José Gaspar, known by his nickname Gasparilla (supposedly lived c. 1756 – 1821), was a purported Spanish pirate, the “last of the Buccaneers,” who is claimed to have raided the west coast of Florida during the late 18th and early 19th centuries. Though he is a popular figure in Florida folklore, no evidence of his existence appears in writing before the early 20th century. His legend is celebrated every year.
The stories of Gaspar are fairly consistent. Most say he was born in Spain in 1766 and served in the Spanish Navy aboard the Floridablanca. Among his early exploits was his kidnapping of a young girl for ransom; some versions give his subsequent capture as the impetus for joining the navy. Simpler versions of the story have him starting a mutiny and becoming a pirate soon after, but more romantic ones say he achieved a high rank and became a councillor to King Charles III. He was popular in the court, but when he spurned one lover for another, the jilted lady levied false charges against him, often said to involve the theft of the crown jewels. To escape arrest he commandeered his ship and vowed to exact revenge on his country through piracy. Renaming himself “Gasparilla”, he patrolled the coast of Spanish Florida for the next 38 years (often 1783 – 1821, approximately the dates of the second Spanish rule of Florida), sacking every passing ship and amassing a huge treasure, which was stored in his fabulous den on Gasparilla Island. Most male prisoners would be put to death or recruited as pirates, while women would be taken to a nearby isle, called Captiva Island for this reason, where they would serve as concubines or await ransom payment from their families.
This is one of several Gasparilla tales that attempt to explain a local place name. One of the most famous involves a Spanish (or Mexican) princess Gaspar had captured. Allegedly named Useppa, she consistently rejected the pirate’s advances until he threatened to behead her if she would not submit to his lust. Still she refused, and he killed her in a rage (or alternately because his crew demanded her death). The captain instantly regretted the deed and took her body to a nearby island, which he named Useppa in her honor, and buried her himself. Some versions identify the lady with Josefa de Mayorga, daughter of Martín de Mayorga, viceroy of New Spain from 1779 to 1782, and contend that the island’s name evolved over time. Similarly, Sanibel Island is said to have been named by Gaspar’s first mate, Roderigo Lopez, after his lover whom he had left back in Spain. Empathizing with his friend’s plight, Gaspar eventually allowed Lopez to return home, and even trusted him with his personal log. Sanibel Island re-emerges in other stories as the headquarters of Black Caesar, a Haitian pirate whose story has become entangled with Gasparilla’s.
Then in 1821, the year Spain sold the Florida Territory to the United States, Gasparilla decided to retire. But while the men were going about dividing up the treasure, they spotted a fat British merchant ship, an opportunity too good to pass up. But when they approached, the intended victims lowered the Union Jack and raised an American flag, revealing that this was no merchant vessel, but the pirate hunting schooner USS Enterprise. In the battle that followed, Gasparilla’s ship was riddled by cannon balls. Rather than surrender, Gaspar chained the anchor around his waist and leapt from the bow, shouting “Gasparilla dies by his own hand, not the enemy’s!” Most of the remaining pirates were killed or captured and subsequently hanged, but a few escaped, one of them being Juan Gómez, who would tell the tale to subsequent generations.
See also Island Legend & Lore