It has been four years since Gregory Hemingway, the third and youngest son of Ernest Hemingway, died. The strange circumstances surrounding his death while tragic were not entirely unexpected, for Gregory Hemingway was as tortured an individual as his father.
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. Gregory's cross-dressing tendencies seem to have blossomed at an early age and it was a practice he continued throughout his life. Ernest was aware of his son's peculiar preferences and it created a great discord in their relationship. An even greater discord would have been realized if Ernest was alive to see his son undergo a sex change operation in 1994.
I remember seeing Gregory speak on the A&E biography: Ernest Hemingway: Wrestling with Life. At one point in the program, he said of his father: "You naturally incorporated his standards which were extremely high and extremely hard to live up to. So as long as you were doing well and satisfying this inner need to do well, it was great being his son, but you felt failure much more acutely I'd say. I wanted him to love me, to love me, yeah." I do believe that Gregory Hemingway was genuine in his comments and that he wanted his father to love him. That love would have been a very positive force in Gregory's life. I am convinced, however, that Gregory Hemingway would have needed much more than a father's love to curb his self-destructive lifestyle.