7

Portobelo

Morgan, abandoned by the French in the South Cays, now showed why he would outshine L’Ollonais. He began by giving a speech. By all reports the thirty-three-year-old Morgan had the common touch and was able to motivate even the most hardened privateer; one of his peers wrote about his “generous and undesigning way of conversing.” Seeing the doubt in his compatriots’ eyes, he “infused such spirit into his men as were able to put every one of them instantly upon new designs,” Esquemeling writes, “they being all persuaded by his reasons that the sole execution of his orders would be a certain means of obtaining great riches.” Among the listeners was an anonymous pirate from Campeche who had rendezvoused with Morgan’s tiny remaining fleet and was obviously judging whether to throw in his lot with them or go off hunting with someone else. Morgan, who “always communicated vigour with his words,” won him over. Soon Morgan’s fleet was back up to strength, boasting nine ships. A further mark of Morgan’s renewed confidence is that he persuaded the pirates to sail without voting on a destination, a violation of the pirate code. Fresh off a defeat, he was reasserting control. Roderick and the other English privateers now formed the backbone of his army.

The privateers sailed to the coast of Costa Rica in July of 1668, and Morgan revealed the target: Portobelo. Some of the pirates protested instantly. The Panamanian city (originally known as Porto Bello) was a major stronghold; it boasted two large castles, the mammoth Santiago and San Felipe de Todo Fierro (the Iron Fort), one on each side of the harbor mouth, bristling with forty-four guns that would fix any enemy ship in a withering fire. (It was also said that the Italian who had laid out the city chose the spot because it stood on a peculiar type of coral that could withstand cannon blasts.) Should a pirate ship miraculously make it past the two castles, farther up the river toward the town there were layers of military redundancy: sentry posts, blockhouses, lookout positions manned by armed soldiers. Near the quay another huge fort was being built by the unfortunates who had been captured at Providence, slaving away during the day and chained in a prison at night. There were only two cities with stronger defenses in the entire Spanish Main: Havana and Cartagena. Even the great Sir Francis Drake had died outside Portobelo harbor, unable to penetrate its defenses.

Portobelo was a seasonal Fort Knox: It was the terminus for the tons of raw silver dug out of Potosí and made into pieces of eight at the king’s mints. For most of the year, it was a tropical hellhole: hot, breezeless, full of “noisome vapours,” a place where various diseases competed for supremacy and fresh victims, where the smell of the rotting, fetid mud that the low tide revealed would blast into a visitor’s nostrils, never to be forgotten. To be posted to Portobelo was the Spanish noble’s biggest dread; it boasted few of the amenities of bustling Cartagena or sophisticated Havana. It existed only for those four or five weeks when the Spanish treasure fleet appeared on the horizon and Portobelo went from backwater to boomtown in record time. Merchants from Peru, Colombia, and the far reaches of the Spanish Empire, including Madrid itself, would pour into the city, sending rents spiraling. The wealth of the king’s dominions, which had been brought up the coast of South America and loaded onto mules at Panama, flooded into the town. The population exploded from 2,000 permanent residents to perhaps 10,000. Traders brought their best slaves. Farmers brought chickens (whose price would increase twelvefold). Two thousand mules were kept at the ready for transporting the king’s treasure; long trains of the sturdy animals that had laced the hills above the town in the days before would suddenly appear in the streets, loaded with jewels and bullion from Peru and beyond. Thomas Gage, while a Dominican friar, had visited the town before a fair and counted two hundred mules entering the town square in one day and dumping their load of treasure there. “Silver wedges lay like heaps of stone in the street,” he marveled; but with the town crawling with Spanish soldiers, no one dared touch a bar. Instead of coins, wedges of silver were traded for the rich spun cloth, the fine muskets, and the hundreds of other goods that arrived from Spain on the treasure ships. The assembled treasure during the fleet’s visit could amount to 25 million pieces of eight, double the king of England’s annual revenue.

Portobelo was the result, in many ways, of one man and one day in the summer of 1544. A young Inca named Diego Huallpa had spent a long morning tracking an elusive deer on the mountain called Potosí in the kingdom of Peru (now Bolivia). The lining of this throat began to parch as he ascended beyond the thirteen-thousand-foot mark, high even for an Inca who spent his life in thin air. But fresh meat was precious, and Huallpa pressed on, determined to claim his prey. As he reached for a shrub to steady himself on the slopes, the plant tore away, and in its thick, dangling roots was entwined something that flashed in the sun, distracting Huallpa. He brushed away the clots of dirt; the metal gleamed under his thumb. Silver, unmistakably.

The Spanish were soon knocking on his door, threatening Huallpa with the rack, one of their earliest imports to the Americas. He pointed them to the mountain. Even when their Indian workers began to dig out piles of silver from the spot where Huallpa led them to, the colonial administrators could not conceive of what they had found. In the next two centuries, Potosí would yield almost 2 billion ounces of high-grade silver ore, at a time when the metal was just as valuable as gold. The entire European economy, tamped down for decades because of a lack of precious metals to serve as currency, took on a new life when the first ships began arriving in Spain groaning under the weight of the mine’s silver bars. The famed city of El Dorado, the city of the Golden Man, drove the conquistadors mad with its tales of unfathomable riches, but it was a myth. Potosí was real. To this day when a Spaniard wishes to talk of any crazily wealthy thing, he simply says, “It’s a Potosí.”

The men seeking the treasure rarely thought of the price paid for each ounce extracted. A Spanish visitor described the Inca workers who recovered the ore. He reported that they worked twelve hours a day, descending as far as seven hundred feet into the mine “where night is perpetual” and the air thick with fumes to gather the ore, and then climbing four or five backbreaking hours to rise again to the surface. If any of them slipped, they’d plunge to their deaths at the bottom of the pit. It was for the product of this misery that Morgan was coming to Portobelo.

To attempt the town, Morgan again had to rally his men, among whom numbered mulatto pirates along with blacks, Portuguese, Italian, French, and English. Many of them considered him crazy even to suggest Portobelo; it was beyond them. But Morgan made them see. “If our numbers are small,” he cried, “our hearts are great, and the fewer we are, the better share we shall have in the spoils!” It was a wonderfully condensed battle cry tailored for pirates: It combined the David-versus-Goliath odds that they seemed to relish in certain moods with the brute economic reality that fewer men meant bigger shares. The pirates quickly signed on.

The Welshman had prepared well. An Indian informant from inside Portobelo had given him an accurate picture of the garrison’s numbers and state of mind. The soldiers manning the various defenses hadn’t been paid in over a year and a half, leading some of them simply to disappear from their posts and others to take up side jobs as tailors or grocers in the town itself, where they slept at night, leaving the castles seriously undermanned. The mammoth Santiago boasted only 75 or 80 men on a typical night, when there should have been 200 trained soldiers on guard. The castle forces were supposed to be backed up by civilian militias (one each for Spaniards, mulattoes, freed blacks, and slaves), but they, too, were depleted by sickness or other duties. Many of the Spaniards were in Panama, away from the miasma that was Portobelo; the loyal blacks were chasing maroons in the hills around the town, leaving fewer than a hundred men able to fight.

And then the pirates stumbled on unimpeachable witnesses: Half a dozen bone-thin and badly sunburned men approached the fleet in a canoe as it headed for Portobelo. It’s not clear if they’d heard rumors of Morgan’s approach or had simply happened on the fleet, but they knew the target city well; it turned out they were some of the long-lost English soldiers from the garrison who had been taken during the Spanish reconquest of Providence and shipped as slaves to Portobelo, where they’d suffered unspeakable torments. As he listened to the men tell of their inhuman treatment, Roderick looked at these half-dead wretches, knowing that the same fate awaited him if he was captured by the Spanish. His anger built to a fever pitch; not in years had he felt so English. He and the others swore they would see the Spaniards bleed for what they’d done to the captives. But two extra nuggets of information tantalized the coolheaded Morgan: The newly freed men reported that an expedition against Jamaica was being planned and that funds were being raised through a levy in the province of Panama. The rumors of war, it seemed, were true. The men also swore that one of their fellow captives was none other than Prince Maurice. Maurice was the king’s nephew who had fought for him throughout the Civil War after a youth spent drinking and dueling in The Hague and elsewhere. He and his brother Rupert had been cruising the Caribbean in 1652 when they’d run into a ferocious storm and Maurice’s ship had disappeared. “He was snatched away from us in obscurity,” wrote one cavalier who had been on the voyage, “lest, beholding his loss would have prevented some from endeavouring their own safety; so much he lived beloved, and died bewailed.” Rumors had flown ever since the sinking: Maurice was dead and at the bottom of the sea; he was alive and being held by the Spanish at Morro Castle in Puerto Rico. Now Morgan had a fix on him. To find Maurice would earn the eternal gratitude of the king, a useful thing considering that Morgan was set to attack Spain in a time of peace. “We thought it our duty to attempt that place,” Morgan wrote in his report on the mission.

Portobelo sat at the southeastern end of a small bay. On the northern shore of the bay sat the fort called San Felipe and on the southern shore, farther in toward the city, sat Santiago, the Iron Fort. An approach through the narrow mouth of the bay was out of the question; the castles were undermanned, but it would take only a few decent gunners to blow the fleet to splinters. Instead Morgan devised a plan based on stealth. The fleet anchored at Boca del Toro, a quiet bay to the southeast of the town. There, according to Morgan’s own narrative, 500 of the men transferred into twenty-three canoes that the ships had been towing or carrying. These were the same type of forty-foot, single-sail canoes that Morgan had used in his odyssey to Central America, and now the men bent low over their sides, dipping the paddles into the black water and speeding the boats along with the strong easterly current. The canoes were becoming a Morgan trademark; so was traveling by night. The buccaneers paddled through the darkness “to be ye more undiscryed” and found hiding places on the deserted shore by day, sweltering beneath the trees. They slid under the guns of San Lorenzo, the fort that guarded the river Chagres, and sped on. It was like a journey through the primeval world, uninhabited and tomb-quiet except for the night cries of parrots and the growls of jaguars.

For four nights the fleet of canoes remained undetected until it came upon a fishing boat manned by two blacks and a “zambo”; in other parts of the Americas, the term would come to mean someone who was three-quarters black and one-quarter white; here in the Spanish territories it meant a person who was half black and half Indian. The pirates began to torture the blacks, what the Brethren called “questioning with the usual ceremonies.” [Pirate argot tends to be drier, more English, than the “Avast!” and “Shiver me timbers” flung about by buccaneers in Hollywood films: Escaping from a tight situation was called a “soft farewell”; “a forced loan” was any theft from the Spanish; a pirate’s corpse left out as a warning to others was described as “sun-dried,” while poking captives with knives as they ran around a circle of laughing pirates was a “sweat.” These intermingled with sailor lingo such as “belly-timber” (food), “fudled,” (drunk), and “Davy Jones” (the devil’s minion), who lived at the bottom of the sea, aka “Davy Jones’s locker.”] The Negroes refused to guide the pirates to Portobelo. Morgan had learned the lesson of Puerto del Príncipe—the cutlasses came out, and the pair was soon fed to the sharks. The zambo quickly agreed to cooperate.

Finally the men arrived at a position between the Isla de Naranja (Orange Island) and the shoreline, within sight of the castles of Portobelo. There were a total of four fortifications to overcome, beginning with a lightly manned blockhouse called La Ranchería, where sentries watched the coastline for unfamiliar ships on the southern shore of the bay that led to Portobelo. Two miles away, on the outskirts of the town, sat Santiago Castle. Then one reached the town center, with its merchant houses, churches, and slave quarters. Beyond the town proper, just off the shoreline in the shallow harbor itself, waited the still-uncompleted San Gerónimo fort, which the captured Englishmen had been working to finish. Across the harbor, on the northern tip of the bay, sat the final obstacle: San Felipe, guarding all entries and exits from the harbor.

The men guarding these forts were a cross-section of the Spanish populace. Some had joined the Spanish army as early as age ten, fetching wood and cleaning the boots of the regular soldiers, and worked their way up the ranks. The bulk of them would have been from the lower classes, while the officers were often wellborn. Both were seeking their fortune in the New World. They were more rooted than the privateers; many of them were married and had side jobs such as cobbler or grocer; they had houses in the town and children to care for. They were often not hugely experienced: A minority of them would have been in battle before, although some of the older ones might have seen action in Flanders or elsewhere on the Continent. And they came from a long and proud tradition that decreed that death was preferable to surrender or defeat. But in the New World, that tradition seemed distant and in some ways beside the point: The armies of Spain’s traditional enemies were thousands of miles away. Not to mention that they often went for months on end without pay, which hardly endeared their king to them.

As it approached the prize, Morgan’s lead vessel was spotted by a group of sharp-eyed Negro woodcutters, who reported the rogue ship to the mayor of Portobelo. Reluctantly, as he’d have to pay for the expedition himself, the mayor sent out a canoe to inquire just what the vessel was: merchant, slaver, pirate, or advice ship? The people in the town were not unduly concerned with the matter: One boat sailing up the river was not much of a threat. As the canoe set out, the fleet, under cover of night, was angling toward the shore where the zambo advised a landing. The men had been given their assignments; they’d checked their powder, cleaned their guns one last time, adjusted their pistols in their belts, made sure they’d tapers to light them, sharpened their cutlasses, and ate a last bit of turtle or boucan to fortify them. Now they grimly eyed the spot on shore and drove the canoes forward. There was nothing left to say; the battle was imminent.

In the middle of the night, Morgan’s spotter detected movement ahead, a silver flash against black. It was a paddle splash from the mayor’s canoe. The Spaniards must have noticed the fleet at the same time and instantly recognized that these were not Dutch traders or slavers but corsairs, because they turned and raced for home. The fleet could not hope to catch them; instead Morgan concentrated on getting his men ashore. An hour later the men heard the gravelly crunch of wood hitting a beach. They’d hit their target: Buenaventura, three miles from Portobelo. They’d skirt the shoreline and attack the city from the west. An Englishmen who had been one of the prisoners at Portobelo now took over as point man; he and three or four pirates were sent forward to take the sentry, “if possible, to kill him upon the place,” so that he would not fire his musket and raise the alarm. The men did one better: They captured the man and brought him back to Morgan, his hands tied and, no doubt, his legs weak with terror. Morgan asked the sentry about the local defenses while the other pirates stood close, cutlasses unsheathed, eyeing him meaningfully. “After every question,” Esquemeling tells us, “they made him a thousand menaces to kill him, in case he declared not the truth.” To ensure that his information was accurate, the man was marched bound and gagged at the head of the column as they made their final approach along the treasure road, pounded to a hard patina by the mules carrying Potosí silver. Any volley from an ambush would kill him first.

The pirates reached the blockhouse on the outskirts of the city at La Ranchería and found it guarded by five men. The soldiers were told to surrender, “otherwise they should all be cut to pieces, without giving quarter to any one,” but the men answered Morgan’s shout with a quick barrage; two pirates sank to the ground, wounded. Screaming that they’d avenge the English captives, Roderick and the others swarmed over the blockhouse, put the men there to the blade, and soon had it under control. But the element of surprise was gone; the reports of the muskets could easily be heard in the city itself. Now Morgan shouted at his men to hurry as the town’s startled residents struggled from their sleep. Groggy and confused, they asked each other what the shots could mean and then heard more, repeated insistently. When the citizens looked out to the harbor, they saw the mayor’s canoe surging toward shore, the men in the boat firing their muskets and yelling, “To arms! To arms!” The canoe passed Santiago Castle, and, according to Spanish reports on the attack, the men cried to the soldiers there, “The enemy is marching over land!” The soldiers ran for their muskets, while families in town uncovered their silver plate and jewels from their hiding places and rushed to throw them down wells or bury them in their yards.

The attack was a test of the Spanish colonial military, and the first sign was actually good. The sergeant on duty at Santiago lowered the castle gate so that the part-time grocers and bartenders who slept in the town could make it back, a smart move for an undermanned fortress. But things went downhill from there: The sergeant went to report to the lord of the castle, or castellan, Juan de Somovilla Tejada, and found the man still asleep in his bed. The sergeant informed his superior that the infidels were inside the city, but the lord simply brushed him off, saying it was only the English escapees causing trouble. The sergeant insisted: This was a large body of men, not the six pathetic souls who had fled Santiago in rags. Survivors of a shipwreck, the yawning castellan replied. His subaltern must have bitten his lip as he informed his lord that as he spoke, hundreds of armed corsairs were racing across the beach toward the castle. At this the castellan rose from his bed.

Morgan’s men had indeed arrived at the beach near the foot of the castle, gasping for breath, having double-timed it the two miles from the blockhouse. And here Morgan experienced a crisis of faith. Seeing the soaring stone walls of the fortress, which rose out of the sand like some medieval Spanish colossus, he lost his nerve. “Many faint and calm meditations came into his mind,” Esquemeling wrote, in an account backed by Spanish sources. The Brethrens’ prisoners reported an even more nerve-racking scene, with the admiral reaching for the throat of the Indian guide and screaming, “We cannot go that way! This is a trick to slaughter us all!” It was a rare break in composure for Morgan, who was, in the pirate vernacular “pistol-proof”: calm under fire. His men soon laughed him out of his terror, and one of the former English prisoners told the captain that Santiago’s defenses were far less formidable than they looked. Morgan nodded, took a deep breath, and gave the command. The pirates burst in two groups from their hiding place and went tearing toward the castle.

One group aimed at the base of the castle walls, while the other angled off and headed toward a hill that would give them a commanding view of the castle’s rear. The men ran across the open space expecting at any moment to be atomized by a blast of grapeshot, but Santiago’s constable of the artillery had mistakenly loaded the cannons with ball (a large cannonball designed to sink ships) and not partridge (small balls designed for killing men). The only cannonball that was fired at the men came nowhere near hitting them and instead kicked up a sheet of white spray as it slammed into the blue harbor waters. The main group of pirates, exhilarated at their survival, hugged the castle walls as they made their way past the fortress to the city streets, onto which they burst “firing off their guns at everything alive, whites, blacks, even dogs, in order to spread terror.” They met only token resistance and took control of the town within minutes. Now that they had Portobelo by the throat, they had to slowly disarm it, like a handler defanging a snake. First in their sights was San Gerónimo, the partially finished, lightly manned fort that lay across an expanse of water. The castellan there replied to the demands for surrender by saying that the men “would fight unto death like good soldiers”; it was the response the king expected of his officers. But he was bluffing: Spain’s decay was immediately evident at Gerónimo: The soldiers found only a single working cannon that could cover the direction from which Morgan’s assault had to come, and there was only damp powder to charge it. The Englishmen hid behind some canoes as Morgan and his commanders tried to gauge the depth of the water, to see whether canoes would be needed and what approach would be best. In the middle of their deliberations, a few of the fort’s former captives strolled by and began walking out into the water toward the walls of Gerónimo. The pirates watched as the captives failed to sink; the water, in fact, came up only to their knees. Laughing, the other pirates charged after them. Utterly exposed but by now scornful of the Spanish gunners, the men splashed their way across the gap. The castellan, seeing that his handful of men had no chance, surrendered; the first of the castles belonged to the pirates. Now the twin teeth at the mouth of the harbor, through which Morgan’s ships had to pass to load the expected treasure, had to be neutralized.

In the city they found something to give them added motivation: the remaining prisoners from Providence. They were discovered chained in a dungeon, “eleven English in chains who had been there two years.” But Prince Maurice was nowhere to be seen, only a clue that would continue the romantic myth of the man: “We were informed that a great man had been carried…six months before to Lima or Peru, who was formerly brought from Puerto Rico.” Having freed the English hostages, the men set out for Santiago, which they’d simply run past on their way to the city. The smaller squadron of men had remained on the hill overlooking its walls, picking off any Spaniard who dared stick his head above the ramparts. The French muskets were earning their ridiculous prices: With the pirates “aiming with dexterity at the mouths of the guns,” the Spaniards found they “were certain to lose one or two men every time they charged each gun anew.” The long-term advantage lay with Morgan, but the defenders inside could postpone the inevitable defeat almost indefinitely: Scaling the fort’s sheer walls under fire would be a nightmare. So Morgan, now fully committed to the ruthlessness his trade demanded, decided to use one of the most controversial stratagems of his career.

Namely, human shields. Morgan “ordered ten or twelve ladders to be made,…so broad that three or four men at once might ascend by them.” He then had his men bring him a selection of the prisoners, chosen with care to appeal to Spanish sensibilities: the august (Portobelo’s mayor), the religious (friars and nuns), and the wretched (several elderly men). Shaking, the prisoners were marched at the head of a column that passed through the city streets and then out onto the open road that led to the castle. Now the Spanish could see what was happening: Their leading citizens screamed at them for God’s sake not to shoot, while the pirates—ladders, grenades, and cutlasses in hand—crouched behind them. It was a terrible dilemma for the men inside, but finally the gunners opened up, spraying the particularly lethal chain shot (two small balls of iron connected by an iron chain, designed for ripping apart the masts of enemy ships, which would rotate with a terrifying keen before beheading or delimbing anyone it caught in its path) into the advancing crowd. Two friars fell wounded, and the chain shot found one English victim. The rest of the party pushed the human shields out of the way and began hacking at the wooden gate with their axes and lighting it with their torches.

At the other side of the fort, a separate scenario was unfolding. A squadron of privateers had taken advantage of the spectacle unfolding at the main gate to slip away and stage a rearguard action. They scaled the walls of the fort with ladders while the Spanish fought them off with everything they could find, including “great quantities of stones and earthen pots full of combustible matter.” It took an extreme form of courage to climb a ladder into the barrel of a musket, but this was the privateer style: fast, unrelenting attacks that depended as much on psychological terror as they did on sharpshooting. “We must have put up a pretty stiff fight,” wrote Raveneau de Lussan of another battle; “in a word, we must have fought like regular filibustiers.” The men swarmed over the ramparts and cut down the last of the defenders in their section of the castle, then raised the infamous red flag. Red stood for “no quarter”; every enemy met under it would be sacrificed. None of the various black banners later used by the pirates—ones adorned with skull and crossbones, skeletons, hourglasses, spears, and bleeding hearts—was as terrible in the sight of their enemies, as black meant quarter would be given to those who surrendered. The pirates assaulting the front gate of the castle soon breached it and joined up with their compatriots. Seventy-four of the Spanish defenders lay dead, including the castellan. Morgan in the entire operation lost eighteen and thirty-two wounded, one-eighth of the number who had staged the attack. Roderick had a deep gash from a Spanish sword on his thigh; he was carried screaming to where the doctor was treating the wounded. Hours later, after the more badly wounded had been treated, the doctor held a sword in a blazing fire and then walked over to Roderick. Three buccaneers held him down as the doctor positioned the sword flat over the wound, then pressed it into the flesh. Roderick fainted from the pain, but the wound was cauterized. He’d sleep until the next day.

On the horizon, San Felipe remained in Spanish hands, but the pirates felt, with justification, that they’d accomplished enough for one day. They got so drunk that “fifty courageous men…might easily have retaken the city.” There was soon news of far more than fifty men who were intent on doing just that; the Spanish would not take the capture of one of the Main’s jewels so lightly. In Panama, just seventy miles away, a horseman brought the news of the city’s capture to the president of Panama, Don Agustín de Bracamonte, the rider arriving just one day after Morgan had begun his siege of Portobelo. Bracamonte instantly knew how the capture would be received in Madrid: It was as if Morgan had seized a state mint and was now cavorting in its vaults. When reacting to crisis, Spanish administrators believed devoutly in consensus, drawing as many important people into the process as possible, thereby sharing out the blame and reducing their chances of being summoned back to Madrid and prison. Calling a junta, or council of war, would be standard operating procedure. But young and new in his position, Bracamonte ordered that the city’s militias be organized immediately to save Portobelo. Drummers walked the city streets calling the men to arms. “I swore to God,” Bracamonte testified, “that I would leave on Friday morning and be at Portobelo on Saturday.”

Back in Portobelo only the final castle, San Felipe, stood between Morgan and the city’s riches, and on the second morning of the raid he set out to take it peacefully. Two pirates in a canoe rowed out to the castle to deliver the surrender terms, but apparently Spanish honor was not quite dead: The canoe was met with a barrage from the castle guns. Morgan must have sighed wearily. The Spanish were defending a lost cause. The fortress held only 49 soldiers, and they were in bad shape, sharing just four pounds of bread and some wine among them. Nevertheless, this handful of men stood in the way of clear passage for his ships through the harbor mouth, so Morgan sent 200 men in eleven canoes to take Felipe. Two Spanish prisoners were acting as guides (at gunpoint), and one of them, Sergeant Juan de Mallveguí, had a plan: After landing on the shore near the castle, he led the pirates along a path that would bring them directly in range of the gunners above. Seeing what was about to happen, his compadre, Alonzo Prieto, asked him whether he’d lost his mind. They’d die along with the infidels. Mallveguí was undeterred. It was very possible, he told his friend, that God would save them for their good intentions and, if he didn’t, it was better that they should both die and kill all the English than the castle be lost. Prieto blanched. “Oh, no, amigo,” he told Mallveguí, “I have a wife and children and I do not want to die.”

It was a conversation between old Spain and new Spain. In the old country, Mallveguí’s plan would have been considered a thing of genius. Death was its own moral drama for the Spanish; to die well was superior to living well. Mallveguí’s plan would bring a public martyrdom (witnesses were essential, as they were needed to spread the word of one’s behavior) connected to nobility—in fact, to the king himself, as it was his castle they’d be dying for. The honor this glorious death would bring to Mallveguí would be incalculable. The Spanish thought differently about these things: In the fifteenth century, the poet Jorge Manrique wrote that there were actually three stages to earthly existence, not two; to the temporal life and the afterlife he added the afterglow of one’s name, which was most important of all. This “chivalric religion” was strong in Spain and had been for centuries. A witness to the kingdom’s battles against the Italians wrote, “These crazy Spaniards have more regard for a bit of honor than for a thousand lives.” But honor mattered far less in the New World, which was more sensual and more attuned to the here and now. Prieto wanted to go home and eat a beefsteak with his wife. The king was far away, and one could not eat or make love to honor.

The debate ended with the sound of wood on skull. The English had among them ex-captives who knew the town’s layout well, and one of them, having realized what was happening, cracked the butt of his musket against Mallveguí’s head. The pirates changed course and soon began probing the castle’s defenses, sending one group of men to set fire to the main gate, while others staged a series of charges on the fort. The Spanish repulsed the assaults at the cost of only five men, but with little food and no reinforcements on the horizon, their situation was grim. The castellan huddled with a lieutenant and gave him some awful news: “We shall have to surrender.” The soldier was shocked to hear those words from the mouth of a fellow Spaniard. Surrendering San Felipe, and thus Portobelo, to the heathens would be a sharp loss to the Catholic cause. “We must fight to the last man,” the lieutenant said in reply. But the castellan ignored him and soon had put his name to the terms of surrender. The other officers were appalled, and the pirates added insult to injury when they reneged on the generous terms of capitulation, which preserved a shred of honor for the king’s troops by allowing them to leave the castle with their muskets at their sides and their flags flying high, and stripped the men of all but their swords. The Spanish stumbled out of the castle like slaves. The castellan soon suffered an attack of conscience and was granted his last wish: poison, which he gulped down. The pirates who had dishonored him were soon extracting every last piece of eight from the locals and the men and women who had fled into the hinterlands.

They also came across some information to tantalize Modyford back in Jamaica. “The Prince of Monte Circa,” Morgan later reported, “had been there with orders from the King of Spain to raise 2,200 men against us out of the Province of Panama.” This was added to the earlier intelligence that Morgan had gathered on the approach to the city: Seventy men “had been pressed to go against Jamaica,” a levy had been exacted to raise funds, and “considerable forces were expected from Vera Cruz and Campeachy, with materials of war to rendezvous at the Havannah….” Morgan had his smoking gun: The plot against Jamaica was real.

The acting governor of Panama was the town’s last hope. But the Spanish Main had the habit of entangling bright ambitions in its tentacles and slowly squeezing the life out of them; almost immediately Governor Bracamonte’s bold moves were countermanded by ennui and distance. His 800 men rushed out of the city into the trails to Portobelo without adequate supplies of food or armament, and days were wasted as the necessary rations caught up with the army. In that time the jungle began to work on the men. Some fell victim to the usual fevers, but others experienced more exotic tortures, like mazamorra, the excruciatingly painful foot disease that would centuries later nearly cripple Che Guevera’s army on the approach to Havana. As they got closer to the besieged city, refugees met them and gave them news: The castles had fallen, and the pirates were everywhere and strong. Bracamonte sent for urgent assistance to Cartagena and Havana, where the Armada de Barlovento, with orders to exterminate the pirates, was stationed. Messengers flitted through the trees and set out in canoes to race down the coast. But Morgan was smarter than he’d been in Puerto del Príncipe and was not going to wait for the collected armies of the empire to arrive. Bracamonte would have to face Morgan alone.

So began an exchange of letters, with Morgan’s first:

Señor, tomorrow we plan to burn this city to the ground and then set sail with all the guns and munitions from the castles. With us we will take all our prisoners…and we will show them the same kindness that the English prisoners had received in this place.

The reference to the men in the dungeon was ominous, but Morgan’s insouciant tone (he signed himself “Henrrique”) must have been even more daunting for the Spanish noble. The pirate also included eight conditions for the surrender, including the price for the return of the city unburned: 350,000 pesos ($17.8 million), a tremendous fortune. Morgan proposed a unilateral cease-fire so that the ransom could be brought to the city, and he demanded that the castles surrender all of their artillery.

Bracamonte responded with consummate disdain. “I take you to be a pirate,” he wrote back, “and I reply that the vassals of the King of Spain do not make treaties with inferior persons.” He expressed nothing but contempt for the people of Portobelo, who had allowed themselves to be overcome by corsairs. “And if you decide to decapitate the prisoners,” he finished, “you will excuse me for not ordering you to do it.” Many pirates would have been goaded by Bracamonte’s taunt; one can only imagine L’Ollonais’s bug-eyed response. But Morgan felt himself to be a highborn gentleman, fully the equal of this Spanish noble. His answer was pure acid:

Although your letter does not deserve a response, since you call me a pirate, despite that I am writing you these lines to ask you to come quickly. We are waiting for you with great pleasure and we have gunpowder and bullets with which to receive you. If you do not come very soon, we will, with the favour of God and our arms, come and visit you in Panama. Now, it is our intention to garrison the castles and save them for the King of England, my master, who since he had a mind to seize them, has also a mind to keep them. And since I do not believe that you have sufficient men to fight with me tomorrow, I will order all the poor prisoners to be freed so that they may to go to help you. As to whether I will order them decapitated, I respond that I will not. I am not so bloody as to kill people in cold blood, as the Spanish are used to doing.

Morgan hated being called a pirate; in his mind, he was a soldier of the English king. He’d come to the New World to make his name and his fortune from weaker men, not to be called a criminal.

As the missives shot back and forth, the governor was receiving his own intelligence from those who had escaped the pirates. A pair of Spanish sailors told him that the French defection from the pirate fleet after Puerto del Príncipe, when they’d supposedly gone to join L’Ollonais, was a ruse: They’d actually agreed with Morgan that the English would attack Portobelo, which would cause the leaders of Panama to raise a rescue force. When that army left Panama, the French would attack the defenseless city. It was a terrifying thought to men who had left their women, their children, and their fortunes back in Panama. Bracamonte finally attacked, but it was a halfhearted attempt. Squads of men were sent into Portobelo to retrieve captives (and some Catholic images the English were sure to desecrate if they got the chance) but they were not to try to take back the castles. There was only one pitched battle, which Morgan exaggerated hugely: “The 5th day arrived the President of Panama with 3,000 men,” he reported, “whom [the pirates] beat off with considerable damage.”

Another barrage of letters passed between the adversaries after the attack. Bracamonte wrote, “In case he departed not suddenly with all his forces from Porto Bello, he ought to expect no quarter for himself nor his companions, when he should take them, as he hoped soon to do.” Morgan shot back, “He would not deliver the castles before he had received the contribution-money he’d demanded. Which in case it were not paid down, he would certainly burn the whole city, and then leave it; demolishing beforehand the castles, and killing the prisoners.”

Both armies were wilting under the assault from the diseases that made Portobelo so notorious. With the rumors of a French attack on Panama, Bracamonte felt the pressure to settle; he called a junta. One Spanish commander spoke out: “We find ourselves today with just eight hundred men, inexperienced and poorly armed people who, man for man, are not the equal of their enemies.” It had to be said. The soldier continued, “I consider it impossible for us to recover Portobelo and its castles,” he said. “We would get smashed to pieces if we attacked, whichever way we went.” Many of the other officers chimed in their agreement. Bracamonte had at least provided a paper trail showing that he was only bowing to his subalterns’ advice. Finally he relented.

An intermediary was sent into the city under a white flag and found that Morgan, who was also seeing his men sicken and die, would not budge from his price: 350,000 pesos, payable immediately, or the city would go up in flames. The negotiations continued back and forth with, at one point, the Spanish cheekily offering to fulfill half their proposed ransom of 100,000 pesos by a bill of exchange, payable sometime in the future by the kingdom’s Italian financiers, the equivalent of giving a kidnapper a personal check. Morgan declined the offer. At length the deal was struck: 100,000 in ready cash. The booty was raised by the rich merchants of Panama and delivered by mule train: gold coins, twenty-seven silver bars, chests of silver plate, and a backbreaking load of silver cobs. One suspects that the incredible wealth generated by the mines undercut Spanish courage. Why fight when you can pay the hoodlums off? There would always be more silver flowing out of Potosí.

The pirates loaded it onto their ships, along with their own looted treasure and their captured slaves, and bade farewell to the town that had made them wealthy. Morgan had certainly learned from L’Ollonais on this expedition, but he also made a point to report on the pirates’ gallantry. He claimed that the lady prisoners chose to travel with the pirates rather than go to the governor’s camp, finding the Brethren “more tender of their honours” than the Spaniards. It’s a wonder Morgan did not have them begging to return to Jamaica as the pirates’ wives.

The Spanish had actually gotten a bargain in the Portobelo negotiations, but Morgan had proved he could attack the empire’s strongholds at will. Now his reputation would grow immeasurably. Even the president of Panama, after the deal had been struck, succumbed to an “extreme admiration” for Morgan’s feat of arms, “considering that four hundred men had been able to take such a great city, with so many strong castles: especially seeing they had no pieces of cannon, nor other great guns….” He sent a messenger to Morgan, asking the admiral to send a sample of the arms that the pirates had used to take Portobelo. If the story is true, Morgan must have shaken his head: It was not the weapons that had proved themselves; it was the men and their leader. He sent a pistol and a few bullets back, with a note saying that the president should keep the guns for a year, after which he’d come to Panama himself “and fetch them away.” The president, seeing that the pistol was a common type, sent it back with a gold ring and a warning: If Morgan came to Panama, he wouldn’t find the success he’d achieved at Portobelo.

The president would have been well advised not to dare Henry Morgan.

The pirates sailed toward Port Royal with numbers running in their heads. They’d left Portobelo in a rush, and there had been no chance to total up the various “loans” they’d extracted from the Spanish; now the loot had been whisked away and was stored under guard. Did it add up to 100,000 pieces of eight? Or 150,000? Was 300,000 completely out of the question? The worth of the swag they carried fluctuated with the price of silver and gems in Port Royal and the going rate for slaves, so all the way back to Jamaica the men gossiped like accountants. Morgan was known to be dissatisfied with the ransom money, but they’d rifled the fabled city of Portobelo, for God’s sake.

When the ships arrived at their rendezvous point off Cuba, the treasure was piled up, inventoried, and priced. When the total was announced, it came out to 250,000 pieces of eight, plus an unspecified but sizable sum to be gained from the slaves and trade goods they’d seized. In today’s money the Brethren had taken about $12.5 million in Portobelo. The average pirate received about 240 pieces of eight, or $12,000, plus any compensation for injuries he might have suffered or bravery he might have displayed. In a time when an average laborer in London earned the annual equivalent of $3,500, the ordinary pirate had collected a minimum of three-plus years’ wages in the expedition, enough to set himself up in business or buy a good piece of land or a long stretch of unrestrained debauchery. Anyone who lost an arm earned the equivalent of ten years of a London workingman’s salary. Most of the pirates, like Roderick, would choose to spend their money on pure pleasure, a decision that will lead to one of the great mysteries at the heart of the Brotherhood.

In Spain the news of Portobelo’s fall and the pirates’ rich haul was bitter news in a bitter season. The kingdom was bowing under the lash of one misfortune after another. The issue of money was especially galling: The Crown had been cash-strapped since the reign of Philip IV. There were days when the royal larder was nearly empty and the queen would be offered a rancid, midget chicken that “stank like a dead dog.” During one meal, Queen Mariana had requested a bit of pastry and was told the castle’s pastry chef would send no more desserts until an overdue bill was paid. Mariana, the daughter of the unimaginably rich Hapsburgs, took a ring off her finger and told her servant to go out into the street and find her a pastry at any cost. Her fool, appalled, gave the man a coin and put the ring back on her finger. It would embarrass everyone to have such a story get out.

Morgan’s haul was not a huge loss to the Crown’s coffers; when the treasure ships arrived, they brought millions in pieces of eight and gems, so to lose a few hundred thousand to a Welsh corsair was not a crippling blow. Besides, the local merchants and traders would be expected to make up their own losses. Only the capture of a galleon or the treasure waiting for a galleon at one of the New World ports would show an immediate result, such as the kingdom defaulting on its loans or canceling a major offensive in its European wars. But the Portobelo raid was important, because it showed the world that the empire was vulnerable. It would spawn a thousand imitators, it would embolden Spain’s enemies, and it would weaken the infrastructure that delivered the treasure.

The king’s poverty was shocking, but more dangerous to the Crown were the plots whirling around the misshapen head of Carlos II. Morgan’s victory found Spain at peace with her enemies for the first time in memory, but at war with herself. As poor as it was in ready money, the Spanish Crown was still a thing of tremendous possibilities. And Carlos’s bastard brother Don Juan wanted it for himself. In 1668, as Morgan sacked Portobelo, the battle was coming to a head. France’s Louis XIV was receiving a steady stream of reports about Carlos’s weaknesses. “The doctors do not foretell a long life,” a French diplomat wrote to the king. “And this seems to be taken for granted in all calculations here.” Louis and the emperor of Austria had secretly agreed to carve up the kingdom and its empire between them as soon as Carlos should die. And Don Juan certainly had his half brother’s frailty in mind. He was the illegitimate son of Philip IV and La Calderona, an actress who had initially attracted Philip because of a piece of intriguing gossip: The Duque de Medina de las Torres told the king that lover after lover had failed to de-flower the young thespian because of a certain anatomical oddity (most likely a thick hymen). The king, who always wanted what he could not have, marched straight off to see her, only to meet the same fate as the other swains. After corrective surgery the two became lovers. Don Juan was born in 1629 and grew up to be one of his father’s favorites of the rumored thirty-two bastards he sired. Philip recognized him in a way he never did his other illegitimate children, and the special treatment gave Don Juan the idea that he was destined for the greatest things. This certainty led him to overestimate his power. The incident of the painting was just one example.

Since a bastard could never be king, Don Juan decided that he must marry one of his half sisters, the legitimate daughter, Maria Theresa, and thus solve the problem of an heir. Even by the incestuous standards of the Hapsburgs, this was beyond the pale. But Don Juan was not to be put off by niceties. He even sent an inquiry to the august theologians at Belgium’s famous Catholic university, Louvain, to see if the pope could grant an exception to divine law and allow the marriage. Nothing came of the idea; in 1665, with the monarchy resting on the slender reed of Carlos II, Don Juan revived it, with his half sister Margarita now in the role of his bride. He had decided to broach the idea when his father invited him for a talk to decide whether the favorite son would be named inquisitor general or archbishop of Toledo, both powerful positions. Knowing he was dying, Philip had been looking for a place for his strong, quick-minded favorite; and he must have considered himself a generous parent to think of bestowing such prestigious titles on a bastard. Little did he know what Don Juan held in store for him.

Don Juan had come up with a novel way of presenting the idea to his father: He’d give him a painting, a very special painting he’d done specifically for this occasion. In the curious portrait, Saturn, the Roman god of the harvest, watches his son Jupiter (the king of all the gods) and his daughter Juno (the protector of marriage) frolicking like lovers. In mythology Jupiter and Juno were married; even if Jupiter cheated scandalously on his sibling-wife. To make his point even clearer, Don Juan had given his own face to Jupiter, while Philip’s mournful visage sat atop Saturn’s body, and Juno became Margarita. Don Juan must have thought the work of art would give the idea of the scandalous union some precedent, along with a subtle message: You and I, Father, are like gods; we are above human laws. The painting does not survive, but it must have been grotesque. You have to sympathize with Philip as he was presented with the painting. He was a sick, exhausted man and probably expected some loving tribute from a dutiful son. Instead he was handed this piece of pornography, which would have brought back to him the (now much regretted) sexual voraciousness of his youth. After comprehension set in, Philip turned away in disgust. The awkward gesture had gone terribly wrong, and the king never agreed to see Don Juan again.

One would have expected Don Juan’s ambition to be checked by his father’s reaction to the marriage idea, but he was beyond embarrassment. With Philip IV fresh in his mausoleum, he turned his sights on the new reigning power, Queen Regent Mariana; specifically, he targeted the queen’s confessor, Father Nithard, a Jesuit who was casually hated by the Spanish man in the street for being Austrian and so close to power. Don Juan tried gambit after gambit to draw the dour Jesuit close to him, first supporting the priest’s pet cause: the making of the Immaculate Conception into an article of faith. The belief in Mother Mary’s chastity had not been recognized as official dogma by the church (and would not be until 1854), and now Don Juan declared himself a wholesale advocate of its adoption. It was ironic that the amorous Don Juan would choose virginity as his secret devotion, but he revealed to Nithard that indeed it was. Nithard took him up as an ally. Don Juan also met secretly with the confessor to ask him to intervene on his behalf: His carnal urges were so strong that he could no longer observe the vow of chastity he’d sworn when he’d been appointed to religious offices. As usual with Don Juan, he had the perfect resolution: He’d resign all his offices, marry the niece of the elderly king of Poland, and take the throne for Spain when the monarch died. It was a pipe dream, as were so many of Don Juan’s schemes, but it was wrong to underestimate him: He was young, dark, virile, and unmistakably Spanish. The folk identified with him against the pale, foreign-born Mariana.

Don Juan’s maneuvers—including a marriage to the Arch-duchess Claudia Felicidad when the Polish option turned sour—all came to nothing. Meanwhile Nithard’s star was rising even higher. When Mariana named him as inquisitor general, the Spanish were outraged. Sensing an opening, Don Juan played all his cards and arranged the Jesuit’s murder. Before it could be carried out, the plot was exposed, and Don Juan fled to Barcelona, where his supporters gathered around him into a rebel army intent on purging the foreign influence from the Spanish throne. Spain seemed ready to tear itself apart. It was not until the pope stepped in that negotiations began. Don Juan set one condition for his cooperation: the removal of Nithard. “If by Monday the fellow has not left by the Palace door for ever,” he said, “I shall go with my men on Tuesday and throw him out of the window.” Nithard left Spain for Rome; Mariana was weakened, and Don Juan went into exile. At the center of these swirling currents of hate and intrigue, Carlos II sat as a spectator. When told that Nithard was gone, he cried out, “What evil there is in the world!”

Queen Mariana retained power, but she was ruling with a five-man junta, with members from the grandees (the highest level of Spanish aristocracy), the church, and the state bureaucracy, while a subservient body, the Council of State, directed foreign affairs (at Mariana’s direction). It was not a structure that lent itself to action. So it was with Portobelo. The junta de guerra of the Council of the Indies, a subset of a subset of the Council of State, met to discuss the raid on February 17, 1669. At first the junta declared all-out war on the Brethren: The galleons and the Armada de Barlovento, along with any available ships that could be mustered to the cause, would be sent out to retake Portobelo and smash the pirate ring. Not only that, the junta decreed that should the fleet find that Portobelo was in Spanish hands, they were then to turn and attack the source of all the trouble in the West Indies: Jamaica itself. As long as the island remained in English hands, the region would not be safe for the workings of empire.

The watering down began immediately: The galleons could not be spared, as the Crown was too dependent on Potosí silver to divert the ships to other missions. The supply could not be interrupted even to protect the supply. A commitment was made to strengthen the New World’s defenses, but the governors of the Main had heard that before. Like any addict, Spain thought only of short-term fixes. “We certainly do not wish to impede [the treasure ships]…,” the council decided. “If we did, the Royal Treasury would be starved of its returns in silver and the Kingdom would be starved of its commerce that the silver fertilizes.” And so the boats would keep hauling treasure and not hunting pirates.

The reaction to Portobelo exposed a hypocrisy: Spain’s rulers told themselves they’d conquered the New World for God. But when it came time to truly defend it, it was the treasure that they wanted from the territories. The souls of the settlers, the land itself—they had to be sacrificed so that the kingdom could survive another day. The soldiers and administrators in the New World had learned a harsh lesson: Their safety was to be forfeited for the larger good. It was as cogs on the conveyor belt that delivered the king’s treasure that they mattered.

Spain protested the capture of Portobelo vehemently. Months after the raid, an English diplomat was still getting an earful, “many storms and loud outcries…not only from ye Minister but from ye common people, upon the assaults on the maineland and depredations at sea committed on them by our privateers.” But the English were in no mood to apologize. It was Spain who had devised the policy of “no peace beyond the line,” and if the Spaniards wanted to live by the sword, they could die by it, too. The English responded to the protests by reciting instances of Spanish violences against their own: this ship captured, this captain detained or tortured, this town burned to the ground. They also brought up the plans for the invasion of Jamaica that Morgan had uncovered. “It is almost certain that the Spanish had full intention to attempt this island but could not get men,” Modyford, Morgan’s protector and ally, told his superior back in London. “And they still hold the same minds.” When the Crown’s share of the Portobelo loot was brought to London, the Spanish ambassador immediately filed a claim in the High Court of Admiralty for its return to Madrid and was just as quickly denied. Behind this tough stance was the king’s desire to negotiate a new treaty that would allow the English a free hand to trade with the Spanish colonies. For that he’d sell out Morgan and the privateers in a moment. But until he got it, Spain needed the English more than they needed Spain.

The queen regent did have one original idea: to steal a page from England’s book. Mariana decided that Spain would authorize its own privateers to fight Morgan and his ilk. It was a natural solution, but a rather embarrassing one for a nation that had not thought in terms of empowering individuals to do its work since the days of the conquistadors. Nevertheless, the queen had no other good options and sent notice to her governors that the vassals of her son the king were to move against the English “with every sort of hostility” and expel the enemy from the territories they’d captured. From now on, Morgan would have to deal not only with the Armada de Barlovento and the garrisons of the Main’s towns but with any Spanish adventurers who cared to challenge him. One in particular would take the queen’s letter to heart.