 The Legend of Jose Gaspar, The Pirate
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
the 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 his 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.
 Gasparilla’s Treasure
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.
Additional information
about Jose Gaspar or of Tampa’s annual Gasparilla
Pirate Fest may be found at:
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