The Legendary Jose Gaspar (Gasparilla, The Pirate)
The Legend of Gasparilla
For more than a century, the legend of Jose Gaspar, the “last of the buccaneers”, has conjured up visions of adventure, treasure and furious sea battles. Jose Gaspar, a respected, Spanish naval officer who turned pirate, stills inspires that annual Gasparilla festival in Tampa, Florida.
But who was Gaspar, and how many of the activities attributed to him are true?
Examining the legend of Gasparilla (as he called himself) is a convoluted exercise. There is no single, reliable source of information. Multiple, often conflicting, stories exist about the pirate, his victories, and even his death.
What follows is one of those stories…
The Early Years
Jose Gaspar was born in Spain near Seville in 1756. He was reported to be "small in body, perhaps, but imbued with the stamina of a Spanish fighting bull". Gaspar was from an upper-class family and possessed a cultured, gallant personality. However, despite is aristocratic upbringing, Gaspar was a bit of a rogue. At age 12, he kidnapped a young local girl and held her for ransom. He was captured and the judge gave him the choice of entering the Royal Spanish Naval Academy or going to jail. He chose a life at sea over a stint in the Graybar Hotel.
Once in the Navy, he demonstrated great skills in tactics and weaponry. He displayed bravery and cunning in battle. He rose through the ranks, becoming a lieutenant, a captain, and then an admiral of the Atlantic Fleet before becoming a naval attaché at the Court of Charles III in 1782. He was 27 years old.
While at the Court, he became romantically involved with several women (all at the same time). It was a perilous game, but one that matched Gaspar’s love of danger and adventure. The game could not go on forever, of course. He publicly jilted the daughter-in-law of the King, in favor of another woman of the Court.
Outraged and spiteful, the daughter-in-law conspired with the prime minister to frame Gaspar for stealing the Spanish crown jewels. Upon hearing news of his imminent arrest, ordered by Charles III, Gaspar commandeered a ship, the Floridablanca, and escaped. Swearing an oath to revenge his treatment by Spanish officials, he resolved to plunder any ship flying the flag of Spain. The year was 1783.
Gaspar took the Floridablanca and escaped to the Gulf coast of Florida. He established his base in Charlotte Harbor (near modern-day Fort Myers). He adopted a new name and the career of Gasparilla, the Pirate began.
A Pirating We Will Go
For the next 38 years, Gasparilla attacked merchant ships from all countries, not just Spain’s. By some accounts, he plundered over 400 ships. His own diary boasts of 36 victories by 1795 alone.
Widely regarded as fearless and ferocious, Gasparilla showed no mercy in battle. He routinely, killed all passengers and crew, with the exception of beautiful women (whom he made concubines). Occasionally, women from wealthy families were held for ransom on Captiva Island (some claim that this is how the island got its name).
His ship roamed the west coast of Florida and down to Cuban waters in search of prey. There where times where he did not sail alone. To pursue a particular big prize, we would temporarily join forces with other pirates operating in the area, including the famous Jean Laffite.
The Death of Gasparilla
After decades of pirating, Jose Gaspar decided to retire. He was sixty-five, an extraordinarily old age for an active pirate. The Florida peninsula was now in American hands, and there has been a determined and unrelenting effort by the Americans to destroy the pirates that preyed in their waters. The combination of age and the aggressive pursuit of the American Navy motivated Gasparilla into contemplating retirement.
In December 1821, he announced to his crew that he was going to quit the pirate’s life. He said that he would divide up all of the spoils with his crew and retire to live a life of luxury.
On the day that the spoils of many years of pirating were to be distributed, a rich British merchant ship was seen passing near Gasparilla’s hideout. Seeing a chance for one last score, Gasparilla took off in pursuit of the fat target. Just as the ship came within cannon range, the British ship dropped its colors and ran up the flag of the United States! Dozens of cannon were instantly uncovered from its deck and aimed at Gasparilla’s ship. Jose Gaspar had fallen into a trap. The seemingly helpless British ship was actually the U.S. Navy’s warship – the USS Enterprise.
A fierce battle ensued, but the end was inevitable. The American cannonballs, repeatedly punctured Floridablanca’s hull, while still more shattered her masts. The Floridablanca was sinking as the USS Enterprise approached to finish the job.
Rather than be captured, Jose Gaspar climbed to the bow of his ship and yelled “Gasparilla dies by his own hand, not the enemy’s”. He wrapped the anchor’s chain around his waist. Still holding his cutlass high in one hand he jumped into the dark waters and instantly disappeared below the waves. The life of Jose Gaspar - Gasparilla the Pirate - and his reign of terror on the seas was over. The remainder of his crew were either killed or captured. Those captured were later tried as pirates and executed in New Orleans.
When the British merchant ship (which later turned out to be the USS Enterprise) was spotted, Gasparilla and his crew were about to divide their spoils. The treasure of many years had been loaded into twenty large chests. Filled with gold and jewels, the chests were sitting on the beach when the merchant ship was spotted.
Gasparilla left 10 of his most trusted men with the treasure chests while he took the rest of the crew in pursuit of the merchant ship. The ten men witnessed the battle with the USS Enterprise from shore. Seeing the Floridablanca go down, then loaded the chests into a longboat and slipped, unnoticed, up the Peace River to a place called Spanish Homestead. Spanish Homestead was owned by Lady Boggess. The pirates bribed Lady Boggess with a small part of the treasure, ensuring that she would not divulge their location if the Americans pursued them to the area.
The ten pirates spent the next day burying the remainder of the chests in different spots along the streams and swamps of Peace River. They then burned their longboat and disappeared forever, apparently never to return.
Near Spanish Homestead, $300,000 in gold coins was found years later – this may have been part of Lady Boggess’ hush-money. Regardless, the remainder of the $30 million dollars in gold and jewels still remains undiscovered in the Peace River area.
Gasparilla, Man or Myth?
Shrouded in mystery, the very existence of Jose Gaspar is a controversial subject. For those wishing to review a carefully-documented examination of the history of Jose Gaspar, please examine The Legend of Gasparilla: Myth and History of Florida’s West Coast by Andre-Marcel d’Ans.
Was Juan Gomez Gasparilla? Read Demystifying the lives of Juan Gomez: from Pirate to Pilot by Carrie Caignet
Additional information about Jose Gaspar or Tampa’s annual Gasparilla PirateFest can be found at: