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.

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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. You can still see the chains in the walls where horses were tied up after they transported chunks of ice into the building when it served as an ice house. At the very center of the Saloon grows a huge tree that disappears through a hole in the roof. This is the infamous “hanging tree” from the branches of which convicted pirates and murderers were strung up and hung. Their ghosts are said to still haunt the place. Hundreds of license plates, business cards and countless women's bras hang from the ceiling and walls. Every bar stool is painted with the name of a famous person who visited or frequented the bar.

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Photo credit: www.huffingtonpost.com

Next to the pool table, exposed in the cement, lies the grave marker of a young woman named Elvira Edmunds that was discovered, along with the skeletal remains of dozens of people, when the old floor boards were removed during renovation. These are presumed to have come from the time when the building was a morgue.

There is another grave of one Reba Sawyer located at the foot of the hanging tree. The legend goes that Reba Sawyer was cheating on her husband, having secret rendezvous with another man at Captain Tony's Saloon. Her husband didn’t find out until after her death, but when he did, he was so enraged that he pulled her tombstone out from the cemetery and dumped it inside the bar, saying “this is where she wanted to be, so this is where she will stay”.

According to historian Tom Hambright, many of these stories including the names “Reba Sawyer “ and “Elvira Edmunds” were invented by Tony Tarracino to keep his patrons interested and engaged.

“He loved to tell a good story, and he made up a lot of them about the saloon,” writes Dave Lapham in Ghosthunting Florida. “If a story went over and interested people, he’d keep embellishing it, dragging it out as long as possible. After all, if people were in his bar listening to his stories, they also were drinking. It was good for business.”

Tom Hambright is also of the opinion that the building was neither a morgue nor an icehouse. Tom says that Key West didn’t have a morgue until recent times, although some places were used as makeshift morgues at times of natural disasters or epidemics. The icehouse theory is also questionable since the walls are too thin, and there was sufficient evidence that there was an icehouse at another place.

Whatever be the truth, the legend of Captain Tony's Saloon lives on. With live entertainment every afternoon and a live band every night, the place is very popular among locals and tourists alike.

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