Sunday, December 5, 2021

The Legend of the Pirate Gasparilla

A portion of Bernard Romans Florida Map of 1774.

A portion of Bernard Romans Florida Map of 1774.

According to local lore the famous pirate Jose Gaspar was born in Spain in 1756 and joined the Spanish navy as a boy until age 27 when he mutinied and commandeered a ship to the Gulf of Mexico. Gaspar’s decision in 1782 to rebel, and leave his wife and children forever, was because his theft of the Spanish Crown jewels had been detected. A price was declared on his head and he swore a vengeance on all Spaniards.

Leading a group of escaped convicts, Gaspar with his stolen ship established a home base in 1783 in the area of Charlotte Harbor, north of the present day Fort Myers on an Island he named “Gasparilla.” He is said to have also taken that name for himself as it means “Gaspar the outlaw.” From 1783 until 1821 Gaspar and his pirate crew attacked many ships, killing the crew and male passengers, but reserving beautiful young women as their personal slaves and concubines. Rich or influential women were also held as captives and secreted away on an island later to be known as “Captiva” until a ransom was paid. These efforts resulted in Gaspar and his crew accumulating immense treasures which they hid along on the islands of Florida’s southwest coast.

In this thirty-eight year period many stories abound about this local pirate, the most popular one being that of “The Little Spanish Princess.” In 1801 Gasparilla captured Josefa de Mayorga, the beautiful daughter of a Spanish Viceroy from Mexico along with eleven noblemen’s daughters who were headed on a ship to Spain with a treasure of gold.  Also on the ship was a cabin boy, Juan Gomez, age twelve, who was born in 1781 on the Portuguese island of Mauritius and moved with his family to Bordeaux in France.   Gasparilla tried to sway the Princess with his treasures, but she continued to reject him. Finally fed up with her contempt for their leader, Gasparilla’s crew persuaded him to behead her. Gasparilla remained inconsolable after her death and Useppa Island is named for the Princess Josefa.

With Juan Gomez’s life being spared by Gasparilla, he joined the pirates and became such a trusted member that, by 1805, Gomez was sent to Spain on a secret mission to murder an enemy of Gasparilla’s. While in Europe on this mission, but before he could accomplish the assassination, he was captured by Napoleon’s army and forced into the French army.   Juan Gomez performed so well in battle that the Emperor Napoleon himself congratulated him for his valor, but despite that praise, Gomez later chose to desert and escaped to the sea. By 1818 Gomez was on a slave ship that, in a remarkable coincidence was captured by his old mentor Gasparilla allowing Gomez to rejoin the pirate crew he had left 13 years earlier!

Being tired of the pirate life Gasparilla, in 1822, at age 65, decided to end his pirate days and promised to split up all of his ill-gotten treasure, estimated to be worth thirty million dollars, with his crew. His crew was filled with the anticipation of receiving the money.  However, before this happened, they saw a large merchant ship flying an English flag and decided to complete their careers with one more spoil of war. Upon



attacking this prize, they quickly discovered, to their horror, that it was an American warship, the USS Enterprise, in disguise, heavily armed and firing directly on the pirates. The battle went badly and Gasparilla chose not to surrender, but instead wrapped an anchor chain around himself and jumped into the sea, all the while crying out “Gasparilla dies by his own hand not the enemy’s.” Meanwhile, most of the rest of the crew were hung by the yardarms or later put to death in New Orleans. One of the crew escaped to later tell the story of Gasparilla. That man was Juan Gomez also known as John Gomez.

Gomez tells the story that fifteen years after he survived the battle with the USS Enterprise, he was serving in the Second Seminole War as a volunteer scout under General Zachary Taylor (later President Taylor) and on December 25, 1837 fought in the battle of Lake Okeechobee. While in Taylor’s service, Gomez carried a letter to a Colonel Smith on the Caloosahatchee River, but lost his way and wandered the woods for five weeks living on roots and berries. Close to dying, Gomez was, fortunately rescued and brought back to life at Fort Thompson.

Prior to the Civil War, Gomez was in Cuba near Morro Castle when he was chased by unknown assailants, but escaped detection by hiding under the seat of a fishing boat, later to paddle to sea. After starving for three days, he was picked up by a schooner heading to Key West. By the time of the Civil War Gomez was a blockade runner along Florida’s west coast running in provisions and smuggling cotton out to support the efforts of the confederacy. “His experience during the Civil War would fill a book” according to an article in 1889 in Forest and Stream.

John Gomez is mentioned in numerous history books of Collier County and for many years he and his wife lived on Panther Key which is a remote Island between Marco Island and Everglades City. Gomez would regale visitors with stories of his exploits as a pirate including that he personally forced a number of people to walk the plank to their death. He further enjoyed telling people that he was the brother-in-law of Gasparilla and that the pirate had buried a large lost treasure in a cave located in the Caxambas hills on Marco Island.

Finally, the life of the old sailor ended with an accidental drowning in 1900 where similar to his mentor Gasparilla, Gomez was in a boat when his leg got caught in a net, causing him to fall overboard and drown. According to his own account John Gomez would have been 122 years old at the time of his death.

Take the test: how much of the above is fact or fiction? Clue: Look for three separate items that you think are true and read the next issue of The Coastal Breeze to find out the answers!

Craig Woodward moved to Marco Island in 1968 and has practiced law in Collier County since 1980.  For many years Craig has led a history tour of the Island for the Chamber of Commerce’s Leadership Marco program. He has a home in Everglades City and a deep interest in local and Florida history.

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