Every year over half a million people gather in Tampa, Florida, for the the Gasparilla Pirate Festival. It’s a celebration of the exploits of Jose Gaspar, better known as the 18th century Spanish pirate, Gasparilla. But there is no proof he even existed, at least not in written history.
The first information we have is from the 20th century, and even then there is no reliable source of information. Yet many mysterious and conflicting legends about him persist to this day.
Most stories about Gaspar say he was born in Spain in 1766 to an upper class family. He was apparently fairly short but was still very appealing to the ladies of his day – and he had a bad temper. In some of the more romantic tales of his life, Gaspar supposedly rose to a high position in the Spanish king’s court, but then got involved with too many of the ladies there. When Gaspar spurned a relative of the king she conspired to frame him for stealing the crown jewels!
In more practical tales Gaspar’s first villainous act was the kidnaping of a young girl from the Spanish court. (Supposedly, Gaspar was only twelve at the time.) Legend has it that he held the girl for ransom. When he was finally captured the judge gave him the opportunity to avoid prison by joining the Spanish Navy.
However it happened, the young man ended up at sea. In some legends, Gaspar led a mutiny on a navy vessel, in others he commandeered the prize vessel of the Spanish Navy and sailed it off as his own. In either case he vowed revenge against Spain, and he became a pirate.
The Pirate Life For Jose
Assuming the name “Gasparilla,” Gaspar raided the coast of Spanish Florida for the next 4 decades, attacking every passing ship (Spanish or otherwise) and building a huge treasure for himself in the process. Gaspar chose a small isolated island for his home base and named it Gasparilla in his own honor. Here he is said to have buried much of his wealth.
Crews of captured ships were given the option of joining Gaspar’s pirates or walking the plank. Male passengers were murdered, while women captives were taken to a nearby island to serve as concubines for the pirate crew. The lucky few who came from wealthy families were held on the island until a ransom was paid for them. To this day that island is called “Captiva”.
One of the most interesting legends surrounding Gasparilla states that he and Jean LaFitte stole the money for the Louisiana Purchase during the 1800s. They supposedly buried the money somewhere along Coral Creek near what is now Placida, Florida. It is even said that Robert E. Lee visited the area before the Civil War to search for that treasure.
The Fatal End
Gasparilla lived the pirate life well into his later years. He is credited with raiding over 400 ships between1789 and 1821. Finally, at age sixty five, legend has it that he decided to retire and enjoy the treasure he amassed. Since the United States had stepped up efforts to capture and destroy all pirates, it had become an extremely dangerous profession any way.
In 1821 he told his crew he was quitting the pirate’s life, and that he would share the treasure (since estimated to be worth $30 million) with them before he left. As it happens, on the day chosen for dividing the treasure, someone in the crew spotted a British merchant ship sailing by. Life-long pirate that he was, Gasparilla couldn’t pass up the chance to make one last huge score, so he took off in pursuit.
The pirate ship quickly caught up to the merchant marine and stood ready to board the helpless vessel. But as soon as the pirate ship was within cannon range, the British ship dropped its colors and ran up a United States flag. Jose Gaspar, world-famous pirate of almost forty years, had fallen into a trap. The “British merchant ship” was actually the USS Enterprise, and it had come equipped for battle.
Although Gaspar and his men fought fiercely, the end was inevitable. Gaspar’s ship was sinking and the Enterprise was approaching fast to finish off the pirates. But Jose Gaspar refused to be captured. According to the legends, he climbed to the bow of his ship, wrapped the anchor chain around his waist, and jumped into the Gulf. It is said Gaspar was holding his cutlass high in one hand as he sank to his death.
The Continuing Mystery
The major mystery of Gasparilla’s life still remains, though. What happened to the treasure the pirates were dividing? Legends say there were twenty huge chests spilling over with gold, jewels and other treasure. The chests were on the beach when the merchant ship was spotted, and it is said Gasparilla left ten of his most trusted men with them when he sailed off.
Here things get even more murky… The ten pirates obviously saw the pirate ship go down. Supposedly they loaded the chests into a boat and sailed up the Peace River to hide the treasure.
In some stories, they ended up at a place called Spanish Homestead. Here they bribed the owner with some of the treasure so she would point any pursuers in the wrong direction. The ten spent the next day burying the chests in different locations along the Peace River. They then burned their boat and disappeared.
Part of the legend apparently was true as $300,000 in gold coins was found years later near Spanish Homestead. However, none of the remainder of Jose Gaspar’s $30 million treasure has ever been recovered!
Whatever is true of this infamous pirate, his life was certainly interesting and filled with mystery.