Photo of the Gasparilla Fest Pirate Ship Floribanca in Tampa Bay

As you look forward to Super Bowl LV in Tampa on Sunday, have you ever wondered about the history of the Tampa Bay Buccaneers team name? To understand the significance of buccaneers in Tampa’s culture, you must first know the story of the notorious pirate named Jose Gaspar.

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While a lot of people will visit Tampa Bay this year to watch the Bucs and Tom Brady play in the Super Bowl, another annual event is essential: the Gasparilla Festival.

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The Gasparilla parade has been a tradition in Tampa for over 117 years, occurring on the last weekend of January every year. The Gasparilla season centers around a pirate named Jose Gaspar, a pirate known as the “Terror of the Gulf.” 

But did this “Jolly Roger” ever exist? Many historians don't believe he did. If not, then the Gasparilla Festival might be based on a lie. Like almost all stories about the pirates of the Caribbean, myths and mystery shroud the legacies of the men themselves, and the Gasparilla festival is based on a myth surrounding a man named Jose Gaspar. 

Jose Gaspar was a pirate in the late 1700s and early 1800s. There are several different accounts of his origins in the pirating life. One report states that Gaspar kidnapped a girl as a young man and held her for ransom but was caught and forced into the navy. He learned how to sail and eventually led a mutiny against the captain and took control of his new pirate ship. 

Another version of the story states that Gaspar was a nobleman who rose high in the Spanish Royal Navy ranks. He achieved such fame that he became a personal counselor of King Charles the Third of Spain. He had multiple loves, and once one of them found out about the others, she told the King that Gaspar had planned to steal the crown jewels. Upon learning of the plot against him, Gaspar stole a Royal Navy ship and set sail, swearing vengeance on his country.

Image of Jose Gaspar

In yet another version, Gaspar was a Spanish admiral of a somewhat questionable character who did steal the Crown Jewels. When he was discovered to be the culprit, he stole the Spanish navy’s most prized ship and abandoned his family to become a pirate. In this version King George the third had his mother, wife, and children killed. When word got back to Gaspar, he swore to sink every Spanish ship he came across.

In all versions of the story, he settled in the Spanish occupied territory of southwest Florida. He named his pirate ship the Floriblanca and turned to a life of piracy. He established his base on Gasparilla Island and quickly became a terror of the Gulf of Mexico. 

He favored attacking Spanish ships but quickly started attacking any vessels he came across regardless of their flying flags. Gaspar and his crew amassed great wealth and infamy. 

But Gaspar had an increasing fear of getting caught. He had heard about other pirates who had gone to Nassau and other pirate havens, only to be captured by pirate hunters. So Gaspar decided to use his wealth to create an island fortress where pirates could come and safely drink and trade. He used the island of Gasparilla and built a home on the nearby island of Boca Grande. His house was said to be luxurious and grand. 

Map of Pirate Island in Charlotte Harbor

The nearby island of Captiva is rumored to have been named thus because Gaspar would keep his female hostages there until ransoms were paid. One of the stories about Gaspar includes him kidnapping the princess of New Spain. Unfortunately for her, Gaspar wanted her to become one of his harem of women, and she rejected his advances. He told her he would kill her if she didn’t come with him. She chose death. Her name was Useppa. 

He had such regret over his actions that he carried her body to a nearby island and buried her himself. He then named the island Useppa after her. It is unsure if Useppa ever existed, but it’s speculated that she was Josefa de Mayorga, daughter of the viceroy of Spain from 1779 to 1782. However, no evidence has exists to support these claims

Legend also has it that Sanibel Island was named by Gaspar’s first mate after his wife, who he left back in Spain. This sentiment moved Gaspar so much that he allowed his first mate to return to Spain to be with his wife. Supposedly, the first mate took along with him a journal that detailed Gaspar's exploits. But no evidence of this journal has ever surfaced.

Almost all the story versions agree that Gaspar died in late 1821, just months after Spain transferred Florida to the Americans for five million dollars. After nearly forty years of being a pirate, Gaspar decided to hang up his hat. He gathered his crew on the island of Gasparilla to divide up his massive thirty million dollar fortune, six times the price it cost to buy Florida. 

While they were dividing the loot, one of the crew spotted a ship on the horizon. Believing it was an English merchant ship, the crew of the Floriblanca took to the seas for one last expedition. When they got close enough to notice, the boat wasn’t an English merchant ship. Instead, it was the USS Enterprise. 

The USS Enterprise was a pirate hunting ship that caught wind of Gaspar’s location. The sides of the boat were ironclad, making it hard for cannonballs to penetrate. After an intense battle, the Floriblanca was riddled with holes and taking on water fast. Gaspar, rather than being taken alive, tied chain shot cannonballs around his neck and jumped into the ocean.

Or so the story goes because that is all historians can prove, that it’s a story. No evidence has ever surfaced proving that Jose Gaspar or Gasparilla ever existed. There are no records of his service in the Spanish navy, royal courts, or in any legal documents. 

As for Gaspar being the most feared buccaneer in the gulf, he certainly wasn’t mentioned in any newspapers or books at the time. There is also no mention of the USS Enterprise ever coming into contact with a ship called the Floriblanca or chasing down Jose Gaspar. 

Jose Gaspar’s private pirate island, which consisted of more than a dozen buildings, has never been discovered, despite numerous archeological attempts to uncover them. And of his thirty million dollar fortune, not a single professional or amateur treasure hunter has ever found a single coin.

Theories About the Legend’s Source

One of the few survivors of the ill-fated last journey was John Gomez. John Gomez was a real man who was recorded on several US census counts. Perplexingly on each one, he was of different age and from diverse backgrounds each time. 

Gomez was somewhat of a local legend. He was known for his hunting and fishing skills and would often charter people out on fishing expeditions or hunting trips. It was on these trips that he would recount the tales of his early years as a pirate who sailed alongside Jose Gaspar. 

Most of the information historians have today about Gomez’s life comes from personal letters and some newspaper clippings. He is the only source of information we have about the life of Jose Gaspar. 

Due to his age and the date on which Gaspar died, Gomez would have had to be a young teenager when he was part of the crew. Some accounts state that he was the first mate. Others say that he was a cabin boy. Either way, Jose Gomez seems to be where the legend started, or at the very least the first and only documentation of Gaspar’s exploits.

The legend of Jose Gaspar arguably started with a brochure from the Gasparilla Inn. In the early 1900s, the newly constructed city of Boca Grande on Gasparilla island became a tourist destination. The tourist brochure told the legend and exploits of Jose Gaspar, the “Terror of the Gulf.” 

The author of this pamphlet was Pat Lemoyne, a publicist for the Charlotte Harbor and Railway company, which owned the resort. The cover featured an illustration of Jose Gaspar with blood dripping off the page. The stories inside were said to have come directly from Jose Gomez, who claimed to be the last remaining member of the Floriblanca’s crew. 

The brochure also claims that on the island was a forty feet high mound and under that mound was the last of Jose Gaspar’s treasure and hundreds of dead bodies. This was said to entice people into coming to the island to find the treasure for themselves. The promotion worked. People started to flock to the island in search of treasure.

Photo of Old Tampa

In 1923, Francis Bradlee got his hands on a copy of the brochure, and assuming the facts in it were true, he included them in a book he was writing called Piracy in the West Indies and Its Suppression. 

This cemented Jose Gaspar’s legacy as it was later used as source material in several other books. Each author put their own spin on the tale, each time growing larger and larger, causing differing accounts of his background and accomplishments.

The author of the original brochure, Pat Lemoyne, gave a speech to the Fort Myers chamber of commerce in 1949, in which he confessed the whole story was a lie. He is quoted saying the entire thing was a “cockeyed lie without any fact in it.” 

He told the group assembled that he had made it all up based on the fanciful stories told by Jose Gomez, who claimed he was a pirate and who sold fake treasure maps for a pretty penny to the gullible wealthy tourists. His confession came too late. Jose Gaspar had already become a pirate legend, whether fact or fiction.

The Gasparilla Festival

In 1904, the city of Tampa created a Gasprillia-themed parade under the leadership of the “Ye Mystic Krew of Gasparilla.” Which at the time was modeled after the Mardi Gras parade in New Orleans. 

The parade’s first iteration had the Mystic Krew members riding through town on horseback wearing pirate costumes while citizens trailed behind them cheering them on. The following year the Krew, again dressed like pirates, drove sixty cars through downtown Tampa. 

The parade gained so much popularity that they decided to add some pageantry to it. In 1911 the Krew added a story to the parade, where the pirates invade Tampa. As the years went on, the parade became more and more elaborate. 

In 1954 they built a replica of the Floriblanca ship. They sailed it into Tampa, where the pirates pretended to take the mayor of Tampa hostage until he surrendered the key to the city to the pirates, and then the parade was officially started.

Old Photo of the Floribanca in the Gasparilla Day Parade

Today, the Gasparilla festival is one of the largest parades in the united states. Drawing crowds of over 300,000 people and generating more than $20 million in local revenue over the last weekend in January. It’s been a tradition of Tampa bay for 117 years.

So are the legends of Jose Gaspar real? Or were they just an elaborate way to bring in tourists? The members of Ye Mystic Krew said it best in 2004 when they released the following statement:

“Whether Gasparilla, the pirate, actually existed or not is a moot point. The legend exists, and that's what matters. The story of Gasparilla and his pirates has lent a certain flair of mystery and adventure to Florida's West Coast since the late 1800s. And on that legend, Ye Mystic Krewe of Gasparilla was founded 100 years ago.”


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