What is the first bar that comes to mind when you think Key West? Most likely Sloppy Joe’s, the famous watering hole of Ernest Hemingway is a Key West tradition steeped in history. Founded on the very day prohibition was repealed, December 5, 1933. The bar actually went through a of couple name changes before Sloppy Joe’s was chosen with encouragement from the infamous Ernest Hemingway.
Fearless rum runner/bootlegger & speakeasy operator Joe “Josey” Russell and his friend, customer and fishing companion Hemingway formed a special bond during the writer’s residency on the island. After the inevitable failure of “Operation Dry America” Russell found himself on the up & up as a genuine saloon keeper and business owner of a dump called the “Blind Pig” which cost him a whopping three dollars a week to lease the building. The pig was located around the corner where Capt. Tony’s Saloon still stands. (Fascinating history there too!) http://www.capttonyssaloon.com/ Built in 1852 the building served 2 important purposes. It was an ice house (very important due to the heat in Key West) and the city morgue (also very important due to the heat in Key West).
Thought to be haunted, the bar now houses the “hanging tree” where 16 pirates and a woman who took a knife to her husband and 2 children met their maker. Known as The Lady in Blue, (nicknamed for the color of her dress during the hideous killing spree and the color she turned during the ….)
In 1898 a telegraph was housed in the same building. Famous for informing the world during the Spanish–American War that the battleship Maine was destroyed, when the news came from Havana to Key West.
Over the following decades it housed speakeasies, a bordello, a cigar factory and an early gay bar. The Navy forbade their men from patronizing the establishment which was ultimately forced to close and remain empty for quite some time until Anthony Tarracino opened its doors in 1958 as Captain Tony’s.
Not long after Joe Russell attained the Blind Pig in 1931, the ratty ramshackle establishment added a dance floor and changed its name to the "Silver Slipper" where in addition to gambling, gossip and ten cent shots patrons could now kick up their wobbly heels.
An Old Havana bar and fish market where Joe “Josie” Russell and Hemingway spent considerable time while in Cuba was owned by another friend, Jose Garcia Rio. Joe’s Cuban bar was ridiculed as being sloppy due to constantly melting ice that made a big mess of the floors….. Hence Havana’s aptly monikered “Sloppy Joe's”. One thing led to another….. and one drink led to another…. and the Silver Slipper became the now famous Sloppy Joe’s at the urging of Hemingway!