The most notorious and successful pirate was Jose Gaspar, better known
as Gasparilla. His methods were black and bloody, and he stands out
among all the pirates who used Florida to bury their wealth. Leaving
Spain at an early age, he sailed to the West Coast of Florida. He soon
picked a good spot in Charlotte Harbor, and began to build his pirate
kingdom. His headquarters were at Boca Grande, on what is today known
as Gasparilla Island. In the following years, he accumulated a board
estimated at $30,000,000. It is said that he and his brother buried all of
his money on the islands in and around Charlotte Harbor. In all, he
buried 13 casks and chests of treasure in the vicinity of his
headquarters. His men, who numbered in the hundreds, also buried their
smaller caches on these islands.

All had been going along fine for Gasparilla until the year 1822. The
American Government then decided to get into the act and sent a Navy
squadron to end his career. One day Gasparilla prepared to attack a
merchantman, but to his surprise, it turned out to be a United States man-
of-war. When he finally realized that it was a warship, it was too late. The
notorious pirate then committed suicide by wrapping a heavy chain
around him and jumping over the side. His ship soon followed him to the
watery depths. The ship contained $1,000,000 in assorted treasure, and
should be there today. Charlotte Harbor is an ideal spot to go treasure
hunting. Just pick any island and start digging, because Gasparilla’s loot
is buried on many of them, including Cayo Pelau.

Another of Gasparilla’s undiscovered treasures, amounting to several
thousand dollars, was buried on Anastasia Island, south of Matanzas
Inlet. The site was recorded as being a three-hour walk south of St.
Augustine. It has been stated that he never returned for the chest.


The Pirate Gasparilla


The ship Orleans, of Philadelphia, a large, heavily armed vessel bound
from New York to the West Indies, was robbed off Cape Antonio, in
September, 1821, by an equally large piratical corvette mounting at least
fourteen guns. The crew of the Orleans offered but a faint resistance and
were probably overawed by the size of the pirate and the number of
freebooters on her; many of the Orleans' men afterwards joined the
pirate, with, it was said, but little urging. The latter was commanded by
one Gasparilla, a noted desperado of the blackest die; his headquarters
were in the island of Boca Grande, on the west coast of Florida; this
place is now a noted and fashionable winter resort, and one of the small
islands in the neighborhood is named for Gasparilla.

Goods to the value of $40,000 were taken from the Orleans. Most of the
marauders appear to have been Spaniards and Portuguese, with a
liberal sprinkling of Negroes. After robbing the ship, Gasparilla wrote, in
the French language, a note to a United States naval officer, a
passenger on the Orleans, as follows:

At Sea, and in Good Luck.

Sir:

Between buccaneers, no ceremony; I take your dry goods, and, in return,
I send you pimento; therefore we are now even. I entertain no resentment.

Bid good day to the officer of the United States, and tell him that I
appreciate the energy with which he has spoken of me and my
companions-in-arms. Nothing can intimidate us ; we run the same
fortune, and our maxim is that ‘the goods of this world belong to the
strong and valiant.

The occupation of the Floridas is a pledge that the course I follow is
conformable to the policy pursued by the United States.



Richard Coeur de Lion



On April 20th, 1820, the “Robert Fulton” left New York on her first
voyage, and plied regularly until 1825, when, owing to indifferent financial
results, she was sold to the Brazilian Government and her machinery
taken out. While a steamer she had averaged four days from New York
to Charleston, four days from Charleston to Havana and three days from
Havana to New Orleans.

A century ago the merchants and bankers, and even the government,
made but little use of cheques and drafts in transmitting money from one
place to another; it was customary, dangerous as it was, to send actual
specie in boxes or kegs; more rarely, bank notes. It was not long before
the financial community availed themselves of the “Robert Fulton” for the
carriage of funds, offering as she did far greater possibilities of safety.

On one of her trips, in 1822, it leaked out that she was to have on board
a very large sum of gold, over $100,000, partly government funds, in
transmission to New Orleans, besides a large consignment from a firm in
New York to some merchants in Havana. In some way, probably through
the before-mentioned confederate in the United States, Gasparilla, the
well-known pirate, learned of the rich consignment and laid a clever trap
to seize the “Robert Fulton” and her treasure. Of course it was of no use
to attempt to chase the steamer with even the swiftest sailing craft, but
Gasparilla arranged that he and a dozen or more of his most
venturesome “friends” should lay in wait for her off the Cuban coast in a
large open boat, impersonating shipwrecked seamen. In response to
their distress signals, the “Fulton” would, naturally, stop to pick them up,
and the pirates, carrying concealed weapons, would improve the
opportunity by swarming on board the steamer and seizing her before
the crew and passengers could recover from their surprise.

A schooner belonging to Gasparilla was to have been in the near
neighborhood, to which the treasure was to be transferred, and the
freebooters would then at once make off in her, first damaging the
“Fulton’s” machinery so that she could not pursue them. It was not, it
would seem, their intention to hurt anyone on the steamer unless
resistance was offered.

However, “the best laid plans o’ mice and men gang aft a-gley,” and in
this case, it was said, one of Gasparilla’s gang, having a grudge against
him, revealed the whole plot, with the result that a United States man-of-
war escorted the “Robert Fulton” and her rich lading safely to her
destination.

Through the kindness of Robert S. Bradley, Esq., of Boston, president of
the Charlotte Harbor and Northern Railway Company of Florida, a most
interesting, and, it is believed, accurate account of the famous, or rather
in­famous, Gasparilla, is here reproduced. It was originally printed in
pamphlet form, to be distributed among the patrons of the railway and
the Boca Grande Hotel, but the story proved so thrilling that the little
brochure went out of print rapidly and is now quite rare.

This narrative was compiled by the writer from incidents told by John
Gomez, better known as Panther Key John, a brother-in-law of Gasparilla
and a member of his crew, who died at the age of one hundred and
twenty years, at Panther Key, Florida, twelve miles below Marco, in the
year 1900; also from records left by John Gomez, Jr., the cabin boy on
Gasparilla’s ship, who was kidnapped by Gasparilla, and who witnessed
the death of this pirate and all on board his vessel. He died and was
buried at Palmetto, Florida, in 1875, at the age of seventy years.

While it is almost impossible to obtain exact information concerning this
outlaw, owing to the numerous and conflicting accounts, the writer has
tried to put into readable form a few of these stories concerning
Gasparilla, and has only used such accounts where two or more sources
agreed. However, it is well to keep in mind that owing to the long lapse of
time between the death of Gasparilla and the present year nearly all old
landmarks have gone.






The Story of Gasparilla

The romantic age of the Gulf is past, the days when pirate bands preyed
upon the peaceful merchantman, stole his goods, and carried away his
women passengers, have gone, but romance still holds sway in the minds
of each of us, and in the pirate Gasparilla we find a story that is full of the
spice of romantic adventure, that abounds with thrills, and causes the
pulse to beat just a little faster at some daring exploit, the eyes to fill with
water at some touching story, or the fists to clench in the good American
way at the brutal butcheries that authentic documents show were
committed. Gasparilla has gone, his pirate gold lies hidden somewhere
on the isles of Charlotte harbor, but the bleached bones of his murdered
victims, with the stories that have drifted down from past generations,
give to the world a synopsis of the life and death of Gasparilla the terror
of the Southern Seas.

His name was Jose Gaspar (Gasparilla meaning Gaspar, the outlaw). He
stood high in the graces of the Spanish Court, so high indeed that he
filched the crown jewels. Jose was also an officer of high standing in the
naval affairs of the Spaniards. Some records give him the honor of being
what we would call an admiral. His theft discovered, he deserted his wife
and children, gathered together a nice lot of cut-throats, stole the prize
vessel of the Spanish fleet, and escaped. This happened in the year
1782. A price was declared upon his head, and it is stated, when
Gasparilla heard this decree, he swore eternal vengeance upon all
Spaniards in general, and commenced to destroy the commerce of Spain.

The Gulf of Mexico at that time being a rendezvous for pirate fleets,
Gaspar settled in Charlotte Harbor and built upon the shores of what is
now called Turtle Bay twelve houses, where, under guard, his female
captives were placed, all male prisoners being killed when cap­tured. The
buildings were constructed of palmetto logs, and arranged in a semi-
circle close to the water’s edge.

About one hundred yards farther inland the burying ground was
discovered several years ago, containing not only the bones of his men,
but the skeletons of his murdered women captives. Many a touching
story has been unearthed when the ghostly remains were uncovered.
Stories of great strong men who died in the fight, of women who died to
save their honor, and of nobility we even find a trace, but these are only
traditions, and the story of “The Little Spanish Princess,” as told by old
Panther Key John Gomez, we will relate later on.

Close to Turtle Bay lies the little Isle of Cayopelean. Upon this island
stood a burial mound fifty feet high and four hundred feet in
circumference at the base, built centuries earlier, it is thought, by the
Mound Builders of a prehistoric race. Excavations in this mound have
produced ornaments of gold and silver, together with hundreds of human
skeletons. On its summit Gasparilla constructed an observation tower,
where always a grim sentinel was stationed and looked across the warm,
smiling waters of the Gulf for a victim.

The present Isle of Gasparilla the pirate named for himself. Taking the
best of everything when a capture was made, he chose the best of the
islands in Charlotte Harbor for his own secret haunts. It is said that Jose
was saluted the King of the Pirates, and his home on Gasparilla Island
was regal in its fittings.

Some writers have said that Gasparilla joined Pierre LaFitte, the famous
French pirate, while others have stated on good authority that LaFitte
joined Gasparilla’s band, contributing a boat and thirty men.

While taking the census of 1900 two gentlemen stopped at Panther Key
and spent the night with John Gomez. The race of the old buccaneer was
nearly run, but all through that night he told a story of piracy that could
scarce be believed, yet it was a dying man that was clearing his soul
before his Maker. He told of the looting of ships, the massacre of
innocents, and last of all, when his life had nearly passed, he told the
story of “The Little Spanish Princess,” whose name he did not remember.
He told where the body would be found, and a sketch was prepared
under his direction, and in recent years in the exact location as described
the skeleton of a beheaded woman was found. This is the story.

In the early days of the year 1801, a princess of Spain sailed in great
state for Mexico. While in that country she was royally entertained by its
Ruler, and to show her appreciation to the Mexican people she prevailed
upon the nobles to allow her to take eleven of Mexico’s fairest daughters
away with her to be educated in Spanish customs. A treasure of much
gold, bound in chests of copper, it is said, was in cargo. When about
forty miles from what is now Boca Grande, Gasparilla engaged them in
combat, killed the crew, took the gold, and carried away as captives the
princess and the eleven Mexican girls. The princess he kept for himself,
the maids were divided among his men. The little Spanish princess
spurned the one-time favorite of the King, and Gasparilla swore that if
she did not return of her own free will the affections lavished upon her,
she would be beheaded, and the story goes the threat of Gaspar was
fulfilled. Far away from her native land, alone on a tropical isle, the little
princess still lies in the lonely bed made for her by Gasparilla. The night
birds sing in the dusk and lull her spirit to rest in the evening, and the
moon throws kindly shadows o’er the spot where royalty sleeps.

From members of Gaspar’s crew many a strange story has drifted down
concerning him, his traits, his ways, his passions. He was polished in his
manners and a great lover of fashionable clothes; fearless in fight, and at
all times cruel in his nature. Concerning women he was fanatical, and his
houses were always filled with captives. It is stated beauty was essential
with him. He kept for himself a certain number of picked beauties, but so
fickle was his nature that when an additional capture was made and a
new face appealed to him, one of his old loves must forfeit her life to
make room for the new favorite. That this was true there is no doubt, as
the graveyard of Gasparilla tells its own terrible story.

In 1819, the United States, having obtained, under the Louisiana
Purchase in 1803, the states bordering on the Gulf, made war upon the
robber bands. On Sanibel Island a conference was held by all the
pirates, and with the exception of Gasparilla, Baker, Caesar, and old King
John, all sailed away, to be heard of no more.

Nearly two years later, the war on piracy becoming too severe, Jose and
his crew agreed to divide their wealth, which was then estimated at thirty
million dollars, to give up piracy, and live as honest men the rest of their
lives. This was decided upon and plans made accordingly.

In the spring of 1822, while getting together his treasure for division,
which at that time was hidden in six separate hiding places, he cited what
appeared to be a large English merchantman just off Boca Grande Pass.
It is said his greedy eyes lit with pleasure at the thoughts of just one more
victim before his piratical days were over. Closely following the shore-line
of the Gulf, he slipped into Charlotte Harbor through what is now known
as Little Gasparilla Pass, crept around Gasparilla Island, and gathered
together his crew. Great excitement reigned when the plans were
unfolded. The band of eighty men was divided into two parts, he
commanding thirty-five men, LaFitte thirty-five, while ten were left in
charge of the camp. At about four in the afternoon Gasparilla and his
men dashed through the Boca Grande Pass for the English prize; fast
overtaking the fleeing ship, the black flag was hoisted, and his men stood
ready with the grappling hooks, but suddenly the English flag floated
down and the Stars and Stripe. pulled in place; in a moment guns were
uncovered on deck, and Gasparilla, realizing that he was in a trap,
turned to flee. His boat, disabled by the shots from the war vessel and
capture staring him in the face, he wrapped a piece of anchor chain
around his waist and jumped into the sea. His age at his death was about
sixty-five. His crew was hanged at the yard-arms, with the exception of
the cabin boy and the ten men left in charge of the captives, they having
escaped to the mainland. Panther Key John was in this gang. The cabin
boy was carried to New Orleans, where he remained in prison ten years.

LaFitte, watching the battle from afar, turned and fled, but the next
morning his boat was captured and sunk off the mouth of the Manatee
River. Whether he was captured at this point is not known, as so many
conflicting stories arose concerning him, still it is a positive fact that he
was buried at New Orleans.

For thirty years the craft of Gasparilla was visible from Gasparilla Island,
lying five miles off Boca Grande Pass, but the sand has now completely
covered the wreck.

The treasure of Gasparilla still lies unmoved. The bones of the bold
buccaneer, with his pirate ship, have vanished, but legends from the
fisher-folk say that some times in the dead of night, off Gasparilla Island,
when the waves are singing a lullaby to the weary and the wind is
whispering soft messages through the palmettos, the phantom fleets of
the pirate crew arise from their ocean resting places and pursue, as in
days of old, the ghost ships of the merchantmen.



Note: From “Piracy In The West Indies And Its Suppression,” by Francis
Bradlee, 1923.
Famous Pirates of Florida