Had Morgan known what was out there waiting for him, he might have demanded bigger ships. Modyford’s informants had understated the danger. The long-awaited Armada de Barlovento, the fleet of six vessels designed to protect the Spanish Main, had finally arrived in the New World after decades of bureaucratic death matches between the Council of the Indies and the navy. “The only reason that forced Her Majesty to convene the Windward Fleet again,” wrote a Spaniard from Mexico, “was the great destruction caused by the enemy pirates. The enemy is hostile and has destroyed the commerce of the region.” The armada’s arrival instantly changed the balance of power on the open seas. These were not the usual Spanish galleons, their decks cluttered with trade goods, bales of silk dresses stuffed into spaces where guns should have gone, their crews facing the interference of lawyers and notaries. These were heavy warships bristling with cannon, manned by competent soldiers, and far superior in firepower to any pirate ship in the world. They were even commanded by an admiral, Alonzo de Campos y Espinosa, who had been given one and only one mission: “to clean the coasts of the Indies of the pirates which infest them.” Henry Morgan was not public enemy number one for the Spanish quite yet, but he was climbing toward the top of the list. And if he and his small ships ran into the armada on the open sea, he and his glorified dinghies would be quite literally blown out of the water.
As he walked his decks, Morgan would have passed among men from every corner of the Old World and the New: There were adventure-minded English youths like Roderick, French Huguenots who had fled religious persecution, English freethinkers and jail-birds, old hands from Cromwell’s New Model Army still dressed in the legendary scarlet coats, now tattered and stained; there were Portuguese adventurers, escaped slaves, mulatto sons of Spanish fathers and black mothers; indentured servants who had jumped aboard trade ships and made their way to freedom; perhaps an odd Dutchman or two. In the Old World, they would have been in a jail cell or working as disgruntled serfs. On Henry Morgan’s ship, they were one move away from being a captain or just filthy rich.
The pirates called their council. “Some were of the opinion ’twere convenient to assault the city of Havana under the obscurity of the night,” Esquemeling writes. Havana was “one of the most renowned and strongest places of all the West Indies,…defended by three castles, very great and strong.” But among the pirates were men who had been held prisoner in those castles, and they said that “nothing of consequence could be done, unless with fifteen hundred men.” Morgan had less than half that. Other city names were tossed out and debated, until a consensus formed around the city of Puerto del Príncipe. One of the buccaneers knew it and gave two things to recommend it: The town was rich and, sitting forty-five miles inland from the Cuban coast, had never been raided by pirates. Buccaneers loved fresh, untouched cities, and here was one grown prosperous on the trade in animal hides. The motion was approved, and the pirates set out for the Gulf of Ana María.
But Morgan’s illustrious career was almost deep-sixed before it even began in earnest. A Spanish prisoner who was being held by the pirates escaped from the ships and began swimming toward shore. The pirates, who didn’t think the man could understand English, had let him listen in on their council, and as soon as he reached Puerto del Príncipe, he began to tell the terrified townspeople exactly what Henry Morgan had planned for them.
This was a problem that would plague Morgan’s career and the career of many other marauders. It was nearly impossible to keep the element of surprise in an attack. If one approached a city by land, there were often settlers or Indians who would send a warning to the target settlement; if one approached by sea, fishermen and lookouts could often give the enemy at least a few days’ warning, especially as ships were dependent on a good wind to make landfall and could sit becalmed for days, in full view of their opponents. And with so much money at stake, men regularly informed on the pirates for rewards and for special treatment. The pirates themselves would brag about upcoming expeditions, especially when drunk, and the Spaniards had spies everywhere. Loose lips did sink ships, and that included pirate ships.
The Spaniards immediately began to dump their plate into the local wells and dig holes for their money. The governor, who was a former soldier and knew his defensive strategy well, ordered “all the people of the town, both freedmen and slaves” to lie in ambush for the English, and he instructed that trees be cut down and laid in the buccaneers’ path, to slow their approach; fortifications were also thrown up “and strengthened with some pieces of cannon.” Eight hundred men were rounded up; Morgan, who had landed by now, marched on the town with 650.
Morgan immediately began to show what he’d learned in the Jamaican jungles. Finding the approaches to the town impenetrable, he took his men into the woods, where progress could be made only “with great difficulty,” but which took the pirates safely past the ambushes on the trail. After a long, sweaty march, the pirates emerged onto a plain, la Savana, that lay before the city. The governor spotted the advancing ranks, now formed into a semicircle, and sent his cavalry to break them up. The pirates did not flinch: Their spirits roused by the sound of their drummers and by marching behind the flag of the Brethren, they began picking off the riders as they swept toward them. The assault was broken, and the skirmish on la Savana devolved into a classic, head-to-head, open-field battle in which marksmanship was all-important. The French muskets proved their worth: Soon the governor went down, and more and more Spaniards were dropping one after the other under the privateers’ wickedly accurate shooting. Finally, “seeing that the Pirates were very dextrous at their arms,” the Spanish relented and the men turned toward the wood line to try to escape. Morgan and his men did not let them get far; “the greatest part of them” died as they retreated. The battle had taken four hours. The Spaniards lost most of their men, the pirates only a few.
Within an hour Morgan was on the outskirts of the city, where the pirates found the people holed up in their houses, taking pot-shots at them. This was too much for Morgan; he’d won the city fair and square. He sent the following message to the town’s men: If you surrender not voluntarily, you shall soon see the town in a flame, and your wives and children torn in pieces before your faces. The Spanish relented, and Morgan had all the prisoners locked up in several of the city’s churches. After pillaging the empty homes, Morgan then sent his men out into the countryside, “bringing in day by day many goods and prisoners.” There was wine, too, and the privateers guzzled it like water.
The admiral then turned to an old pirate standby: ransom. Four prisoners were sent into the adjacent woods to find the people who had fled and demand money for the imprisoned families. The four returned a few days later to tell Morgan they’d been unable to find anyone and asked that he give them fifteen days to complete the job. Morgan agreed. A few hours after the four messengers had left, some of the privateers returned from pillaging and reported they’d taken substantial booty and also captured a Negro who was in possession of letters. When Morgan read them, his eyes must have narrowed with fury. The missives were from the governor of Santiago, capital of the adjoining province. In them he told the prisoners to delay paying any ransom and to “put off the Pirates as well as they could with excuses and delays; expecting to be relieved by him within a short while, when he’d certainly come to their aid.” Morgan had been double-crossed. As the men had swilled the local wines and fell over themselves collecting booty, an army was being organized to defeat them.
Morgan began barking out orders. He told his men to load the ships with all the treasure and demanded that the Spanish slaughter and salt five hundred head of cattle for his men, which they did along with the buccaneers in great haste. Finally the beef was loaded—after an unfortunate incident in which an English privateer stole the marrow bones from a cow being slaughtered by a Frenchman. As they walked to a dueling spot, the Englishman “drew his sword treacherously” and fatally wounded the other man in the back. The French were ready for war right the
re on the beach, but Morgan had the man arrested and promised his Gallic allies justice once they returned to Port Royal. The French grumbled but agreed.
The Spanish were impressed by the raid. The governor of the province that included Puerto del Príncipe wrote to the queen regent to express his shock and outrage at what the privateers had done. He reported that he’d charged his sergeant major and another officer with misconduct, because the rugged country and long distances should have enabled a much smaller force to destroy the buccaneer army. The privateers were less thrilled. They sailed off to the South Cays and counted up their booty, which came to a disappointing 50,000 pieces of eight (or $2.5 million in today’s dollars). It sounds like a windfall, but when deductions were made for the king’s share, for Morgan’s and the captains’ and the surgeon’s and carpenter’s take, for injuries, and with the remainder being split among 650 men, the seaman’s share was hardly a small fortune. And besides, Port Royal, where many of them made their homes, was one of the most expensive cities on earth in which to live, as nearly everything except rum and food had to be imported from Europe. “The sum being known,” reports Esquemeling, “it caused a general resentment and grief, to see such a small booty; which was not sufficient to pay their debts at Jamaica.” Roderick was among the complainers. His share would barely pay his back rent, let alone allow him the bacchanal he’d been dreaming of for weeks. From a callow youth, Roderick had grown into a shrewd, toughened buccaneer, with hardly an ounce of fat on him. For the first time, he looked at his leader with a cold eye.
The mission could not stop now; another city would have to be hit. Morgan’s reputation, his future as the admiral of the Brethren, was at stake. If he returned with such a small payday, he might be voted out of power. Already some elements of the force were withdrawing their confidence. The Frenchmen pulled out of the mission, even after Morgan used “all the persuasions” he could think of to convince them to stay. It was a shocking blow.
And Morgan must have known exactly what had gone wrong: He hadn’t been cruel enough. Failing to torture the captives, as most pirates would have done, and allowing them plenty of time to raise their ransom, went against the proven methods of buccaneering. A follower of the gallant Mansfield, he’d played the gentleman, only to have the Spanish string him along, toy with him as if he were an amateur. His softness had cost him dearly. The French made this point clearer when they left Morgan to join one of the legitimate monsters of the pirate world, Francis L’Ollonais. In his report on the adventure, Morgan would say that the Gallic pirates “wholly refused to join in an action so full of danger,” but danger was never the point. It was leadership. L’Ollonais represented the pirate code at its most extreme, but Morgan could not afford to ignore his methods. The privateers would sail with whoever found them the most gold, and L’Ollonais was a rising star who was making his boys rich. Morgan would have to meld his ideas with those of a ruthless killer if he were to avoid another embarrassment.
Born Jean David Nau, L’Ollonais got his name from the Sands of Ollane, the region in Brittany where he was raised. He came to the New World as an indentured servant and, after serving his time, arrived on Hispaniola as a free man. He joined some of the original boucaniers and then graduated to the Brethren at Tortuga. The pirates had not seen his like before; L’Ollonais was an innovator, as well as a complete and utter sociopath. His career gives an idea of what Morgan was competing against. The Frenchman began as a common pirate, boarding ships with the other men. “He behaved himself so courageously,” Esquemeling tells us, “as to deserve the favour and esteem of the Governor of Tortuga.” The governor recognized a good prospect and gave L’Ollonais his own ship “to the intent he might seek his own fortune.” (One can be sure that the governor got his cut of any proceeds.) Word of the Frenchman’s extreme cruelty immediately began to spread throughout the West Indies. “It was the custom of L’Ollonais that, having tormented any persons and they not confessing, he’d instantly cut them in pieces with his hangar [cutlass], and pull out their tongues,” Esquemeling tells us, “desiring to do the same, if possible, to every Spaniard in the world.” He delighted in putting men to the rack and in “woolding,” or tying a stick around a victim’s forehead and tightening with turns of a stick until the interviewee’s eyeballs popped out of the sockets. But that was standard procedure, on both sides of the war between Spain and its enemies in the New World.
After outfitting his ship, L’Ollonais ran into bad luck when he was caught in a storm off Campeche; his ship was destroyed, and he and his men were forced to swim for their lives. When they made it to dry land, they were hunted through the forests by the Spanish, who killed many and wounded their captain. To survive, L’Ollonais “took several handfuls of sand and mingled them with the blood of his own wounds,” then smeared the mixture all over his face and hands. Lying down among the slaughtered men, he played dead. When the Spaniards left, he disguised himself as a local and insolently marched into town; mingling with the Spanish, he overheard them calling to his ex-crewmen, now held prisoner, “What is become of your captain?” “He is dead,” the men replied. “With which news the Spaniards were hugely gladdened, and made great demonstrations of joy, kindling bonfires and…giving thanks to God Almighty for their deliverance from such a cruel Pirate.”
Returning to Tortuga, L’Ollonais scared up another ship and crew and set out to exact his revenge. The governor in Havana was informed by residents of a seaside town that L’Ollonais had risen from the dead and was again terrorizing them; he sent a small warship with ten cannon and fifty soldiers, ordering them not to return until they’d “totally destroyed those Pirates.” (He even sent along a Negro executioner, who was told to hang every pirate except L’Ollonais, who was to be brought to Havana for special attentions.) L’Ollonais and his men stormed the ship on its arrival, boarding even in the face of barrages from its cannon. One by one the captured crew members were brought up from the hold and were beheaded. Finally it was the executioner’s turn; the terrified man begged L’Ollonais for his life. “This fellow implored mercy at his hands very dolefully…and [swore] that, in case he should spare him, he would tell him faithfully all that he should desire to know.” L’Ollonais must have laughed at that; as if he were not going to find out everything he wanted anyway. He got the information he needed and promptly lopped off the man’s head. Only one man was spared, and he was sent back to the governor’s office in Havana with this message:
I shall never henceforward give quarter to any Spaniard whatsoever; and I have great hopes I shall execute on your own person the very same punishment I have done upon those you sent against me. Thus I have retaliated the kindness you designed to me and my companions.
Morgan would learn this: Pirates depended on their reputation for cruelty. If townspeople knew ahead of time that you cut off people’s heads for withholding information, they tended to talk a lot more readily. Armies surrendered. Mayors bargained. Loot materialized. It was the difference between seeing the Hells Angels pulling into your isolated town versus some strangers from the next county. You might be willing to take your chances with the latter, especially if you were guarding money built up over a lifetime of brutal hardship. But not with the Hells Angels—and not with the pirates. The Angels’ winged skull insignia sends the same message as did the pirate’s flag: You know who we are. Do as you’re told.
Some pirates cultivated a reckless image: The first description that civilians throughout the Americas repeated over and over again when retelling their encounters with the Brethren was “barbarous”; the second was “crazy.” “I soon found that death was preferable to being linked with such a vile crew of miscreants,” wrote Philip Ashton, a young fisherman captured by pirates in 1722. The Spanish tended to torture captives according to a formula: There were probably in the advice ships crisscrossing the Atlantic booklets full of exact instructions for how to pull out a man’s toenails for stealing a loaf of bread. The Inquisition’s brutality was institutional
. The pirates’ was often just insane. One buccaneer, Raveneau de Lussan, recounted that captives were often ordered to throw dice for their lives; whoever lost, lost his head. Blackbeard took this management philosophy to a new level. The pirate commander was once drinking in his cabin with the pilot and another man. Without any provocation he drew his pistols underneath the table, cocked them, blew out the candle, crossed his hands, and fired the guns. One of the men was shot through the knee and lamed for life, while the other escaped shaken but unhurt. Blackbeard did not have any quarrel with either man, which naturally led one of them to ask him why he’d shot them. “He only answered by damning them, that if he did not now and then kill one of them, they would forget who he was.” [Emphasis in the original.]
This strategy also meant that the craziest often rose to the top of the trade. “He who goes the greatest length of wickedness,” wrote Captain Johnson, the author of A General History of the Robberies and Murders of the Most Notorious Pirates, “is looked upon with a kind of Envy amongst them, as a Person of a more extraordinary Gallantry.” One Captain Taylor was pointed out as being popular for all the wrong reasons, “a great Favourite amongst them for no other Reason than because he was a greater Brute than the rest.” But other pirates were, after all, simply young men from coastal cities in England who had wanted a little adventure; they were not born lunatics but decent men who had sought out adventure and gold, not orgies of violence. A schism can sometime be detected in pirate narratives: Captain George Roberts was captured by pirates off the coast of the Cape Verde Islands in 1722; he was used to the rough ways of seamen, but the pirates’ wanton cruelty appalled him. Roberts had the guts to try to challenge them and eventually gave a speech to the whole crew about God and conscience. When he finished, the men responded:
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