Robert Searle’s St Augustine raid and the founding of South Carolina

In this week’s Florida History Podcast we discuss a critical event that led to the building of the Castillo de San Marcos in St Augustine.

May 28, 1668 was the 82nd anniversary of Sir Frances Drake’s successful raid on St Augustine. That afternoon the 120 soldiers guarding St Augustine had been put on alert as an unfamiliar ship came into the Inlet. But in fact it was a delivery of flour from Veracruz, the annual provisions that the residents and soldiers of St Augustine so needed to survive. The next day those provisions would come ashore. 

However, that night a fisherman came ashore screaming having been shot twice by Pirates. The soldiers heard the screams and within minutes a hundred pirates under Searle’s command were ashore. 

Allen & Ginter (American, Richmond, Virginia) John Davis, Stabbing the Sentry, from the Pirates of the Spanish Main series (N19) for Allen & Ginter Cigarettes, ca. 1888 American, Commercial color lithograph; Sheet: 1 1/2 x 2 3/4 in. (3.8 x 7 cm) The Metropolitan Museum of Art, New York, The Jefferson R. Burdick Collection, Gift of Jefferson R. Burdick (Burdick 201, N19.16)

The pirates were before long everywhere in the town. People stormed out of their houses in panic but were easy targets for the English who used the narrow streets of St Augustine to their advantage. By morning, many of the residents had fled into the nearby woods. Nothing in the town was spared and the ship from Veracruz was also overwhelmed by the Pirates. Eventually the pirates left after ransoming off their prisoners for food and supplies. The pirates however refused to release Native Americans or freed African slaves and they took them back to Jamaica. 

Searle’s midnight May 28/29 raid left 60 residents of St Augustine dead and finally convinced Spanish authorities to secure and fortify the town in the most expensive way possible – with the building of the Castillo de San Marcos. 

Searle’s raid resulted in the escape of Henry Woodward from captivity. The lessons Woodward took from his time in Florida led directly to the founding of Charles Town and the successful pacifying of some Native Americans in the Carolina’s. 

With the founding of Charles Town, Spain began to see its Florida Colony as an essential bulwark against rivals and a line of defense for its Caribbean colonies. St Augustine was a critical stop on Spain’s commercial shipping routes and had been proven once again vulnerable to English attacks. 

Absent the gold of other Spanish colonies in the Americas, Spain actively looked for those who would “serve” the crown in its military and economic needs in Florida. This included enticing slaves from English territories to flee to Florida and achieve freedom if they converted to Catholicism. 

This decision would alter the relationship between Florida and its neighbors to the north for the next 90 years. In fact, African runaway slaves and Native Americans would prove exceedingly loyal to defending Spanish Florida from English invasions during the 1700’s.  

In addition, the massive Castillo de San Marcos was built at great expense to the crown to protect Florida from future English aggression. 

One comment

  1. […] week on The Florida History Podcast we will discuss the period of time from Robert Searle’s raid on St Augustine in 1668 to the formation of Fort Mose in 1738 as well as the War of Jenkins Ear that involved free […]


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