3

Morgan

On the island of Jamaica, Philip’s inheritance was not yet lost to the English. A killer’s game of cat and mouse was under way. The Spanish holdouts had retired to the mountains, and the English held the shore and the new town of Cagway; beyond that was enemy territory. To English boys from Coventry or Dover, everything past the tree line or the small town was terrifying: when they’d slept on the shores of Hispaniola at night, the sound of the giant crabs emerging from the ocean and scuttling across the beach had shot them bolt awake; it sounded exactly like the clatter of bullet cartridges on an infantryman. And then there were the fireflies that were mistaken for the lit fuses carried by soldiers to light their muskets. Convinced that the Spanish soldiers were closing in on them, they stayed tense, trigger-happy until dawn. Even after they’d lived on the island for weeks and begun to grow accustomed to its sights and sounds, the beauty of the place turned sinister at night, when the oddly humanlike jabbering of the monkeys crescendoed with birdcalls and unidentifiable screams (animal? human?) to a deafening roar. For all along they knew that their true enemies—the former slaves—were watching.

Gage had been wrong: The blacks had not turned against the Spanish; they’d disappeared into the jungle and become excellent guerrilla fighters. “They grow bold and bloody,” Major Sedgwick wrote, “a people that know not what the laws and customs of civil nations mean, neither do we know how to capitulate or discourse with them, or how to take any of them.” The soldiers could not even find their hiding places and were forced to send to England for hounds. The malnourished survivors of the invasion sent patrols into the bush to smoke out the last of the resistance; when they went in numbers, they were safe. But when hunger tempted a lone Englishman to walk out of the cleared settlement where his mates stood guard with muskets, into the trackless jungle, different rules applied. Tempted by the fish in the streams or the hope of capturing an iguana or guinea hen, a soldier might head out into the bush, then stop and listen. The jungle emitted a stream of snaps, low calls, whirls, and clicks; he understood none of it. He went on. All along, the black guerrilla was tracking him soundlessly, to English eyes a shadow among shadows, sensed but not seen. When the famished soldier at last let down his guard to chase a lizard or hook a fish, something would flash in the corner of his eye, and a machete would cleave his skull from the crown forward.

Each side knew the stakes. When the English search party would see the vultures circling above and find their dead mate, the mutilations would be gruesome. Officers suffered worse fates: Captured and force-marched to the other side of the island, they’d be interrogated under torture (with methods learned from the masters of the Inquisition), then shipped off to the salt mines of the Main or the dungeons of Cuba, to which death was often preferable. (One captured English soldier told the Spaniards what they wanted to hear: that the Jews of Flanders, recently allowed into England, had financed the invasion—a complete falsehood.) The black guerrillas captured by the whites might face a punishment similar to that dealt out to disobedient slaves on Barbados, reported by an Englishman. The “rebellious negro” was chained flat on his belly and fire was applied to his feet until he was gradually burned to ashes while still alive. Others were starved to death with a loaf of bread hanging just out of reach, and they were known to gnaw the flesh off their own shoulders before dying. It was in this atmosphere that Henry Morgan came of age as a soldier.

His deliverer—the man whose life had brought Morgan to Jamaica—did not live to see his rise. Thomas Gage succumbed to disease early in 1656; in the records of the Admiralty, his widow successfully applied for back pay in the amount of one pound 6 shillings and 8 fourpence, his last appearance in the ledgers of English foreign affairs. At the end of his book that had led the English nation to the shores of Jamaica, Gage had compared himself to one of the spies sent into the land of Canaan, Moses’s emissaries who had gone in search of the promised land and returned to describe a place filled with milk and honey, with clusters of grapes so large that two men had to carry them. (Gage did not mention that they also told their people of the strongly fortified cities and that “the land through which we have gone as spies is a land that devours its inhabitants.”) He saw himself as the scout for the great Protestant empire soon to rule the New World, and perhaps even a martyr, like his Catholic ancestors. “I am ready to witness with the best drops of blood in my veins,” Gage wrote. “Though true it is that I have been envied, jealousied, and suspected by many.”

One would be naïve to take him at his word; our last glimpse of Gage brings us closer to his true character. It finds the ex-friar serving as the interpreter for the English commanders as they negotiate the surrender of the Spanish. Surely Hispaniola had been an appalling embarrassment for him; his sunny predictions had cost lives, and he was forced to witness his fellow Protestant crusaders falling left and right. But in the Spanish report on the invasion, he has recovered from any embarrassment, and we find him yelling at the sargento mayor of Santiago de la Vega (later Spanish Town) about insufficient supplies, basically lording it over his old compatriots. The writer’s dislike of the man comes through; he describes Gage as a man full of “noisy menaces” who “took the habit of Saint Dominic…and, ordained a priest, returned to England and fell from the Faith.” When the Spanish claimed that Jamaica belonged to them, having been granted to them by Pope Alexander and occupied for 140 years, Gage shot back that Cromwell had taken the island for the English and that “not right, but might of arms gave them possession,” tossing in that the pope had failed to snatch away Henry VIII’s realm when the king turned against him and adding “other blasphemous, licentious words.” At this the Englishmen began laughing.

Gage had come to the Americas in search of a religious crusade, but he little realized that the war he was relishing would take a far different shape: It would be a confrontation not between two traditional faiths but between two radically different visions of men and society. Cromwell’s “banners of Christ” had been folded up and put away; in their place would come the flag of the pirates, whose way of life was utterly foreign to both Catholics and Protestants. Port Royal would not mark the beginning of Spain’s replacement with another theocratic empire. The town and its pirates would follow another path, one focused more intensely on the individual than on the kingdom of belief.

The English eventually hunted down the remaining guerrillas, and the invasion fleet dispersed to ports back in Europe. Some of the former soldiers settled down to lives as farmers; it was immediately clear that the island’s soil was rich, perhaps as rich as that of the fabulous moneymaker, Barbados. Still, in the early years the ex-soldiers and the other adventurers who were making the real money had turned to a new trade: privateering.

Privateers were sailors from one nation who had been given permission by their monarchs, contained in documents called letters of marque—also called letters of commission, or simply commissions—to attack and capture enemy ships. Licensed marauders of the seas, they ranged from pirates simply looking for a tissue of legal protection to men who thought of themselves first and foremost as patriot soldiers. A pirate had no commission; he usually attacked anyone and everyone he came upon, regardless of nationality, and he was hanged on sight if captured and given no protection as a prisoner of war. Privateers were supposed to share their “purchase” (treasure) with the nation they represented; the English owed 10 percent to the lord admiral and 6 to the king. Pirates kept what they stole. Privateering was invented by a cash-strapped Henry VIII of England, who had no navy to attack the French (it having been sold by Parliament to pay his debts); he came up with the idea of issuing commissions to three private captains for the purpose of causing havoc with French shipping. Privateers were completely respectable; nobles often signed up when in a financial pinch.

Piracy was much older and threaded through the history of all seafaring nations. Julius Caesar had been captured by pirates off the island of Pharmacusa and spent thirty-eight days gambling and declaiming his own verses with the corsairs; he joked that when he won his release, he would come back and crucify all of them, which the pirates found hilarious. When he’d bought his release, he quickly borrowed a fleet of ships, tracked down the pirates, and crucified them. St. Patrick was seized by pirates, who sold him as a slave in Ireland. On his return from his battles with the Turks, the ship of Miguel de Cervantes, later the author of Don Quixote, was intercepted by Barbary pirates, and he spent five miserable years as an Algerian captive, repeatedly attempting to escape.

Who were the pirates of the West Indies? They were an assemblage of runaway slaves (the famous maroons), political refugees, disaffected sailors, indentured servants whose masters had tossed them off the plantation, hard-bitten adventure seekers, the flotsam and jetsam of the New World. They will play so vital a part in the coming battles, and they shared enough common characteristics and experiences, that it will clarify things to profile a typical pirate/privateer. There is enough information on the privateers who served under Morgan to give us a detailed composite picture of an average member, drawing from the experiences of various members of the Brethren of the Coast, as the pirates and privateers of the Caribbean were known. We shall call him Roderick.

Roderick was nineteen years old, short (five foot four being a common height in those days), English (as most of Morgan’s men were), and unmarried—in one survey of Anglo-American pirates from 1716 to 1726, only 4 percent had taken a wife. He was blue-eyed, lean, and quite strong for his size. Roderick had grown up in Dover, one of the great seaports of England, which were veritable factories for sailors and pirates. He went to the docks not only out of tradition (his father and grandfathers had earned their living on the water, rolling into their hovels after six long months away with tales of Morocco and Corsica) but because he had an itch for adventure and newness. He looked with astonishment on friends who became clerks or cobblers. One English sailor wrote that he “always had a mind to see strange countries and fashions,” while another said that his mind was “engrossed with voyages, the longer and more dangerous, the more attractive.” By signing up as a sailor, Roderick was already marking himself out as a breed apart. But when his merchant ship, undermanned by the owners in order to save money and pack more trade goods aboard, was spotted and captured by a pirate ship on its way to Barbados in 1660, Roderick faced a dilemma. He and his mates were brought out of the hold, marched up on deck to face the outlaw crew, and offered the chance to join up. They’d heard many tales of real-life pirates in the waterfront dens; who could resist the story of John Ward, a working-class English boy who had sailed off to Algiers, converted to Islam, assembled a pirate flotilla that could rival the Venetian navy, captured ship after ship loaded with spices and treasure, and built a palace of alabaster and marble where he lived out his life in unimaginable luxury? But the men who were lined up across from Roderick were more frightening than romantic. One had his eye shot out; another was missing an arm; a few had facial scars obviously left by a Spanish cutlass. They could hardly be called white men anymore, so blackened with the sun was their skin, so crisscrossed by their surprisingly delicate tattoos. The flint-lock pistols on silk strings that were their permanent accessories and their most prized possessions hung gaily around their necks, and their outré clothing—silks, damasks, and velvets in eye-smacking colors—announced the fact that their latest victim had been a French merchantman. Their captain gave a short, surprisingly persuasive speech. “We sing, sweare, drab, and kill men as freely as cakemakers do flies,” he boasted. “The whole sea is our empire where we rob at will.” Any man who joined up would get an equal share. All could vote on their missions and their policies. Toward the end he mentioned briefly that they’d be taking the ship’s carpenter, whether he was willing or not, as they’d lost their last one on a raid against a coastal town on the Spanish Main. But everyone else was free to choose.

Roderick considered. His life on the merchant ship was dull and underpaid; the captain whipped the men occasionally when he drank to excess. The nautical life had not yet matched his conception of it; Roderick wanted greater excitement and greater rewards. He looked down the line of crewmen and saw two other men step forward, and with sudden conviction he strode across the twelve feet of planking that separated sailors from pirates. He had just made a sizable leap: from law-abiding citizen to hunted criminal. You could go no further astray in the seventeenth-century world, except perhaps by proclaiming yourself a child of Satan or killing a man, and the new pirates would get ample opportunity to do the latter. The pirates looked at him as he approached their line, and the captain nodded slightly. Roderick turned and stared down at the deck, unable to meet the eyes of his former mates. He’d just left everything he knew.

The Spanish had helped create this petri dish of malcontents. If they’d allowed legal trade with their colonies and opened up their cities in the New World, these vagabonds would most likely have been incorporated into a thriving economy and become respectable workers in the region’s booming industries. The hard cases among them would have been hunted down by the English and French authorities and punished for interfering with trade. But the Spanish resisted—for them, trade was not a virtue in itself but only a tool to achieve the worldwide divine kingdom. By hoarding the riches and preventing these men from finding a place in the world, Spain slowly built its own perfect enemy, an enemy diametrically opposite in almost every respect.

Roderick and the West Indian pirates had a special ancestor: the boucaniers. These outcasts got their name from boucan, the process of smoking strips of beef obtained from the cows that ran wild on Hispaniola (brought there by the Spanish in a failed attempt at raising livestock), which these hunters would shoot, butcher, and then cure expertly over a pit fire. The tangy, preserved strips of meat could be traded with passing ships for everything a man needed. The boucaniers found their way to the forests of Hispaniola in the early decades of the 1600s, a diverse assortment of political refugees, religious refugees, escaped Negro slaves, outright criminals, and disgruntled or abused servants. They were Scotch, Irish, Dutch, French, and mulatto, and they were all radicals in one respect—they rejected everything a good bourgeois looked for in life. Last names were not to be used; some had pasts they did not wish to discuss. (With one stroke they dissolved everything a Spaniard worked toward his whole life.) Women were not allowed into their camps, on pain of death; instead the cow killers paired off with matelots (literally, “bedmates,” but used to connote friendship) for lifelong, probably sexual, relationships. The boucaniers used flat stones for plates and hollowed-out calabashes for cups. They shared everything; no one had more food, liquor, or ammunition than the others. These backwoods communists topped off their lifestyle with a very basic appearance: They wore homemade suits fashioned of cow skins that were covered with layers of dried blood so thick that it looked like black tar.

What they’d created was a male fantasy of escape from all civilizing influences: women, heritage, children, and money. No one had power over them; living on the far-flung edge of Western civilization, the boucaniers were freer than almost anyone else in the world. This gift they’d give to their inheritors, the men with so many names: pirates, buccaneers, filibustiers, corsairs, and the more decorous privateers. The Spanish looked on the buccaneers and their inheritors as vermin. They were godless, without culture or meaning to their lives. Their system was no system; it was as if they were savages who had freely chosen to reject all that the Spanish held dear. And they were trespassing on the divine kingdom. So the Spaniards hunted them.

When the Spanish soldiers began to track them down like the cattle they survived on, many of the buccaneers fled to wide-open ports where another kind of living awaited them. The island of Tortuga attracted many of the French buccaneers, while the Jamaican town now named Port Royal in honor of the new king of England, Charles II, became another destination. In the five short years since the English had arrived, Port Royal had been transformed from a killing ground into “the wickedest city in the world.” Privateers had turned Cromwell’s new city on a hill into a Sodom and Gomorrah. It was a thriving outpost of English civilization and a serious annoyance to the Spanish, two of Cromwell’s objectives when he sent the expedition out from Portsmouth. But, spiritually speaking, it was a disaster.

Roderick, our representative pirate, gaped at it when he first arrived in 1660. The town had 4,500 white residents and 1,500 Negro slaves. There were eight hundred houses eight years later, three hundred more than its competitor, New York, with more taverns and brothels than the rest of the English colonies combined; forty new licenses for drinking houses were issued in the month of July 1661 alone. And it was so rich that, in 1662, the government proposed building a mint on the island, to melt down and coin the piles of silver and gold plate that the privateers were bringing in. Port Royal lived and prospered not by an English proverb but by a Dutch one: “Jesus Christ is good, but trade is better.” When Roderick strode down from the docks, he saw a town bathed in the light of the Jamaican sunset, its shops and houses thrown into relief by the big blue mountains hovering behind them, its streets covered with a layer of golden sand and coral dust that cushioned Roderick’s steps as he made his way toward the bars that lined the waterfront. He could not believe how smartly dressed the local merchants were. Riding through town in fine carriages pulled by six horses, jeweled rings on their fingers and shod in shiny leather boots, they were the equal of Dover’s richest gentry. Port Royal had the romance of a civilized oasis about it. But then Roderick walked toward the pirate haunts such as the Bear Garden, which looked like any of the rough joints you might find in Portsmouth or London. There was a blast of singing and shouting as he passed by the open door. Lingering there, he saw that bets were being thrown down at the cockfight pit dug right into the tavern’s sandy floor. Pirates spilled past him into the night air and invited a local man, at gunpoint, to have a glass of rumbullion, a potent grog. Down the street others had carved a hole in a wine barrel, and local whores were taking their turns dancing in the spray. It looked like the kind of place where a thug off a corsair ship might murder someone whose face he didn’t like or where you might come across a newly arrived privateer having his way with a prostitute in an alleyway off the harbor.

There was one difference from his home in Dover that Roderick noticed immediately: Here the pirates seemed to own the place. Never before had he seen bad men act as if they were the law.

In Port Royal the privateers were commanded by Christopher Mings, whom the great diarist Samuel Pepys had described as “a man of great parts and most excellent tongue among ordinary men.” The son of a shoemaker, Mings had climbed his way through the ranks from cabin boy to captain by sheer force of will. In 1659 he led a privateer expedition against the Spanish Main, taking and pillaging in succession the towns of Campeche, Coro, Cumana, and Puerto Cabello. At Campeche his subordinates (who may have included a young Henry Morgan) advised a sneak attack by moonlight, but Mings scoffed at the idea as being beneath an English seaman; he sailed into the harbor in broad daylight, with his trumpeters sounding the attack and his drummers beating a martial tune. The fort fell in the first attack, surprise or no surprise. And when he returned to Port Royal, Mings’s boats were brimful with Spanish loot, estimated at a value of 1.5 million pieces of eight.

It is notoriously tricky to give present-day equivalents for seventeenth-century money, but a very rough estimate can be obtained. The math goes like this: In the late 1600s, four pieces of eight were worth about one English pound. One English pound in 1670 would be worth £115 today. And £115 British today equal $204 U.S. So divide that $204 by four (as it took four pieces of eight to equal one pound) and you have $51. That’s how much modern buying power in the local Wal-Mart a single piece of eight might get you. Or you can forget all that and just think of a piece of eight jingling in Roderick’s pocket as worth $50 or more.

In today’s dollars Mings had just snatched $75 million. It was an immense fortune, and it surged into Port Royal’s taverns, goldsmith shops, and merchant houses. The only entity that didn’t profit from the raids was the English government: When Mings refused to give the lord high admiral his share, he was sent back to England for trial.

Mings returned to Jamaica in 1662, having been freed by an indulgent Charles, who was grateful for Mings’s support during the bad days of the Civil War. The raiding began again. Next on his list was Santiago, the second-largest city in Cuba after the jewel of Havana, too strong even for the privateers. The mission was to be Henry Morgan’s initiation into the trade: He was the captain of one of the twelve ships that sallied forth to try their luck against the Crown’s forces. The fact that he’d already achieved the rank of captain suggests that Morgan had proved his talents as a soldier during the guerrilla wars and that his talent for leading men—and making alliances with those richer or more socially prominent—was already evident. Morgan’s family and their illustrious military history also probably earned him a foot in the door, reputation-wise. But everything after that he earned himself.

On September 21, 1661, Morgan and the other adventurers were given a hero’s send-off, with wives, whores, and merchants lining the shore to cheer the boys away. It was the middle of hurricane season, which runs from June to November, and the ships tacked to Negril in Jamaica and then headed north for Cuba at three knots. Off the coast the fleet encountered a surprise: a ship already anchored near a cay, commanded by none other than Oliver Cromwell’s scapegrace nephew, Sir Thomas Whetstone. Whetstone’s background was not unusual for a gentleman pirate. The Restoration of Charles II had brought with it a return to pleasure, and Whetstone had thrown himself into the whirl of parties and plays, spending wildly; he was soon being hounded by creditors. Luckily, he’d sided with the Royalists and not his uncle during the Civil War, and King Charles had released him from debtors’ prison with a loan of £100, with the understanding that he’d recover it on the high seas. Charles did not grant him a commission, however, so he was operating as a full-fledged pirate. His crew was almost entirely Indian, natives who had been forced off their land by the Spanish. They were out for more than treasure. Whetstone and his Indian crew soon joined Mings’s expedition.

A council of war was held aboard Mings’s forty-six-gun ship, Centurion, and a final battle plan was worked out. Santiago was a defender’s dream: The port sat on a bay accessible only through a long, thin channel, sixty yards wide at its narrowest, with high cliffs towering on either side. At the entrance to this channel stood the Castillo del Morro, a major fort whose guns could easily reach any ship attempting to sail through the gap. Another battery of guns sat at the cliff’s foot, just below the Castillo, adding more firepower. And in this age of sail, the winds at the mouth of the channel were notoriously tricky.

For the seventeenth-century sailor, winds were animate creatures, the physical manifestations of minor demigods and demons. Roderick believed they lived on mountain summits or in the hollows of caves, awaiting their orders to go and blow up a storm or hasten a ship to its destination, orders given by their commander, the great North Wind. The South, East, and West each had its own personality, as did all their various subalterns, from North by Northwest down to harbor breezes. Seamen imagined that the winds led sailorly lives; shouted into action by the blustery voice of the North, they’d go out, whip up a hurricane, then retire exhausted to the top of an Alpine peak for a game of cards or some storytelling over rum punch. These gales had feelings: They could be offended, wounded, or flattered, and sailors often called out to them encouragingly as they passed. Each had its own peculiar sound, which the mariner claimed to know by heart: lazy murmurs, keening gusts, voices angry or mournful. It is a testament to the loneliness of the seas and how much power wind had over the sailor’s life.

The breezes off Santiago were chaotic and difficult to predict, so the men decided on a direct attack up the mouth of the channel. Capricious or nonexistent breezes slowed the fleet’s pace, but on October 5, the men spotted the Castillo del Morro, towering over the entrance to the bay. By now the fleet had swelled to twenty ships with late arrivals from Port Royal, and the captains used telescopes to gauge the action of the wind at the channel mouth. Old hands who had sailed this way before knew that at dusk an onshore breeze would kick up; Mings decided to use it.

He swept the fleet in to the village of Aguadores at the mouth of the San Juan River, two miles from Santiago. The Spanish, who thought the attack would have to wait until the next day, were startled to find riders arriving from Aguadores saying that the English were pouring off their ships onto the rocky shore. By nightfall Mings had landed 1,300 men without losing a single soul. The privateers lit fires and waited for morning. At Santiago the troops were put under the command of Don Cristóbal Arnoldo y Sassi, a well-connected Spanish-Jamaican who had led the Jamaican guerrillas in their battles with the English invaders. Perhaps the governor hoped for some of the guerrillas’ success in picking off the English; but this was to be an old-fashioned frontal attack. The next morning the English marched to Santiago and, just after sunrise, sent wave after wave of musketeers toward the castle. The Spanish broke in short order, with Arnoldo leading the retreat. The privateers spent five days looting the town, taking anything that could be resold for the tiniest sum, down to the iron fixtures in the church. During the whole operation, Mings lost only six men to enemy fire, while twenty succumbed to sickness. When he sailed into Port Royal on October 22, the crowds along the shore erupted in celebration. Roderick and the boys flowed off the ship and straight into the taverns. By now our nineteen-year-old privateer was an experienced binge drinker. The pieces of eight jingling in his pocket promised weeks of nonstop carousing. He’d killed his first man at Santiago, a Spanish musketeer he’d shot in the face with his pistol, now tucked safely into his leather belt. Roderick would spend all he’d earned on rum and women, but Morgan, although it is likely he dropped a few cobs in the taverns, husbanded most of his share for the future. His plans were grander than Roderick’s.

The raid on Santiago was a preview, in miniature, of Morgan’s expeditions to come, which shows how much he learned from the irrepressible Mings. One more expedition to Campeche, which netted the privateers fourteen Spanish ships in addition to the usual assortment of trade goods and silver plate, and Morgan was ready to set out on his own. Privateering was confirmed as a business proposition: Fabulous riches lay strewn across the length and breadth of Central America, and Mings had proved that the rabble London had flushed out of its sewers and its army ranks could take it when motivated. Now the English blade had been placed at the jugular that fed Philip IV’s empire. Soon Morgan would begin to press it home.

In London the man who had set the invasion of Jamaica in motion was gone. Cromwell had died in 1658, and his Puritan revolution seemed to dissolve like morning fog. In his place came a far different man, Charles II, whose biography was touched early and often by piracy. The new king’s father, like many of the Stuarts, had married a Catholic, Henrietta Maria of France. This had enraged conspiracy-minded Protestants like Thomas Gage, who were always prone to rumors of papist plots to take over the country. When she was pregnant with Charles II, Henrietta had sent to France for a Catholic midwife. Her dwarf and dancing master were sent by sea to retrieve the woman but were captured by pirates and delayed past the blessed event. The man in the street rejoiced: Charles II was guided into the world by faithful Protestant hands.

At his birth, fortune-tellers predicted that Charles would be drawn to mathematicians, merchants, learned men, painters, sculptors—and sailors. Astrologers foresaw a man with a “mincing gait,” a high-pitched voice who would be lucky in both marriage and war. Charles’s father once stated that “the state of the monarch is the supremest thing upon earth: For kings are not only God’s lieutenants, and sit upon God’s throne, but even by God himself are called Gods.” His son, however, came of age in a much more uncertain world. He had to fight for power from his exile in France, flitting in disguise through enemy ranks, endangered and hungry. He’d even turned pirate for a brief moment when he sailed up the Thames and held merchant ships for heavy ransoms to raise money for his armies. Cromwell’s death in September 1658 opened the way for Charles II to assume the throne, and he’d be the monarch whose court would be enriched and scandalized by Henry Morgan’s raids. He brought the Restoration to England, and with it a spirit of debauchery of which Morgan and his boys would have approved. By his return to the throne in 1660, Charles was a canny, passionate man with few illusions; in the marvelous description of one historian, he was “life-bitten.”

Charles inherited a monarchy with few assets and many lurking enemies. The main players in Europe were at war with each other for most of the seventeenth century, seeking dominance and riches, but only four were vying for colonies in the West Indies: France, England, the United Provinces, and Spain. During Charles’s reign France was the rising power, rich and led with supremely cynical brilliance by Louis XIV. Spain, despite her recent military losses, was still Spain; it was difficult for the English, who had been raised on tales of her immense power, to believe she was really as depleted as she seemed. The United Provinces (the modern Netherlands) were tough and resourceful and had a powerful navy that was increasingly able to challenge any of the European fleets. And England was dependent on its West Indies privateers to do the work of empire. Other countries of varying degrees of potency—including the behemoth Austria (the Holy Roman Empire), Sweden, Italy, Greece, and Russia—were not active in the Caribbean arena, while Portugal was preoccupied with Brazil. In the mid-and late seventeenth century, European nations switched allies constantly in their bids for domination on the Continent and in the New World. Religious affinities and popular opinion meant little in this furious grab for power: Protestant kings would ally themselves with Catholic monarchs one year and then switch sides the next. The colonies of the New World were chess pieces in this ever-changing game, to be milked for money to fight European wars and to trade away if absolutely necessary.

So when Charles went looking for a bride, it was power and not love that he sought. Eager for cash and new markets, Charles gazed longingly at Portugal, who wanted desperately to have England as an ally. Only recently freed from the iron grip of Spanish dominion, Portugal held rich colonies in the East; it dominated the vital trade in spices that went back to 2600 BC, when Egypt’s rulers fortified with hot pepper the diets of the workers building the pyramids of Cheops. Portugal was weak, and if it collapsed, its rich possessions might fall into an ally’s waiting hand, giving England lucrative assets around the world: “Bombay as the mart for the trade of all India,…Tangier as a centre for the commerce of the Mediterranean, and…Jamaica as the key that would unlock to England the great Spanish treasuries in America.” Besides which, the Portuguese had placed a well-funded spy in Charles’s court, and he distributed bribes high and low. Spain reacted with panic to the threat of an English-Portuguese alliance, but Philip IV had little money to spare for greasing the palms of Charles’s men. Portugal was offering the fabulously rich Catherine of Braganza, daughter of their monarch, while the daughterless Philip (again hampered by the mortality rate of his legitimate children) countered with the ruler of Parma’s daughter. But many doubted whether he’d be able to deliver the huge dowry he promised.

Jamaica was a pawn in this great game. When Charles was in exile, he’d signed a secret agreement with the Spanish to return the island and crack down on the privateers if Philip IV, his friend and fellow debauchee, would supply him with 6,000 troops. But once he returned to power, the giveback seemed inadvisable. Merchants were doing a busy trade with Jamaica, and they were furious that he’d think of returning the island to the Spanish. From an island full of renegades and drunks, Charles began to see Jamaica in a new light: as “the navel of the West Indies,” “a window on the power of Spain.” Philip, on the other hand, kept bidding up the price for the return of it; he was desperate to regain his inheritance.

But the Portuguese bribe, and the promise of more to come, won the day. Charles would keep Jamaica and accept Catherine; in 1662 he announced his engagement. Catherine brought not only her plain and retiring person but also Bombay, Tangier, and £300,000 (approximately $61.5 million in today’s dollars) to the union. The announcement caused a “great passion” in Madrid; the breach with England was now official. There were even rumors that the fleet Charles sent to retrieve his bride would double the insult by intercepting the galleons from the Americas and ransacking them. It wasn’t true, but the gossip only pointed up Spain’s nervousness. The empire seemed under attack on every front.

Having decided on holding Jamaica, for the next ten years Charles did little to govern it. When the Council of Jamaica shipped back a copy of its new laws for approval, the document was mislaid—for a decade. The “fit of absent mind” continued; policies often shifted with the winds and with whether a pro-or anti-Spanish adviser was in favor in Charles’s court. The pirates and their Jamaican allies would have a relatively free hand to roam the Caribbean, with one edgy eye on London but with a remarkably free hand to strike at will.

Charles’s snatching back of the Jamaican offer was another disappointment for Philip IV. His torments only intensified as he grew older and in 1661 were capped by one overriding concern: a male heir. If he did not produce one, on his death Europe would be plunged into a war of succession and his empire would be carved up by his enemies, his family’s legacy scattered to the winds. Philip felt that by denying him a son, God was mocking him, the great seducer, the man who had illegitimate children stashed all over Madrid. How better to illustrate that fact than the fates of the royal sons, starting with Baltasar Carlos, who had died one after the other? How could his bastard sons thrive while his heirs withered and died? It was clearly a message: God would not allow any product of Philip’s legitimate pleasures to survive, as punishment for his darker ones. To say, as one writer has, that Philip was “possessed of the greatest capacity for sexual pleasure recorded of any modern monarch” is unprovable, but he’d certainly rank high—and yet not one of his heirs had made it to adulthood. In 1661 his last surviving legitimate son lay dying.

In the early days of that January, the monarchy was desperately striving to save the last boy, three-year-old Felipe Próspero. One religious leader had led a pilgrimage of devout Spaniards to the convent of the Barefoot Nuns, praying for the boy’s survival. The bodies of revered saints were moved from sacred site to sacred site in an attempt to appease God; the incorruptible corpse of San Isidro, whose body miraculously had never decayed, was laid beside Felipe’s crib, as were the ashes of San Diego Alcalá. But it was all in vain. On January 11, the boy passed away and plunged his father into fresh despair. Philip wrote to a friend, his mind divided between two calamities:

I assure you that what has most exhausted me, much more than the loss of my son, is to see clearly that I have vexed God and that he sent this punishment to castigate my sins. Pray to Our Lord that He may open my eyes, that I may perform His holy will in all things…. There is nothing new in the English situation.

There was only one hope left: Months before, Philip had deliberately slept with his queen, Mariana, one last time as an insurance policy against Felipe’s death. Now she was pregnant, and a few days after the death of Felipe she went into labor. The eyes of Europe—certainly of its monarchs in France and Vienna—were turned toward Madrid as the fate of Spain was decided.

As Mariana prepared to give birth, she was brought to the Tower Chamber, which had been made ready for her. Around the room had been carefully placed the royal family’s most sacred relics: There was a Roman nail from the cross, three thorns from Jesus’s crown on Golgotha, an actual fragment of the cross. The relics represented the physical connection between Jesus and his heirs on earth, the Spanish monarchy. As the contractions came quicker and quicker, Mariana was bled. And then on Sunday, November 6, the news came: It was a boy, Carlos Próspero. The French king instantly sent his spies to check on the health of the child. The Spanish court proclaimed him “most beautiful in features, large head, dark skin, and somewhat overplump,” but the French communiqués painted a much different picture: Carlos was so small and tender that he was placed in a box of cotton. “The crown was firmer on his head than the ground now beneath his feet,” one spy reported. But Philip was satisfied. “Our Lord was pleased to give me back the son he had taken from me,” he wrote. With an heir, however fragile, in place, Philip had fulfilled his last duties to his ancestors, and his spirits improved.

The news did not. The raids of Mings’s privateers were just more in a continuing stream of bad omens: droughts, plagues, and a disastrous loss to the Portuguese army in 1665. A possible cause was uncovered when the authorities raided a suspected counterfeiter’s house and found secreted away two plates; on them was engraved a heart pierced by an arrow and the words “Philip IV son of Philip III and Margaret” on the first and another man’s name on the second, along with some biblical verses and the chilling words “Thou are mine and I am thine.” Witchcraft was suspected, and the investigation went on for months, with the woman who lived at the house interrogated by the Inquisition. Delving deeper into the sorcery, Philip’s court priests confiscated the small bag the king had always worn around his neck to keep him safe. Instead of the relics it was believed to hold, inside were a portrait of Philip pierced with pins, a book of charms, and other tools of the devil. Convinced at last that they’d found the source of Spain’s disasters, the ecclesiastics burned the contents.

But the true devils lay to the west. Henry Morgan was beginning his career in earnest.