Gregory Hemingway is the third son of Ernest Hemingway and his second wife Pauline Pfeiffer.
Gregory graduated from the University of Miami Medical School and practiced medicine in New York and Montana. In 1988, his medical license was revoked by Montana authorities due to his alcoholism.
In addition to alcoholism, Gregory struggled with mental illness, drug abuse and ultimately had sex reassignment surgery.
Gregory's 1976 book, Papa: A Personal Memoir explores his strained relationship with his father. He comes to the conclusion that: "I felt profound relief when they lowered my father's body into the ground and I realized that he was really dead, that I couldn't disappoint him, couldn't hurt him anymore."
Gregory was married four times and was the father of eight children: Patrick, Edward, Sean, Brendan, Vanessa, Maria, John and Lorian.
On September 26, 2001, Gregory Hemingway was walking around naked in Key Biscayne, Florida. He was carrying a woman's dress and high heels. He was arrested on an indecent exposure charge and sent to the Miami-Dade Women's Detention Center. He died there of heart failure on October 1, 2001.