THE SACK OF ST. AUGUSTINE:
CAPT. ROBERT SEARLE'S RAID OF 1668

March 1, 2008

St. Augustine, Florida, that “noble and loyal city,” is the oldest inhabited European settlement in North America.  Founded by Don Pedro Menendez de Aviles in 1565, it was a valuable outpost of the Spanish Empire, serving as a haven for the imperial treasure fleets sailing from the New World to Spain.  For over a century and a half, beginning with Sir Francis Drake’s raid in 1586 and ending with General James Oglethorpe’s attack in 1743, English troops and buccaneers repeatedly tried to wrest this strategic port from the Spaniards.

In 1655, Oliver Cromwell’s “Western Design” resulted in the capture of Spanish Jamaica, thus providing English freebooters with a safe base from which to plunder the Spanish Main.  The Golden Age of Piracy had begun!  In 1668, Capt. Robert Searle and his privateers sailed from Jamaica to loot the silver ingots held in the royal coffers at St. Augustine.  Under the cover of night, they slipped into the harbor and attacked the sleeping town, killing sixty people and pillaging government buildings, churches, and homes.  The devastation wrought by these bloodthirsty pirates prompted Spain’s Council of the Indies to issue money to build a massive stone fortress on Matanzas Bay to protect the city.  The Castillo de San Marcos still stands, an enduring reminder of Florida’s exciting heritage!