Don’t Push Your Luck: The Saga of the Pirate Gasparilla

There’s nothing better than a pirate story, except a pirate story that offers buried treasure worth millions of dollars. Of all the buried treasure stories we’ve covered, this one may be the most authentic, and is certainly the most celebrated. So, pull up a chair, pour yourself a pint of spiced rum (it’s five o’clock somewhere) and travel with us back in time to the mid-eighteenth century when mighty sailing ships ruled the seas and being a pirate was, sometimes, a lucrative career choice.

Around 1756 José Gaspar was born in Spain, by most accounts to a fairly aristocratic family. He was described as being small in stature but large in ambition, which manifested itself early in life when he kidnapped a 12 year old local girl, holding her for a fat ransom. After getting arrested he was given a choice between joining the navy or going to jail. Opting for the navy, he quickly rose, eventually becoming Admiral of the Atlantic Fleet, then a naval attaché at the Court of Charles III in 1782 at just 27. At court he was romantically linked with several women, apparently all at the same time. After publicly jilting the king’s daughter-in-law in favor of another woman, a plot was hatched to frame him for trying to steal the crown jewels. Getting word of his pending arrest, Gaspar commandeered a ship named the Floridablanca, thus launching his career as a pirate.

Florida has a long history of being home to pirates and smugglers and Gaspar, who went by the pirate name Gasparilla, was one of the most successful pirates of all time and certainly the best known. The NFL football team the Tampa Bay Buccaneers and the Gasparilla Pirate Festival are dim echoes of the time when the Florida Gulf Coast was rugged and inhospitable; the perfect place for pirates to hide out between raids. Gasparilla set up his base just north of modern day Fort Myers, near Charlotte Harbor at the mouth of the Peace River. Still today you don’t have to get very far from a road to find yourself in some the most remote and inhospitable territory the Florida swamplands have to offer. If the heat, humidity and mosquitoes don’t get you, alligators, crocodiles (because alligators just aren’t scary enough) and every crawling, biting, stinging thing you can imagine are waiting to finish the job. There’s a reason Gasparilla was able to hide there for so long.

For nearly four decades Gasparilla raided ships of every nationality, by most counts between thirty-seven and forty ships before 1795. Another reason he was able to operate so long is Gasparilla didn’t leave any witnesses to tell the tale. The crew and passengers of captured vessels were killed, except for good looking women that he kept as concubines. Occasionally he would ransom high value women held on Captiva Island, where most locals believe the island’s name was derived.

Over the years Gasparilla and his men accumulated a lot of treasure and, like most pirates, buried it in chests in and around modern day Gasparilla Island and Boca Grande. This is where an amazing tale takes an even more bizarre turn. After decades as a pirate Gasparilla decided to retire. That retirement was partially because by the early 1800s the newly formed country of the United States was tired of having pirates operating out of its waters and decided to crack down. Gasparilla was tired anyway, being at a very old age for a pirate, and set about dividing up the treasure and disbanding his crew. And that’s where the story nearly ended.

With the treasure packed up and ready to disperse, Gasparilla spies what he thinks is a slow British merchant ship off the coast of Gasparilla Island. He decides on one last score and heads out after the fat target. When the Floridablanca, now an old ship, gets within cannon range the British ship strikes its colors and drops its facade to reveal that was actually an American man-of-war loaded with cannon, bizarrely named the USS Enterprise. It was a trap and Gasparilla sailed right into it. A fierce battle ensues but the Floridablanca is outgunned and outmatched and after taking numerous hits below the waterline and rigging she starts to sink. Vowing not to be taken alive Gasparilla wraps himself in anchor chain and, still brandishing a cutlass, jumps overboard into the gulf. The crew members who weren’t killed in the fight were later hanged as pirates in New Orleans.

Watching from the shore with boats full of treasure, the crew sees the Floridablanca lose the fight and quickly escape up the Peace River with the treasure to a place called Spanish Homestead. There they used some of the treasure to bribe Spanish Homestead’s owner, the intriguingly named Lady Boggess, to hide them from the Americans. The remaining pirates buried the rest of their treasure somewhere in the narrow, twisting channels of the Peace River and disappeared from history.

Years later $300,000 in gold coins was found near Spanish Homestead, a hint that the legend has at least some element of truth to it. According to accounts that treasure, and much more buried by individual crew members over the years, is still out there on the islands around Port Charlotte. One chest was allegedly buried near Lettuce Lake, an area which is now a state park…that anyone can poke around in… It’s certainly a story to contemplate while sipping your rum and planning your next vacation.