The capture, sack and burning of the city of Panama in 1671 marked the climax of one of the most extraordinary campaigns in military history — perhaps the most remarkable aspect of which was the fact that it was not a military campaign at all. The ‘army ‘ that reduced the second largest city in the Western Hemisphere to ashes did not act on behalf of any nation, sovereign, religion or political ideology.

No, these were men motivated solely by the spirit of free enterprise. They were, in point of fact, a gang of criminals — pure, unadulterated pirates.

The leader of this enterprise was equally remarkable. Indomitably courageous and charismatic, Henry Morgan had a rags-to-riches life that would have made a fine subject for a Horatio Alger novel had he not also been one of the most rapacious, ruthless and unprincipled villains of his age.

Born the son of a farmer in Llanrhymney, Wales, around 1635, Henry Morgan had no inclination to follow in the father’s muddy footsteps and left home to seek his fortune. Control over how to seek that fortune slipped from his personal grasp, however, when he was shanghaied, shipped off to the West Indies and sold into indentured status in Barbados.

Labor was a problem in the 17th century West Indies. When native and even imported Indians were used up, black Africans and white Europeans were imported. In the case of the Europeans, a system of indenture rather than outright slavery was often practiced. Young men were deceived by unscrupulous agents who ultimately sold them into bondage. Many were transported for petty crimes or for debts as small as 25 shillings. Others were simply kidnapped.

Indentured whites in the West Indies were not necessarily treated better than black or Indian slaves — in fact, it was often quite the reverse. Blacks and Indians in perpetual bondage represented capital assets to their masters, who therefore had a vested interest in their welfare. Since the whites were indentured for a given period of time, the master had less to lose if they died, particularly near the end of their service. In addition, the period of indenture — ostensibly three years among the French and seven years for the English — could be prolonged indefinitely. Many served 15 to 20 years.

Those, like Henry Morgan, who managed to survive to regain their freedom were usually released penniless, homeless, without prospects in the New World and without any means of returning to the Old World. Hardened and embittered by their ordeal, they often drifted together with others of their own kind and turned to crime. They also soon discovered that crimes directed against politically expedient victims were not only profitable but officially condoned. The nationality of those victims changed throughout the course of the century as wars and alliances came and went. For political, religious and especially economic reasons, however, the favorite targets were Spanish.

In the middle of the 17th century, Spain still possessed the greatest empire in the world. ‘New Spain ‘ included the entire coast of the Gulf of Mexico, all of the territory that is now Florida to California; Mexico and all of Central America; the islands of Cuba, Puerto Rico and Hispaniola; and all of South America with the exception of Portuguese-owned Brazil. Furthermore, the Spaniards had seemingly ended up with all the territory producing gold and silver. For more than a century they had been shipping it home by the galleon-load.

It was little wonder, then, that the other European colonists were envious of Spain. They scratched out a living on a few fever-ridden little islands that the Spaniards had not seen fit to take, while casting covetous glances at the treasures ships outward bound from Mexico and Panama.

That was particularly the case on the English island of Jamaica. Discovered by Christopher Columbus in 1494, Jamaica had been captured by the English from Spain during the course of a serendipitous campaign in 1655. Because the island lacked gold, the Spanish didn’t consider it important enough to mount a serious retaliation.

With the benefit of hindsight, noting Jamaica’s domination of the Yucatan Channel and the Windward Passage, two of the principal Caribbean trade routes, Spain’s failure to retake the island seems to have been a serious strategic blunder. In any case, by the mid-17th century was common knowledge that if a suspicious cargo was to show up in Port Royal, Jamaica, few questions would be asked.

At some point after the English conquest, Henry Morgan, having survived his indenture in Barbados, was recruited by a pirate crew. Posterity is indebted to John Esquemeling, a Dutch former slave who served as a pirate under Morgan, for his detailed description of typical 17th century pirate articles (i.e., the pirates’ code). Salaries were based on a strict commission basis of ‘no prey, no pay ‘ and were doled out by shares, except in the case of certain specialists, such as the carpenter (who received 100 or 150 pieces of eight) and the surgeon (who provided his own medicine chest and received 200 or 250). At the end of the cruise, the profits, if any, were divided up and each of the crew received a single chare, except for the master, who got five or six, and the mate, who received two.

Provisions were to be distributed twice a day in equal portions, regardless of rank, and generally consisted of stolen livestock. One captain was known to roast Spaniards alive for refusing to show him where he could steal pigs.

Surprisingly, the pirate articles included liberal disability compensation. For the loss of a right arm, 600 pieced of eight or six slaves were stipulated. A left arm or right leg was worth 500 or five slaves, while a left leg was, for some obscure reason, only worth 400 or four slaves. Eyes and fingers were valued equally at 100 or one slave.

Having prospered at his new profession, Morgan and a few of his new associates pooled their resources and bought a ship. He evidently made a good impression on his companions, because they chose him as captain. He also impressed his future patron, Captain Edward Mansvelt.

Mansvelt (or Mansfield) was an ambitious old Dutch pirate from Curacao who was one of the first to gather large enough numbers of freebooters to attack whole towns rather than just individual ships. He became a sort of pirate godfather, in control of numerous ships and hundreds of men. His pirates had attacked Cartegena and had been known to raid overland as far as the Pacific coast of South America. This old reprobate must have recognized qualities of leadership and ruthlessness in Henry Morgan similar to his own, for he made the young Welshman his ‘vice admiral ‘ on his latest and most audacious enterprise.

In 1665, England was at war with the Netherlands and the governor of Jamaica, Sir John Modyford, commissioned Mansvelt to capture the Dutch island of Curacao on England’s behalf. Mansvelt accepted the commission, but had no intention of carrying it out. It wasn’t that the old villain had any compunction about attacking his own countrymen — he simply had something more ambitious in mind.

After departing Port Royal, Mansvelt and Morgan took the 15 ships and 500 men they had assembled and, instead of sailing southeast for Curacao, sailed southwest for Central America. Mansfelt intended nothing less than the establishment of his own permanent island base, as an independent’state ‘ from which he could rule and raid as he pleased.

The island Mansvelt selected was called St. Catherine and, judging from contemporary descriptions of its position, it may have been the island now known as San Andrés, about 100 miles east of Nicaragua.

There, or near there, a landing was made under cover of darkness on the night of May 2, 1665. And since St. Catherine’s was sparsely populated and poorly guarded, the pirates made short work of the Spanish defenders. Leaving 72 men to fortify the island under a French pirate from Tortuga called ‘Le Sieur Simon, ‘ they set the garrison’s survivors ashore near Portobelo and proceeded to plunder coastal villages. When Mansvelt and Morgan learned that the governor of Panama was preparing to attack them, they decided to quit while they were ahead. They returned to Jamaica to divvy up their profits and recruit reinforcements.

The victorious pirates were welcomed enthusiastically by the Port Royal business community, which featured a somewhat lax moral outlook. Mansvelt found a cool reception awaiting him form the Jamaican authorities, however. Not only had he countermanded Governor Modyford’s orders, but his island stronghold was viewed as a potential threat to British commerce. Undeterred, Mansvelt set sail once more, this time on a northeasterly course. If he couldn’t replenish his fleet in Jamaica, he could simply go elsewhere.

The destination this time was an island off the northwest coast of what is now Haiti. The Spanish mariner who first discovered this nasty little plague spot thought it looked like a giant tortoise, and as part of French-speaking Haiti it is still called Isle de la Tortue. It is better known, however, through the Spanish rendering as Tortuga.

The isle of Tortuga first and nominally had been settled by the Spaniards, but they had been driven out by French squatters, who eked out a living planting tobacco and hunting the wild hogs with which the island was infested. The hunters were known as boucaniers, which might be translated as pork purveyors, or ‘bacon-eers, ‘ and is the origin of the word ‘buccaneer. ‘

Mansvelt never returned to his ‘island state, ‘ St. Catherine. In 1666, soon after arriving in Tortuga, he died suddenly — whether from natural causes or by foul play is not recorded. In any case, Henry Morgan succeeded him as the de facto head of the international criminal empire Mansvelt had founded.

Meanwhile, things had not gone well for the pirate garrison left behind on St. Catherine. The governor of Panama, Don Juan Perez de Guzman, dispatched a force of 520 men in four ships to retake the island. Le Sieur Simon, bribed by the Spaniards, betrayed the garrison, which was overpowered on August 15, 1666. In addition, when a pirate relief ship arrived on September 10, Simon personally piloted it into the harbor and betrayed its crew as well.

At that point, Henry Morgan’s unprecedented pirate rampage began. By 1668, his power and prestige were sufficient to assemble 12 vessels and 700 men, both British and French, for the sack of the Cuban town of Puerto del Principe (now called Camagüey). The raid yielded a satisfactorily profitable 50,000 pieces of eight.

Influenced by Mansvelt, Morgan still had designs on Panama in mind. After the obligator post-raid interlude in Jamaica, Morgan sailed for Portobel with nine ships and 500 men. Portobelo was the eastern terminus for Panamanian trade, and all the gold from Peru passed through that port on to Spain. Its harbor entrance was flanked by two fortresses, manned by a permanent garrison of at least 300 soldiers.

‘If our number is small, ‘ Morgan is supposed to have declared to his men, ‘our hearts are great. And the fewer…we are…the better shares we shall have in the spoil. ‘

A frontal assault was out of the question, due to the formidable defenses, so Morgan landed at Puerto Pontin, about 25 miles west of Portobelo. Leaving 100 men behind to handle the ship, 400 pirates marched through the jungle and, attacking Portobelo from the landward side, achieved complete surprise. The first for was quickly taken, its defenders massacred and the magazine blown up.

The second fort’s commander, however, had time to organize his defenses, so Morgan ordered his men to fabricate scaling ladders. Self-sacrifice was not a characteristic pirate trait, so local priests and nuns were conscripted to carry the ladders. Even so, many of Morgan’s men were killed or wounded in the assault, but they successfully stormed the fortress. The Spanish commander fought to the end, threatening to pistol any of his men who tried to surrender, but to no avail. He was eventually killed and the pirates took possession of the town.

After the customary interlude of rape, murder and pillage, Morgan sent a ransom demand to the governor of Panama: 100,000 pieces of eight for the town and its inhabitants. He also sent along a pistol as a symbol of how easily he had taken Portobelo and declared that in a year he would return and take his pistol back again. The governor scorned Morgan’s boast, but he duly paid the ransom.

Most of the money the pirates made ended up in the pockets of the pimps and publicans of Port Royal, so Morgan had no trouble in rapidly recruiting men for his next project, a proposed raid on the Venezuelan port of Maracaibo. The Sapniards, under Don Alonso del Campo y Espinosa, had only three ships against Morgan’s seven, but they were regular naval warships with properly trained crews and their flagship alone packed more firepower than the pirates’ entire fleet. Anchored in the shelter of the guns of a fortress at the harbor entrance, Espinosa was confident in spite of Morgan’s insolent demand for his surrender. When informed that the pirates were preparing a fire ship, he dismissed the threat on the grounds that the pirates ‘lacked the wit ‘ for such a tactic.

On the morning of April 30, 1669, the pirates attacked. Stripped of its armament, filled with combustible and disguised with wooden guns and a scarecrow crew, the fire ship led the pirate fleet. At the last moment, the fire ship’s 12-man skeleton crew set it alight, grappled the Spanish flagship and abandoned their own vessel. With their flagship ablaze, the Spaniards were thrown into confusion. The pirates boarded and captured one of the Spanish ships and the remaining one was scuttled by its crew. The fortress’ discouraged garrison who had witnessed the entire debacle, soon surrendered. The Maracaibo raid grossed the pirates 250,000 pieces of eight in ransom money alone — not counting pillage.

Henry Morgan’s success and prestige as a pirate leader was such that, the next time he called for recruits, lo less than 2,000 men in 37 ships turned out. They rendezvoused at Tortuga on October 24, 1670, and learned that the target this time was to be the city of Panama itself. The self-governing articles were particularly generous, with captains receiving eight shares, disability compensation for all hands and even a bonus of 50 pieces of eight for conspicuous acts of bravery. Morgan himself was done for one percent of profit of the entire enterprise.

On December 20, the pirate fleet once again appeared off the isle of St. Catherine. Morgan wanted to use it as a base of operations for the coming raid on Panama and he also wanted to expunge the disgrace of its capitulation to Panama’s governor five years before.

This time it was the Spaniards who would be betrayed. Although the island, now a Spanish penal colony, was defended by 200 troops in nine forts, its governor had made a secret deal with the pirates whereby he agreed to place himself in a position to be captured by them. Once in the pirates’ hands, he could claim that they had coerced him into giving up the forts. He allegedly belied that such an intrigue would preserve the lives of himself and the island’s 450 inhabitants without his losing face with the Spanish authorities by surrendering.

Along with loot and provisions, the second fall of St. Catherine’s gained the pirates 48 cannons, 170 muskets and more than 30,000 pounds of gunpowder. More important, they had acquired the services of three Spanish criminals who agreed to guide them across the Isthmus of Panama.

Morgan determined that the best route to Panama was up the Chagre River, the mouth of which, defended by a fort, lies just west of the present day city of Colón. Morgan detached a force of 400 men in five ships to deal with the fort. Chagre, however, proved to be a very tough objective. The Spaniards knew the pirates were coming this time and were prepared for them. They had more than doubled the garrison to 314 men, improved their defenses and increased its artillery to 20 guns.

The pirates had no choice but to launch a frontal assault and they were driven back with heavy casualties. Chronicler Esquemeling asserted that one of them, struck by an arrow, was responsible for reversing that state of affairs. The wounded pirate was so infuriated that he pulled the arrow out of hi body, wrapped a burning rag around it and shot it back over the wall with his musket. As chance would have it, that missile lodged in the Spanish magazine. The resulting explosion devastated the fort and gave the pirates their opportunity to storm the walls. By then, Morgan’s expedition had lost more than 100 men killed and 70 wounded before the walls of Chagre.

Morgan had left 130 pirates behind to garrison St. Catherine, which he still intended to maintain as a permanent base. Next, leaving 500 men at Chagre, which was to be his base for the Panama expedition, he led an army of 1,200 remaining pirates into the Panamanian jungle on January 8, 1671.

The Spaniards, correctly interpreting the pirates’ intentions, adopted scorched earth tactics. Spanish and Indian ambushes prevented the pirates from foraging in small groups and the villages they encountered were invariably deserted and stripped of anything of value or succor to them. By the fifth day, Esquemeling noted that there were, for the first time, ‘many complaining of Captain Morgan and his conduct…and desiring to return home. ‘ Despite the hardship, however, the force of Henry Morgan’s personality, the undeniable power of greed and the fact that these former slaves were inured to such privation, all contributed to the successful conclusion of the march.

On the ninth day, January 17, the pirates were finally able to feed themselves properly, having encountered a few head of horses and cattle that the Spaniards had overlooked. That night, they jubilantly camped within sight of Panama. Morgan, however, was worried was concerned. He was dependent upon the interrogation of prisoners as a vital source of intelligence, but the Spaniards’ evasive tactics had prevented the pirates from taking a single prisoner during the entire course of their march.

The Spaniards had two squadrons of cavalry and four regiments of foot staioned at Panama. Outnumbering the supposedly exhausted and overextended pirates by more than 3-to-1, they were confident of victory. They had even taken the precaution of posting a detachment of 200 cavalry behind the pirates to cut off their inevitable retreat. Morgan’s men, for their part, had come too far and suffered too much to turn back empty handed. They were also too well aware that few of them would survive if they had to retreat.

On the morning of January 18, 1671, 3,600 Spanish troops marched out of the city of Panama was one of the most extraordinary armies ever assembled — 1,200 criminals, Englishmen, Dutch, French, blacks, Indians and even a few renegade Spaniards. At their head stood not a prince nor a general, but a former Welsh plowboy and onetime Barbados indentured servant. Henry Morgan had come to retrieve his pistol from the governor of Panama.

The Spaniards began the battle by launching their cavalry against the pirates, with their infantry in support. The ground in front of the pirates was boggy, however, and the cavalry could not maneuver well. Frustrated by the soft footing and the pirates’ accurate musket fire, the Spanish horse was compelled to withdraw. The Spaniards next tried stampeding a herd of cattle into the pirate ranks, but most of the terrified animals simply ran away from the noise of the battle and the few that reached their lines were shot by the still-hungry pirates, who were grateful to the Spaniards for supplying them with the makings of a victory barbecue.

After two hours, most of the Spanish cavalry had been cut down and the few survivors fled. Seeing their horse desert them, the infantry fired one more volley at the pirates, then down their muskets and fled after the cavalry. The Spanish dead totaled some 600, with scores more wounded and taken prisoner. The pirates had lost heavily as well, but nevertheless they were determined to press home their attack. Spanish prisoners revealed — under torture — that there were still 2,400 troops left to defend the city, the outskirts of which had been fortified with trenches and artillery batteries.

That afternoon, the pirates assaulted the city itself. After three hours of fierce fighting, the exhausted Spaniards were overrun. The second largest city of the Western Hemisphere, a thriving mercantile community of more than 7,000 households, had fallen into the hands of a gang of thugs, who immediately began pillaging it. Morgan ordered his men not to drink any wine under the pretext that the inhabitants had poisoned it. It seems more likely that he was concerned that the Spaniards, who still greatly outnumbered his own force, might be encouraged to counterattack if the pirates degenerated into a drunken rabble.

Fire broke out in several quarters of Panama soon after the looting began. Morgan had traditionally accused of ordering the city burned, but such behavior would contradict his usual modus operandi. Morgan regarded the towns he captured as hostages, to be destroyed only in the event of a ransom not being paid. He had a great deal to lose and nothing to gain by such an act of arson.

Panama continued to burn for four weeks. During that time, the pirates searched the adjacent coast and outlying islands for hidden caches of loot, until Morgan learned some of his men were planning to dessert in one of the Spanish ships and go into business for themselves in the Pacific. Morgan could not afford to see his army split up in a hostile country, so he ordered all captured ships’ masts cut down and burned.

On February 24, the pirates began the march back with 175 pack animals laden with treasure. They also brought along 600 prisoners of all ages, most of whom were ransomed before they reached Chagre. Halfway across the isthmus, Morgan ordered his entire army to be stripped and searched, himself included, in order to ensure that no one was concealing any valuable from the communal coffers.

Once back at Chagre, Morgan tried to extort a ransom for that town as well. When it became clear that no money would be forthcoming, he ordered the town and its fortifications demolished. While his men were engaged in that work, Morgan slipped out of port with most of the loot, leaving his former companions at the mercy of the Spaniards.

The remaining pirates soon split up into smaller groups of men, many of whom were eventually tracked down and killed by the vengeful Spaniards. A few managed to escape, including the resilient Esquemeling. His memoirs, published in Amsterdam in 1678, caused a sensation in Europe. They were later translated into Spanish in 1681, and into English in 1684.

Henry Morgan returned to a Jamaica much changed from the one he had left. In the Treaty of Madrid, signed in 1670, England had agreed to suppress piracy in return for Spanish recognition of its sovereignty in Jamaica. In 1672, Morgan was transported back to England to be tried for piracy, but he was received rather more as a romantic hero than as a vicious criminal. Relations with Spain deteriorated once again, and in 1674 he was made a baronet. Later that year, he returned to Jamaica as Lieutenant Governor Sir Henry Morgan, even serving as acting governor from 1680 to 1682. He died in 1688 — rich, respectable and an enduring contradiction to the adage that crime does not pay.

This article was written by Robert Guttman and originally published in the October 1991 issue of Military History magazine.

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