British Piracy

During the 1590s there were an average of 14 English expeditions to the Caribbean every year, with as many as 25 in 1598. That led by Francis Drake and John Hawkins in 1595- 96, aimed at San Juan de Puerto Rico and Panama, was the largest, comprising 27 ships, 1,500 seamen, and 2,500- 3,000 soldiers, but it met with even less good fortune than Drake’s solo foray a decade earlier. Hawkins died on the outward passage, and the Spaniards, long since forewarned of the impending English attack, had time to reinforce Puerto Rico with 1,500 fresh troops from Spain. When his attack was consequently driven off with considerable loss Drake sailed for Nombre de Dios, raiding along the coast of the mainland as he went. Nombre de Dios was found largely deserted, and he seized the fort and burned the town. He then despatched 900 men, organised into five or seven companies under his lieutenant, Thomas Baskerville, to traverse the Isthmus and take Panama, but after marching through torrential rain for three days these encountered stiff Spanish opposition on the fourth and, with their provisions and powder ruined by the downpour, they were obliged to withdraw. Re-embarking its landingparty, the fleet then sailed along the coast of Honduras and Nicaragua, its crews contracting dysentery en route after landing to find water. When Drake himself died of the `bloody flux’ in January 1596 command devolved on Baskerville, who called an end to the disastrous expedition and sailed for home with the remaining 14 or 15 ships (several having either been lost to the enemy or scuttled in consequence of having insufficient men left to crew them). It was left to another celebrated English corsair, George Clifford, Earl of Cumberland – author of a dozen raids between 1586 and 1598 – to succeed where Drake had not in capturing San Juan de Puerto Rico, which he did in 1598 with a fleet of 18 ships and 1,000 men. He had intended to hold the port permanently, but once again unsustainable losses to tropical disease obliged the English to withdraw without installing a garrison. The frequency of such semi-official English ventures subsequently declined, there being only ten altogether between 1600 and 1603, when the long-running Anglo-Spanish conflict effectively came to an end.

The majority of pirate flotillas operating in American waters initially consisted of no more than a single ship equipped for both fighting and trading, accompanied by a smaller vessel of a type called a pinnace or patache, which, having a shallow draft and being provided with up to 18 oars a side as well as sails, was better suited to the inshore work called for in coastal operations. The pinnace might displace as little as 20 tons and could have a crew of as few as 20 men or as many as 70, but carried little or no armament beyond a number of small versos (1-11/2 pdr breech-loading swivels). No raiding force recorded in the first half of the century ever comprised more than 800- 1,000 men and six vessels, of which two at the very least were pinnaces. During the 1550s, however, the French despatched larger fleets which included royal warships as well as privateers, and carried sizeable contingents of troops for deployment ashore. The ten ships which sailed under François le Clerc in 1553-54 constituted the first of these more substantial ventures, and included two royal warships and three or four pinnaces. Most English expeditions of the period 1572-1603 were of three ships or less. Only those which received royal backing were any larger, being sometimes accompanied by royal warships (two served under Drake in 1585-86, and five in 1595-96). Drake’s expedition of 1572-73 appears to have been unique in carrying three prefabricated pinnaces aboard one of its two ships, which were unloaded and re-assembled when he arrived at his destination in the Gulf of Darién. Pinnaces were sufficiently important to the success of a privateering enterprise that expeditions were generally abandoned if the larger ships lost touch with them for any reason, while the pinnace commander sometimes decided to utilise the advantages of his vessel for his own profit, abandoning the accompanying ship to go a-roving on his own.


Drake knew from experience that a surprise assault was critical to their success. They laid in wait, crouching by the side of the jungle path for what must have seemed an eternity before the tinkling of mule bells rang sweetly in their ears. Suddenly, the gallop of a lone horse coming from the wrong direction warned Drake that all was not as it should be. Before the rider could be stopped he had alerted the muleteers to head back, and that the pirate Drake would pounce on them any moment. The Spanish cleverly separated out the silver shipment from the more valuable gold—estimated at some £35,000 ($12.32 million or £6.66 million today)—and sent the mules carrying the silver on into Drake’s arms. Realizing that they had been discovered, Drake and Pedro decided that it would be too risky to return to base the same way they had come, and opted instead to boldly take Venta Cruces. The raiding party marched through the town, burning and pillaging as they went. Any casualties incurred were in defense of property, not in brutal murder, according to reports both Spanish and English. Drake had also ordered his men that the women must remain “inviolate,” and he even entered homes to reassure the women personally that none of them would be raped. While there is no excuse for the terror Drake and his raiders inflicted on their victims, this level of humanity in the sixteenth century—let alone in the twentieth or twenty-first—is remarkable.

Now that he had made his strike, Drake once again lay low, hoping to trick the Spaniards into believing that he had left the Caribbean with his paltry treasure. While his good “Plymouth lads” grumbled about the heat, humidity, and their ill-luck, the Cimarrones tended the sick and injured and made moccasins for the foot-sore rovers. Drake marveled at their strength, their courage, and above all their loyalty. “Yea many times when some of our company fainted with sickness or weariness,” Drake wrote later, “two Cimarrones would carry him [the sick] with ease between them two miles together, and at other times (when need was) they would show themselves no less valiant than industrious and of good judgement.”

After their retreat, there was little else to do than plan their next raid for the spring of 1573, and capture a prize that would hopefully keep them well provided in victuals and water. Then, nearly a month after they had rejoined their ships following the Venta Cruces raids, a large French ship bore down on them just off Cativas Headland near Nombre de Díos. Her captain, who had been looking for Drake for some five weeks, was none other than the Huguenot corsair Guillaume le Testu. Le Testu was no ordinary pirate. He had been the personal protégé of Admiral de Coligny, and was captaining a ship for the merchant adventurer Philippe Strozzi.

Le Testu was well known to Drake. After all, Le Testu had taken part in the French colonial adventure to Brazil, and Drake admired the French challenge in South America to the Spaniards. So when the Frenchman asked for water, and explained some of his men were ill, Drake ordered provisions to be sent aboard; then he asked Le Testu to follow him to one of his storehouses so that they could be fully replenished. When they finally anchored, the Huguenot captain gave Drake a gilt scimitar that had been a gift of his dear, now butchered, leader, Admiral de Coligny. This devastating news, and the carnage that had ensued in France, shocked and angered Drake, making the gift all the more dear.

The two men had already respected each other before they ever met, but once in the same cabin together, that respect grew into mutual admiration. Le Testu showed Drake his invaluable folio atlas of fifty-six maps that he had drawn based on his own experiences, and which had been dedicated to Coligny some years earlier. This treasure of experience would have driven home the fact to Drake of how poor English knowledge of the seas had truly been. Le Testu had been a royal pilot at Le Havre, and had been born and bred with the sea coursing through his soul like Drake. The main difference between the two was that Le Testu had high-level contacts in Coligny and, lately, André Thévet, Catherine de’ Medici’s chaplain. Drake had to make his own way through hard graft. What is striking from this encounter of great “pirates” is that Le Testu would have not been a corsair or outlaw if he had adhered to the Catholic faith.

Naturally, Drake and Le Testu fell in together, and agreed on how to mount another raid on the trajín. Le Testu believed that if they attacked closer to Nombre de Díos, after the gold and silver shipments had been separated at the Chagres River, the soldiers would be more relaxed as their journey was nearing its end. It would be easier to box them in or, preferably, disperse the mule train’s defenders more easily, he ventured. Drake agreed.

On March 31, 1573, the combined Cimarrone, English, and Huguenot forces stole into the jungle. Cimaroon scouts edged forward in the night, returning to their positions before daybreak. The trajín had nearly two hundred mules in all and an escort of around forty-five poorly armed, barefoot soldiers.

The assault was rapid and deadly. The Cimaroons led the charge. Within the first few seconds, a Negro harquebusier fired at Le Testu, wounding him in the stomach, and killing a Cimaroon. The attackers surged forward regardless, shouting fierce battle cries and shooting off their weapons. The Spaniards quickly recognized that if they stayed and defended the trajín, it would be a turkey shoot, and they would be the turkeys. While they turned tail and ran, the raiders leapt onto the baggage and prized open the chests. The mules were carrying more than 200,000 pesos de oro ($23.24 million or £12.56 million today). What made the prize sweeter was that 18,363 pesos de oro ($2.13 million or £1.15 million today) personally belonged to the King of Spain.

The fifteen tons of silver looted was hastily hidden in burrows made by land crabs, or under fallen trees. They had to be quick about it, though, since again, they were only two leagues from Nombre de Díos. Half of the gold was loaded back onto the mules and carried to the mouth of the Francisca River, where their pinnaces were waiting. But Le Testu was mortally wounded, and he knew it. He told Drake to go ahead and leave him, that he would guard the silver until they could return. The last thing Le Testu wanted was for Spanish soldiers to cut off their retreat to the sea, and Drake reluctantly agreed. Two of his men volunteered to keep him company, while the others marched laboriously away.

Two days later, after yet another torrential downpour in the jungle, the raiders arrived at their rendezvous. But instead of their own pinnaces, they found Spanish shallops. Had the pinnaces been captured? How would they escape back to their pirate’s haven? the men asked. Had the Spaniards wrecked the Pasco and dashed their hopes of returning home? Drake knew from experience that action would keep these worries from overpowering his men. As ever ingenious, he instructed them to make a raft from fallen trees, binding the trunks together and using a slashed biscuit sack for its puny sail. It wasn’t pretty, but it just about floated. After the Spaniards rounded the headland, Drake and three men waded out in their ludicrous tree raft, at times sailing waist high in seawater, before they spotted the Bear and the Minion, nestled in a safe harbor nearby. As Drake boarded the ship, he broke into a sudden smile and brought out a quoit (disc) of gold from his shirt. Their voyage had been made.

After his men had been brought safely on board, the Cimarrones came forward with the sad news that captain Le Testu had been killed. Drake said a prayer for the Frenchman’s soul and gave the order to weigh anchor. It was unsafe to return for the silver. Their voyage had been made, thanks in large part to the Cimaroons and the Huguenots, with whom he gladly shared their prize. They had been away for more than a year, and more than half of them were dead, including Drake’s two brothers.

In an incredibly swift and uneventful crossing of only twenty-three days, Drake and his remaining crew pulled into Plymouth harbor on Sunday, August 9, 1574. All the good men and women of the town were at prayer in St. Andrew’s Church, listening to their vicar’s sermon, when a murmuring among the parishoners grew into a roar. Drake had returned, they whispered to one another. One by one they left, until finally the entire flock deserted its preacher and raced to the waterfront to welcome home their heroes.

The French

In the absence of their own navigational charts, early French raiders depended heavily on the knowledge and experience of disaffected Spanish pilots, Benzoni recording in the 1540s that `it was some Spaniards, practised in that navigation, who led the enemy, so that the French also became as familiar with those waters as the Spaniards themselves’. It was, for instance, a Spaniard who guided five French ships into Cartagena harbour in 1544, where they landed 100 men and sacked and burnt the town. Before long, however, French corsairs knew as much about navigating in the Caribbean and the Atlantic sea-lanes as their Spanish counterparts, and had accumulated sufficient intelligence of Spanish strength in the region to enable them to launch their attacks with impunity. Benzoni noted that `although in the beginning they restricted themselves to the vicinity of Hispaniola and San Juan de Puerto Rico, yet when those districts ceased to yield rich prizes, they frequented more of the islands, and even some of the provinces on the mainland’, pillaging towns and capturing ships wherever they went. The audiencia of Santo Domingo reported in 1541 that French corsairs `knowing the weakness of these ports landed in many of them, in full daylight, [and] burned and robbed some without meeting any resistance’. Very few Spanish attempts to repel pirate landing-parties were ever successful, and at least some of those that were owed their success more to bribery than force of arms. Indeed, Blasco Nuñez Vela (1539) considered that 300 corsairs could seize any coastal town on the Spanish Main that they cared to, regardless of its size or strength, and it is readily apparent from the sources that the Spaniards’ poor leadership and lack of adequate arms virtually guaranteed the pirates success on land. So long as they managed to avoid the larger and more heavily-armed Spanish warships sometimes despatched against them there was also very little that they needed to fear at sea.

Normal French raiding practice, as recorded by a Spanish eye-witness in 1571, was for the crew of the pinnace to make the attack while the larger ship stood offshore, the booty being subsequently transferred to the ship, which would periodically return to Normandy to sell it. This is exactly how Sores went about attacking Havana in 1555, when he landed the bulk of his men by means of his pinnaces and ships’ boats to outflank the town’s defences and launch an overland attack from the rear. On this particular occasion the French set fire to the fort’s gates to smoke out its garrison after several hours of fighting. The Spanish governor had meanwhile rallied the population (which, as was customary under such circumstances, had fled inland with the greater part of its portable valuables at first site of the corsairs) and returned with such armed men as he could muster, but was beaten off. Drake employed much the same tactics in his attack on Santo Domingo in 1586, putting his landing-party ashore several miles away to launch a surprise attack from the rear while his main fleet kept the town’s defences occupied from the seaward side. This became the characteristic modus operandi of English privateers thereafter.

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