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To be the son of a great man is a
high fortune, a considerable advantage.
But it is likewise an oppressive burden,
a permanent derogation of one's ego.
Dr. Gregory Hemingway, Ernest's youngest son, was a demonic, Dostoyevskian figure. Handsome and dynamic, yet reckless and self-destructive, manic and at times insane, he was an extreme case of transgender tragedy and a salutary warning. He struggled throughout his life with inherited mental illness and suicides, had four marriages, four divorces and eight children, and many personal failures. He was also brilliant and gifted, practiced medicine in New York and Montana, and wrote a penetrating memoir of his father. My cautionary tale—partly based on personal relations with Greg—describes his bizarre and fascinating life, and explains the complex reasons for his manic depression, serial marriages, compulsion to wear women's clothes and deep-rooted desire to change his sex. Despite his recurrent disasters, the impulsive and irrational Greg emerges from all his ecstasies and dangers as suffering and sympathetic, brave and weirdly impressive.
Greg, Ernest's son by his second wife, Pauline Pfeiffer, was born in Kansas City in November 1931. Both parents wanted a daughter: Ernest had two sons and Pauline hoped to please him. When Greg was born, Ernest was disappointed and Pauline felt guilty. Both resented the infant whose difficult birth had threatened Pauline's life and who turned out to be the wrong sex. During his childhood, Greg felt ignored and unloved. Ernest and Pauline took many long trips away from home and left him to be brought up by the severe and frightening nanny, Ada Stern. A silent, tyrannical blue-eyed Germanic spinster from