Most trips to Key West include a stop at its most famous bar, Sloppy Joe’s on Duval Street, but for those who want a little literary history and a whole lot of morbidity with their cocktail, the “Sloppy Joe’s” where Ernest Hemingway used to sit and drink is right around the corner on Greene Street, now known as Captain Tony’s Saloon.
Josie Russell established Sloppy Joe’s on Greene Street in the 1930s, and when the rent was raised by a dollar per week in 1938, the bar relocated to its more well-known site on Duval. The building that was formerly Hemingway’s watering hole underwent various changes until it was purchased by Captain Tony Tarracino, who established Captain Tony’s Saloon.
The building has a lengthy and gruesome history, dating back to the early nineteenth century. Visitors will see a big tree within the bar; this was the gallows tree in the open courtyard where judgments were held, and the structure was eventually erected around it.
At least 75 persons were hanged here for piracy, along with other criminals. Ironically, the tree is still alive; it stretches through the roof, and despite Hurricane Irma removing much of the top, at least six inches of the tree can still be seen above the building. Surprisingly, it still develops twigs and leaves inside the dimly lit pub.
Throughout its history, the structure has served as a morgue, bordello, telegraph office, speakeasy, and cigar factory. During refurbishment work in the 1980s, the floorboards were removed, revealing the bones of 15-18 persons.
Among them, a gravestone for a young woman named Elvira Drew was found. Elvira was married in her mid-teens to a 50-year-old abusive alcoholic. Elvira died in 1822 at the age of 19, hanging on the winter solstice over two centuries ago for murdering her husband; self-defense was not a credible reason at the time. Her tombstone now rests beside the pool table indefinitely, or at least until the pub is renovated again.
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Another gravestone in the bar beneath the ancient hanging tree belongs to Reba I. Sawyer, a Key West native who lived from 1900 until 1950. Following her death, her husband discovered scandalous letters between his wife and another guy. The letters described their trysts and how they planned to meet at Captain Tony’s Saloon. The widower husband pulled his cheating partner’s tombstone into the bar, positioned it under the tree, and allegedly said, “This is where she wanted to be, so this is where she will stay”.
There are considerably more bodies under the floor than gravestones–some graves are flat with the existing floor level, while others are beneath it. So wherever you go, you’re treading on someone’s grave. And, before you go, make sure to say farewell to the resident skeleton, who is now propped up and dressed nicely inside the bar.
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