ON HIS last night as a free man, Ernest Hemingway's youngest son slipped on
a demure black cocktail dress and made his way to a small private party in the
upscale Miami enclave of Coconut Grove.
He introduced himself to friends as "Vanessa" and spent much of the evening
in the kitchen, chatting with millionaires in country club attire. Guests say
he didn't get drunk. He seemed to be in good spirits.
"The odd thing about it was, he looked happy," says writer Peter Myers, who
had never seen his old friend dressed as a woman before.
"I'd say he looked about 20 years younger. He looked comfortable." But
things took a rapid turn for the worse, as things often did in the life of
Gregory Hemingway, a doctor who had lost his medical license, a writer who
hadn't published a book in 20 years, a husband who had been divorced from four
Less than 24 hours after he successfully introduced his female identity to
some of his oldest and most respectable Florida friends, he resurfaced in the
nearby community of Key Biscayne.
Perhaps he wanted to celebrate his triumph at a local bar, a friend says.
Maybe he intended to take a walk on the beach.
What is clear is that at about 4 p.m. the next day, Sept. 25, the burly
transsexual was seen parading down a main Key Biscayne thoroughfare, naked,
with a dress and heels in his hand. Taken into custody by an officer who
described him as "very nice" and perhaps mentally unstable, he was charged with
indecent exposure and resisting arrest without violence.
After a medical exam showed he had undergone a sex change, he was jailed -
on a mere $1,000 bail - at the Miami-Dade Women's Detention Center.
On Oct. 1, his sixth day in jail, Hemingway, who suffered from high blood
pressure and heart disease, rose early for a court appearance, began to dress
and suddenly collapsed in his underwear onto the concrete floor.
The third son of the 20th century's most resolutely macho literary figure
had died, at age 69, in a women's jail.
Gregory Hemingway's journey from elephant hunter to bejeweled
exhibitionist, from the boy who appeared to have everything to the prisoner in
cell 3-C2, was long and winding, marked by many detours and numerous
On this much, however, friends and family agree: He suffered from manic
depression, a form of mental illness. Even in a family tormented by chemical
imbalance - Gregory's father, paternal grandfather, uncle, aunt and niece all
committed suicide - the man who sometimes called himself Gloria was notably
"He had hundreds of shock treatments, and he kind of got to like them,"
says Jeffrey Meyers, who wrote one of several major biographies of Ernest
Hemingway. "It was like an addiction. Most people are terrified of shock
treatments. If you read Sylvia Plath's 'The Bell Jar,' it's not something you
would willingly do."
There are many who remember Gregory Hemingway as unfailingly gentle and
generous, but when he was in the manic - or euphoric - stage of his disease he
could be reckless, even violent. He had a string of arrests in Florida and
Montana, where he spent his winters, including one in which he threatened to
expose himself and kicked a police officer in the groin.
Other factors in Hemingway's decline, his associates say, may have included
a chaotic childhood, a complex relationship with his mother and a sometimes
overwhelming desire for acknowledgment from his famous father.
And then there were the dresses.
At the heart of Hemingway's tangled tale was a lifelong flirtation with
femininity that enraged Ernest, that epitome of swaggering American machismo,
and led to a series of father-son confrontations that scarred Gregory as a boy
and haunted him as an adult.
The battles date back to at least the early 1940s, when, according to
Gregory's friend, the poet Donald Junkins, Ernest walked in on Gregory - then
about 10 - while his athletic young son, the skeet shooter with the mischievous
grin, was trying on his stepmother Martha Gellhorn's dress and nylons. Ernest
"went berserk," Junkins says.
Father and son appear to have remained close for several years after that,
with Ernest even tutoring the boy he called Gig for a career as a writer. But
by the time Gregory was 19, he and Ernest were locked in bloody psychological
warfare over the lure of silk and taffeta.
It was a battle that would span much of the son's life and continue for
decades after the father's death.
Ernest Hemingway was a man who got what he wanted: the biggest fish, the
prettiest girl, the Nobel Prize. And in 1931, the man they called "Papa" wanted
The birth of a third son, Gregory Hancock Hemingway, on Nov. 12, was an
added complication in an already shaky marriage.
"My father had wanted a daughter badly," Greg wrote in his 1976 book,
"Papa, a Personal Memoir." "So to my mother, my birth meant that she, or
perhaps I, had blown this last chance to make her lovable egomaniac happy." His
mother, Pauline Pfeiffer, the second of Hemingway's four wives, left much of
Greg's early upbringing to a "'verness" named Ada, who, according to Greg,
tended to respond to even minor misbehavior by screaming, packing her bags, and
fleeing down the stairs. His father was a warmer figure, and although he was
frequently absent - reporting, writing and romancing his next wife - Greg
Strong, stocky and keenly intelligent, the dark-eyed boy, who fed ducks
tenderly and shot them accurately, in many ways resembled his father, who once
said Greg "has the biggest dark side in the family, except me." Father and son
shared a similar steely determination, and by age 11, Greg was showing signs of
the same athletic gifts.
That was when Ernest entered his son in the Cuban pigeon-shooting
championship. Greg defeated more than 140 contestants, including some of the
best wing shots in the world, to tie for top honors. There were articles about
him in the Havana newspapers. His father was thrilled. But if there was
triumph, there was also tumult.
Ernest ran through four wives by the time Greg was 15. He drank heavily and
allowed his young son to do the same. Greg recalls in his memoir having his
father cheerfully prescribe him a Bloody Mary - the boy was maybe 12 - as a
cure for a hangover.
The conflict over cross-dressing had worsened by 1951, when, according to
the standard account of Hemingway family history, Greg, then 19, got in trouble
over his use of a mind-altering drug.
THE incident prompted Ernest to lash out viciously at Greg's mother,
Pauline, in a bitter phone call. The story might have ended there, but
unbeknown to anyone, Pauline had a rare tumor of the adrenal gland that can
cause a deadly surge of adrenaline in times of stress. Within hours of the
phone call with Ernest, she had died of shock on a hospital operating table.
Ernest blamed his son for Pauline's death, and Greg, who was deeply
disturbed by the accusation, never saw his father alive again.
That basic chronology is not in dispute, but the biographer, Meyers, now
acknowledges that there was an element missing. It wasn't Greg's drug or
alcohol use that caused Ernest to berate Pauline shortly before she died, he
told the Tribune.
"I had to cover that over a little bit in my book, because I was very close
to the family and I really couldn't wound them ..." Meyers says. "But Ernest
knew about Gregory's cross-dressing way back in '51, and that was the cause of
the dispute; not, I think I called it, drug-taking or drinking." After his
mother's death, Greg, apparently depressed, interrupted his pre-med studies and
retreated to Africa, where he drank too much and shot elephants - at one point
18 in a single month.
It wasn't until nearly a decade later, in 1960, that he felt strong enough
to resume his medical studies and respond to Ernest's charges. He wrote his
father a bitter letter, detailing the medical facts of his mother's death and
blaming Ernest for the tragedy.
Within months, Ernest showed serious signs of mental illness. The next
year, he would kill himself, and once again Greg would wrestle with guilt over
the death of a parent.
"I never got over a sense of responsibility for my father's death," he
wrote in his memoir, "and the recollection of it sometimes made me act in
If Greg was devastated by the death of his father, he also confessed to a
profound sense of relief. As the body was lowered into the ground, he reflected
that never again would he disappoint the old man.
What followed was perhaps the most productive period of Greg's life. He
graduated from the University of Miami School of Medicine in 1964, and married
what was by now his third wife, Valery Danby- Smith, the mother of three of his
eight children. Living in New York and Montana, he practiced medicine, the
profession of his paternal grandfather.
"He was a physician at heart," says his eldest daughter, Lorian, 49, a
writer. "The passion was there." In 1976, he published his book about life with
his father. Compassionate but unflinching, it opened with an admiring
introduction by Norman Mailer and is still highly regarded by Hemingway
Precisely when Greg's demons caught up with him is unclear, but by the
early 1980s, the storm clouds were gathering. Meyers, who spent a week with
Greg and Valery while researching his book on Ernest in 1983, recalls that
Greg's marriage was breaking up and he was acting in peculiar, and sometimes
"He was very good-looking. He was very smart. I mean, you could have some
interesting talks with him. He was also, always, very crazy," Meyers says.
By the early 1990s, Greg's finances were so precarious - he was routinely
spending every dime of the checks he received monthly from the family estate -
he at one point lived in his beat-up Volkswagen. Apparently considering a sex
change, he had gone so far as to have a single breast implant, leaving the
other side of his chest flat.
He and Valery had been divorced, and his medical license had been suspended
in both Montana and Florida - the reason is not known because officials in
Montana, where the licensing problems originated, say they have lost the
But when he and Junkins, a Hemingway scholar and retired University of
Massachusetts English professor, began running into each other socially in
Miami in 1991, it wasn't his present problems that Greg wanted to talk about.
It was his past.
He told Junkins, who would later serve as best man at Greg's fourth
wedding, about the fit Ernest threw when he caught Greg cross-dressing as a boy.
"Gregory was 60 years old, and this is the first thing he tells me,"
Junkins says. "He says he never got over it: the raging wrath of his father."
Thirty years after his death, Ernest Hemingway was back in his son's life.
By 1995, the final showdown between father and son was well under way, with
Greg rejecting not only his father's hyper-masculine code of conduct, but
masculinity itself, in an act that some consider courageous and others depict
as the final, desperate act of an unbalanced mind.
For the most part, Hemingway lived as a man after his sex change. He had
the same deep voice, the same muscular build. Rather than adding a second
breast implant, he had the first removed at some point in the 1990s.
He stayed with his fourth wife, Ida Mae Galliher, a fine-featured blonde
who drove a Mercedes convertible and was much admired by Coconut Grove's
graying jet-setters. Florida records show the couple divorced in 1995, after
about two years of marriage, but friends say they continued to live together in
Ida's gated coral-rock cottage.
"He was a very heterosexual guy, I guarantee it," Junkins says. "He and Ida
weren't putting polish on each other's nails." Ida, who declined to be
interviewed for this article, told the Miami Herald shortly after Greg's death
that she and Greg remarried in Washington state in 1997.
Hemingway mostly went by the name Greg or Gregory in the Grove, where he
frequented the Taurus Ale House, a neighborhood bar and restaurant, in men's
"He'd hang out in the afternoon, drink beer with us and talk," recalls
Taurus regular Charley Brown, 62, a writer. "And he was just one of the guys."
Rumors about Greg's personal life did flourish, and occasionally he would be
spotted cross-dressing. But in resolutely artsy, often bizarre Coconut Grove,
Greg Hemingway wasn't the most unusual guy in the bar.
"Not by a long shot," Brown says.
Hemingway's apparent reluctance to let go of his male identity could be
explained by many factors, among them the potential for embarrassment. But it
does seem a remarkable coincidence that, in getting a sex change, Greg chose
perhaps the one path most likely to pain and embarrass his father - and then
went on living his life much as before.
It's also interesting to note that when he did assert his femininity, he
sometimes seemed more interested in creating a spectacle than completing a
process of sincere self-transformation.
Perhaps the most dramatic example of that occurred in 1995, when Hemingway,
then 64, boarded a Miami bus, made a series of sexual advances toward the male
driver and threatened to break his jaw.
When police arrived, Hemingway was standing outside an Amoco station,
dressed in women's clothing and talking incoherently. Pulling up his skirt, he
said to one of the officers, "Let me show you that I'm a woman." The police
officer reminded him he was in public and told him to put down his skirt.
Hemingway responded by kicking the cop in the groin. It took three police
officers to handcuff Hemingway, who pleaded guilty to a felony charge of
battery on a police officer, but was never convicted.
The Miami-Dade Women's Detention Center is a long way from the Miami of
snow-white sailboats and gated Spanish mansions where Greg Hemingway celebrated
the running of the bulls at the annual Pamplona Party in Coconut Grove.
A battered pay phone stands outside the center, a bland, four-story
building framed by scrub grass, a highway overpass and a series of rusty pipes
enclosed in a chain-link fence.
Inside, the faint smell of disinfectant lingers in a pale green lobby with
peach trim. A row of broad- shouldered, unsmiling women play volleyball in a
Hemingway, who was examined by a corrections medical staff, was classified
as female and assigned here "basically because of his genital organs,"
according to Janelle Hall, a spokeswoman for the Miami- Dade corrections
"It would have been an injustice to hold him in a male facility," she says.
Hemingway, who died of heart disease and high blood pressure on Oct. 1,
spent the last days of his life on the third floor, in a private cell used for
high- profile inmates. The room is 10 feet by 10 feet, with a steel cot and two
Staff recall him as "a very big, robust, very learned sort of person," Hall
says. "He did not give us any problems." At the jail, his death was just
another in the long series of hard-luck tales common to the place. To the
outside world - his obituary, which referred to his sex change and various
psychological problems, ran in publications across the country - it may have
seemed a scandal and sensation.
But in Coconut Grove, where Hemingway was well known and well liked, it was
a tragedy, a tragedy that some say could have been prevented.
Standing outside the house where Ida Hemingway still lives, handyman Terry
Fox speaks of his friend Greg in the present tense as he fixes the automatic
gate Greg smashed with his car shortly before his death.
"I don't think they should do that to him, ya know?" he says of Hemingway's
incarceration. "We're real upset about that. I mean, the average burglar gets
out the next day."
Lorian Hemingway goes further, claiming that her father didn't receive
vital medication while in jail.
"I do not know to whom to assign blame," she says, "But I think his having
been incarcerated for five days on a bail of a mere $1,000 and having his life
end because he could not have the medication he needed is a criminal act,
outright." Ida Hemingway told the Miami Herald that she called the jail
repeatedly, but that she didn't bail Greg out because she thought he needed
Hall declined to comment on whether Hemingway received his high blood
pressure medication in jail, citing inmate confidentiality. Larry Cameron,
director of operations for the Miami-Dade Medical Examiner Department, declined
to comment on medical details, saying Ida Hemingway had requested that the
family's privacy be respected.
Greg Hemingway apparently did not contact his friends, several of whom said
they would have been more than happy to supply the $100, or 10 percent,
required to secure his release on bond.
Guests cried openly at Greg's small, private memorial service in Coconut
Grove. Hemingway's children spoke of the good times.
"These kids adored him. It says a lot about Gregory," Junkins says. "They
know everything. Of course they do. You know, he was their father."
Exiting the turn-of-the-century Spanish mission church where the service
was held, glancing back at the twin splashes of hot-pink bougainvillea framing
the front door, it must have been easy for those who attended to think
comforting thoughts about God, nature and the afterlife.
But it's not at all clear that the deceased himself would have taken refuge
in such consolation.
If he had proved one thing during his long and torturous battle with his
father's shadow, it was that he, too, was a Hemingway: stubborn and
self-destructive, but also fierce and uncompromising.
Forty years before, he had considered voicing comforting cliches at his own
father's funeral, he wrote in his memoir.
He had envisioned the old man alive, aware and dreaming, a spirit united at
last with earth and sky.
But, he wrote, such visions seemed small to him, and their comfort shallow.
And his father would have considered such visions absurd.
"Atoms can't dream, Gig," he could hear his father say. "No use deluding
yourself, old pal."
Chicago Tribune is a Tribune Co. newspaper.
A Family History
IT'S SAFE to say there are few families as fascinating as the Hemingways. Here
is a brief look at some of the family members and their lives and their
Start, of course, with Ernest. Regarded as one of America's greatest
authors, he won a Pulitzer Prize in 1953 and the Nobel Prize a year later. His
adventures included driving a Red Cross ambulance during World War I, covering
the Spanish Civil War as a news correspondent and living in Africa, where he
went on countless safaris and survived two plane crashes. All pretty macho
stuff. But he also was the boy whose mother, Grace, dressed him and his older
sister, Marcelline, as twins. Some speculate that was the root of Ernest's
attitude toward women - he long resented Grace and refused to attend her
funeral, married four times and had countless affairs. He died in 1961, the
victim of a self-inflicted shotgun wound, after years of physical and mental
problems. He was 61.
Clarence Edmonds Hemingway, Ernest's father, took his own life in 1928.
Suffering from diabetes and depression and facing debts, he shot himself to
death with a Civil War pistol. He was 57 years old.
Grace Hall Hemingway, Ernest's mother, was a former singer and music
teacher. She was extremely protective of her first son. As he grew older, he
rebelled against her nurturing - and later against her criticism of his work.
To friends, he referred to her as "the bitch." She died in 1951 at 79.
Marcelline Hemingway was Ernest's older sister and the sibling to whom he
was closest. She maintained a famous correspondence with her brother for many
years. Marcelline died in 1963, two years after Ernest. She was 65.
Ursula Hemingway Jepson, Ernest's younger sister, having survived three
cancer operations, committed suicide with a drug overdose in 1966. She was 64.
Another sibling, brother Leicester Clarence Hemingway, 67, shot himself to
death in 1982 after a series of health problems.
Carol Hemingway Gardner, Ernest's youngest sister, was estranged from her
brother after he objected to her choice of fiance and she married the young man
anyway. She today is the last surviving Hemingway sibling.
Madelaine Hemingway Miller, nicknamed "Sunny," typed portions of her
brother's novel "A Farewell to Arms," and later played the harp with the
Memphis Symphony. She died in 1995 at the age of 90.
Jack Hemingway, Ernest's oldest son, had a pretty interesting life in his
own right. His godparents were Gertrude Stein and Alice B. Toklas, whom Ernest
had befriended in Paris in the '20s; his early days were recounted in his
father's "A Moveable Feast"; he was a decorated World War II veteran who spent
six months in a German POW camp; and he wrote several books, including one
about his father, and three on fishing. He died in 2000 of complications
following heart surgery. He was 77.
All of Hemingway's former wives are deceased. Martha Gellhorn, his third
wife, died most recently, in February 1998. Gregory's mother, Pauline Pfeiffer
Hemingway, died in 1951 at age 56 of an undiagnosed tumor.
Actress/model Margaux Hemingway, 41-year-old daughter of Jack, died of a
drug overdose in 1996. Her younger sister, Mariel, continues to appear in films
and on TV.
Hemingway's sole surviving child is son Patrick, born in 1928. He continues
to promote his father's memory as a member of the advisory board of the
Hemingway Foundation of Oak Park.