The legend is often told in history books: Jose Gaspar was born in Spain in 1766 and served in the Spanish Navy aboard the ship Floridablanca. Supposedly he became a high-ranking advisor to King Charles III, but had to flee after he was falsely accused of stealing the crown jewels. Vowing revenge on his country and on mankind in general, he renamed himself Gasparilla the Pirate and terrorized the coast of Spanish Florida for the next 38 years. Purportedly his headquarters was on Gasparilla Island, and he kept women as concubines on Captiva Island.
In 1821, that fateful year Spain sold Florida to the United States, Gasparilla considered retiring from his pirate ways but was tempted to have one last adventure in plundering a British merchant ship. That ship, however, turned out to be the American pirate-hunting schooner, the USS Enterprise - which overtook Gasparilla's ship and disabled it in short time. Refusing to surrender, Gaspar attached himself to the anchor and jumped, shouting "Gasparilla dies by his own hand, not the enemy's!"
Problem is, despite this story having made it to scholarly journals, it's uncertain today whether there's a lick of truth to any of it. There's no verifiable record of Gaspar having actually existed, with the first known mention of him being in a railroad company advertising brochure circa 1900. A young pirate who supposedly witnessed Gasparilla's suicide was one Juan Gomez (note same initials) who claimed to be the world's oldest man and regaled impressionable Florida tourists with specious tales of his pirate days in the 19th century.
None of this stops the Gasparilla Pirate Festival from taking place every year in Tampa, however. Nor should it. If Gasparilla wasn't real before, he most certainly is now, manitous and thoughtforms being what they are.
The festival is less about historical accuracy than a damn good excuse to dress up in pirate gear and drink mead. It's become something on a par with Mardi Gras in New Orleans, with parades, floats, and actual Krewes that plan and plot all year round for the event. And also, of course, scantily-clad folks covered in beads.