TRAVELS OF DURSMIRG VOLUME IV THE ROGUES OF ST. AUGUSTINE AND OTHER SOCIAL MISFITS Chapter 5
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Chapter 5 ST. AUGUSTINE’S FOUNDING
Here is a chronological look back at the external forces that began the initial European settlement of the “Oldest City”;
It wasn't until the French established a small outpost in north Florida at the mouth of the St. Johns River in 1564 that
the Spanish again took notice of this desolate piece of isolated real estate because they did not want their lucrative
trade routes threatened.
The greedy Spanish didn't particularly want Florida but then they didn't want anyone else to have it either, so they
staked claim.
The Spanish conquistadors plunder from the American Indians of Mexico was being shipped in convoys back to Spain
and they certainly did not want it pilfered along the way especially after all the hard work they went through stealing it in
the first place.
A brief recap and the timeline of historical events beginning with the first Europeans landing in America after the Norse
Vikings, (The following stories can be found expanded upon in appendix 2 of this volume.)
1492 Christopher Columbus first set foot on American soil in the Bahamas, returning to Spain with only his two smallest
ships and part of his crew.
1493 Columbus made a second voyage to America this time with 17 ships and 1,500 men. Not finding enough gold he
begins to trade in slaves.
1498 Columbus made his third voyage with six ships and landed in the shores of South America at the mouth of the
Orinoco River…his first landing on continental America, and returned to Spain in chains.
1502 Columbus makes his fourth and final voyage to America with four caravel ships and 150 men. He reached
Honduras, Costa Rica, Panama and Cuba. He encountered the Chontal Mayan Indians from Tabasco, Mexico in their
sea-going trading canoes in the Bay Islands of Honduras in the Caribbean Sea, a days sail from the Yucatan
peninsula. Columbus became the first European to make contact with the Maya, pirating their cargo of cacao and
abducting the passengers and crew for slaves.
Note; Columbus had no idea of the value cacao or chocolate would have in world trade.
An interesting note; the Maya of the Yucatan were mentioned in the logs of both Columbus and Ponce de León. They
stated evidence that the Taino Indians and the Calusa in Florida had knowledge of the sophisticated Maya civilization in
the Yucatan of Mexico.
1513, Juan Ponce de León sailed from Puerto Rico, where he was governor to present day Florida to become the first
European other than the Vikings to set foot on North American soil. On this seven month voyage he also ranged as far
west as the Yucatan in Mexico.
Ponce de León survived his return trip back to Puerto Rico and there promptly croaked from his everlasting eternal
prize...a gift in the form of an arrow planted in his chest from the very Florida Indians he had set out to plunder and
conquer.
(Between 1502 and 1565 there were no less than twenty Spanish, Portuguese, Italian and French explorers coming to
America.)
1565, 52 years after Juan Ponce de León and 73 years after Christopher Columbus, Don Pedro Menendez de Aviles
established St. Augustine as the first permanent European settlement in North America.
As mentioned earlier the fact that both the Spanish Canary Islands, off Africa and St. Augustine are at approximately
30º north latitude would make Menendez’s trans-Atlantic crossing relatively simple. With the primitive navigational
devices of the day this would be their best option to make good a known landfall.
Menendez quickly got his fill of Florida’s hardscrabble existence and set sail back to Spain but before he left he gave
instructions to the settlers and soldiers; “Don’t do anything until I come back.”
Well, he never did return and it is rumored that this is why St. Augustine stayed a stagnant little suck hole for the next
three hundred and fifty years!
(Read the expanded story in Appendix 2 of this volume.)
In 1763, after years of Spanish rule, little St. Augustine, the capital of Florida had a little over three hundred stone
dwellings mostly with thatched roofs, a population of 2,446, 124 slaves and 26 soldiers and no roads out of town.
The Spanish heyday was nearly over, Mexican gold finally dried up and the Spanish inquisition ran out of steam and
heretics to purge.
Above is the 1763 Spanish map depicting the poor little outpost of St. Augustine with its only access to the
outside world being the ocean inlet. As the map clearly shows after over one hundred years of occupancy
little progress was made in carving anything out of the surrounding wilderness. (Note; the shallow sand
depicted in the center foreground of this map would become a vast and treacherous area of breaking surf
at high tide.)
1783 at the Treaty of Paris the Revolutionary War between the US and Britain is ended. In a separate agreement
Britain gives Florida to Spain.
1821 Spain sells Florida to the US for $5,000,000
1845 Florida becomes the 27th state in the US.
When Florida became the twenty-seventh state in 1845 it entered the Union as a slave state.
The very next year the United States declared war on Mexico and Florida lost fifty-five of its young men to the conflict,
surprisingly St. Augustine only lost one.
St. Augustine’s status as state capital was changed to Tallahassee, (where Jackson enjoyed a huge land grant in
appreciation of his resolution of the Indian problem) so St. Augustine would again remain a stagnant little suck hole until
the end of the century when Henry Flagler arrived with his pockets full of those dirty Yankee dollars.
This wasn’t enough flag changing over little St. Augustine and next in 1860 when the United States had a civil war and
sure enough Florida became part of the CSA, (Confederate States of America).
1865 The Confederate States of America is defeated and Florida returns to the US.
This is the old fort, St. Augustine’s number one tourist attraction known as Castillo de San Marcos that was renamed
Fort Marion after Florida became part of the Union and was pressed into service as a military prison almost exclusively
for Native American Indians.
The above recent photo does not capture many of the original features like the water moat that surrounded it that was
still functional up into the 1960s. Also originally the entire structure had been plastered with stucco.
In the fort’s long history it was never engaged in a losing battle.


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This is the Seminole Chief Osceola who honored a truce to negotiate and was then betrayed and captured along with seventy one warriors and six women. He was put in irons then forced to sign a document to validate a new treaty
go to chapter 6
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