On May 28, 1668, the Spanish presidio of San Agustin (St. Augustine, Florida, USA) awaited the arrival of a supply ship bringing flour from Veracruz, in New Spain (Mexico). That morning, the Centinela de Anastasia, the watchtower on Anastasia Island across Matanzas Bay from the city, sighted an approaching vessel and sounded the alarm. A drum summoned the town’s garrison—120 men—to arms. The ship hove to and anchored two leagues off the inlet.
The harbor pilot went out in his launch to identify the newly arrived vessel and guide it safely into the bay. As the launch drew closer to the ship, its crew hailed the Spaniards lining the gunwale. Climbing on board, the pilot and his crew found themselves the prisoners of English buccaneers. Captain Robert Searle (alias John Davis) had captured the Veracruz ship off the coast of Havana and was using it to approach San Agustin undetected. As the pilot drew near, the freebooters in hiding had forced the ship’s crew to stand at the rail to give the appearance that all was well on board.
That afternoon, the townspeople saw the pilot’s launch sounding the inlet—standard procedure prior to bringing a vessel into the harbor. This lessened their concern over the ship’s lack of identification. The vessel remained at anchor, however, even when tide and wind favored entry into the bay. The Governor of Florida, Don Francisco de la Guerra y de la Vega, later claimed that the vessel had fired the two cannon shots prearranged as the identifying signal.
At about 9:00 that evening, a second alarm was sounded. The Centinela de Matanzas, the watchtower on Matanzas Inlet, 14 miles south of San Agustin, had sighted a small ship nearing the presidio. Many in the town thought it was the local frigate, which had left for Havana 50 days earlier and was expected back at any time.
Searle, however, had also captured this frigate off Havana and more of his men were approaching San Agustin aboard it. The coincidence of two vessels being expected and two vessels appearing off the bay certainly seemed to indicate that they were Spanish. At last, the governor ordered the garrison soldiers to rack their matchlock muskets with the town guard at the main guardhouse, a quarter mile from the city’s fort, and go home to sleep.
As the darkness deepened, over 100 pirates slipped into the pilot’s launch, the launch of the Veracruz ship, and two large piraguas (native canoes) they had been towing behind their ships. They forced the town’s pilot to guide them over the bar into Matanzas Bay, planning to coast along the western, landward shore of Anastasia Island and ascend the San Sebastian River on the uninhabited side of the city. They would then fall upon Government House, the seat of local authority and residence of the royal governor, and the decaying wooden fortress at daybreak.
At about 1:00 on the morning of May 29th, Corporal Miguel de Monzon was fishing in his piragua on Matanzas Bay—probably opposite the more settled part of San Agustin, south of the plaza (or town square). He heard the muffled sound of oars pulling across the water and immediately began rowing toward the town wharf to report the event. The corsairs, who had already traveled a quarter mile along the inner shore of Anastasia Island, must have seen or heard him. They raced after him and shot him twice as he reached the shore. Despite his wounds, Monzon shouted a belated warning and managed to reach the safety of the fort. Behind him, the pirates stormed ashore.
The townspeople of San Agustin had been caught completely by surprise. Shouting, cursing, bands of cutthroats scattered through the narrow streets, seizing or shooting the frightened, half-naked inhabitants as they emerged from their houses. The royal accountant, Juan Menéndez Marques, and his brother, Antonio, ran to the guardhouse. Shortly after they had left their house, freebooters burst in and captured their family. The Marques brothers found the guardhouse looted and deserted. They then hurried to Government House—all was silent there, as well. The brothers then decided that the city’s fortress would be the next place to look for help. As they ran toward the stockade with 10 or 12 men who had joined them, the buccaneers fired upon them.
When the uproar began, Sergeant Major Nicolás Ponce de León the Younger, senior officer of the presidio’s garrison, was at home, being treated for a skin ailment. Rousing himself, he rushed to the guardhouse to find it already pillaged. Then, as the pirates gathered at the stockade to storm it, he shepherded 130 bewildered men, women, and children—including 70 unarmed soldiers—to safety in the woods a league away. The din caused Captain Enrique Primo de Rivera, an unemployed veteran, to leave his pregnant wife in her parents’ house and race to the fortress to volunteer. In the church, the parish priest, Father Francisco de Sotolongo, destroyed the icon of the Holy Redeemer to prevent possible desecration at the hands of the heretics. He then chose to become a prisoner so that he could watch over the captured ladies and maidens, fearing the corsairs might dishonor them. Estefania de Cigarroa, daughter of Major Salvador de Cigarroa (then absent in Mexico), emerged from her house with her younger sister in her arms. A pirate’s bullet killed the child and pierced Estefania’s breast.
Upon landing, another group of marauders ran straight to the guardhouse. The town guard stationed there, too few to put up a fight, fled to the fort. The raiders paused to loot or destroy the weapons left there the previous day when the alert had been cancelled and then crossed the north end of the plaza to Government House.
Awakened by the uproar, Governor de la Guerra y de la Vega looked out a window, saw the buccaneers nearing Government House, and began descending a stairway on the wall facing the plaza. He had to get to the fort and direct its defense, one of his primary duties as governor. A hail of musket fire cut down his secretary, Miguel Alonso de Ojeda, and forced the governor back into the house. He escaped through a hidden door and, with the freebooters on his heels, safely reached the stockade.
Reformado Adjutant Isidro de Reinoso was on sentry duty at the fortress that night of May 28—29. He was making his rounds when he heard the tumult caused by the filibuster’s landing. Reinoso notified the lieutenant of the fort, Captain Mateo Pacheco Salgado, who immediately alerted the entire garrison. The stockade’s gate opened to admit the town guard from the guardhouse, Accountant Menéndez and his brother, and the handful of men with them. Menéndez, being a royal official, ordered the powder magazine to be opened and ammunition distributed to the soldiers present. Just then, Governor de la Guerra arrived and took command of the 33 men within the stockade’s rotting wooden walls.
Before its cannons could be loaded, Searle’s crew attacked the fortress. For an hour and a half, the corsairs repeatedly tried to storm the walls, only to be driven back by heavy musket fire. During the battle, one of the defender’s powder kegs exploded, severely burning Adjutant Reinoso’s hands and legs. Firing at the glowing matchcord carried by each Spanish musketeer, the brigands were able to kill five of the defenders and wound five more. The buccaneers finally withdrew, with 11 men dead and 19 wounded.
By failing to watch the stockade closely after their repulse, the pirates allowed Governor de la Guerra y de la Vega to improve his defenses. Messengers were secretly sent from the fortress to urge every soldier they could find to report to the fort. By daybreak on May 29th, seven soldiers had arrived. Major Ponce and his 70 weaponless men soon followed them. Also with the daylight, two vessels joined the Veracruz ship—the captured San Agustin frigate and Searle’s own craft, the 60-ton/8 gun Cagway. All three sailed into the bay, passing the ineffectual cannon fire of the fort, and anchored just out of range of the Spanish guns.
The raiders on shore returned to the unfinished task of systematically sacking San Agustin. The king’s treasury yielded 138 silver marks, which had been salvaged in 1667 from the Nuestra Señora de las Maravillas, a galleon of the Tierra Firme fleet which sank in the Bahama Channel in 1656, with 5 million pesos aboard. The royal warehouses were robbed of 760 yards of sail canvas—including a ready-made mainsail, a foresail, a frigate’s main topsail, and a launch’s main topsail—and 25 pounds of wax candles intended for Mass.
The parish church and the Franciscan convent’s chapel were stripped of their ornaments, the replacement of which later cost 2,066 pesos. The hospital was pillaged. Homes were carefully searched for jewels and other valuables. The booty was loaded aboard the Cagway and the ship from Veracruz. As the looting drew to an end, the pirates seized the royal treasurer, José de Prado, who had refused to abandon his house. Also captured were some local natives and mestizos (persons of mixed European and Native American ancestry).
On the afternoon of May 29th, Governor de la Guerra rallied his forces and sent out a sortie to drive the pirates from the city. He detailed artillery Captain Nicolás Esteves de Carmenatis to command two parties of 25 men each (under Adjutant Francisco Ruiz Canizares y Osorio and Ensign Diego Díaz Mejía) and execute the operation. Between 3 and 4:00, Esteves sallied from the stockade, unaware that only 40 buccaneers were still ashore. The soldiers went reluctantly, displaying little military experience and less enthusiasm. After they had received fire, wounding both Canizares and Díaz, the governor recalled the troops “so that the enemy would not kill them as if they were sheep.”
At about 9:00 that evening, the last 30 pirates who remained ashore rowed back to their ships. The sack of San Agustin had lasted 20 hours. Behind them, the buccaneers left a grief-stricken people—60 of their relations and friends were dead.
Yet with the tears came prayers of thanksgiving, for the raiders did not set sail immediately, carrying off their prisoners. On May 30th, Searle sent Governor de la Guerra y de la Vega a message, offering to ransom his captives—about 70 men, women, and children—in exchange for water, meat, and wood. The governor accepted, but in return asked for some much-needed flour, as well as the prisoners. The same day, as a gesture of good faith, the women—their honor intact—were released before the other captives.
Over the next six days, the ransom was paid. On June 5th, the treasurer, the priest, the harbor pilot, the crews of the Veracruz ship and the San Agustin frigate, and other prisoners were put ashore. At the last minute, Searle refused to release any native, black, or mestizo residents, explaining to Father Sotolongo that his letter of marque from the governor of Jamaica permitted him to sell as a slave anyone who was not a full-blooded Spaniard. (NOTE: Searle’s claim was, in fact, neither here nor there. Sir Thomas Modyford, governor of the English colony of Jamaica, had repealed all letters of marque in June of 1667. Searle’s raid on Spanish Florida was therefore piracy, not privateering.) Sotolongo remonstrated that these prisoners were freedmen and that many had Spanish fathers, but in vain. The corsairs sailed from Matanzas Bay amidst the thunder of the useless guns in the old wooden fortress.
With the return of the captives, one cause of the pirate attack on San Agustin became known—revenge.
According to Spanish records, Father Sotolongo laid the blame for the disaster squarely on Governor Francisco de la Guerra y de la Vega. Since his appointment to Florida in December 1664, the bachelor governor had become familiar with several of the local ladies.
For three years, he had shamelessly kept one of these women in Government House. Because San Agustin had tolerated this public sin, said the priest, God had visited the town with a drought, a storm, two ships lost, and now this buccaneer’s attack. (NOTE: The governor was guilty as accused. Spanish colonial law forbade a royal appointee to marry into the local families where he was stationed during his term of office. This had not, however, kept Don Francisco from falling in love. His mistress was the highly connected Dona Lorenza de Soto y Aspiolea, who bore him three children out of wedlock. Each was adopted by the couple as a “child of parents unknown.” Within a week of the arrival of Don Manuel de Çendoya, Florida’s next governor, Don Francisco and Doña Lorenza were married.)
This scandalous situation was complicated by the arrival of a Frenchman in 1666. Pierre Piquet (or Pedro Piques) was appointed surgeon of the Florida presidio in April of that year. His personal and professional reputation was impeccable. For reasons unknown, perhaps due to jealousy, the governor treated Piquet badly. On one occasion, he publicly slapped the surgeon in the face and dismissed him from his post. Piquet asked for the settlement of his accrued pay (slightly more than 200 pesos), which Guerra approved, only to have that amount seized on the irrelevant pretext that the surgeon was a Frenchman. When the War of Devolution broke out between France and Spain in 1667, Piquet was ordered to leave San Agustin, boarding the frigate that sailed for Havana on April 8, 1668.
The Frenchman was furious and ready for revenge. He saw his opportunity when English corsairs captured the presidio’s frigate off Havana, after seizing the Veracruz ship bound for Florida. According to witnesses, Piquet encouraged Searle to sack San Agustin, describing the lay of the land, the garrison’s strength, and the city’s defenses.
Lourdo Hernández, the frigate’s captain, tried to point out flaws in the surgeon’s plot, but to no avail. Searle was convinced and decided to use the captured Spanish vessels to surprise the presidio, with his own ship following out of sight.
It is likely that another cause of Searle’s raid was the English settlers in Carolana, newly arrived from Barbados. From their colony at Charles Town (later Charleston, South Carolina, USA), they at least tacitly encouraged the attack, the best indication for this being the presence at the time in San Agustin of another non-Spanish physician, the famous spy, Dr. Henry Woodward, who departed with Searles. Some historians claim that the main mission of the surprise attack was not so much to sack San Agustin as to free Woodward.
Woodward remains one of the most enigmatic English explorers of the period, intimately tied to the history of the Carolana settlement and its challenge to Spanish Florida. He was among the original English settlers and it was his first priority to learn about the country and its natives, including their languages. He entered the unexplored interior, traveling beyond the Chattahoochee River. In the 1660s, he appears to have been the first Englishman to trod the soil of what is today the central Florida Panhandle. Upon his return to the Atlantic coast, he encountered the Spaniards at their old settlement of Santa Elena, near what soon became the 1670 demarcation line between Spanish Florida and English Carolana. There, apparently, he was captured and carried to San Agustin. The governor of that city, Don Francisco de la Guerra y de la Vega, was surprised to receive a letter from Woodward in Latin, requesting baptism into the Catholic Church. Governor de la Guerra treated him more as a guest than as a prisoner. The learned doctor lived with the parish priest, Father Francisco de Sotolongo, a graduate of the University of Mexico, during the period of catechism. While in residence, Woodward noted a great deal about the Spanish status in Florida. Some historians believe that he might have allowed himself to be captured in order to spy out the Spaniard’s strength. After the sack of 1668, Woodward sailed from San Agustin with Searle’s buccaneers.
The ransomed Spanish captives also bore news that caused much apprehension in San Agustin. They identified the marauders as Englishmen from Jamaica. Furthermore, the buccaneers who remained aboard the vessels to guard the captives had sounded the harbor, plotted the sandbars, noted the technique for channel navigation, and recorded the local landmarks. They claimed that they would return with a greater number of ships, men, and artillery to seize and hold San Agustin for their king, Charles II of England. This information, with the fact that the town had not been burnt to the ground, lent credence to the threat of the pirates.
To the Spanish, such a prospect was indeed grim. San Agustin, though small and isolated, was the keystone in the defense of Florida. And Florida was important, not as a land rich in natural resources, but as a way station on Spain’s greatest commercial route. Each year, galleons bearing the royal banners sailed past the keys and beaches of Florida, following the Gulf Stream on their way to Cadiz. In these galleons were millions of ducats worth of gold, silver, and jewels from the mines of New Spain and Peru, and all of Europe knew it.
Florida’s position on the lifeline connecting Spain with her colonies gave this sandy peninsula great strategic importance. Spain’s Council of the Indies knew that Florida must be defended to prevent enemies from using its plentiful harbors as havens from which to raid the Spanish treasure fleets. Besides, Florida’s lee shores and deadly reefs joined with hurricanes in the narrow Bahama Channel to wreck many stout ships. Scores of mariners were cast away on the inhospitable coast. Florida must be made safe for them, as well as unsafe for Spain’s enemies.
It was a sizable defense problem. The French triggered the solution in 1564 when they established Fort Caroline, a colony named for their young king, CharlesIX, near the mouth of Florida’s St. Johns River. The French settlement drew the Spanish admiral, Don Pedro Menéndez de Avilés, to Florida in 1565. He founded the San Agustin colony and forthwith massacred the Frenchmen, some of whom had already begun raiding Spanish shipping. Now, with this small, fortified presidio on one side of the Bahama Channel and growing Havana on the other, Spanish ships could pass with some assurance of safety from the ports of New Spain to the Old World.
Where the sword of Spain went, the cross went also. Gradually, a system of missions developed in Florida, reaching north and west as far as the Chesapeake Bay and Alabama. These missions had to be protected from hostile aborigines, as well as Europeans, so the defense of Florida became a dual operation. The unceasing hunt of naval patrols for pirates, storm-wrecked vessels, and starving castaways was paralleled on land by fast-marching patrols along the native trails and swift-moving piraguas in the coastal waterways. San Agustin was the presidio’s capitol and the base for all these operations.
After the buccaneer raid of 1668, the city was utterly destitute. Notwithstanding, the sack of San Agustin was a blessing in disguise, for it shocked the ponderous Spanish bureaucracy into action. The governor of Havana, Don Francisco Oregon y Gascon, lent 1,200 pesos for masting and rigging the presidio’s frigate, thus insuring San Agustin’s communication with its supply bases in Cuba and New Spain. The viceroy of New Spain, Don Antonio Sebastián de Toledo Molina y Salazar, Marques de Mancera, released the 1669 situado (or payroll) of 76,172 pesos, with an additional 1,200 pesos for general repairs, weapons, gunpowder, and lead for bullets. He also promised 75 men to bring the garrison’s troops up to authorized strength. Furthermore, the presidio was allowed to keep an 18-pounder bronze cannon that had been salvaged from the wreck of the Nuestra Señora de las Maravillas.
It was Mariana, Queen Regent of Spain, ruling during the minority of her son, Carlos II, who gave permanent aid to San Agustin in three decrees addressed to New Spain’s viceroy. On March 11, 1669, she ordered him to pay the Florida situado on time and add an adequate amount for building the fortress proposed by the presidio’s governor. Next, on April 10, she commanded him to support a full 300-man garrison in Florida, instead of the customary 257 soldiers and 43 missionaries. Finally, on October 30, she enjoined him to hear the views of Don Manuel de Çendoya, Florida’s newly appointed governor, on an effective fortification and provide for its construction. Even so, it would be four more years before the multiple levels of the royal bureaucracy could translate the resolutions of the Queen and her Council of the Indies into funds, troops, and a day of groundbreaking for the new stone fort. The Castillo de San Marcos was finally completed in 1695 and still stands, an enduring reminder of Florida’s exciting heritage.
SOURCES
P. K. Yonge Library of Florida History, University of Florida, Gainesville. Stetson Collection.
Archivo General de Indias (hereafter AGI) 54-5-10/97, Governor Francisco de la Guerra y de la Vega of Florida to the Crown, St. Augustine, March 18, 1665, 2 ff.
AGI 54-5-14/134, The royal treasury officials of Florida—Accountant Juan Menéndez Marques and Treasurer José de Prado—to the Crown, St. Augustine, June 30, 1668, 10 ff.
AGI 54-5-18/70, Accountant Juan Menéndez Marques of Florida to the Crown, Florida, July 4, 1668, 7 ff.
AGI 54-5-20/89, Father Francisco de Sotolongo of St. Augustine to the Crown, St. Augustine, July 4, 1668, 5 ff.
AGI 54-5-18/71, Captain Antonio de Argüelles of Florida to the Crown, St. Augustine, July 6, 1668, 5 ff.
AGI 54-5-9, Governor Francisco de la Guerra y de la Vega of Florida to the Crown, St. Augustine, August 6, 1668, 7 ff.
AGI 54-5-18/73, Sergeant Major Nicolás Ponce de León of Florida to the Crown, St. Augustine, August 6, 1668, 5 ff.
AGI 54-5-10/106½ , Governor Francisco de la Guerra y de la Vega of Florida to the Crown, St. Augustine, August 8, 1668, 3 ff.
AGI 54-5-18/76, Governor Francisco Davila Orejon Gaston of Havana to the Crown, Havana, October 29, 1668, 12 ff.
AGI 2-4-1/19/2, Crown to the Viceroy of New Spain, Madrid, March 11, 1669, 4 ff.
AGI 54-2-2/14, Viceroy Marques de Mancera of New Spain to the Crown, Mexico, April 20, 1669, 89 ff.
AGI 2-4-1/19/1, Crown to the Viceroy of New Spain, Madrid, October 30, 1669, 7 ff.
AGI 54-5-18/81, Manuela Rodriguez (widow of Corporal Miguel de Monzon) of Florida to the Crown, St. Augustine, January 26, 1670, 7 ff.
AGI 54-5-19/1, Reformado Adjutant Isidro Reinoso of Florida to the Crown, Havana, March 31, 1670, 18 ff.
AGI 41-5-34/9, Don Gabriel Bernardo de Quiros to the Casa de la Contratacion, Madrid, May 6, 1670, 10 ff.
AGI 41-5-34/9/3, Crown Secretary Francisco Fernandez de Madrigal to the Casa de la Contratacion, Madrid, December 18, 1670, 3 ff.
AGI 58-5-20/29, Crown to the Governor and Royal Treasury Officials of Florida, Madrid, February 24, 1671, 2 ff.
AGI E de C 155, legajo 2, Demanda puesta por los Jueces Oficiales de la Real Hacienda de la Ciudad de San Agustin de la Florida contra Gobernador Don Francisco de la Guerra y de la Vega, sobre lo que se llevo el enemigo de cuenta de Su Magestad en la entrada que hizo, que va remitida con la residencia a los senores del Real Consejo para los articulos contenidos en la sentencia. St. Augustine, August 20, 1671, 38 ff.
AGI 54-5-18/93, Adjutant Diego Díaz Mejía of Florida to the Crown, St. Augustine, March 15, 1672, 5 ff.
AGI 54-5-18/91, Reformado Adjutant Francisco Ruiz de Canizares y Osorio of Florida to the Crown, St. Augustine, March 29, 1672, 13 ff.
AGI 54-5-14/147, Reformado Sergeant Major Salvador de Cigarroa of Florida to the Crown, November 3, 1678, 3 ff.
Arana, Luis R. The Basis of a Permanent Fortification. El Escribano, v. 6. St. Augustine, FL: St. Augustine Historical Society, October, 1969.
Arana, Luis R. Aid to St. Augustine after the Pirate Attack, 1668-1670. El Escribano, v. 7. St. Augustine, FL: St. Augustine Historical Society, July, 1970.
Arana, Luis R. and Albert Manucy. The Building of Castillo de San Marcos. St. Augustine: Eastern National Park & Monument Association for Castillo de San Marcos National Monument, 1980. p. 7-13
Gannon, Michael. The New History of Florida. Gainesville, FL: University Press of Florida, 1996. p. 103-104
Waterbury, Jean Parker. The Oldest City: St. Augustine, Saga of Survival. St. Augustine, FL: St. Augustine Historical Society, 1983. p. 54-5
Warning Orders for March 2008 event
A More Complete Account of the Original Attack
Biography of Captain Robert Searle
Rules and Guidelines for the Event
Rules and Guidelines for Black Powder Weapons
Rules and Guidelines for Swords and Edged Weapons