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Piratical History of Port Royal

Author: Chris Rule

Avast there, shipmate! We meet once again for a look at another pirate stronghold...welcome to ‘the wickedest city on earth’, Port Royal,’d be real difficult to find a more wretched hive of scum and villainy anywhere else in the Caribee – what say we drop anchor a whiles and explore?


(Illustration: Map of Jamaica, including a detail of Port Royal)

The island of Jamaica is situated 90 miles south of Cuba. It is the third largest island in the Caribbean and covers an area of 4411 square miles, with mountains running east to west through its middle. The mountains to the east are the highest, rising to 7402 feet at Blue Mountain Peak, so named because of the trailing mists that colour it’s slopes. There are large, low coastal plains, particularly in the south and west parts of the island, known as the Great Morass, crossed by numerous rivers and streams. Upon its discovery in 1494, Columbus claimed that it was “the fairest island eyes have beheld; mountainous and the land seems to touch the sky...”

Jamaica’s vegetation, geography and climate vary quite considerably: at Mandeville in the hills, you’ll be needing to sleep with a blanket on your bed; the East Coast, liberally showered with warm rain from the high country, has dense, lush jungle-like foliage; the Blue Mountains are Jamaica’s backbone; the central plain contains the Cockpit Country, where rain has etched the limestone landscape into bizarre formations and rimming the North Coast, you’ll find one beautiful beach after another.

The island fairly vibrates with colours, scents and sounds – royal palms and coconut trees, orchids abound, poinciana and flaming poinsettias, many-hued hibiscus, bamboo, breadfruit and banyan trees (but care is needed around the latter, for they are said to be inhabited by ‘duppies’ or ghosts). All of this is accompanied by the songs of over 200 varieties of birds, lizards and tree frogs. The Arawak Indians, Jamaica’s first inhabitants called the island ‘Xamayca’ – land of wood and water.

The town of Port Royal is found on the southeast coast of Jamaica (and geographically situated at the centre of the Caribbean, very handy for any trading or piratical expeditions you might be a-plannin’!). Built on the Palisadoes Peninsula (originally called Caguaya), a narrow, 10 mile-long spit that forms a natural breakwater protecting Kingston Harbour, the town is underlain by a submerged coral ridge topped by sand, silt and gravel deposited over thousands of years by westerly currents.

The Palisadoes is arid and sparsely vegetated, fringed on its harbour side by mangroves that shelter a small number of crocodiles and nesting colonies of pelicans and frigate birds. The spit has no fresh water, no crops can grow on its barren sand and all supplies have to be brought in by boat, yet thanks to its excellent harbouring facilities (there are six fathoms of water so close to the beach, that ships can tie right up to the wharves and warehouses), in the closing years of the seventeenth-century, it ranks as the most flourishing seaport in the Caribbean. Due to the extraordinarily large size of Kingston Harbour, it was described by one seventeenth-century visitor as “one of the marvels of the World, for it is capable of holding all the ships of Christendom.”


The original inhabitants of the island of Jamaica were the Arawak Indians, who probably traveled over from South America around 700 AD. A gentle folk, the Arawaks lived in small villages of conical-shaped thatched huts, making a living from farming and fishing. They were blessed with an abundance of food and appeared to be a friendly race, described by Columbus as “honest and content with what they have...a peaceful and generous people.”

The Arawaks were short and slightly built, averaging at about five feet tall. They had bronze coloured skin, broad faces and black shiny hair, which they wore in a topknot. They prized pointed skulls and to attain this desirable shape, babies’ heads were pressed between wooden slats.

The women gathered food while the men hunted, fished or tended to the fields and the abundance of food available afforded the Arawaks plenty of leisure time. They evolved skills as potters, carvers, weavers and boat-builders. They were particularly adept at weaving cotton into clothing and hammocks for trading with neighbouring islands. The early Spanish visitors even had them weave sailcloth for their ships.

The Spaniards noticed other habits that the Arawaks had formed: a ball game akin to volleyball that the Arawaks bet on; getting incredibly drunk on maize alcohol; smoking dried leaves and snorting a powdered drug through a three-foot tube called a tabaco.

It was Columbus who brought the island to the attention of Europe after having sighted it on his second voyage to the New World in 1494. Columbus spent a year on the northern coast of the island when he and his crew were marooned at St. Ann’s Bay during his fourth trip (1502-03).

What little is known about the Arawaks is learned from a priest who had accompanied Columbus. When the Spanish arrived in Jamaica, there were somewhere between 60,000 and 100,000 Arawaks inhabiting the island. By the time the English took over the island in 1655, they had disappeared – killed off by imported diseases or the cruel treatment from their Castilian overlords. Some, it is said, chose to kill their children and commit suicide by drinking poisonous cassava juice rather than succumb to the ordeal of Spanish rule.

For a while, Jamaica was considered to be the personal property of Columbus and when he died in 1506, the title passed to his son Diego, who appointed Jamaica’s first governor, Don Juan de Esquivel. Esquivel founded a settlement at Sevilla la Nueva (close to St. Ann’s Bay) in 1510. Unfortunately, the colony had established itself near an area of swampland and proved to be an unhealthy and unproductive site.

In 1534 the Spanish moved the island’s capital south near the River Cobre to Saint Jago de la Vega. It was soon discovered that Jamaica held no gold and once they learned this, the Spanish took little interest in the island. They did however, plant tobacco, sugar cane and banana and raised cattle along with some hogs. In time, African slaves were brought over to replace the ill-fated Arawaks. At this point in time, Jamaica was little more than a stocking-up point for ships on their way to far richer prizes in the Caribbean and South America. The colonies on Jamaica, however, languished and were seen as weak targets; constantly harassed by French, English and Dutch pirates who had begun to ply their deadly trade throughout the Caribbean. For many years, Jamaica remained an underdeveloped backwater, a third-rate colony ripe for invasion.

It was Oliver Cromwell, setting his ‘Grand Western Design’ into motion in 1654 that was responsible for the English invasion of Jamaica. The plan was to destroy the Spanish trade monopoly in the New World and accrue English holdings in the Caribbean. He amassed a fleet and under the joint leadership of Admiral William Penn (father of the founder of the US state of Pennsylvania) and General Robert Venables and sent it off to conquer the Spanish-held Caribbean Islands – their first mission: capture Santo Domingo, the capital and principal port of Hispaniola.

The expedition to the New World was badly equipped and poorly organised – its forces described as “a wicked army of bullies, common cheats, thieves and lewd persons.” Even Venables himself described his expeditionary force as “unruly raw soldiers, the major part ignorant, lazy, dull – officers that have a large portion of pride, but not of wit, valour or activity.”

Despite leaving England with 3,500 men and stopping off at other English-owned islands throughout the Caribbean to pick up enough reinforcements to bring their number up to almost 8,000 aboard 38 ships, the invasion force had trouble taking Santo Domingo. Hindered not only by inadequate supplies of provisions, arms and munitions, the campaign was also ineptly organised. Deciding against a frontal assault, the troops were to be landed six miles west of the port. They were actually deposited more than thirty miles from their target and had to make an exhausting trek through dense jungle and swampland. Just to make things worse for the invaders, no food or water had been provided. All chance of a surprise attack had evaporated and they were constantly fired upon by Spanish snipers.

(Illustration: Santo Domingo)

Then the English leaders decided that rather than attack Santo Domingo straight away, they would set up camp for a week. The Spaniards used this time to strengthen their defences and bring in reinforcements of their own. All the while, tropical fevers were doing their worst to the English troops. When the assault was finally made, it was a shambles. The English forces were badly trained, poorly armed troops wracked by disease and starvation. The battle went on for three days as the Spanish defenders stoutly repulsed the English troops. The ‘invaders’ eventually had to admit defeat and after burying their numerous dead, clambered back aboard their ships and left the island.

Although Penn and Venables quarreled about just who was to blame for the failure of the attack, they both agreed that it would be an exceptionally bad idea to go back to Cromwell empty handed. They had to take some Spanish territory to offer as a consolation, besides, if they didn’t find somewhere that could offer up victuals, most of the men would be dead before they could reach England. But it had to be an easy target – that ruled out Havana, San Juan in Puerto Rico and the heavily fortified ports on the mainland. They settled on Jamaica. The island’s meager defences were known to the world at large and to the English in particular.

As the sun rose on May 10 1655, the English fleet entered Kingston harbour. There was a brief resistance put up by the handful of Spaniards manning the small fort at Puerto de Caguaya, but they soon fled to spread the alarm in Saint Jago de la Vega. Instead of following hard on the heels of the fleeing Spaniards and taking the town by surprise, once again the English set up camp, waiting for the rest of the troops to land. This gave the inhabitants of the town all the time they needed...

When the English did enter the town the following day, they found it deserted except for a few Negro slaves. They had taken everything of value with them and even worse, especially to the men who had been hungry since leaving England, they had taken all the food and driven the cattle from the surrounding plains and into the hills.

The Spanish governor, who assumed the attack was just another raid for plunder, sent some men into town, lead by two officers named Ysassi and Duarte de Acosta, to find out what the ransom was going to be this time. When he learned that the attackers were actually an invasion force bent on taking possession of the island, he was surprised, but made the best of it. He managed to stall Penn and Venables for almost a week, by pretending to be considering the harsh terms of surrender that they had demanded. This was long enough for him and his people to send all their valuables, their women and children and their aged and infirm to the north coast to be evacuated to Cuba, while the able-bodied men and loyal Negro slaves, under the leadership of Ysassi, prepared themselves for a long siege of guerrilla warfare.

The English eventually figured out that they had been tricked and sent search parties out to find the Spaniards. All of their sorties were unsuccessful and on a number of occasions suicidal as well, due to the ambushes set up by the Spaniards, who were at a supreme advantage due to their intimate knowledge of the terrain. Without any other course open to them, the English dug in as events went from bad to worse. The parties that were sent out to look for food also met the same fate as those out searching for Spaniards. The task of planting crops was also made just as dangerous and although they managed to get the job done, they couldn’t expect crops to pop up overnight and the invaders were driven to eat dogs, rats, snakes and lizards. By January of the following year, this diet combined with the devastation wrought by dysentery, malaria, yellow fever and the actions of the Spaniards reduced the original number of eight thousand men to just over two and a half thousand. Penn and Venables, acting in their usual feckless manner, decided that Jamaica was an unhealthy place and returned to England. Upon their arrival home, a furious Cromwell immediately imprisoned them in the Tower of London.

Cromwell was extraordinarily displeased with his consolation prize but decided that it should be kept at all costs. He sent reinforcements and a close friend, Major General Robert Sedgewick, as military governor. A proclamation was also made that anyone over the age of twelve who was willing to travel to Jamaica, would be granted thirty acres of free land. But news of the hardships to be suffered out there had spread and there were few takers. For several years the English kept a tight grip on the island they now considered theirs, even though they only held Saint Jago de la Vega and a few scattered outposts (all within a 10-mile radius of the town). The Spaniards still felt they owned the island and bolstered by arms and reinforcements from other Spanish colonies, continued to harry the English and held most of the island.

There was one bright spot in this world of misery and squalor that surrounded the English – Port Royal. From the moment of their arrival they realised that the cay with its deep waters and absence of shoals was the best site for a port and named it Cagway, a corruption of Caguaya. They also realised that it was the key factor in the defence of the entire harbour and began building fortifications soon after their arrival. When the fort was completed in 1657, they moved their headquarters from Saint Jago de la Vega, or Spanish Town as it was now becoming known, to the cay. It was found to be the safest place on the island for the English to be; although Saint Jago de la Vega was attacked on several occasions, no guerrilla war band was foolish enough to go anywhere near the ships and guns that guarded the cay.

As it turned out, the cay was also a healthier place to live than the mainland as it had little rainfall and as a result, fewer fever-carrying mosquitoes. Despite it having no fresh water supply, being covered in barren soil and all supplies having to be brought in by boat, a busy little civilian community soon grew up there.

Even though Spain’s attitude towards Jamaica had been exceedingly casual, the seizure of the island by the English made the Spaniards realise that the loss of it presented a very great and real threat to their other colonies in the New World. War was declared on England and plans formulated to re-take the island of Jamaica. Unfortunately for the Spanish, their ships were needed at home and the war against England was draining the royal coffers, so the plan had to be delayed. As an alternative, a plan was drawn up that suggested an invasion force be made up from neighbouring Spanish colonies and the Viceroy of Mexico was placed in charge. Little was accomplished. Many of the colonies had problems of their own as due to the lack of finances from home, they had to fund their own defences against the increasing number of pirate attacks. Besides, although the guerrilla forces already on the island numbered under a thousand men, they continued to harass the English and caused more problems than any invasion force could.

The English soon learned that they were fighting a losing battle against the guerrillas and came to the conclusion that the best defence is a good offence. For the spearhead of this attack they used the weapon that was quickly making the English the most feared power in the world – its navy. Penn had taken most of the ships with him when he left in 1655, leaving only a dozen or so frigates and a handful of smaller craft under the command of Vice-Admiral William Goodson, which he managed to put to good use.

Goodson’s forces were joined in 1656 by the 44-gun frigate Marston Moor, captained by a Christopher Myngs. Although Myngs was a Royal Navy officer, he quite happily employed a sizable contingent of freebooters. Myngs and Goodson fought well together, embarking on many raids against the Spanish in their island colonies and also on the mainland. Cruising the Caribbean, Myngs took many Spanish and Dutch ships, claiming them as prizes. Myngs was annoyed and frustrated when all but one of the ships were released on technicalities.

(Illustration: Christopher Myngs)

In 1657, Goodson’s small fleet approached the island’s north coast and engaged Ysassi and the Spanish guerrillas at Ocho Riós and managed to rout the Spanish forces. Shortly afterwards, Goodson returned home to England complaining of ill health and left the fleet under Myngs command. Myngs fought the Spaniards again in 1658 at Rio Nuevo. Managing to slip his men ashore, Myngs’ forces pulverized the Spanish, took their artillery as a prize and had it installed at Cagway. The English were victorious, but the Spaniards were not destroyed.

Myngs went on to make further raids against the mainland, attacking settlements along the coast. The English fleet burned Tolú (today in Columbia) and devastated Santa Marta, also intercepting three Spanish merchantmen bound from Cartagena to Portobello. Profits from these attacks were limited as the inhabitants were warned of their coming and had had time to hide their valuables. Myngs split up his fleet, hoping to achieve surprise attacks with a smaller force. The Marston Moor and two other ships raided Cumana, Puerto Caballos and Coro on the Venezuelan coast. They also learned to pursue the locals inland and managed to capture a large silver shipment, consisting of more than 20 chests, each containing 400lb of silver ingots, belonging to the Spanish Crown, at Coro. The entire haul was valued at over a quarter of a million English pounds and Myngs split the booty with his men, refusing to keep a share for the governor and the English treasury as was ordered.

(Illustration: Sacked!)

On his return to Port Royal, Myngs was arrested. Myngs claimed that the prize taken at Coro was ‘coined money’ to the value of £50,000 and the authorities suspected that a large part of the haul had been plundered. Myngs did not deny that some looting had taken place, but dismissed it as customary behaviour amongst privateersmen. The officials took a dim view of this and believing Myngs to be “unhinged and out of tune” sent him back to England to stand trial by the Admiralty on charges of embezzlement.

In 1660 it was learned that Ysassi was still hiding out in the north and claiming to be the legal ruler of the island. A small force was sent on a difficult march overland to track down the guerrilla camp. Ysassi and his band of over a hundred men were found encamped in a swamp.

At the time, Ysassi was unwell and the guerrillas were being lead by his second-in-command, Raspuru. Although they were outnumbered, the English advanced boldly and Raspuru received a killing blow almost immediately. Ysassi quickly ran away and evaded capture. Almost half of the Spanish forces were killed and others were captured. Not a single English soldier died. The Spaniards who did escape with Ysassi clambered aboard dugout canoes and sailed for Cuba. To this day, the spot from which they departed is known as Runaway Bay.

This marked both a beginning and an end – the beginning of Jamaica as an English colony rather than a beleaguered military outpost and the end of Spanish domination of the island. When the English monarchy was restored in 1660, it was feared that King Charles II, sympathetic to Spain, would give Jamaica back to the Spanish Crown. It surprised many when he announced his intent to keep the island and began making extensive efforts to entice settlers to make the voyage to Jamaica. People began to flock from England and other colonies. Now that the country was free and colonists could roam freely without fear of reprisal from Spanish guerrillas, plantations began springing up all over the coastal plains and even in the foothills.

The fortifications that had been begun on Cagway finally made Jamaica’s largest harbour almost impregnable. No ship ever managed to enter it by force. The deep water close to the beach enabled ships to unload directly onto the wharf and they could sail up onto the beach for careening. Also, once inside the harbour, ships were protected from violent storms and hurricanes. To celebrate the return of the English monarchy, its name was changed from Cagway to Port Royal and the fort was christened Fort Charles.

Even though settlers were spreading out all over the island, the settlement at Port Royal continued to be the most densely populated area and within a few years, the cay was so jammed with houses and other buildings, that the settlers had to fill in the marshy area that separated the cay from the Palisadoes so as to provide more room for expansion. The reason for so many people flocking to Port Royal is easy to explain – money. From the beginning, gold, silver, pearls and precious stones were circulating in the streets and much of it came from plunder.

The first civilian government of Jamaica, its councilmen and courts of justice all met at Port Royal and in 1662, the first civilian governor, Lord Windsor, arrived on the island. Windsor was accompanied by a familiar figure – that of Christopher Myngs. It seems that upon his arrival back in England, Myngs found the country distracted by the restoration of Charles II and as he had been an early public supporter of the monarch, he was cleared of all charges after a sympathetic hearing in June of 1660. By the end of the year, he was restored to his position in the Royal Navy but because of many upheavals, he did not actually set sail for his return to Jamaica until April 1662, when he conveyed Lord Windsor, the governor aboard the 46-gun Centurion.

Around this time, many more merchants began to open shops and set up booths in the streets, trading for booty taken from Spanish fleets. They also obtained Spanish money by a more direct means – contraband trade. Spain held a monopoly on trade with its American colonies, but it was unable to enforce it. Even under the best of circumstances, Spain’s meagre fleet was unable to adequately supply its colonies with enough of the goods they needed: cloth, tools and other European goods. And since Spain was unable to supply its colonies with those much needed goods, the English at Port Royal were happy to meet their demands – at a hefty profit.

Port Royal, being at the centre of the Caribbean, inevitably became the centre for this contraband trade. And so, through plunder and contraband, many of the riches of Spanish America found their way to Port Royal and what had been a deserted cay only a few years ago became the most important trading centre in the New World.

It is no surprise that a community so committed to worldly gain should also devote itself to worldly pleasures and Port Royal became notorious for its lack of moral discipline and sexual restraint. Reverend John Taylor claimed Port Royal to be “the most wicked and sinful city in the world.” And if the measure of its licentiousness was the amount alcohol consumed by its inhabitants, then wicked and sinful it indeed was. In 1661, the town council issued over forty new licenses for taverns, grogshops and punch houses during the month of July alone.

A resident of Port Royal wrote to a friend in England in 1664: “rum punch is not improperly called Kill-Devil; for thousands lose their lives by its means. When newcomers use it to the least excess, they expose themselves to imminent peril, for it heats the blood and brings on fevers, which in a very few hours send them to their graves.”

The letter is obviously exaggerated about thousands of people losing their lives from drinking Kill-Devil, but it was most certainly potent stuff. One of Jamaica’s later governors, Sir Thomas Modyford reported that “the Spaniards wondered much at the sickness of our people, until they knew the strength of their drinks, but then wondered more that they were not all dead”’.

At first, the military stationed there and the sailors of the fleet, behaving like any soldier or sailor loose in a town, contributed to the town’s bad reputation. They were soon joined by women eager to separate them from their money. A common sight in any tavern on any given night was a sailor with a girl draped over each arm recklessly spending Spanish pieces-of-eight taken in a recent raid. Towards morning, badly hungover and with empty pockets, he would generally find himself alone, bereft of female companionship.

Very soon the ranks of the revelers were swelled by adventurers, assorted cutthroats and the men whose exploits were to bring Port Royal its lasting fame: the buccaneers. They came from all over the Caribbean but many came from the island of Tortuga (see The Piratical History of Tortuga elsewhere on this site). At the time, the French occupied Tortuga and drove out any buccaneers who were of a different nationality and made the island off-limits to any who were not French. As the English authorities were encouraging buccaneers to bring their contraband trade into Port Royal, the hospitality was quickly accepted. Even though they were granted letters of marque (a government license to seize enemy property), they were still regarded as pirates by the Spanish but to the English, they had a standing as an unofficial navy. The citizens of Port Royal enjoyed the two-fold blessing of plunder and protection.

Port Royal’s buccaneers were a mix of men, from unstable sociopaths to brilliant leaders like Henry Morgan. One of the first to arrive and certainly one of the least savoury was a squat barrel-chested Dutchman with a terrible temper who was known as Roche Brasiliano. Exquemelin once described him when drunk “he would roam the town like a madman. The first person he came across, he would chop off his arm or leg, without anyone daring to intervene, for he was like a maniac. He perpetrated the greatest atrocities possible against the Spaniards. Some of them he tied or spitted on wooden stakes and roasted them alive between two fires, like killing a pig...” In his more sociable moods, he would buy a huge barrel of wine and sit in the street, inviting passers-by to partake in a drink with him. Few refused as the offer was usually made with a pistol in his hand.

(Illustration: Roche Brasiliano)

Another pirate who arrived closely behind the English was Bartolomeo Portugues, a bold and ruthless man who was plagued by bad luck. As he was prowling the coast of Cuba in a small boat with only 30 men and 4 guns, Portugues happened upon a larger ship. The pirates boarded her but were beaten back by the Spanish crew. They gave it a second try and even though half of his men were either killed or wounded, Portugues took the ship. Their haul was 70,000 pieces-of-eight and 120,000lb of valuable cacao beans. Due to contrary winds they were unable to return to Jamaica, so the pirates made for western Cuba. As they neared Cape San Antonio, they were captured by three Spanish ships, sailing from Mexico to Havana. The Spaniards relieved them of their plunder.

Soon after, a severe storm forced the ship carrying Portugues and his men to return to Campeche. The townspeople recognised Portugues as the leader of a band of pirates who had ravaged the Yucatán coast and as he had previously managed to give them the slip, he was kept aboard the ship as they erected a gallows in the town.

Portugues, who spoke good Spanish, overheard sailors discussing what was to be his fate. During the night, he killed the sentry with a stolen knife and taking two stoppered, earthenware wine jars, leaped overboard and used them to float ashore. After a difficult journey through 120 miles of wilderness, he reached El Golfo Triste (Sad Gulf) on the eastern tip of the Yucatán Peninsula. He eventually managed to find a buccaneer ship to take him back to Jamaica.

(Illustration: Portugues and the wine jars)


With a canoe and 20 men, he returned to Campeche and took the ship on which he had been held prisoner. As they were in a canoe, the Spaniards must have thought he was smuggling contraband trade from the town and did not stop him. Although all the gold had been removed, there was still plenty of valuable merchandise aboard. But Portugues’ bad luck still haunted him.

The ship ran aground on the Isle of Pines, south of Cuba. The survivors clambered aboard a canoe and made way back to Jamaica once again. From there they immediately set off in search of fresh booty. According to Exquemelin, Portugues “made many violent attacks on the Spaniards without gaining much profit from marauding, for I saw him dying in the greatest wretchedness in the world.”

Shortly after his own arrival, Windsor instigated a much tougher line to be taken against the Spaniards. Spain regarded all foreigners in the Americas as interlopers and to challenge this policy, Windsor had brought with him instructions to make a proclamation offering privateering commissions and a call for volunteers for a major operation against the Spanish. Within three days, 1,300 men, a great number of which were buccaneers, had mustered and ten other vessels joined Myng’s Centurion, including a tiny craft commanded by a 27 year-old militia captain named Henry Morgan.

Myngs was to lead his men against Santiago de Cuba, which had been the Spaniard’s main base for their planned reconquering of Jamaica and was much loathed by the English. Myngs fleet left Port Royal in October 1662 and having rounded Point Negril at the western end of Jamaica, made way for a rendezvous east of their Cuban target, where they met with Sir Thomas Whetstone and seven other privateers. In a conference aboard the Centurion, it was decided that they would take the town in a frontal assault, bursting into the port and taking them by surprise.

However, Myngs had to change his plans as they neared the towering harbour castle that guarded the approaches to the town. They were unable to close in because of faint, erratic breezes. He decided to sail directly for land and by nightfall had put more than 1,000 men ashore. The next morning, they fought their way into the town and took possession of the vessels in the harbour before pursuing the fleeing Spanish inland. Five days of this action “proved not very advantageous, their riches drawn so far off that we could not reach it.” In frustration, the freebooters razed the town and Myngs used 700 barrels of gunpowder to demolish the fortifications and principal buildings. After five days of calculated destruction, Myngs reported that “the harbour castle lies mostly level with the ground.” It would take the Spaniards more than a decade to rebuild the stronghold.

Myngs and his men returned to Port Royal in early November. The entire assault had cost only six men killed during fighting and another twenty to accidents and illness. Upon his return, Myngs found he had been elected to the council in his absence.

(Illustration: A view of Port Royal from the sea)

Encouraged by this success, the privateers ‘all went to sea for plunder’, but Myngs remained in port until December when he called for another expedition. The freebooters once again marshaled as the Centurion was refitted. Soon a dozen ships were ready and in late January of 1663, they got under way. Sailing around the Yucatán Peninsula in early February, Myngs managed to sneak almost a thousand men ashore, four miles west of Campeche and under cover of the night, began to march on the sleeping city.

At first light, Spanish sentries spotted his ships at anchor along with larger men-o’-war farther out to sea and sounded the alarm. But they were too late – the freebooter army burst out of the nearby woods and rushed the city. Despite the surprise attack and being heavily outnumbered, the 150 militiamen put up a valiant resistance. A bloody firefight ensued and Myngs received serious wounds to his face and both thighs while leading the charge. He was carried back to the Centurion and Mansveldt, a captain from one of the other ships, assumed overall command. After a heated battle, during which the Spanish defenders fought from the rooftops, hurling down not only musket fire, but also stones and hot oil, the Spaniards were eventually overcome and 170 prisoners were rounded up as the city’s thatched huts were put to the torch.

The next morning Antonio Maldonado de Aldana entered and agreed a truce in exchange for the good treatment of the prisoners. Despite his injuries, Myngs remained in control and released four prominent captives with a message to Maldonado offering to spare the city and release the rest of the prisoners unharmed if the raiders could draw water from the nearby Lerma wells. He also added his regrets that he could not come and meet his Spanish counterparts as he was impeded by his wounds. The Spanish agreed and as a token of good faith, Myngs released all but six of his most important hostages before obtaining the water. Towards the end of February, his fleet got under way, carrying with it a great amount of booty and 14 vessels found in the harbour.

The heavily laden fleet slowly made their way back to Port Royal, but due to contrary winds and currents, didn’t arrive until the end of April. Myngs’ wounds required a lengthy convalescence and so in early July the Centurion set sail for England.

When the second Anglo-Dutch war threatened in late 1664, Myngs was promoted to Vice-Admiral and was knighted for his involvement in the Battle of Lowestoft in June 1665. In June of the following year, he was abaord the HMS Victory during the brutal ‘Four Days of Fight’. With the battle raging, Myngs was shot through the throat but refused to leave the deck, remaining upright and compressing the wound with his fingers until a second bullet passed through his throat and lodged in his shoulder. He lingered a few days but eventually died at his home in Goodman’s Fields, Whitechapel. In his eulogy, Samuel Peyps described him as a “very stout man and a man of great parts and most excellent tongue among ordinary men.”

After his departure, the pirates and privateers continued Myngs’ policy of keeping Spain on the defensive and the benefits they bestowed upon Port Royal were financial as well as military, as just about everybody on the island profited from their raids. The merchants in town would buy goods plundered from the Spaniards, tavern owners were there to mop up a good share of the spoils (the privateers were all too keen to spend their money on drink) and even the local farmers made money by provisioning the ships before an expedition. Considering how much interest the townspeople had in the success of the raids, its small wonder that there was dancing in the streets whenever pirate vessels returned to port after a successful voyage.

As soon as a lookout at Fort Charles spotted a returning vessel, it would fire a cannon as a signal to the townsfolk that the fun was about to start. Everybody dropped what they were doing; merchants closed shop, on occasion courts suspended their sessions and people came a-running. As soon as the ship was tied up to the wharf, the King’s officials rushed aboard and took their ten percent of the booty (the Crown’s share in return for issuing letters of marque). Next the creditors who had financed many of the raids arrived, to make sure they were on hand as the booty was unloaded. The ship captains would ensure that the rum flowed freely, on one hand to celebrate the success of their raid, on the other to soften up the potential buyers. Presented to those gathered was the plunder – all manner of luxury items, silks, laces and brocades, jewelry, reliquaries and chalices from the Spanish churches and slaves captured on the raid – all sold to the highest bidder. Then the privateers, each with a share of the proceeds would manage to quickly spend it in the taverns, at the gaming tables and in the numerous brothels of the town.

During Windsor’s brief rule, Jamaica’s government changed from a military to a civil one – the new rule was by law instead of court-martial. Windsor disbanded the standing army and established a militia. He also had orders to take the buccaneers’ island of Tortuga, which was at the time under French governorship, but he didn’t do it. He left Jamaica after only ten weeks, stating ill health to be the reason for his leaving, but Samuel Peyps, in his diary, claimed that Windsor was just too lazy for the job.

Upon his departure, Windsor named Chancellor Lyttleton deputy governor. Lyttleton’s time in office was an unhappy one. Just before he was knighted and ordered to ship out to the West Indies, Lyttleton had married. His wife was a member of the minor nobility and was not in good health. While in Port Royal, she claimed, in a letter to a friend, dated Sept. 3rd 1662, to be “not at all well, being troubled with the symptoms of consumption.” Lady Lyttleton concluded the letter by saying “the truth is, I can say no more of anything for I am already so weary I know not what to do...” She died the following January, after months of suffering. Their infant son followed her five days later. In spite of his grief, Lyttleton carried on as best he could.

The marauding against the Spanish continued and Port Royal prospered. But while the privateers operating out of Port Royal might be prospering, it was an unhappy place for Lyttleton, an officer of the Crown working on a salary in a climate that was dangerous to Englishmen. In 1663, he wrote to London asking to be relieved of his post.

In reply, King Charles II, who had heard of the many raids against the Spanish, after telling the Spanish ambassador, the Duke of Medina, that he disapproved of the actions, wrote back to Lyttleton telling him that, while he admired the daring exploits of the Port Royal privateers, such things should really cease. They interfered with planting, which in the long run would prove more profitable. Charles II had no doubt enjoyed seeing Spain suffer such defeats and he certainly enjoyed the wealth that the privateering commissions brought him personally and so didn’t actually order Lyttleton to outlaw the privateering. It seemed to be expected to continue and so the bewildered Lyttleton did nothing to change the situation.

A report was sent to London in October 1663, informing the King that the Port Royal fortifications were only half finished and cost were increasing. Food supply was better and prices were lower, but less new settlers than expected. There was still too much privateering and too much sickness. Once again, Lyttleton asked to be relieved. He said that the island needed a man who wanted a career in the West Indies, not a man continually yearning for London; the governor should be a planter and an active man eager to encourage this island’s growth. He himself was not such a man. The widower was finally granted permission to go home in May 1664.

Port Royal came to know some livelier days after Lyttleton’s departure and under the new governor. King Charles II followed Lyttleton’s advice and offered the post to Thomas Modyford, a man who had already established a career as a landowner in the Indies and governor of Barbados. Modyford was exceedingly enthusiastic to accept the post and sent a wealth of proposals for Jamaica’s expansion to the King.

Modyford arrived in Port Royal on June 4th 1664 and he immediately attended to a number of matters, one of the first being a law passed against “tippling, cursing and swearing.” After Myngs’ raid on Campeche, Spain had appealed to England for an end to hostilities. Charles II obliged and so Modyford was also ordered to suppress privateering. The truce meant very little however, as the semi-official expeditions of the Myngs ‘variety’ were soon replaced by ventures born purely from alehouse conspiracies. More and more of the island’s inhabitants had given up their normal occupations and taken to the sea to enjoy the more lucrative business of privateering. This, claimed Charles II, was detrimental to the island’s growth and prosperity. Modyford came down hard on several of Port Royal’s buccaneers, punishing them severely to hopefully make an example of them. He soon learned the error of his ways, however, as the general response was to desert the port and head for the friendlier waters around Tortuga. This led to such a precipitous decline in Port Royal’s commerce that Modyford changed his mind and began to tolerate and eventually openly support ‘peacetime privateering’...or piracy, within a few months of his arrival, a move met with the approval of most of the island’s inhabitants.

(Illustration: Pirates ‘tippling’)

Not all of the plunder that reached Port Royal came from lawful privateers. Many did not want to give a tenth of their gains to the English Crown and so refused letters of marque and remained true pirates. During the early years of the town, the governors and royal officials were powerless to take action against them because of their great numbers, so they enjoyed the same privileges as the privateers.

The aforementioned Portugues was one of the first rogues to achieve notoriety, as was the brutal Roche Brasiliano. After a successful raid against Havana, the carousing and debauchery that followed set a record even for the degenerate town of Port Royal. Brasiliano contributed more heavily than any other pirate to Port Royal’s reputation. Fortunately for everyone, his career lasted only a few years. When he left on a voyage and was never heard from again, few, if any missed him.

Brasiliano’s excesses were unusual – the majority of pirates and privateers took their pleasure in less sadistic ways than the mad Dutchman. But it was not uncommon for a man to find life ashore more dangerous than at sea. Many who had survived Spanish gunfire met their end in a wharfside tavern, embroiled in one of the many duels and drunken brawls for which Port Royal was notorious. They had the run of the town and few attempts were made to stop them, for the locals feared they might make their base elsewhere, taking with them the protection and plunder they offered. Some of the more righteous citizens did try complaining to the authorities, but no action was taken – what was a little disturbance of the peace in return for the profits and protection from invasion offered by these ruffians?

The exploits of a number of other pirates made them legends in their own time. There was Lewis Scot, who captured and destroyed Campeche a few years after Myngs’ attack. There was John Davis who traveled deep into Guatemala and other Spanish colonies in Central America, managing to take a fortune in plunder while leaving a trail of destruction behind him. Edward Mansveldt, the privateer who had assumed command of the raid against Campeche when Myngs had been wounded, marched his men overland across Central America to attack Spanish settlements on the Pacific. But towering above them all, was a man whose name is as much a part of Jamaican history as its discoverer Columbus – Henry Morgan.

(Illustration: Henry Morgan)

Well, shipmate, we’re goin’ to have to leave it there for now...the sun is long over the yardarm an’ that means it’s time to heave anchor an’ get out of here...come back real soon an’ I’ll tell ye all about the greatest pirate who ever lived – Sir Henry Morgan. Ye’ll learn all about his life, his battles, his career and his death. I’ll also be tellin’ ye about the frightful events on June 7th 1692 and the struggles of the people and pirates of Port Royal in the aftermath of the great don’t want to be missin’ it, so’s I guess I’ll be seein’ ya!

Sources & further reading:

Buccaneers & Marooners – Pyle, Howard: Rio Grande Press 1990
Buccaneers & Pirates – Gilbert, John: Hamlyn Publishing Group Ltd. 1975
Buccaneer Harbour: The Fabulous History of Port Royal, Jamaica – Briggs, Peter: Simon & Schuster 1970
Buccaneers of America – Exquemelin, A.O.: Penguin Classics 1969
Buccaneers of America – Exquemelin, A.O.: The Folio Society 1969
Buccaneers of America – Exquemelin, A.O.: Rio Grande Press 1992
Caribbean Companion, The A-Z Reference – Doyle, Brian: Macmillan Press 1992
Caribbean Pirates – Alleyne, Warren: Macmillan Education Ltd. 1986
Exquemelin & the Pirates of the Caribbean – Shuter, Jane: Raintree Streck-Vaughan Pub. 1995
Exploring the Drowned City of Port Royal – Link, Marion Clayton: National Geographic Vol. 117 No. 2 February 1960
General History of the Robberies & Murders of the Most Notorious Pirates, A – Johnson, Captain Charles: Conway Maritime Press 1998
History of Pirates, The – Konstam, Angus: The Lyons Press 1999
Jamaica – Baker, Christopher: Lonely Planet Publications 1996
Jamaica – McLeod, Catherine: Berlitz Publishing Co. Ltd. 1994
Life Among the Pirates – Cordingly, David: Little, Brown & Co. 1995
Pillaging the Empire: Piracy in the Americas 1500-1750 – Lane, Kris E.: M.E. Sharpe Inc. 1998
Pirate Port: The Story of the Sunken City of Port Royal – Marx, Robert E.: World Publishing Company 1967
Pirates Adventurers on the High Seas – Marley, David: Cassell 1997
Pirates an A-Z Encyclopedia– Rogozinski, Jan: Da Cappo Press 1996
Pirates and Privateers of the Americas – Marley, David F.: ABC-CLIO Inc. 1994
Pirates – Johnson, Captain Charles: Creation Books 1999 (pretty much the same as the book ‘A General History of...’, but with an extra 233 pages containing a further 17 chapters, although it doesn’t have the number of illustrations that the Conway book has)
Pirates Fact & Fiction – Cordingly, David & Falconer, John: Collins & Brown Ltd. 1992
Pirates Terror on the High Seas – Cordingly, David (ed.): Turner Publishing 1996
Pirates’ Who’s Who – Gosse, Philip: Rio Grande Press 1924
Port Royal Rediscovered – Marx, Robert E.: Doubleday & Co. 1973
Spanish Main, The – Wood, Peter: Time Life Books 1979

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Christine Markel Lampe (a.k.a. Jamaica Rose) of the excellent No Quarter Given (
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Jim McEvoy, Collector of Spanish, American and Dutch shipwrecked coins and artifacts – a very generous and helpful man and a pirate to boot!
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All of the fine folks who subscribe to the Pirates e-mailing list (see the ‘Sailing the Cyber Seas’ page on the No Quarter Given website for more details)
And a final mention to the meanest, dirtiest, most scurrilous pirates to ever (dis)grace the Spanish Main – Morgan Daniels, ‘Boy’ Tom Trevellian, Eduardo de Souza, Dr. Esteban Salcedo, Owen Hawkes, Lecker Vife, Daniel Gough and Algernon Farharr.