In many of the locations that I love to visit most (Cuba, Miami, the Florida Keys), Ernest Hemingway is synonymous to Jimmy Buffett. The name alone embodies the good life, masculinity, the alpha male, sport-fishing, marina life and living the ultimate coastal American dream. Hemingway is often used as an adjective to describe homes, lifestyles, boats, and even cats. Look alike contests for grey bearded men, yacht clubs where affluent boat owners can dock, family estates from days gone by and even a men’s cologne and a darn good bottle of rum bear this famous name.

I originally heard about John Hemingway while reading Mozos, A Decade of Running with the Bulls by Bill Hillman. John is the grandson of the Nobel Prize Laureate, Ernest Hemingway. Hillman mentions John in the book after meeting him in Pamplona, Spain for Fiesta (the running with the bulls). Hillman also referred to John’s book, Strange Tribe, which documents the bizarre relationships between Ernest and his son Greg and later Greg’s relationship with his son John.

John Hemingway

Strange Tribe, John’s memoir, vividly charts his unorthodox upbringing with a crossdressing father who was absent for extended periods of time during some of his critical years. His father, Greg, also had an interesting and often strained relationship with Ernest, who had a bold sense of masculinity both in his writing and his lifestyle. The book charts a tangled web of sexual confusion, marriage, divorce, mental health, and strained family dynamics.  The gripping read left me with more questions than answers, as it dissected the splintered family history of one of America’s favorite literary heroes.

I had the chance to talk with John, who now lives in Montreal, by phone about his memoir, his new novel “Bacchanalia”, and of course Ernest. John is somewhat removed from the fame and attention that comes with having Ernest Hemingway for a grandfather. He set out on his own path long ago, living 20 years in Italy, and now residing with his wife in Canada. John still participates in family promotions such as with Hemingway Pilar Rum in Key West but for the most part, he sticks to his own writing. In addition to publishing his memoir and novel, John is currently working on a collection of short stories and another novel.

Do you feel that the complicated family relationships that you describe in your memoir helped you to grow and shape you into the person you are today?

You know, it required me to get to the root of my father’s behavior. For a long time in my life, I just did not connect on any level my dad with Ernest. I mean, Ernest was a macho guy. But after doing some research, Why shouldn’t they have a connection? You don’t think of Ernest Hemingway and my father, who was a cross dresser and eventually had a sex change, as having a connection but, there is a connection. After an extensive dive into his writings, Ernest was what I would call “straight with a chaser”.  He was complicated. He was macho, very much so. He enjoyed hunting and deep-sea fishing. He was nearly killed in the First World War when an Austrian shell landed in the trenches where he was. He was also heavily influenced by poet and fascist sympathizer Ezra Pound as well as writer Gertrude Stein, a lesbian who introduced him to Pamplona. He then asks me to remind him of the question. I do and he concludes that family is important to the Hemingways and that loyalty is important, too. They all helped shape him.

My mother-in-law has described Ernest’s writing as “dripping with testosterone”. Would you say that in some way his lifestyle and his writing was an attempt to overshadow his confused (Ernest was dressed as a girl when he was young and made to play the cello) upbringing?

You know, I mentioned Gertrude Stein because she was an open lesbian and a tremendous impact on my grandfather’s style. However, Ernest wasn’t just Gertrude Stein. His mother was rumored to be bisexual. His father suffered clinical depression and eventually killed himself. But Ernest was intensely passionate about hunting, fishing, the outdoors, and biology. He was able to convey his experiences in his writing. I think he took on the style and personality of everyone around him.


Would you say that Ernest would be proud of your writing today?

(long sigh ) I don’t know. I think he would like some of it. He probably would be vey critical. I think he would like Bacchanalia because it’s based on my own experiences and feelings. Also, the spirit of Fiesta hasn’t really changed that much in the hundred or so years that have passed since the publication of his book. I would be proud, of course, if he did like it but I’ll never know.

Would you say that you have the same adventurous spirit and like having the same types of “bold” experiences that your grandfather enjoyed?

I like things like running with the bulls, hunting, and fishing. One of my dreams that I hope I can see through is to sail across the Atlantic. I did a lot of sailing when I was a kid but that was mostly small boats.

Do you have any involvement with the family to promote the Hemingway brand and help to keep the legacy of your grandfather alive?

The family licenses the name to the Hemingway Rum Company. I’ve actually been down to Key West to help promote it and sign bottles of the Pilar rum along with my book. I also do some speaking occasionally. I don’t really commercialize anything personally, however.

I personally have a fascination with Cuba that it seems we share. So, I want to ask…do you have any idea if Ernest had a personal relationship with Fidel Castro?

I don’t think he had any direct involvement in the Revolution, but he would have certainly been aware of the ongoing issues with the Batista regime. I am sure he probably supported a lot of the ideas of the revolution such as helping the poor, health care initiatives, and access to education. They [Cuba] produce some of the best baseball players in the world. There’s a lot that unites the US and Cuba. It’s more than just politics. As someone who was born and raised in Miami, it’s probably the largest Cuban occupied city outside of Havana. (He never answers the question on the relationship with Fidel… )

How did the running with the bulls become such a prominent part of your family’s history from your grandfather down to you?

John Hemingway with friends at Fiesta

My grandfather was introduced to Pamplona through Gertrude Stein. She felt he would understand it. Ernest never actually ran with the bulls. He played with the cows and was more of an observer. He liked to party at fiesta. Apart from me, my brother Sean has run with the bulls. I have been about 17 times, myself. It’s a cool thing. Total adrenaline. There’s a lot of partying and debauchery. It will be interesting to hear your opinion of the book if you have never been. People who have tend to like it because it reminds them of their own experience. I’m curious to get your thoughts as someone who has never witnessed it first-hand.


What is it like living in the shadow of a Nobel Laureate and perhaps America’s most famous author?

It was more difficult when I was younger because I was still trying to find my own voice as a writer. It’s difficult to write with someone else’s voice. You should always try and write with yours. My ability will be inherited but it will be different from my grandfather’s. Also, I am not trying to compete against anyone. I really admire the guy and I think he is a great writer, but my competition is with myself. First, he’s my grandfather. You can relate to that. I could never idolize him as a writer as some of my friends do because I am so connected with the family. It is much more personal than that. I never knew him…he died when I was 11 months old. I admire him as a writer but to me, he’s the father of my father.


I have a bit of a fascination with the Hemingways. Occasionally, I enjoy a Pilar Rum with ice along with a cigar and dream about a lifestyle that seems almost unimaginable. We have even had a couple of “Hemingway dinners” (yes, we actually call them that) with friends. Now, after this interview, I’m more curious than ever. I just ordered John’s book, Bacchanalia on Amazon. I am looking forward to reading it and sending him my feedback.

I am impressed with the way John has emerged from the shadow of his grandfather to make a name for himself as a writer. The interview was only a short excerpt from our conversation. He’s a great storyteller, a trait that I’m certain is hereditary. I am also looking to a post COVID-19 life where I hope to make a trip to Pamplona and experience Fiesta with John, who I’m sure has plenty of stories to share!

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