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Hemingway’s Key West Years 1928 – 1939

Hemingway lived his dreams, as shown by this grade school assignment. ( KW Museum)   Click for a larger view.

Thank you for your patience. The more I researched about this larger-than-life man, the more contradictions I encountered. The Hemingway Resource Center website suggests, “To find the truth about Hemingway, look first to his fiction.”

I did just that, along with gathering information from the Key West Museum, chatting with Key West historians, and poring through published biographies and online sources. If you find Hemingway a fascinating figure, too, you may wish to read his work and research to draw your own conclusions.

Ernest Miller Hemingway was an accomplished writer by the time he and his second wife arrived in Key West. John Dos Passos, his friend at the time, had recommended they stop there for a holiday on their return from Paris in April 1928.

Like many tourists to the tiny island, Ernest and Pauline were instant converts and determined to settle there. Perhaps it reminded them of the foreign lands they loved, while still part of the United States, situated as it is on the southernmost tip of Florida’s westward archipelago. After three years of renting apartments, the couple purchased a house in Old Town with money loaned by Pauline’s uncle.

907 Whitehead Street

Hemingway wrote the final draft of his bestselling A Farewell to Arms at their new home on 907 Whitehead Street, rising early each morning to write. He also published works such as Death in the Afternoon, Green Hills of Africa, and two of his most beloved short stories, “The Short Happy Life of Francis Macomber” and “The Snows of Kilimanjaro” during his Key West years. As for his family life, Pauline gave birth to two sons during this time, and outfitted their property with a luxurious 20′ x 60′ pool, carved out of the island’s coral bedrock for $20,000 in 1938.

At home by the pool (Courtesy Hemingway House)

When the midday tropical sun drove him away from his writing, Hemingway gravitated toward the water or his favorite watering hole. Whether his time away from home was a consequence or cause of an unhappy marriage, only Pauline and he would know for sure. Whatever the case, Papa Hemingway as the macho persona developed during this decade.

On land, Papa continued his lifelong enjoyment of boxing. The backyard of a brothel in Bahama Village constructed a boxing ring where he spent many happy hours. This site is now home to the popular Blue Heaven restaurant. According to R. Andrew Wilson’s Write Like Hemingway, Papa “was known to exaggerate his own experience in the ring,” athough Key West historians assure me he did spar with locals and won quite often.

He enjoyed his drink as much as the next man, spotted at Sloppy Joe’s most afternoons. The original Sloppy Joes was located on 428 Greene Street and has been renamed Capt. Tony’s Saloon. (The current Sloppy Joe’s bar at the corner of lower Duval and Greene came to be when the owner refused to pay a rent increase at the former site and relocated in 1937.) Joe “Josie” Russell, the bar’s owner, is said to have cashed a $1,000 royalty check for Hemingway when all the banks refused, earning him a close friendship with the writer.

“Tag and Release. Not!”

Papa was an avid fisherman, the photos of him throughout present-day Key West establishments an apparent  testament to his prowess. The picture to the right can be seen at the Turtle Kraals Bar & Restaurant.  For his extended fishing trips to Havana, Papa would charter Josie Russell’s boat. Fans of Hemingway’s final novel, The Old Man and the Sea, may be interested to learn that the character, Santiago, was inspired by Papa’s Cuban mate, Carlos Gutierrez. According to Hemingway’s personal accounts, this mate had fished marlin for forty years and was a gifted storyteller. Photos, including one of Carlos Gutierrez with Papa, can be viewed here.

Why did Papa ultimately leave Key West?

At some point in his island adventures, Hemingway met journalist Martha Gellhorn, his future third wife. As with Pauline while still married to Hadley, he had an affair with Martha before divorcing Pauline in 1940. In addition, his last book written in Key West, To Have and Have Not, was considered by many critics to be second-rate. Some say he moved on with a new wife to a new life for a rebirth of his career. Although he owned the house until his death in 1961, Ernest Miller Hemingway’s life in Key West ended in 1939.

Was Hemingway an example of art imitating life, or life imitating art? Or were both so intertwined it’s impossible to separate the legend from the writer?

What are your thoughts about Hemingway, either as a historical figure or American writer?

20 comments on “Hemingway’s Key West Years 1928 – 1939

  1. I’ve never read any of his work it never called to me to do so. Maybe it was the “macho” persona that turned me off. I have to admit you do make him sound interesting to me.

    1. Hi Donna! I plan to share some of my Hemingway favorites in future posts. Maybe I’ll inspire you to read a few pieces of his work. Note that his macho attitude is far stronger in his non-fiction work than in his fiction. I admire his writing and the effect it had on modern American writers; not necessarily his life choices.

  2. Fascinating Jolyce. I’m sure it took hours to research and write this post, so thanks soooo much for putting this together for us.

    P.S. All your posts have convinced me that I MUST visit Key West. So could you tell what’s the best time for tourist season? (not took overcrowded, but I like the weather really hot.) 🙂

    1. Hi Nicole! I’m excited to have garnered your interest in my favorite town. We like to getaway in mid-July to experience the quiet, the heat, and the mini-lobster season. We’ve gone in August but be prepared for more rainy weather and potential hurricanes the later in the summer you go. Early October is quiet also, and the weather is still quite warm.

      Feel free to contact me via email if you’d like to discuss more. Happy Spring! 🙂

  3. Great post. “Like Leessons of a Legend” by Captian Tony Tarracino tells great stories of Old Key West. It is not the easiest read but you will get a ton of interesting Key West tidbits.

    1. Hi Jeff! Thanks for the suggestion.

      You’re so right. I’ve only touched the tip of the iceberg that was Hemingway. There’s so much KW lore about his involvement with rumrunning during prohibition, his friendships (ie Charles Thompson), and his political leanings during the Spanish Civil War. And then there’s the writing…

      Thanks for stopping by. Happy Spring!

  4. He was an interesting man, but I don’t enjoy reading Hemingway. This area always looks beautiful. I must get there at least once in my lifetime! Great post, Jolyse. Fascinating.

    1. I find some of his short stories quite unsettling and thought-provoking. Of his novels, I liked The Sun Also Rises and The Old Man and The Sea but couldn’t get through For Whom the Bell Tolls. I also read (and enjoyed!) Nathanial Hawthorne, Willa Cather, Theodore Dreiser, and Henry James. Perhaps the history buff in me is why. His precise, succinct newspaper-style interspersed with poetic touches appeals to me as well.

      Thanks for your kind words, Julie. If you travel to Key West one day, I hope it brings you the joy it has us. 🙂

  5. This was so interesting. Like Julie, I don’t enjoy reading Hemingway, but he was a fascinating character. Which brings me to a question you asked at the end of your blog:

    “Was Hemingway an example of art imitating life, or life imitating art? Or were both so intertwined it’s impossible to separate the legend from the writer?”

    Have you ever heard “Saturday Night” by the Eagles? One of the lines of the song says, “Someone show me how to tell the dancer from the dance.” So my answer to your question is that Ernest Hemingway created his own mythology and the mythology became the writer. Jim Morrison did that. So did Elvis. And Janis Joplin. 😀

    I enjoyed reading this. Thanks for going to the trouble of researching and writing it.

    1. Thanks for stopping by, Catie, and for sharing your perspective. Hemingway’s interviews and non-fiction would lead one to believe he’d be the kind of person to create his own mythology. I’m happy you found the post interesting. I have many other stories about Hemingway–to be explored at another time. He fascinates me the way Elvis or Marilyn Monroe may someone else.

        1. I think you may surprise yourself. Some of his short stories have stayed with me for decades–poignant and stark. I love his unique mix of poetic devices with a newsman’s style. Quite raw, yet elegant too.

    2. Which the Eagles borrowed from the last lines of W.B.Yeats’ “Among School Children”. Check it out. I wrote my 1993 dissertation on Hemingway and few realize what made his prose so fascinating was that he was a failed poet (see his 88 poems) and used his poetic sensibilities in his pride fiction. The first paragraph of A FAREWELL TO ARMS is his finest poem. He also was more an intellectual than a boxer, with one of the largest libraries if any American author. Yet people only see the machismo he cultivated for the purpose of his fictional persona.

  6. I think of the reference to one of his books, “The Moveable Feast” in one of my favorite movies, “City of Angels” when I think of Hemingway. He’s accomplished a great deal in the short number of years that he lived, and I hope for all that he’s contributed to American literature (and culture), he has found peace.

  7. Wow! Great post, Jolyse! I never knew most of that about Hemmingway. Thanks for doing all the research and sharing. I think I could write a few good books there. What an awesome place. 😉

  8. Also, just a curiosity. But before becoming a professor of English Lit and Creative Writing I was an actor. I filmed a tv pilot in 1983 FEEL THE HEAT for three weeks in Key West many of my scenes were shot in Joe’s where Hemingway ‘s large photo figures prominently. Inspired, I wrote my first published poem followed years later by my own fiction.

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