The building housing Captain Tony's Saloon has a history as colorful as the town of Key West itself. When first constructed in 1852, 428 Greene Street was an ice house that doubled as the city morgue. In the 1890s, it housed a wireless telegraph station. The telegraph's most important utilization came in 1898, during the Spanish–American War. The battleship Maine was destroyed, as the news came from Havana to Key West and it was reported all over the world from this building.In 1912, the building was home to a cigar factory. Later, it was a bordello and a bar popular with the Navy until it was forced out of business. After that, it became several speakeasies, the last of which was named The Blind Pig, specializing in gambling, women, and bootleg rum.
Founded on December 5, 1933, the bar's most famous patrons were Ernest Hemingway and the infamous rum runner Habana Joe. The original location at the time Hemingway frequented Sloppy Joe's is a few doors down to the west, just off Duval Street, at 428 Greene Street, and is now called "Captain Tony's Saloon".
The bar went through two name changes before settling on Sloppy Joe's with the encouragement of Hemingway. The name was coined from the original Sloppy Joe's bar in Old Havana, that sold both liquor and iced seafood. In the Cuban heat, the ice melted and patrons taunted the owner José (Joe) García Río that he ran a "sloppy" place.
The bar is the site of the Ernest Hemingway look-alike contest, started in 1981. It is well known as a tourist attraction, with live bands and slushy drinks. On November 1, 2006, it was added to the National Register of Historic Places.