It seems as if pirates and the Florida Keys should go together like rum and lime. And they do, in the sense that stories of pirates are often passed around by barstool historians while sipping rum. Contrary to their legendary status, there are scant accounts of pirates physically being on the island chain. Did they frequent the Florida Reef like bands of sharks in search of an easy meal? Absolutely – what better piratical prey than a ship floundering on the reef?

The most common form of piratical activity associated with the Florida Keys occurred when pirates would intercept a ship out at the reef, bring it back to one of the creeks separating the islands, and conduct their piracy in relative privacy. Rear Admiral Casper F. Goodrich studied the evidence of piratical activity in 1818 and published his findings in the “U.S. Navy Proceedings Magazine,” Volume 42. Among a number of other incidences involving pirates, Goodrich noted, “To these must be added the ship Emma Sophia, from Hamburg to Havana, which was boarded on December 19, by a piratical schooner of 30 tons, 1 gun, 30 men, between Bahama Bank and Sal Key Bank. The ship was sent to a small port formed by the Florida Isles and the Martyr’s Reef, and was plundered to the tune of $5,000.”

More often than not, however, these legitimate pirate stories take a back seat to the more legendary tales told in and about the Florida Keys. Take, for instance, the one about the dozen or 18 pirates strung up and dangled from the hanging tree growing in the middle of the legendary Captain Tony’s Saloon. 

Beyond the lack of supplemental documentation supporting the claim, it was the pirate-based motives of Commodore David Porter who arrived on Key West in 1823 with the mission of eradicating the pirates of the West Indies that punches the biggest hole in the story. It is universally agreed that Porter was quite good at his job. One of the things that made him so effective was that, unlike his predecessor Commodore James Biddle, when capturing pirates (even suspected pirates), Porter would hand them over to the English to deal with as they saw fit.

Unlike the American system of justice where pirates were taken into custody and tried before a judge, the English could simply have them hanged without any formal hearings. This is not to say that no one has ever dangled from Captain Tony’s legendary tree — a great deal of sh*t has gone down on this island chain since the days of piracy and the best legends are always based on kernels of truth. 

The legend of the hanging tree at Captain Tony’s is just one in a long list of pirate tales that have been told and retold. After all, pirate stories and this particular island chain should go together like, well, rum and lime. As for any piratical connection to Captain Tony’s, however, beyond the legendary Captain Tony himself, it more than likely begins and ends with the well-dressed skeleton hanging behind the bar.

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