Sloppy Joe’s, Captain Tony’s, and the Fight for Hemingway’s Barstool

Where did Papa Hemingway refuel after long days of fishing and writing in Key West? Owners of both Sloppy Joe’s Bar and Captain Tony’s Saloon claim to be the favored watering hole for the Pulitzer and Nobel Prize winner. Was it Sloppy Joe’s, an up-scale bar which rakes in $10 million in profits each year from thirsty tourists? Or is it Captain Tony’s, a drinker’s bar with no pretensions to décor, no food, and no umbrellas in the drinks? Which bar stools did Hemingway sit on?

In Hemingway’s time, Prohibition led enterprising individuals to run profitable, and illegal, side businesses. Joe Russell, one such businessman, met Hemingway when the writer came looking for some good Scotch. It was, they say, the beginning of a beautiful friendship. Through name changes and an impromptu move down the block, Hemingway wiled away the hours on Sloppy Joe’s wood bar stools, even modeling a character in To Have and Have Not after his friend, fishing companion, and drinking buddy, Joe Russell.

Not so, claims the former owner of Captain Tony’s Saloon, Tony Tarracino. The original Sloppy Joe’s was run by Joe Russell, yes, but in the building where Captain Tony’s is now – a former city morgue, no less. Tony himself is quite the character – on the run from the mob in New Jersey, he came to Key West. Another fishing buddy of Hemingway, Tony claims his counter stools were the ones Hemingway drank his Scotch and mojitos. Who is right? Who is the “original” Sloppy Joe’s? Ernest Hemingway wrote, “I know now that there is no one thing that is true – it is all true.” So whether he drank at one, the other, or more likely, both bars, doesn’t really matter. If in Key West, do what Hemingway would do: grab a drink from both and go fishing.