Legend of Gasparilla

January on the Gulf Coast of Florida means Pirates! Most notably is the Gasparilla Festival which takes place this time every year. But while everyone enjoys the party and fun of dressing up in your favorite pirate gear, not everyone knows the whole story of the most famous pirate to roam the waters around Sanibel – Jose Gaspar or Gasparilla.

If you have never heard the legend of “Gasparilla”, he was purportedly a Spanish nobleman turned Pirate, and last of the true Buccaneers, who plied the quiet waters around Sanibel and Captiva from 1783 until his violent and spectacular death in 1821. While there is significant disagreement and a definite lack of historical evidence for his existence, it is beyond dispute that the story of Gasparilla has had a major impact on the area from Sanibel north to Tampa since first gaining popularity in 1900.

According to some versions of the legend, Gaspar was a high ranking Naval officer and Councilor to King Charles III of Spain. After being falsely accused by a spurned lover, and faced with imprisonment or worse, he brashly stole the crown jewels, commandeered a ship, and vowed eternal revenge on the country which betrayed him. Gaspar rechristened himself “Gasparilla” and his ship the “Floriblanca”. He then fled to the West Coast of Spanish Florida in 1783 where he turned to piracy.

Gasparilla made his home port on a small isolated key he named Gasparilla Island and soon became the most dreaded scourge of the Gulf of Mexico. Gasparilla claimed dozens of ships, and amassed an enormous fortune in gold, silver, jewels and artifacts.  Ships were burned and sunk, men were put to the sword or enslaved, and women were held captive on a small island whose name still conjures ghostly images of the captives it held – Captiva Island.

Many of the other islands in the area still bear the mark of Gasaparilla. In one of his most infamous exploits, he captured a beautiful Spanish princess named Useppa, whom he soon fell in love with. When she would not give herself willingly to him, he killed her in a lustful rage. He was immediately overcome with sorrow and regret, and stricken with grief, he took her to a small island where he buried her, naming the Island Useppa in her honor. Sanibel Island also allegedly owes its name to Gasaparilla, when he gave his first mate the honor of naming the island after his beloved, who he had left behind in Spain.

In 1821, Spain sold Florida to The United States, and after nearly 40 years haunting the eastern Gulf of Mexico, Gasparilla and his crew decided to divide the treasure and retire from piracy. According to apocryphal accounts, the hoard had been hidden in 13 different locations, and the crew had already gathered together six of these at a camp along the barrier islands. On a sun-drenched afternoon in the Spring of 1822, Gasparilla sighted what appeared to be a slow-moving and heavily-laden merchant ship laboring north along Sanibel and Captiva towards Boca Grande Pass. The band of eighty men decided to grab one last easy prize before giving up the pirate’s life. Gasparilla took 70 of his best men onto the Floriblanca, while 10 were left ashore to guard the treasure. The ship stayed hidden from view, shadowing her prey from Pine Island Sound and Charlotte Harbour, before hoisting the black flag and springing through Boca Grande Pass, cutlasses and grappling hooks at the ready.

As they pulled alongside to claim the prize, the merchant ship suddenly lowered its British merchant colors, raised the Stars and Stripes, and dropped her false, painted-canvas sides, revealing a bulletproof hull and fourteen brass 6-pound cannons. Gasaparilla and his crew immediately realized this was no merchant ship, but was the USS Enterprise, the star of the American West-Indies Squadron, which had already destroyed or captured thirteen pirate, slaving or smuggling ships, and whose commander was responsible for ending the reign of the great pirate Jean Lafitte just one year earlier.

The Enterprise opened fire with all of her guns, and added to that the musket fire of her ninety veteran crewmembers. Gasparilla attempted to come-about and flee, but the Floriblanca was quickly disabled by the thunderous wall of cannon fire and musket balls, and began to break-up under the withering barrage. Faced with capture, and grievously injured, having lost his hand to a cannonball, Gasparilla wrapped himself in the anchor chain, raised his sword and shouted “Gasparilla dies by his own hand, not by the enemy’s!” and leapt from the bow into the deep. Of his crew aboard the Floriblanca, all but one was killed in the fighting or captured and summarily hanged. The ten men left on shore witnessed the final moments of the Floriblanca, then fled into the mangroves with the treasure and escaped.
According to at least one account, the sole survivor on the Floriblanca was a former Spanish missionary turned pirate named Juan Francisco del Oro. Del Oro was nicknamed Diablito, or “little devil”, possibly in acknowledgement of his denunciation of the church in favor of a life of piracy. As Gasparilla wrapped himself in the anchor chain and plunged over the side, Diablito snatched up the map of the 13 treasure troves and Gasparilla’s severed hand still bearing his jeweled signet ring.   Diablito then followed Gasaparilla into the gulf, and swam to shore, and according to this account, made his way north to Fort Brooke, where he died of yellow fever in 1829.

For the next 100 years or so, the legend of Gasaparilla faded into obscurity until a railroad worker named Ernesto Lopez stabbed his shovel into the wet muck below the Cass Street Bridge in Ybor City.  While working on a construction project near the Tampa waterfront in the 1930’s, Ernesto uncovered a copper-bound wooden box buried deep in the muck while digging a foundation.  Upon opening the weathered wooden chest, Ernesto made an incredible discovery. Inside he found a stash of Spanish coins, an old, crumbling, treasure map and a grisly, skeletal severed hand, still wearing a ring with the name “Gaspar” engraved upon it. This was believed to be the severed hand of the dread pirate Gasparilla, along with a handful of his cursed treasure, and a map showing the locations of the rest of his lost pirate hoard.  This was big news at first, but the Great Depression quickly eclipsed talk of pirates, and just as mysteriously as it had appeared, the box containing the skeletal hand was lost again for another 80 years.

Finally, in 2015, while cleaning out her grandfather’s attic, Maria Lopez, great-granddaughter of Ernesto, made national headlines when she re-discovered the box. Since the discovery, Maria and her brother have taken the box and its contents to several experts at antique stores in the Tampa Bay area, who have declared the contents as “gruesome and authentic.” Meanwhile, somewhere beneath the water off Boca Grande Pass, the rest of Gasparilla’s skeletal remains wait patiently, still wrapped in rusting chains, and guarding the treasure he paid for with his life.   If you think you have what it takes to find the treasure buried somewhere on the beaches of Sanibel and Captiva, contact us at Select Vacation Properties, and book your stay on these historic islands!

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