October 22, 2001 12:00 PM

In her five years on the police force in upscale Key Biscayne, Fla., Officer Nelia Real had never seen anything like what appeared on the median strip of the town’s main thoroughfare at noon on Sept. 26: a naked senior citizen clutching spike-heeled shoes, a black velvet dress, shredded panty hose and flowered thong underwear. “He had a necklace and two rings, and his nails were painted a plum color,” says Real, 43, who booked the flasher on charges of indecent exposure and resisting arrest without violence. “First he told me his name was Gloria,” she says. “In the car, he told me it was Greg.”

More surprises were to come. The suspect confessed that he was the son of Real’s favorite author—Ernest Hemingway. “It was an honor to be talking to this guy,” she says. But since the “guy” (also the uncle of actresses Mariel, 39, and Margaux, who committed suicide in 1996) had had a sex-change operation, he was remanded to the Women’s Detention Center in Miami.

That was Gregory Hemingway’s last stop. Five days later, while awaiting a court hearing, he was found dead in his cell at age 69 of a heart attack. For many who knew him, the scenario was sadly predictable, given his family history of mental illness. A manic-depressive and a physician who lost his license after he failed to get a state-mandated psychiatric evaluation in 1988, he had seemed more tormented with each passing year. Out of touch with many of his relatives, he shared a Coconut Grove cottage with the former Ida Mae Galliher, 59, his fourth and fifth wife (divorced in ’95, they remarried not long afterwards). He had been arrested before: for harassing a Florida bus driver and assaulting police officers in ’95 and for throwing a glass at Ida in ’96. And he was turning increasingly to cross-dressing, a longstanding compulsion.

“He would come in and ask me if there were any nice bachelors he could meet,” says Mo Wilson, a bartender who sometimes served Hemingway at Key Biscayne’s Sand Bar. Adds musician Louis Archambeau, a Sand Bar performer: “He always said something about being a Hemingway. He wanted to be noticed.”

He had longed for that since childhood. The son of Nobel Prize winner Ernest and his second wife, Pauline Pfeiffer, Gregory was born in Kansas City, Mo., and grew up in Key West, Fla., and elsewhere, winning sporadic attention from his world-wandering parents. “The best thing my mother did for me was get me a good nanny,” he said in 1999 of Pfeiffer, who died in 1951. The youngest of three boys (Patrick, now 72, is an editor; Jack, a conservationist, died last year at 77), “he did so many things to please his father,” recalls Jeanne Porter, 73, a childhood friend, “including becoming a champion pigeon shooter in Cuba when he was 10.”

After a stint as a professional game hunter in Africa, Gregory attended the University of California and then medical school at the University of Miami. He practiced family medicine in Jordan, Mont., married five times, and had eight children. In 1976 he wrote Papa: A Personal Memoir, a much-praised biography of Hemingway, but his mental illness—inherited perhaps from his father, who killed himself in 1961—was worsening. He once said he had had shock treatments 98 times.

He wed Ida, a retired auto executive, for the first time in 1992. She refuses to discuss his sex-change operation and says his transvestism was his own business. “Don’t we all have our personal whatevers?” she asks. “He was a wonderful husband, with an enormous sense of humor, and very kind.” But she knew he was in trouble in early September, when he disappeared from the couple’s ranch in Montana. Making some frantic calls, she learned of his arrest. “He must be at peace,” she says of his death, “after the tortured life he had.”

His daughter Lorian, 49, also a writer, hopes the world will remember more than his pain. “What I would hope for him is that there would be sympathy and respect,” she says. “He was not a sideshow oddity; he was a man with problems. He was a good human being.”

Kim Hubbard

Siobhan Morrissey, Linda Trischitta and Denise Sypesteyn in Miami, Alexandra Hardy in Los Angeles and Steve Barnes in Arkansas