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Jose Gasparilla Early Years

Jose Gasparilla was born into an aristocratic family in 1756. As a young man who grew up near the ocean in Spain, he quickly developed an attraction to adventure and a love for the sea. At the age of 18, he entered the Naval Academy in Barcelona, an institution for training prospective officers in the Spanish Navy. Jose quickly rose to the rank of Lieutenant by the age of 22. His first assignment was on the sloop-of-war, Florida Blanca, a vessel carrying 8 cannons and a crew of 40. In 1783, Gaspar’s ship, along with the rest of the Spanish fleet, was defeated by the British, and thus Spain’s plans for world conquest came to an end. Gasparilla and others aboard the Florida Blanca became discouraged and saw their dreams of adventure on the high seas all but disappear.

It was at this point that Jose Gasparilla led a group of other adventurous souls to mutiny. They seized control of the ship and sailed west to Florida, abandoning their home country of Spain and effectively became pirates. On the long voyage across the Atlantic, Gasparilla changed his name to the more piratical “Gasparilla” and likewise changed the ship’s name to the Jose Gasparilla.

Gasparilla’s life as an aristocratic officer in the Spanish Navy was therefore transformed into that of an adventurous, treasure-seeking pirate. However, Gasparilla was unlike other pirates of the 1700s, most of whom were ruthless, lowlife misfits of society. He was well educated, well mannered, and well-read in the classics. He was reportedly strikingly handsome with faultless attire. When he was a cadet at the Naval Academy in Barcelona, not only did he develop his fighting and swordsmanship skills, but he also polished his social graces as he mingled with the ladies. Although there were other members of Gasparilla’s mutinous crew who were also well-educated and experienced officers, most of them were ordinary, tough, “enlisted men” and all were experienced sailors.  In stark contrast to Gasparilla was his First Lieutenant, Roderigo Lopez, a coarse brute, lacking in any social graces. He was described as having bushy eyebrows and a hawk-like face and was always looking for trouble.


Jose Gaspar’s Time in Florida

Gasparilla and his crew made landfall in Florida and settled in the Charlotte Harbor area. The many barrier islands protecting the mainland provided a well-disguised headquarters from which Gasparilla and his band of pirates could easily prey on unsuspecting ships and offered an excellent refuge in which to hideout. He named one of the larger islands after himself and named another one Sanibel in honor of the girlfriend of his First Lieutenant Lopez. Gasparilla named one island Captiva, where he kept the women from his many captured ships. Another island was named after one of Gasparilla’s especially beautiful mistresses, Joseffa, who he chose to keep away from the other captive women. Through various translation changes through the years, “Joseffa” Island was ultimately changed to Useppa Island.

It was from these tarpon-filled waters that Gasparilla’s reputation as a skillful pirate grew. An excerpt from his neatly written personal diary states that 36 ships were captured during the 11 year period from 1784-1795.  Gasparilla thus began collecting a fortune in coins, jewels, and other riches, most of which have never been found. Many more ships were captured, including one seized near Cuba in 1795, an excellent fighting ship, far superior to the original  Jose Gasparilla. The existing cannons were painstakingly transferred to the newly captured ship, named Jose Gasparilla II, which now boasted 14 guns.


Jose Gaspar’s Love Life

When a ship was captured, the choice of death or joining Gasparilla’s crew was given to those captured. It goes without saying that Jose Gasparilla’s piratical crew began to grow. Captured women were given the option of marrying one of his crew or being sent to Captiva Island. If marriage was chosen, a ceremony was held and the marriage covenant was to be strictly enforced.

Although Gasparilla was an educated, well-groomed pirate and ladies man, things did not always go according to plan. On one occasion, Maria Louise, a beautiful Spanish princess, was returning to Spain from a trip to Mexico with 11 Mexican princesses who were to be educated and married in Spain. Gasparilla captured their ship, along with their 11 well-stocked dowries, and fell madly in love with the Spanish princess. However, when this beautiful young lady rejected his offer of romance, he had her beheaded.

Despite his reputed ruthless nature, it has also been said that Gasparilla had a softer side as well. On one occasion, his First Lieutenant was growing weary of the pirate’s life and after 13 long years longed to return to Spain to see his love, Sanibel. Gasparilla not only gave Lopez his consent but extended his blessing to his long time friend and supplied a ship and several men to accompany him back to Spain. Another example of his more humane personality involves the story of Ann Jeffries, an English girl who was en route from New Orleans to Liverpool. Her ship was seized by Gasparilla and the captives taken to Gasparilla Island. While on land, Gasparilla fell in love with Jeffries, however, she informed him that she had fallen in love with one of his own crew, Batista Fuentes, a handsome, well-educated man from a prominent family. The two young lovers thought that Gasparilla would surely have them killed when he demanded that they accompany him and his crew on a raid. Instead, he chased down a merchant ship and demanded that the captured ship transport Batista and Ann Jeffries to England and that its captain marries them on board ship, once they were out of sight of the Jose Gasparilla II.


Jose Gaspar & The United States Navy

The exact number of ships that were captured by Gasparilla is unknown. However, no more unsuspecting ships would be captured by the then infamous Gasparilla after December of 1821. The United States was growing tired of these menaces to society and declared war on piracy in 1820. Spain was also interested in putting a stop to their ships being captured, primarily because of one Jose Gasparilla. U.S. Naval officers were given permission to hang captured pirates on the spot, without the benefit of a formal trial. Because he was now 65 years old and because of the increasing pressure of the government to rid its shorelines of pirates, Gasparilla decided it was time to retire. On December 12, 1821, he called his crew together to announce that it was time to call it quits, divide up the treasure, and live out their remaining days in luxury. Just as they were about to unearth their many years of accumulated treasures, a British merchant ship was spotted on the Gulf of Mexico horizon. Being the greedy, adventure-seeking lot that they had always been, Gasparilla’s crew persuaded him to go after that one last ship. As the Jose Gasparilla II quickly overtook the lumbering merchant ship, the British flag was suddenly lowered and a United States flag was hoisted to the top of the U.S.S. Enterprise, a U.S Naval warship that had disguised itself as an unarmed ship of goods. This vessel was under the command of Captain Lawrence Kearney and a bloody battle ensued in which many of Gasparilla’s crew was killed and the Jose’ Gasparilla II was rendered disabled, burned, and out of gun powder. When he saw the U.S. Navy rowboat approaching his lifeless ship, Gasparilla wrapped a heavy anchor chain around himself and jumped into the Gulf of Mexico. In this last defiant act, as he plunged into the water with his sword held high over his head, he said, “Gasparilla dies by his own hand, not the enemies.”


Jose Gaspar – Man or Myth

Most of Gasparilla’s crew was killed during this final battle, however, there were 12 survivors – 11 men and a cabin boy named Juan Gomez. Gomez had been captured on a Spanish ship in 1812, joined Gasparilla’s crew of pirates, and was to become the last survivor of this piratical group. He served a jail term and was released, yet the 11 men that were captured during Gasparilla’s final battle were tried and executed in New Orleans.

It is from Juan Gomez that many of the tales of Gasparilla have been generated. He loved to spin his tales of adventure on the high seas and of the vast amount of Gasparilla’s treasure that was never found. He eventually migrated to Panther Key, in the 10,000 Islands area of Florida, where he became known as Panther Key John. In 1900, Gomez drowned while fishing for mullet at the alleged age of 120.

The legend of Gasparilla was later given national attention when G.P.LeMoyne, a press agent for the Charlotte Harbor and Northern Railroad Company of Florida, printed Juan Gomez’s adventurous pirate stories in a pamphlet for tourists. This publication, which described the piratical heroics of the infamous Jose’ Gasparilla, was to bring visitors to the Boca Grande area to purchase property and to visit the Gasparilla Inn.

The preservation of the legend of Gasparilla can also be credited to Edwin D. Lambright, once the respected editor of the Tampa Morning Tribune. In 1936 he wrote “Life and Exploits of Gasparilla, The Last of the Buccaneers.” Around the time of the Gasparilla Invasion and the Florida State Fair, Lambright occasionally published portions of his Gasparilla story in the paper, further authenticating the legend of Jose Gasparilla.

Webster’s dictionary defines “legend” as “a story coming from the past; one popularly regarded as historical although not verifiable.” There is little doubt that the legend of Gasparilla has existed since the 1800s and has provided many adventurous and colorful stories for the residents of Florida’s Gulf Coast, especially to those in the Tampa Bay and Boca Grande area. Whether or not Jose Gasparilla ever existed is not important. The legend does exist and on this remarkable story, Ye Mystic Krewe of Gasparilla was founded over one hundred years ago in 1904.

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