Gregory Hemingway

Gregory Hemingway was born in 1931, the son of Earnest Hemingway and his second wife, Pauline Pfeiffer. He was known to have had impressive marksmanship like his father, but who’s cross dressing tendencies tended to put a strain on their relationship. Gregory attended the University of Miami, Medical School, and eventually acquired his medical license. Never fully recovering from his father’s suicide nor the tragic death of his mother; he often suffered from bouts of alcoholism, depression, and run-ins with the law. He also wrote a book called” Papa: A Personal Memoir”, published in 1976, entailing his constant need for his father’s approval, and the relief he voiced burying his father, never having to worry about disappointing him again. Gregory, also known as Gigi, was married four times and fathered at least seven children. He was found dead in his prison cell in 2001, while dressing for a court appearance. Since then there has been a bitter feud over the remaining estate estimated worth somewhere around seven million dollars.

Gregory and his father had a fair relationship marred by arguments about his cross dressing tendencies. Earnest once even entered his son in a Cuban pigeon shooting contest, and he beat out over one-hundred and forty contestants, satisfying his father greatly. Though there were happier times, the great novelist suffered from alcoholism and was stubbornly overbearing. In a weird twist of events, Gregory’s mother died from shock, shortly after a heated phone call from Earnest concerning their sons cross dressing. Unknown to anybody she suffered from a rare tumor of the adrenal glands, that when stressed released a lethal dose of adrenaline. Gregory’s father blamed his son for her death, but his son would later send him a letter confirming the medical details. Guilt ridden, Earnest started showing signs of mental instability shortly afterwords. Armed with a shotgun, Earnest killed himself, adding to the long saga of deaths within the Hemmingway family tree.

Gregory fought a lot of personal demons stemming from his Father death, and endured a lifetime of instability. He took his cross-dressing as far as getting one breast implant, which he later had removed. In the 1990’s his finances were in shambles and Greg was known to spend every check he received from the family estate. Greg was known to be very friendly and generous by friends, but reckless and sometimes violent during fits of erratic behavior. He was arrested several times, dressed like a woman and resisting arrest. He divorced his fourth wife Ida in 1995, two years later after a confirmed sex change operation they apparently remarried in 1997.In 2001 he was arrested for indecent exposure and resisting arrest, and was placed in the women’s annex of the Miami county jail. Gregory collapsed and died from complications involving high blood pressure and cardiovascular problems, he was 69 years old.