Historic Dates: June 6, 1586 – Drake’s Raid

Returning from his “Great West Indies Raid,” Sir Francis Drake and an English fleet of 23 ships, with more than 2,000 troops, happen upon the Spanish presidio of San Agustín; now St. Augustine.

Drake determines to attack the town.

The royal governor of Spanish Florida, Don Pedro Menéndez Marqués, has evacuated the settlement some days earlier after receiving warning from Hispaniola. However, with 70 or 80 men, he resolves to hold the unfinished log fort (called San Juan de Piñillo, on Matanzas Bay) as long as possible.

On June 7th, Drake begins his attack, landing artillery and 1,000 men across the bay on Anastasia Island.

Throughout that day, the opposing forces engage in an artillery duel, exchanging cannon fire across the bay. Capt. Christopher Carleill, commander of Drake’s infantry, himself puts a cannon-shot through the Spanish ensign flying over the fort.

Realizing he can hold the fort no longer and worried about leaving the hidden townspeople undefended, Menéndez withdraws under cover of darkness. That night, the soldier/interpreter/entrepreneur, Juan Ramírez de Contreras, who was later killed and eaten by the Surruque in 1597, leads native auxiliaries across the bay in guerrilla raids on the English camp.

With daylight on June 8th, Drake marches into the town unopposed, occupying San Agustín for several days.

As soon as the Spanish had left the town, local natives looted it.

Drake’s men now finish the job, burning the town, the fort, and the surrounding fields and groves. They strip the presidio of 14 cannons, tools, and all else of value, including a pay-chest with 6,000 ducats.

Three garrison deserters (one French, one Flemish, one Spanish) join the English at San Agustín and three black slaves desert to the Spanish.

After the demolition of San Agustín, Drake and his fleet leave the Spanish settlers to starve in the Florida wilderness and continue on their homeward journey to England, sailing north to call on the year-old English colony at Roanoke Island in present-day North Carolina.

Written by Davis Walker and posted courtesy of Florida Living History, Inc. www.floridalivinghistory.org

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Photo credits: © 2010 Historic City News contributed photograph