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The Pirates of San Augustín

By Cindy Vallar

Sir Francis Drake                     Robert Searle                    Andrew Ranson               Nicholas Grammont
On 28 August 1565, a fleet of Spanish ships reached the coast of Florida. Those on board celebrated the festival of Saint Augustine, a philosopher and bishop who lived most of his life in Algeria. Eleven days later, Admiral Pedro Menéndez de Avilés stepped ashore in northeast Florida near a Timucuan village, and dubbed the new colony he founded San Augustín (Saint Augustine).

  Spanish galleonAdmiral Pedro
              Menéndez de Avilés
Spanish Galleon and Admiral Menéndez

Although taking possession of this part of the Spanish Main for his king, this was not his only task. Menéndez was a combat veteran and naval strategist. Together he and his brother, Álvaro Sánchez, developed the convoy system that brought the treasures of the New World to Spain, and Pedro served as captain general of the treasure fleet. He had also organized groups of vessels who frequented Caribbean waters in search of pirates. Now, he had a new duty – rid the territory of interlopers and heretics.
The year before (1564) French Huguenots established Fort Caroline in present-day Jacksonville, territory belonging to Spain since first claimed by Juan Ponce de León in 1513. On hearing this news, Felipe II ordered Menéndez to take care of the problem. He and his men arrived in late August 1565 at the same time as reinforcements for the fort, under the leadership of Jean de Ribaud (also spelled Ribault), did. The Spaniards tried to board the French ships, but having no success in that venture, Menéndez sailed his vessels and men south to where he founded St. Augustine.
Rather than wait for the Spaniards to return, Ribaud decided to attack them at their new colony. As the French ships reached their destination, a hurricane hit. Shipwrecked down the coast from
San Augustín, Ribaud and his men headed north. In the meantime, Menéndez took advantage of Ribaud’s absence and attacked Fort Caroline. That garrison was unable to put up much of a fight and soon surrendered. Those Frenchmen still alive were slain, while the women and children were sent to Puerto Rico. Menéndez renamed Fort Caroline, Fort San Mateo, then headed south to meet up with the survivors of the French shipwrecks who were marching north to San Augustín.1
The Hugenots were exhausted and hungry, and Menéndez used this advantage to persuade them to surrender the next day. During the night, however, some of the Frenchmen had second thoughts and fled. One hundred eleven men submitted themselves the next morning, only to be slain. A mere sixteen were spared the death sentence. On 11 October, the remaining Huguenots, including Jean de Ribaud, surrendered. As he had with the previous shipwrecked victims, Menéndez never promised to keep them alive. He merely said he would do what God commanded him to do. Again he massacred 134 out of 150 men. Legend says they had to die not because they were French, but because they were Luteranos (Protestants), and Felipe II was the defender of the true faith, Catholicism. The site of the executions earned the name “Matanzas,” which means “slaughters.”
By the time Governor Juan Fernández de Olivera arrived to take control of the government in 1610,
San Augustín had become a place for exiles – rebellious officers and friars – and many soldiers had records for indebtedness, petty thievery, vagrancy, or rioting. The walls of the timber fort were so dry, it was feared that firing a single cannon would ignite the logs. Fifty years later the city was more respectable, with 700 inhabitants and seventy Franciscan friars. The garrison boasted three hundred men on its payroll, including soldiers, officers, sailors, a treasurer, surgeon, barber, smith, amourer, locksmith, slave overseer, and chaplain.
Even in its early years, San Augustín attracted another group of men to its shores because of its location. Situated near the Bahama Channel, ships sailing to Europe had to pass nearby. Hidden behind Anastasia Island, the inlet provided an ideal place from which pirates could watch and wait for cargo-laden vessels to pass. But the Spanish arrived first and – knowing the pirates might target them – they built watchtowers on Anastasia Island and posted sentries in them to scan the ocean and send word of any impending danger.

Felipe III of SpainSir Francis
Felipe III of Spain (left) and Sir Francis Drake (right)

Two decades after the founding of San Augustín, Sir Francis Drake set sail with a fleet of about twenty-five ships and 2,300 men. He planned to attack Spanish ports in the New World, thus interrupting the deliveries of gold and silver to King Felipe III’s coffers and weakening one of England’s main foes. Drake’s forces sacked Santo Domingo, then Cartagena, before beginning their voyage home. Unable to successfully attack Havana, Drake sailed north along Florida’s Atlantic coast in search of possible targets.
As they neared San Augustín on 27 May 1586, lookouts spotted the watchtower on Anastasia Island near the mouth of the Matanzas River. William Biggs, one of Drake’s men, kept a journal of what happened at San Augustín, which Master Thomas Cates eventually published.

[E]arly in the morning, we descried on the shore a place built like a beacon, which was indeed a scaffold upon four long masts raised on end for men to discover to the seaward, being in the latitude of thirty degrees, or very near thereunto. Our pinnaces manned and coming to the shore, we marched up alongst the river-side to see what place the enemy held there; for none amongst us had any knowledge thereof at all.
Here the General took occasion to march with the companies himself in person . . .  and, going a mile up, or somewhat more, by the river-side, we might discern on the other side of the river over against us a fort which newly had been built by the Spaniards; and some mile, or thereabout, above the fort was a little town or village without walls, built of wooden houses . . . . We forthwith prepared to have ordnance for the battery; and one piece was a little before the evening planted, and the first shot being made by the Lieutenant-General himself at their ensign . . . . One shot more was then made, which struck the foot of the fort wall, which was all massive timber of great trees like masts. The Lieutenant-General was determined to pass the river this night with four companies, and there to lodge himself entrenched as near the fort as that he might play with his muskets and smallest shot upon any that should appear, and so afterwards to bring and plant the battery with him; but the help of mariners for that sudden to make trenches could not be had, which was the cause that this determination was remitted until the next night.

In the night the Lieutenant-General took a little rowing skiff and half a dozen well armed, as Captain Morgan and Captain Sampson, with some others, beside the rowers, and went to view what guard the enemy kept, as also to take knowledge of the ground. And albeit he went as covertly as might be, yet the enemy, taking the alarm, grew fearful that the whole force was approaching to the assault, and therefore with all speed abandoned the place after the shooting of some of their pieces.

About this time, the English heard music drifting over the water. The fifer played “The Prince of Orange’s Song,” and when he finally reached the English, they found him to be Nicolas Borgoignon.2 This Frenchman had spent the past six years as a prisoner of the Spanish. He told the English that the enemy had fled the fort.3

Upon this intelligence the General, the Lieutenant-General, with some of the captains in one skiff and the Vice-Admiral with some others in his skiff, and two or three pinnaces furnished of soldiers with them, put presently over towards the fort, giving order for the rest of the pinnaces to follow. And in our approach some of the enemy, bolder than the rest, having stayed behind their company, shot off two pieces of ordnance at us; but on shore we went, and entered the place without finding any man there.
When the day appeared, we found it built all of timber, the walls being none other than whole masts or bodies of trees set upright and close together in manner of a pale, without any ditch as yet made, but wholly intended with some more time. For they had not as yet finished all their work, having begun the same some three or four months before . . . .
The platform whereon the ordnance lay was whole bodies of long pine-trees, whereof there is great plenty, laid across one on another and some little earth amongst. There were in it thirteen or fourteen great pieces of brass ordnance and a chest unbroken up, having in it the value of some two thousand pounds sterling, by estimation, of the king's treasure, to pay the soldiers of that place, who were a hundred and fifty men.

Once the fort was secured, Drake’s pirates headed for San Augustín. Snipers emerged from their hiding places, fired a few shots, then returned from whence they came. Sergeant-Major Anthony Powell commandeered a Spanish horse, already saddled, and gave chase. His company followed, but not before Powell was shot. After he toppled from his horse, several soldiers came forward and stabbed him with their swords and daggers before the English could come to Powell’s aid.
Rather than risk any more men, Drake ordered his men to gather any equipment the Roanoke colonists might find useful and to seize twelve of the fourteen cannon, all of which were taken back to the ships. They also sacked the town, but found little of value since the citizens had taken their valuables with them when they fled. His men set fire to the fort and town before sailing north to Roanoke. 4 and 5

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Almost a century after Drake attacked San Augustín, another pirate and his men sacked the unfortified city. Robert Searle, who sometimes used the alias John Davis, used Jamaica as his home base. As with most pirates, his early life is a mystery. The first mention of him in the historical record surfaced in connection with Commodore Christopher Myngs’ expedition against Santiago de Cuba. On 11 September 1662, Searle departed Port Royal, along with Myngs and his force of 1,300 men. Two weeks later they sacked Santiago then returned to Jamaica with a sizeable haul.
What Searle’s did after this is unknown, but on 19 August 1664, the Jamaican Council decided they had to appease King Charles II, who was upset with English raids against his ally, Spain. They chose as their example Robert Searle.
On reading the King’s letter of June 15 last, commanding restitution of captured ships and goods to the Spaniards: ordered that the ship and bark brought in by Captain Searles of the Port Royal be seized and restored to that nation, and also all specie that can be found; that notice thereof be sent to the Governor of Havana; that persons making any further attempts of violence and depredation upon the Spaniard be looked upon as pirates and rebels; and that Captain Searles’s commission be taken from him, and his rudder and sails taken ashore for security. (Marley, 352)
The following year the Second Anglo-Dutch War began, and Searle joined Colonel Edward Morgan’s expedition to attack Saint Eustatius and Saba, which belonged to the Dutch. They sailed from Port Royal in April 1665. Governor Modyford described Morgan’s forces as “chiefly reformed privateers, scarce a planter amongst them, being resolute fellows and well armed with fusils [muskets] and pistols.” (Marley, 352) Soon after he landed, Morgan died from heat exhaustion, but the rest of the English forces captured the island. With no booty to share and frequent arguing over Morgan’s successor, the privateers split up. Searle, a Captain Steadman, and eighty men attacked Tobago, destroying whatever they couldn’t take on their ship.
Three years later, Searle and his men sailed off the coast of Cuba, where they captured a Spanish frigate bound for Vera Cruz and a brigantine on her way to Havana. On board the former was a French surgeon named Pedro Piques. The Spanish governor of San Augustín had slapped Piques in public, then sent him packing. Whether he divulged the city’s vulnerabilities to the pirates can’t be documented, but Searle and his cohorts decided the city would be their next target. Piques might also have told them the treasury contained bars of silver recovered from a shipwreck.
At the time, Searle already sailed in consort with another pirate ship, but he saw the value of these two Spanish vessels and all four sailed north. As they neared San Augustín, the two pirate ships stayed out of sight, while the frigate and brigantine came within hailing distance of the fort on the morning of 28 May 1668. On the two main decks the Spaniards went about their business as if nothing was wrong, while the pirates hid. Unaware of the danger, a launch approached with a harbor pilot, who demanded to know where the ships were from and what cargo they carried. He learned they had sailed from Mexico with supplies for the city. Reassured these were legitimate visitors, the pilot’s men fired two shots, a prearranged signal to the soldiers manning the fort that all was well. Those ashore returned to their normal activities, while the pilot and his men boarded the Spanish vessels.
Normally, the pilot would have brought the ships directly into the harbor, but the vessels remained where they anchored. No one in the town or at the fort seemed suspicious, perhaps assuming the pilot waited for a favorable wind. When night came, everyone went to sleep.
Around midnight, Searle and the other pirates sailed past the fort’s guns into the harbor. Their sneak attack would have succeeded with perfection had Corporal Miguel de Monzón not been out fishing. The darkness and the water carried the sounds of the pirates’ oars as they rowed ashore. Realizing an attack was imminent, the Spaniard paddled his boat toward land. The pirates pursued him, firing their pistols and wounding him twice, but the corporal reached the garrison and woke his sleeping comrades.
The people of San Augustín had little warning and while some eluded the pirates, others were slain or captured as the rogues swarmed through the streets. They plundered townhouses, government buildings, the church, and a monastery. What they could not abscond with, they burned.
The buccaneers lost eleven men; another nineteen sustained injuries. Although many citizens fled their homes for the safety of the fort (which never capitulated) or the surrounding forest, about sixty Spaniards – almost a quarter of the population, died in the attack. Juan Menendez Marques, an accountant, and Antonio, his brother, eluded the pirates just before they breeched the Marques home and captured the rest of the family. Estefania de Cigarroa, the daughter of one of the fort’s officers, tried to flee with her younger sister. A bullet killed the little girl while another struck Estefania in the chest.
Governor Francisco de la Guerra de la Vega evaded the invaders, while Father Francisco de Sotolongo opted to become their prisoner so he could make certain no one dishonored the captured women. In total Searle took seventy children and adults as hostages, which he exchanged for firewood and provisions.6 He did not, however, free any of the Indians, blacks, or mestizos whom the buccaneers had taken, for Searle claimed his letter of marque from the Jamaican governor permitted him to sell anyone who was not a full-blooded Spaniard.
Another person he took with him was Henry Woodward. The Spaniards had captured the doctor several months before, but he was so well liked he was permitted to walk around the city without guards. This allowed him to learn all about the town, its residents, and the fort’s defenses. No record details where Searle, Woodward, and the rest of the pirates went after leaving San Augustín, but several years later someone recorded that the doctor “was carried to the Leeward Isles, where he shipped surgeon of a privateer, but was cast away 17th August 1669 in a hurricane at Nevis.” (Marley, 355) He survived and eventually ended up in Charleston, South Carolina.
Searle and his men absconded with 133 silver marks, 760 yards of canvas for sails, twenty-five pounds of candles, all the ornaments from the convent church, and an untold amount of valuable jewels and utensils.7 They occupied the city for twenty hours before they sailed away.
The next time Searle was heard from was when he arrived in Jamaica in 1670. On 18 March, Governor Modyford wrote:
There arrived also at Port Morant the Cagway, Captain Searle, with 70 stout men, who hearing that I was much incensed against him for that action of St. Augustine, went to Macarry Bay and there rides out of [my] command. I will use the best ways to apprehend him, without driving his men to despair. (Marley, 355)
Searle came ashore the following month and was promptly arrested. That summer Manoel Rivero Pardal and other Spaniards became such a nuisance that Henry Morgan was chosen to lead a retaliatory strike against these corsairs. Searle was released to help and participated in the attack on Panama City, after which he became commander of a small fleet of vessels that he used to ransack the islands offshore. They discovered a large amount of wine on Taboga, which the pirates consumed. For whatever reason, Searle failed to post lookouts, so no one noticed when the 400-ton Santísima Trinidad appeared. Alexander Exquemelin later wrote of the ship that had departed Panama before the pirates attacked:
. . . a galleon, loaded with the King of Spain’s silver, together with all the jewels and treasure of the foremost merchants in Panama. There were also nuns on board, taking their church ornaments and their silver and gold. This ship was armed with only seven cannon and a dozen muskets. Nor was it fully rigged even – it lacked topsails, and was moreover short of water.
          The rovers learned all these facts when they captured a boat sent ashore from this galleon, with seven men in it, to fetch water. According to these men, the great ship could not possibly put to sea without water. But the buccaneer captain had been more inclined to sit drinking and sporting with a group of Spanish women he had taken prisoner, than to go at once in pursuit of the treasure ship.
          Next day he did have the barque made ready to go and hunt down the galleon, but without success, for she had sailed away when the Spaniards aboard her found out that the buccaneers were at sea and had captured their ship’s boat. (Exquemelin, 198-99)
Searle’s attack on San Augustín proved devastating. The pirates’ demand for provisions greatly depleted the town’s available food supplies. They took with them any ship that could navigate high seas, so it took six months before the Spanish monarch learned of the attack via the government in Havana. The ransomed captives had also seen the pirates taking soundings of the harbor and river, which led them to believe the thieves intended to attack again at a later date. Another indicator seemed to confirm this belief: the pirates did not set fire to San Augustín as Drake had done. Such vulnerability convinced the regent, Queen Mariana, that a stronger, more defensible fort was needed, and four years later the stone fortification, which became known as the Castillo de San Marcos, was started.

Castillo de San MarcosCastillo de San MarcosCastillo de San Marcos
Three views of the Castillo de San Marcos today
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In 1683 Alonso de Avecilla sought sanctuary in the home of a Quaker living in the Bahamas. Why? A band of pirates wanted him because he had once lived in San Augustín; they wanted his knowledge of the area in order to prepare their attack on the Spanish city. They cajoled the governor to hand over the Spaniard. Whatever Avecilla shared with them, however, didn’t insure their attack on San Augustín would succeed, for that city’s governor, Juan Márquez Cabrera, received four advance warnings of the impending attack. Three came from his counterpart in Cuba, while the Dutch master of a visiting vessel was his fourth informant.
The pirates planned to go ashore near the Matanzas Inlet, journey fifteen miles to attack the watchtower, and if that proved successful, they intended to sail pirogues up the Matanzas River to their real target. Once they sacked the city, they would transfer their booty to larger vessels before escaping.
Cabrera had no intention of allowing these rogues to walk right in. Additional watchtowers were constructed, one above San Augustín, the other twenty-one miles below Matanzas. In spite of these preparations, the pirates succeeded in their surprise attack on one watchtower as morning dawned on 30 March 1683. The five sentries had fallen asleep, and one was forced to lead the pirates north on the Matanzas River to their destination. Perhaps to make up for his earlier mistake, the sentry led them up a small creek that fed the river, which slowed their progress.
Any surprise the buccaneers hoped to achieve vanished before they even arrived near the city. Having spotted the invaders, another Spaniard was on his way to warn Cabrera. Soldiers in the more distant watchtower had also seen them. They abandoned their post for San Augustín. When they encountered a man out horseback riding, he immediately rode to town to inform the governor.
Cabrera sent soldiers to ambush the pirates, whom the Spaniards thought numbered around forty. The buccaneers who approached, however, numbered more than two hundred, but they had no inkling the soldiers awaited them about a mile southeast of the Castillo de San Marcos. The two sides exchanged gunfire, and the Spaniards forced the pirates to retreat. Before they did, they captured one soldier named Francisco Ruiz. Although they tortured him for information about the fortress’s weaknesses, he told them the Castillo was being reinforced every hour and that his compatriots would ambush the pirates again along Anastasia Island. Then the pirates threatened to kill Avecilla, who was still in their custody, because he had failed to tell them of the southernmost watchtower. Ruiz told them the man couldn’t have revealed that information because the tower had been built after Avecilla left San Augustín.
Knowing they had lost the element of surprise, the buccaneers returned to their ships. They debated for three days as to what to do next. The majority wanted to sail into the inlet opposite the fort and head north in search of provisions, rather than attack San Augustín.
Governor Cabrera had no intention of allowing them to do as they pleased. He sent thirty men in small boats after the pirates to determine their intentions and to harass them whenever possible. The soldiers only found several
sacked villages along St. Johns River and on Amelia Island. The residents of San Augustín remained on alert, while their governor urged everyone to assist in strengthening the fort and erecting temporary defensive posts.
The pirates eventually headed to what is known today as Cumberland Island off Georgia, where they careened their vessels and buried their dead before departing the area. Although they released several prisoners, Ruiz remained in their custody for two years and six months.
In the fall of 1684, the year after the failed pirate attack, a man named Andrew Ranson ascended the gallows for his execution. The residents of San Augustín, including the Franciscans who lived in the nearby convent, watched the executioner place the rope around Ranson’s neck.
Unlike England, Spain did not hang pirates. They garoted them, using a technique similar to the buccaneers’ torture technique of woodling, but with more devastating results. John Swain, who wrote The Pleasures of the Torture Chamber (1931), explained:
The word [garrote] means “cudgel”, and the punishment gets its name from the original form of execution, which was to tie a rope or band around the neck of a criminal who was seated against a post. A stick was then inserted between the cord and the neck and twisted till strangulation ensued. (25)
On the sixth turn of the stick, Ranson collapsed. The executioner twisted the stick once more, but the rope snapped. Ranson fell to the ground, and the friars gathered around to pray for his soul. One of them discovered Ranson still breathed. Claiming this to be a miracle, the Franciscan in charge of the order interceded, threatening the dumbfounded soldiers with God’s wrath if they interfered as the other friars carried the pirate back to their convent and gave him sanctuary.
Who was Andrew Ranson and why was he condemned to death? He was one of the pirates who had attempted to raid San Augustín the year before, but had the misfortune of getting caught.
An Englishman born around 1650, Ranson first came to the West Indies in his twenties. For whatever reason he ended up in a Cuban prison, but the historical record doesn’t reveal how he became a pirate. In 1684 he signed on with Captain Thomas Jingle to raid Spanish Florida. Six ships joined this venture, one of which had participated in the failed attempt to sack San Augustín in 1683.
This buccaneer band captured the frigate Plantanera off the Florida Keys. She was bound for Vera Cruz to pick up the annual funds the Spanish government paid to its officials and soldiers in Florida. By the time the pirates sailed into the Gulf of Mexico, five more ships had joined their undertaking. With this many men, the buccaneers felt they could successfully sack San Augustín, so they set sail for the east coast of Florida.
As they neared the city, a storm hit. When it abated, five pirate ships had disappeared. The remaining buccaneers headed north in search of supplies before they attacked San Augustín. While the larger vessels remained offshore in deep water, Ranson accompanied those sent ashore for food and water. They captured a Spanish sentry, whom they interrogated about the city’s defenses.
During this time, cattle ranchers discovered the pirates’ boat and to prevent their escape, chopped holes in it. Somewhere along the line fifty soldiers surprised and captured the buccaneers. In an attempt to lure their comrades who had remained on the ships ashore, the Spaniards returned the buccaneers to the beach and set an ambush. Andrew Ranson had to stand on the shore and call to his fellow brethren. Assuming all was well, they heeded his request, but the nearer they came to the shore, the warier they became. Suspecting the worst, they quickly returned to their vessels before the soldiers could attack.
Disappointed, the Spaniards took Ranson and the other previously captured pirates back to San Augustín, where they tortured and interrogated them. At Ranson’s trial, a sailor testified that Ranson had beaten him and threatened to decapitate him in an attempt to gain information about the various settlements in Spanish Florida and the treasures they held. Plantanera seamen also testified for the Crown. The pirates were sentenced to an undefined period of hard labor, which was later reduced to ten years. Ranson, whom the Spanish considered to be the man in charge, was sentenced to die. Before his execution, Ranson sought the help of the Franciscans, vowing he was innocent of the charges.

This was why the friars came to Ranson’s aid after the rope broke. Even though the governor demanded the pirate’s return so the execution could be completed, the Franciscans refused. The stalemate went on for several years, and the head friar threatened to excommunicate the governor if he or his soldiers attempted to invade the convent and take away Ranson. Before Cabrera left Florida in 1687, he made certain that those soldiers who had allowed the monks to abscond with Ranson were punished. Some were discharged; others were sent to remote or dangerous outposts.8
After the new governor arrived to assume his duties, he made finishing the Castillo one of his top priorities. Ranson heard of his request for men to assist in the work and sent a message to the governor. Having training as both an engineer and a carpenter, Ranson offered to help if the death sentence was commuted. The Spaniards accepted his offer, and Ranson moved into the Castillo.
Governor Moore of South Carolina decided to attack San Augustín. For two months they laid siege to the Castillo. Moore’s Spanish counterpart offered freedom to all prisoners in exchange for defending the fort. Ranson not only volunteered, but also acted as interpreter during interrogations of English prisoners. After the siege ended, the historical record ceased to mention Andrew Ranson.

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The final chapter in the pirate history of San Augustín occurred in 1686 and involved a successful Frenchman named Nicolas Grammont (also known as “Chevalier” and Sieur de Grammont). Often considered one of the greatest commanders of the flibustiers, his early life is steeped in myth. Was he born around 1650, or earlier? Was his father an officer? Did Nicolas kill a man in a duel at the age of fourteen, then run away to sea? Was his Christian name François, Michel, or Nicolas?
Boucanier --
              predecessor of the buccaneersWhatever the answers, he eventually ended up at Saint-Domingue, where he joined the boucaniers (the original buccaneers), who admired his courage, humor, and openhandedness. A contemporary wrote of him, “He has a particular secret for winning their hearts and insinuating himself into their spirits.” (Marley, 154) He was of short stature, dark complexion, and full of life. He fought primarily on land, using ships to get to his military targets. He seemed invincible in battle, and Spaniards unlucky enough to get captured feared his cruelty.
After France declared war against Holland and Spain in the 1670s, Grammont led the corsair contingent from Saint-Domingue for Vice-Admiral Comte d’Estree’s expedition to attack Curaçao.9 This French flotilla left Martinique on 7 May 1678. Four days later many of the royal warships went aground. While D’Estree returned to Martinique with the few survivors, Grammont and his 2,000 men, aboard nineteen vessels of various sizes, opted to attack Maracaibo instead.
Although the Spaniards defended the fort guarding the approach to the city, they eventually surrendered. The residents fled, including the new, but sickly, Governor Jorge Madureira Ferreira, which allowed the flibustiers to occupy the city on 14 June. One Spaniard wrote of Grammont: “this French enemy was so tyrannical that after taking everything people had, he would torture them unto death, something which not even a Turk nor a Moor would do.” (Marley, 155)
After razing the city, the corsairs left Maracaibo on 28 June. They sacked Gibraltar, then marched to Trujillo, fifty miles farther inland. Even though the fort there was manned by 350 soldiers and had four cannon, the corsairs gained access to the fortification on 1 September. Later, one defender wrote that they did so “by some hills where it seemed impossible to do so.” (Marley, 155) On their return journey the flibustiers plundered Gibraltar again, then set it afire. Not until 3 December 1678, did the French set sail for Petit Goâve, their ships laden with treasure and prisoners.
Grammont’s next venture took them to Caracas. During the evening of 26 June 1680, he and forty-seven men infiltrated the city while its residents slept. They took control of the fort and imprisoned the garrison’s commander and 150 soldiers. When the people awoke, they found themselves at the mercy of the corsairs. They freely plundered the homes and offices, but eventually a new contingent of soldiers arrived to relieve Caracas. Grammont and his men retreated to the beach with their booty and hostages, but the flibustiers did not leave unscathed. Nine buccaneers died and several others were wounded, including Grammont, whose neck had been slashed by a machete. The triumphant return to Petit Goâve was not repeated, however, for most of the treasure and many prisoners died when a hurricane shipwrecked
the flibustiers' ship.
Grammont blockaded Cuba in 1682, sacked Veracruz the following year, and in 1685 raided Campeche. He and his men finally arrived in the Atlantic off the Florida coast on 30 April 1686 with two Spanish prizes. While his flagship and one captured sloop anchored out of sight of the Spaniards, he sent the captured galliot, flying a Spanish flag, to Matanzas to do reconnaissance.
After three days, the galliot still had not appeared, so Grammont headed for Matanzas himself. Along the way, though, they spotted what remained of the prize, which had sunk in shallow water during a storm. At least some corsairs went ashore, but Governor Juan Marquez Cabrera ordered Jose Begambre and twenty-five soldiers to stop them. The two forces fought hand-to-hand for four hours, then the French returned to their ships. Along the way the local natives attacked them, too, which resulted in many deaths.
Once the buccaneers were safely on their ships, Grammont positioned his ship to blockade the inlet leading into San Augustín. A Spanish boat managed to slip past the French and sailed to Cuba for help. Once Grammont learned of this, he and his men chose to sail away without sacking the city. They went as far north as South Carolina. Once there, the corsairs decided to set sail for West Africa. They seized a Dutch ship off the Azores, but that was the last prize Grammont took. Soon after, his flagship went down in a storm. No one survived.
That failed attack was the last time pirates attempted to sack San Augustín. Spain held the city from its founding until the signing of the Treaty of Paris in 1763, which ended the Seven Years War. It then became a possession of the British, who only held it until 1783. At that time Spain reclaimed Florida, and retained it until 1821 when Florida became part of the United States.

1. Three years after the massacre at Fort Caroline, French Huguenots returned. They razed Fort San Mateo and hanged Spaniards who survived the attack.
2. This popular tune honored William Prince of Orange, who had led Dutch Protestant insurgents. He was assassinated in 1584.
3. The fort at the time of Drake’s attack is where the Fountain of Youth Park is now located. The small, unwalled settlement, consisting of wooden houses and shops, lay just to the south of the fort.

4. Drake’s sacking of San Augustín was his last successful raid in the Spanish Main.
5. The same year that Drake left with his armada for the New World, Sir Walter Raleigh sent out an expedition, under the command of Sir Richard Grenville, to establish the Roanoke Colony on the present-day island of Manteo in the Outer Banks of North Carolina. They arrived in July of 1685, but one ship ran aground, destroying most of the colony’s food supply. The following month, Grenville returned to England, leaving behind Ralph Lane and about 100 men. By the time Drake arrived, relations with the local tribes had deteriorated and food supplies had dwindled to such an alarming rate that the surviving colonists opted to return to England with Drake. It is the second group of settlers, who came in 1587, who are better remembered. They became known as the Lost Colony, after the first English child, Virginia Dare, was born in North America.

6. Father Sotolongo, the parish priest, blamed Governor Guerra for Searle’s devastation because the governor had been living in sin for three years in his house. Government officials appointed by the monarch were not permitted to marry local women. During this time Doña Lorenza de Soto y Aspiolea gave birth to three children while the pair remained unwed. Not until the next governor arrived would Guerra finally marry the love of his life.

7. The Franciscans paid 2,066 pesos to replace what the pirates stole from the church.

8. In 1692 the head Franciscan was ordered back to Spain to account for his order’s interference in Ranson’s execution and to prove that not carrying out the death sentence was the proper thing to do. The friar used the severed rope as evidence of a divine miracle at death, but the authorities didn’t agree. Two of the Franciscans were exiled from Florida as a result.

9. The Dutch seized the island from Spain in 1634, and Curaçao became a major slave trading spot for the Caribbean. It was the last major stronghold in this region occupied by the Dutch.

For more information, I recommend these resources:
Barton, Rose. “Robert Searle and the One that Got Away,” No Quarter Given IX:3 (May 2002), 7.
“The Basis of a Permanent Fortification,” No Quarter Given IX:2 (March 2002), 6-7.
“The Basis of a Permanent Fortification,” No Quarter Given IX:3 (May 2002), 6-7.
Biggs, Walter. A Summary and True Discourse of Sir Francis Drake’s West Indian Voyage, begun in the year 1585. Thomas Cates, 1589. 
Castillo de San Marcos: A Brief History. Historic Print & Map, 2002.
Castillo de San Marco Official Map and Guide. National Park Service.
Chartrand, René. The Spanish Main 1492-1800. Osprey, 2006.
Coote, Stephen. Drake: The Life and Legend of an Elizabethan Hero. Thomas Dunne, 2003.
Drake’s Raid, A Detailed History on Searle’s Buccaneers [accessed 12/26/2010].
Exquemelin, Alexander O. The Buccaneers of America translated by Alexis Brown. Dover, 2000.
Fort Matanzas Park Handbook on Augustine.com [accessed 12/29/2010].
History of Saint Augustine on Augustine.com [accessed 12/29/2010].
The History of the Castillo de San Marcos at Augustine.com [accessed 12/29/2010].
Konstam, Angus.  Piracy: The Complete History. Osprey, 2008.
Little, Benerson. The Buccaneer’s Realm: Pirate Life on the Spanish Main, 1674-1688. Potomac, 2007.
Marley, David F. Pirates of the Americas, volume I: 1650-1685. ABC-CLIO, 2010.
The Massacre of the French at National Park Service [accessed 12/26/2010].
McCarthy, Kevin M. Twenty Florida Pirates. Pineapple Press, 1994.
The Oldest City: St. Augustine – Saga of Survival edited by Jean Parker Waterbury. The St. Augustine Historical Society, 1983.
O’Steen, Joseph. “Drake’s Raid on St. Augustine,” Joseph O’Steen Nautical Author Newsletter 3:1 (1st quarter 2006), 2.
O’Steen, Joseph. “French Pirate Attack on St. Augustine,” Joseph O’Steen Nautical Author Newsletter 3:1 (2nd quarter 2006), 6.
“The Story of St. Augustine,” St. Augustine’s Red Train Tour Book (Winter/Spring 2005), 6-38 (even pages only).
Virtual Walking Tours of St. Augustine on Augustine.com [accessed 12/29/2010].
Walker, Davis. “Capt. Robert Searle’s Raid of 1668” on Searle’s Buccaneers [http://www.searles-buccaneers.com/searles_raid_rules.html -- link no longer active 8/3/2015].
Wright, J. Leitch, Jr. “Andrew Ranson: Seventeenth Century Pirate?” The Florida Historical Quarterly 39:2 (Oct. 1960), 135-144. Online

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