Pirates Burned St. Augustine to the Ground Twice

LIBRARY OF CONGRESS, Drawing of St. Augustine and commercial whalers. 


In 1586, pirate Sir Francis Drake was sent by Queen Elizabeth to burn St. Augustine to the ground. 

In 1668, pirate Robert Searle burned St. Augustine, resulting in construction of the Castillo de San Marco, commencing that year.  

In his book, titled the "City of God," Saint Augustine tells the story of a pirate captured by Alexander the Great who reportedly angrily asked the pirate,

"How dare you bully the seas?"

The pirate is said to have replied, "How dare you bully the whole world? Because I do it with a small boat, I am called a pirate and a thief.  You, with a great navy, bully the world and are called an emperor."

Our Nation's Oldest City's namesake, Saint Augustine thought that the unnamed pirate's reported answer was "elegant and excellent."