The True Story of Ernest Hemingway's Favorite Bar

Three places lay claim to the title, but there can be only one.

Photo: A. Palmer/ClassicStock

In the 56 years since Ernest Hemingway died, even the most mundane details of his daily existence have taken on mythical proportions. Where he vacationed as a child, his favorite drink or where he liked to get a baguette are routinely debated by the literary-inclined.

Hemingway lived in Key West for about 12 years, owning a house there that is still populated by the six-toed (supposed) descendants of his beloved cat Snowball. It's also no secret that he was a man who enjoyed a drink or several, routinely spending his evenings in a particular watering hole named "Sloppy Joe's."

Today, Sloppy Joe's on Duval Street is a Key West icon and pridefully plays up their Hemingway connection in every way possible - including plastering his face on t-shirts and hosting an annual Hemingway look-alike contest. Mere feet away and around the corner is another bar, "Capt. Tony's." They too sell merchandise and have taken their own piece of the Hemingway legend by claiming they were "The First and Original Sloppy Joe's." For years, the bars have engaged in legal battles to settle once and for all who can trademark themselves as the original "Sloppy Joes."

Here's the thing, though: They are both wrong.

It was 1918 when Spanish bartender José Abeal y Otero finally got tired of working for others. A decade and a half earlier, he had arrived in Havana from Spain to serve drinks to thirsty patrons. His craft had taken him north to the United States - including bartending gigs in New Orleans and Miami - before coming back to Cuba and getting a job at the "Greasy Spoon." But enough was enough. Using the money he had saved, he bought a small bodega and opened his own bar. It's unclear what Otero first called it, but when old friends from the States came to visit him - who called him "Joe" rather than "Jose - they had a suggestion. According to the bar's 1932 cocktails manual, upon seeing the state of the bar, they exclaimed, "Why Joe, this place is certainly sloppy. Look at the filthy water running from under the counter." They started calling the downtown Havana bar "Sloppy Joe's." The name stuck.

"Sloppy Joe's" on Agramonte and Animas Streets in Havana became a frequent haunt for Americans escaping their country's ban on alcohol. Despite its outer appearance, and according to their own advertising at the time, Otero believed in "genuine" ingredients and the bar was always "supplied with all the best liquors wherever produced, regardless of cost." Otero's clinetelle was diverse — from prostitutes to celebrities like Frank Sinatra and boxer Joe Louis to regular, well, Joes. Hemingway was also a frequent patron. While the opening of Havana's "Sloppy Joe's" predated the author's move there by about a decade, he liked to vacation on the tropical island (there was alcohol there afterall). And he was often joined by his friend and bartender Joe Russell.

At this time, Joe Russell was likely running a speakeasy in Key West. These trips to Cuba with Hemingway also perhaps doubled as rum-running expeditions. But after 13 years of the so-called "Great Experiment, prohibition was repealed. Now running a legal business, Russell was looking to expand so he purchased the old city morgue on Greene Street in Key West. He turned it into a bar and named it "Sloppy Joe's," essentially stealing the name of the more-famous and original establishment 90 miles away in Havana.

While it may not be the first "Sloppy Joe's," today's "Capt. Tony's" was absolutely a regular stop for Hemingway. Hemingway haunt. After all, his buddy Joe Russell owned it. "No doubt, [it] is where he did most of his drinking," says Monroe County historian Tom Hambright, "It was a real dive, though, so I'm sure he didn't take (his wife) there." Literary historians also believe that the bar was the inspiration for "Freddy's" in Hemingway's Key West-centric novel To Have and Have Not. In 1937, perhaps upset that his rent was being raised by six dollars, Russell moved the bar about a half block to Duval Street. One version of the story says that Hemingway financed the move (Hambright says there are no records of this, but doesn't rule out the potential that the author gave his friend cash).

Meanwhile, in 1965, the Castro-led Cuban government shutdown the original "Sloppy Joe's." But in 2013, it was restored and reopened. Reviews are mixed.

In truth, while there is only one original "Sloopy Joe's" and it's in Cuba, Hemingway probably drank at all three bars. As Hambright puts it, the great writer "was not drink-shy."

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