A Hanging Tree, Graves And Hemingway: The Colorful History of Captain Tony's Saloon

There appears to be nothing remarkable about Captain Tony's Saloon housed in a yellow, two-storied building at 428 Greene Street in Key West, Florida. But the inside is steeped in history. Said to be the oldest bar in Key West, what is now Captain Tony's Saloon was the original Sloppy Joe's Bar, where legendary writer Ernest Hemingway spent most of his evenings. It was at Captain Tony's Saloon where well known folk country singer Jimmy Buffett got his start, playing for tips and beers —an experience he later described in the song "Last Mango in Paris." The pub’s other celebrity patrons include Truman Capote, Bob Dylan, Duane Cahill, Tommy Newell, and even John F. Kennedy and Harry Truman, among others. Photo credit: Sam Howzit/Flickr When first constructed in 1852, the building at 428 Greene Street was an ice house that later became the city’s morgue. The building then went through several incarnation becoming first a telegraph station, a cigar factory, a bordello, a gay bar, and several speakeasies specializing in gambling, women, and bootleg rum. Between 1933 and 1938, a local named Joe Russell operated a bar called Sloppy Joe’s at this place, and it became Ernest Hemingway’s favorite watering hole. The writer became so attached to Sloppy Joe’s that when the bar moved half a block down after a rent dispute with the owner, Hemingway insisted on having the urinal. He was of the opinion that “his hard earned money paid for it.” The urinal can still be viewed at the Hemingway House where it remains as a cat trough. The building eventually came into the possession of a colorful character named Captain Tony Tarracino, a local charter boat captain, who turned it into Captain Tony’s Saloon. Tony understood the historical importance of the building and was savvy enough to preserve the various elements of it.