Remembering Gregory Hemingway

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.

Posted on October 02, 2005 | Six comments

I never knew his son had such a tortured life. It would have been difficult, indeed, to have been Hemingway's child, I feel. I'll have to get a copy of the biography when I can.

— Liz | October 07, 2005

Love from your parents can make a you cry with happiness and weep in shame at the same time.

Knowing how much Hemingway disliked violence and useless bloodshed, I think he would have been greatly saddened by his son's death, despite the suggestion that he bore little love for him and was estranged by his curious habits.

Also, I think that if only father and son could have reconciled, it might have prevented a lot of suicides within the Hemingway family.

Never underestimate the power of love or hate.

— ian | October 29, 2005

I have read most of the bio's on EH (Hotchner, Fuentes, L. L. Hemingway, J. Hemingway, Carlos Baker, among others) None told of the Gregory's nature better than "Running with the Bulls" by Valerie Hemingway (Gregory's former wife and personal assistant to EH from 1959-1960). No holds barred and a very personal look into his life.

— Thomas | November 15, 2005

Ernest Hemingway had a difficult childhood and that coupled with his alcoholic bouts and womanizing and constant search for excitement in blood sports lead straight to the loony bin. It's truly a pity that he never gave his progeny the one thing he himself lacked so much: LOVE!

— jeff | June 03, 2009

I love it! This is what makes Hemingway such an intriguing subject. He was nuts - if he hadn't been - we probably wouldn't still be obsessing over him this long after his death. And the fact that his son was a transexual, well, that's just icing on the cake, I'd say.

— rot hamden | September 16, 2009

I had to smile over Ian's comments that Ernest "disliked violence and useless bloodshed." That wasn't Ernest at all. He relished war, illegally participated (as a correspondent) in warfare, claimed to have personally killed Germann (however many, even one is too much) when he was prohibited to carry arms; he would get friends and acquaintances drunk, invite them outside in the dark, punch them in the stomach and leave them lying on the sidewalk; his temper was hair-trigger, always quick to fight, saw most things as a slight, and knocked down the poet Wallace Stevens, a man 20 years his senior. Oh, and he shot a round into the ceiling of his Key West (in anger) and shot off the lock of his writing studio... Oh, he shot no less than five cats dead when a vet could have put them to sleep... And he marooned a three-time Pulitzer Prize recipient on a mosquito-ridden, fresh water-less Dry Tortugas island after an argument... Anyone want to be friends with Pauline instead?!

— Mr. Grey | June 25, 2010