after apparently allaying the impulse to become “a Hemingway hero.”

By the early ‘70s, he was working as an industrial physician in New York City, a job he described as “necessary but dull.”

He said he wrote the memoir of his father to make enough money to flee Manhattan and start a new life.

He chose the wide open spaces of Montana--Hemingway country--and in 1976 took up residence in Fort Benton on the Missouri River where he went to work in a storefront medical clinic on the town’s original Main Street.

“Some of the happiest memories of my childhood were associated with the West,” an exhausted Hemingway told a New York Times reporter after working a late-night shift in the one-story brick hospital.

Hemingway was married four times and had eight children. Hemingway’s last marriage was to Ida Mae Galliher in 1992, in a ceremony in the garden of his father’s old home in Key West. They divorced in 1995, the same year he attended a conference of Hemingway scholars in Cuba, where his father had lived from 1939 to 1959.

In 1992, Hemingway and his brothers, John and Patrick, formed Hemingway Ltd. to license the use of their father’s name, image and signature.

Several years ago, the Hemingway trio fought to collect royalties from tours of Ernest Hemingway’s Key West house and battled with organizers of the annual Hemingway Days festival in Key West over who has the right to use Ernest Hemingway’s name and likeness.

At the time of his death, Gregory Hemingway hadn’t practiced medicine for years, alcohol having caused him to lose his license.

When arrested in Key Biscayne last week, Hemingway was living in the Miami community of Coconut Grove. Hemingway’s arrest affidavit, according to Miami-Dade Police Department, listed the name Gloria as an alias.

In a 1987 interview with the Washington Post, Hemingway said he had spent most of his adult life struggling against the compulsion to dress in women’s clothes. His father, he said, had been aware of his cross-dressing.

“I’ve spent hundreds of thousands of dollars trying not to be a transvestite,” he said. “It’s a combination of things--first you’ve got this father who’s super-masculine but who’s somehow protesting it all the time. He’s worried to death about it.”