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History of the Las Cruces Trail and Adjacent Canal Area
Part 2 - Pirates and Privateers - End of Spanish Rule


A Historic Review of the Events and Persons Associated with the Different Trans-Isthmian Crossings and Routes in Panama
from the Camino Real and Las Cruces Trail, the construction of the Panama Railroad and the subsequent construction and operation of the Panama Canal and the Trans-Isthmian Highway


By Susan Harp,
Darién Information Systems, Inc.

Panama City, Panama

June 1, 2001


Privateers were privately funded naval defense forces that sailed under commissions, also called letters of marque, to protect British, French and Dutch colonies in the Caribbean.  Investors paid for the ships and armed them.  In return, the privateer crew paid the owners a percentage of any ship or cargo they captured.  Spanish ships were the preferred target, as the Spanish monarchy held a monopoly on all trade with its New World colonies.  The Spanish trade ships were few, but were always heavily laden with luxury items on the westbound journey and with gold, silver and other treasures on the return trip.

In addition to the ships, treasure held in Portobelo and Panama City was the target of every privateer’s dream.

In addition to the lure of treasure, hunger played an important part in the raiders’ attacks as well as their success rate.  With hundreds of men to feed, many of their raids were to acquire provisions, by either confiscating food or by holding hostages for ransom payed in food.  The nature of sail-powered travel (long sea journeys, uncooperative winds) frequently led to food shortages on board and thus influenced the privateers’ decisions on when and where to go ashore.  When they sought treasure on land, they carried heavy weaponry and lightened their load by leaving the food behind.  They reasoned that they could steal food from their victims or from the towns and farms they came upon.

Under the British flag

The British had taken Jamaica from the Spanish in 1655 and recruited privateers to defend the island.  But by 1664, a new treaty prohibited privateers operating under British letters of marque from attacking Spanish ships.  The privateers refused to give up a chance to capture Spanish goods and began operating under French or Dutch commissions, leaving Jamaica with little naval protection and vulnerable to attack by the privateers themselves.  The Jamaican governor, Sir Thomas Modyford, knew the only way to entice the privateers back was to issue new commissions that named Spanish ships as legitimate targets.  On March 4, 1666, he began to do so. 

Division of goods

When British privateers captured a ship, their commission bound them to return to Jamaica, where the booty was inventoried and approved by the Admiralty Court.  Detailed rules dictated how the goods would be divided up among the crew, according to rank and risks taken during battle.  First, however one tenth was separated out for payment to the Duke of York (the Lord High Admiral of England and the king’s younger brother) and one-fifteenth was due the King of England.

To benefit Jamaica, certain Admiralty Court fees, including a fee to the governor, had to be paid.  Of the remainder, one fourth was separated for the respective ships of the fleet and their owners, who were frequently plantation men and other merchants based in Jamaica.  The remaining three-fourths was divided into shares and distributed among the ship captain and crew.  For example, boys received a half-share, specialists such as carpenters and surgeons received more than one share, captains got two shares and the admiral received five shares. (Earle, 42)

Privateer’s code

It is important to understand that commissions only addressed the division of goods from ships taken at sea and did not mention anything about land operations.  This created great incentive for the privateers to attack on shore under the pretense of following up on intelligence gathered from Spanish ships.  Booty taken on land was not included in the rules and therefore did not have to be shared with the king or ship owners.  This made Portobelo and Panama City even more desirable targets.

Santa Catalina Island

Just two months after Jamaica restored its privateer commissions, a Dutch privateer, Captain Edward Mansfield, led the first expedition against the Spanish.  The taking of Santa Catalina Island (called Providence by the Brits), marked a new phase in the privateer war against Spain that lasted for four and a half years and ended with Henry Morgan’s sack of Panama.  Technically, Mansfield attacked the island (located just off the Caribbean coast of Nicaragua) without an official commission, but he reasoned that he was really just retaking it, since Spain had captured the island from the British on May 25, 1641, exactly 25 years previously.

English possession of Santa Catalina gave the privateers a place to rest and provision.  The island was strategically close to Cartagena (Colombia), Panama and the main route for Spanish gold.

Panama responds

After Mansfield took Santa Catalina, he released the island’s Spanish governor, Don Estevan de Ocampo, and his soldiers, who hastily retreated to Fort San Lorenzo in Panama.  They reported to Don Juan Perez de Guzmán, Governor of Panama and Captain-General of the province of Tierra Firme.  Don Juan reacted quickly by sending a ship and successfully retaking Catalina just three months later in August.  The English prisoners were sent to Portobelo to work along with Indian and black slaves to build a fort.

These events, the British attack on Santa Catalina and the arrival of English prisoners in Portobelo, set the scene for events that were still seven years away.  A young Brit, Henry Morgan, was part of Mansfield’s crew, and both he and the prisoners were later to play an important role in the 1668 sack of Portobelo and the 1671 sack of Panama City. (Earle, 63)

Sir Henry Morgan attacks, 1666 – 1671

Sir Henry Morgan gained his fame and knighthood as a privateer and the first to successfully devastate all three Spanish strongholds – Portobelo, San Lorenzo and Panama City. 

Panama – the prize

Portobelo was officially the only arrival point for Spanish ships carrying luxury items, such as furniture and fine china, to the new Spanish aristocracy in Peru and Panama.  During the rainy season – April to December – the ships continued on to the fort at San Lorenzo.  Goods then traveled up the Chagres River by boat and then continued by mule along the Las Cruces Trail to Panama City.  During the dry season, goods followed an all-land route from Portobelo by mule train along the Camino Real trail to Venta de Cruces and Panama City.

The two trails paralleled each other as the led out of Panama City, one turning northwest to the Chagres River, the other crossing the river and heading northeast to Portobelo.  Peruvian silver usually followed the land route across the isthmus.  Sailing from Lima be Spanish galleon, it arrived on the Pacific coast and made the arduous crossing by mule to Portobelo for shipment to Spain. 

The governor of Panama avoided using the water route because sending the king’s fortune down the Chagres River and over the open ocean to Portobelo exposed it to pirate attacks.  For many decades, Portobelo held a huge fair upon the annual arrival of the royal fleet from Spain and, simultaneously, Peruvian riches from Panama City.  The residents of Portobelo and Panama became wealthy from this commerce, and at certain times of the year the vaults were full of treasures awaiting passage to Spain.

Fortifications, 1666

 Two Spanish castles, Santiago and San Felipe, and a garrison of soldiers fortified Portobelo.  The Castle San Lorenzo guarded the sea entrance to the Chagres River.  Panama City itself was not walled, as few ships other than the Spanish galleons sailed the Pacific, and a successful land attack from across the isthmus seemed unlikely.  During the 1660s, the garrison in Panama City held about 500 regular soldiers and relied on the additional services of all able-bodied citizens and slaves.  Even with such a small number of soldiers, a serious attempt on the city had not been made since the days of Sir Frances Drake, more than five decades in the past.

Morgan appointed admiral

In late 1667, Mansfield was captured by the Spanish and killed.  Henry Morgan received a new commission with the rank of admiral from the Jamaican governor.  Fearing the Spanish would attack Jamaica, the governor permitted the privateers to apprehend Spanish ships under the pretense of interrogating those on board about Spanish intentions and movements.  Morgan set his sights on Portobelo first.

Morgan’s plan

Incredibly, Morgan’s capture of Portobelo took less than a day.  Growing Spanish complacency, combined with a sneak attack, contributed to its success.  With 12 ships in his fleet, Morgan knew he could not approach Portobelo undetected.  As he approached from Nicaragua, he was surprised to meet six Englishmen paddling in a canoe.  The men had escaped from Portobelo and some part of the Catalina Island prisoners who were forced to build Fort San Geronimo in Portobelo.

The escapees provided invaluable information about the state of defenses in Portobelo and gladly volunteered to take revenge on the Spanish.  They reported that there were less than 500 regular soldiers at Portobelo, the guns and cannons at both forts had been greatly neglected and the gunpowder was damaged by humidity.

Under cover of night

Morgan’s fleet was carrying 23 small boats that they had stolen in Cuba.  With 500 men, Morgan left the main fleet in Bocas del Toro, 150 miles west of Portobelo, and paddled the small boats down the coast of Panama under cover of night, escorted by just one ship. During the voyage, the privateers came upon three men of Indian-black mix, two of whom they killed.  The third saved his life by agreeing to lead them to a safe landing near Portobelo.  They paddled for four nights, passed the castle at San Lorenzo undetected and arrived at Orange Bay.  Remaining under cover, Morgan’s men marched across land to reach Portobelo, arriving at the city just before dawn on July 11, 1668.

Attack on Portobelo

They first had to pass by the castle of Santiago, but their informants had already told them the cannons were in disrepair.  Armed only with muskets and scabbards, the privateers attacked the castle.  Just as reported, wet gunpowder caused many of the Spanish cannons to misfire; others were blown off their tracks when they did fire.  The panicked defenders contributed to the fiasco by misloading the cannons or loading them with cannonballs meant for firing at ships instead of grapeshot that was more lethal for foot soldiers.

Morgan and his crew passed by the castle to take the town first.  The citizens had scant warning of their arrival.  While some of the wealthy residents threw their valuables into water cisterns or in holes hidden in walls, others turned to their guns, only to find the gunpowder supply had been moved to one of the forts to protect it from the humidity.  The privateers quickly rounded up the citizens and held them at the church. 

Santiago Castle

The castle at Santiago still had to be taken, and the element of surprise was over.  After several unsuccessful assaults and heavy losses, Morgan selected some of the town’s friars and nuns and used them as shields to escort his men to the castle’s front gate.  The Spanish soldiers, after some hesitation, did fire on the nuns and priests, but too late to succeed in stopping the privateers.  Historians differ in the exact details of their demise.  Esquemeling’s eyewitness but embellished report says that the religious captives carried ladders that the privateers used to climb the fort’s walls.  Earle writes that the privateers used the captives as shields to walk to the front gate, where the attackers set to work hacking and burning their way through the door.

Meanwhile another group staged a sneak attack from the opposite side of the castle, which had remained almost unguarded.  One group entered the castle and planted a red flag, the signal for the rest of the army to join in the attack.  The castle fell by 10 a.m. (according to Earle, 73), or at least by nightfall (according to Esquemeling, 140) whereby the privateers fell to celebrating with captured wine and with the unfortunate lower-class female prisoners.  Morgan reportedly held upper class women apart for ransom.  In the end, Morgan’s men collected an estimated 250,000 pesos worth of goods and took control of 300 black slaves. (Earle,


The privateers proceeded to torture the citizens to make them confess where their valuables were hidden.  Earle reports that Doña Agustina de Rojas, a lady of Portobelo, was placed in an empty wine barrel that was then filled with gunpowder.  A lit match was held to her face to persuade her to reveal the location of her treasure.  Another woman was laid bare upon a baking stove and roasted because she did not confess, although the money the privateers assumed many of the citizens had hidden may not have existed at all.  Another torture, ‘woolding,’ involved the tying of a band around the victim’s head and tightening it with a rotating stick until his eyes popped out. (Earle, 74)

San Felipe castle

Morgan still had to capture the remaining castle, San Felipe, which was manned by 49 men led by a young Castellan, Alexandro Manuel Pau y Rocaberti.  The castle had no stock of food to withstand a siege, but their weapons were in good order.  They repulsed the first three attacks, killing five of Morgan’s men.  Then some of the attackers found shelter under an overhanging rock on the wall of the castle and began trying to set a wooden gate on fire.  To the surprise of his own men, Rocaberti panicked, sounded a cease-fire and prepared to surrender.  While his own lieutenants were protesting the surrender, the attackers swarmed up a ladder and opened up the main gate.  Realizing he would be branded a coward for the rest of his life, the Rocaberti begged his captors to bring him a flask of vitriol, which he drank.  He died two days later.

Rocaberti was not the only one to commit suicide, as the Constable of Artillery who had neglected to maintain the weaponry and gunpowder at the castle Santiago begged the English to shoot him instead of face his disgrace.  They obliged.

Panama learns of the attack

Within 24 hours, on July 12, Panama City received news of the attack.  The acting governor of Panama was a young nobleman named Don Agustin de Bracamonte.  (The appointed governor, Don Juan Perez de Guzmán, was in jail in Peru, a victim of a jealous viceroy.)  Bracamonte immediately set out across the isthmus on horseback with 800 soldiers and militia to aid in what he assumed would be Portobelo’s defense, since he had not heard of its fall.  They reached Venta de Cruces within a day, but in their haste to leave had brought little food, and the mulatto militiamen had even forgotten to bring their weapons and had no footwear.

The Spanish set up camp and waited three days for food  and shoes to arrive.  At Pequení they met some of the Portobelo refugees, who informed them of Portobelo’s fall.  This shed a new light on their mission, and Bracamonte, keenly aware of Spanish bureaucracy and the necessity of documenting and justifying his every action, called a military junta to decide how to proceed.  The majority agreed to continue their march.  Bracamonte sent a letter to Cartagena, Colombia, requesting help.  The messenger traveled 19 days by foot and canoe before arriving in Cartagena.  By the time a fleet of seven ships left Cartagena on August 31, Morgan had already sailed from Panama.


During his occupation of Portobelo, Morgan released one of the prisoners, Sergeant-Major Antonio de Lara with a letter for the governor.  Morgan sent cordial greetings and informed the Spanish that he would burn Portobelo to the ground and take all the guns, munitions and prisoners unless he received a ransom of 350,000 pesos.

This was a lot of the Royal Crown’s money, much more than was being held in the Spanish garrisons at the time.  Because of the state of Spain’s finances at the time, the soldiers at Portobelo had not received their pay for 18 months, and no supply ship from Spain had arrived for almost a year.  However, the merchants of Portobelo and Panama City were wealthy.  Bracamonte rejected Morgan’s demands, writing back, “I take you to be a corsair and I reply that the vassals of the King of Spain do not make treaties with inferior persons” (Earle, 83)

Morgan replied with insolence, taunting Bracamonte to hurry up and arrive at Portobelo or Morgan would have to go to Panama City.  He even offered to release his Spanish prisoners to help Bracamonte’s inadequate army.  Morgan signed his letter with the epithet “Portobelo, city of the King of England,” (Earle, 84) even though he did not have an official British commission  to invade Spanish territory.

Disease strikes

Both the Spanish and Morgan’s troops began suffering from the unhealthy effects of rainy season.  Unbeknownst to them, the swarms of mosquitoes were infecting them with diseases like malaria and yellow fever, and men in both camps began to sicken.  Although Morgan had only lost 19 men during the attack, many more began to fall.  In the camp at Matapalo, just a mile or two outside Portobelo, Bracamonte’s army began to literally bog down in their low-lying campsite.


A few skirmishes resulted in the escape of some of the Spanish prisoners, the taking of one English prisoner, and the death of eight Spaniards and one of Morgan’s men.  Bracamonte interviewed two ‘escaped’ Spanish seamen, who misinformed him that Morgan’s plan was to distract Bracamonte at Portobelo while a group of French allies marched across the isthmus to sack Panama.  (Morgan, during a previous council of war in Nicaragua, had indeed invited the French to join him, but the French had declined because they doubted he would be successful.)

The pressure was on the young governor to make the right decision:  attack the English who had already taken Portobelo and controlled the heavy artillery, or return to defend Panama City, the stronghold of the Spanish and the vital link to Peru?  After another junta meeting, the majority of the officers voted to return to Panama City.  Records officially note the lack of food and troop illness as additional circumstances, in case their superiors ever questioned the retreat.


They left Captain Francisco de Aricaga to try to negotiate with Morgan.  And negotiate he did, assuring Morgan that 100,000 pesos worth of silver and gold was the highest possible amount they could produce.  Aricaga had the nerve to say the Spanish would pay only 50,000 pesos in cash and the rest in a note of credit from a Genoese slave contractor.

Morgan scoffed at the idea of receiving a note of credit, but kept quiet about his concern that further delay would allow sickness to debilitate his already weak men and the Spanish would take back Portobelo.  He continued to negotiate with the commander of the rearguard, Cristoval Garcia Niño, and came to an agreement for the payment of the entire 100,000 pesos and a prisoner exchange within ten days.  Garcia suggested that the English should show good faith by leaving Portobelo first and then receiving the money and handing over the prisoners from their ships.  Morgan would have none of that, but he did agree to take payment at Portobelo and allow the Spanish hostages to inspect the castle guns to ensure they were not sabotaged.

Garcia hastened back to Panama to report to a grateful Bracamonte, who had found not one French privateer near Panama City and was anxious to find a way to avoid receiving a reprimand for abandoning his rescue mission at Portobelo. 

The payoff

Some of the ransom came from the Royal Treasury, but the majority was borrowed from private citizens.  However, the governor decreed that the city of Portobelo had to pay the money back from the profit made on the next trade.  The citizens of Portobelo would loudly protest this decree when they were at last freed, and many would later file lawsuits protesting the measure.

Nevertheless, on August 3, 1668, two mule trains crossed the isthmus carrying 27 bars of silver worth 43,000 pesos, several chests of silver plate worth 13,000 pesos, 4,000 pesos in gold coins and 40,000 in silver coins.  Morgan, who was well known for his gentlemanly way of speaking, formally thanked the Spaniards, loaded up the ransom with all the other loot he had gathered, and sailed away less than one month after his arrival.

Panama recovers

Morgan had mistimed his attack on Portobelo at about the midpoint of a two-year cycle between the Spanish fleet’s arrival from Europe and Peru.  The next arrival was scheduled for October 1669.  Viceroy Conde de Lemos released Governor Don Juan Perez de Guzmán from prison, and Don Juan arrived in Panama as preparations were being made for the fleet’s arrival from Lima.  He found the city of Panama guarded by only 200 regular soldiers augmented by the town’s militia groups organized by race – white, black, mulatto (white/black) and zambo (black/Indian).  He immediately sent letters to Spain asking for more troops, but help never came. 

When the Peruvian treasure arrived, mule trains carried 5 million pesos of merchandise and over 17 million pesos of silver coin and bullion over the Las Cruces trail to Portobelo. (Earle 140)  Now was the time for the pirates to attack before the royal fleet arrived from Spain!  But the fleet arrived, the treasures were loaded safely and the ships sailed away in early December.  During that brief time, 450 men died of fevers contracted in Cartagena and Portobelo.  The ships had arrived in Panama at the peak of the heavy rains, when disease-carrying mosquitoes were at their height.

Fortifications at Portobelo and San Lorenzo, 1699

Earle writes that the designs of the original castles in Portobelo and San Lorenzo broke many of the rules of good military architecture.  The Santiago castle was surrounded by higher ground that provided good attack positions for snipers.  Another problem was the lack of good construction stone and lime.  Most of the castle blocks were made of cut coral reef.

On the other hand, San Lorenzo’s exterior was built of timber palisades reinforced with sand and earth, and the living quarters were made of earth and straw with palm-thatch roofs.  Governor Guzmán tried to improve defenses at San Lorenzo, but lacked funds.  He did build a new gun platform at sea level to augment defenses stationed at the castle at the top of the cliff.  The fort’s wooden palisades and thatch roofs would later contribute to the fall of San Lorenzo under the attack of Sir Henry Morgan and the largest gathering of privateers ever.

The final attack

In 1670, Morgan amassed a fleet of 38 ships and some 2,000 men for one last attack on the Spanish.  They knew that news of an official declaration of peace between England and Spain would soon arrive in the Caribbean.  During a summit meeting, the privateers chose Panama as their final target over Santiago, Cuba; Veracruz, Mexico; and Cartagena, Colombia.  On Christmas Eve, they attacked Santa Catalina Island, which fell without losses on either side.  Reports say the frightened defenders of the island sent word to Morgan that they would prefer to stage a mock defense, firing into the air, in order to fall with honor instead of surrendering. (Esquemeling, Earle, Minter)

 Fort San Lorenzo

The privateers’ next target was the fort at San Lorenzo, Panama.  San Lorenzo had to be taken before the great pirate fleet could sail up the Chagres River.  Morgan knew their arrival and huge fleet size would immediately be reported to Panama.  Instead, he sent only three ships and 400 men under the command of Lieutenant Colonel Joseph Bradley to take San Lorenzo.  Morgan and the remaining ships stayed at Santa Carolina a few days more, passing the time by systematically destroying the island’s fortifications and guns.

Bradley and his 400 men landed east of the castle and hacked their way through dense undergrowth until reaching a large cleared area next to the fortifications.  They attempted an attack across the clearing in broad daylight.  But accurate Spanish cannon fire and gunfire, accompanied by a shower of arrows, caused heavy casualties, and they fell back into the trees.  An hour later, they attacked a second time, only to be beaten back again.  Near sunset, the privateers successfully reached a ravine near one of the walls in their third attack.  In the failing light, it was harder for the Spanish to pick out their attackers in the ravine, but the sun setting behind the fort made it easy for the privateers to spot the Spanish soldiers’ silhouettes.

Among the attackers was a group of grenadiers who prepared and threw pots containing burning oil, an early-day Molotov Cocktail.  The January dry season had dried out the fort’s palm-leaf roof, and the explosives ignited the thatch.  The fire caused an explosion in a storage room containing arms and gunpowder and the wooden palisades began to burn and collapse.

Turn of events

Much is known of this attack from a published account of and eyewitness and participant in the attack.  John Esquemeling, who served as a barber-surgeon to the privateers, published his account in Dutch in 1678.  The book was very popular, and recounts how the battle turned in favor of the English.  It seems an English musketeer wrenched an arrow from his own shoulder, wrapped a cotton wad around the arrow and fired it from his musket onto the fort’s palm-leaf thatch.  The gun’s blast ignited the cotton, which began to burn the thatch.  Other privateers fired more burning arrows, and the Spanish were soon trying to put out fires with a bucket brigade.

But luck was not with them.

Their prize bronze cannon that had inflicted much damage blew up, ripping up the palisades below it and collapsing a long section of wall on either side.  The grenadiers took advantage of the hole and threw more burning oil pots.  One landed on the main gunpowder room, causing a great explosion.  The fires and explosions devastated and demoralized the Spanish.  Many began to retreat down the cliff and make their way to canoes at the water’s edge.

San Lorenzo falls

With only 150 Spaniards defending the castle, Bradley attacked again at dawn.  He suffered heavy casualties in the first two assaults, but on the third attempt, the attackers entered the fort.  The Spaniard in charge, Don Pedro de Elizalde, and some 70 loyal men refused to surrender and fought until they were all killed.  Equemeling maintains that 30 remained alive and informed the privateers that the Spanish had fortified the way stations along the trail to Panama City.

Despite their success, Colonel Bradley and 76 others suffered fatal wounds in the assault.  Thirty others were killed outright.  While waiting for Morgan to arrive, the remaining privateers began rebuilding portions of the fort with the help of the slaves they had brought from Santa Catalina or captured from a nearby village.  They had to make the fort defendable in order to guard against a Spanish counter-attack.

Esquemeling’s description of the battle at Castle San Lorenzo (pages 189-190)

“At last, after many doubts and disputes, resolving to hazard the assault and their lives desperately, they advanced towards the castle with their swords in one hand, and fireballs in the other.  The Spaniards defended themselves very briskly, ceasing not to fire at them continually; crying withal, “Come on, ye English dogs! Enemies to God and our king; and let your other companions that are behind come on too, ye shall not go to Panama this bout.”  The pirates making some trial to climb the walls, were forced to retreat, resting themselves till night.  This being come, they returned to the assault, to try, by the help of their fire-balls, to destroy the pales before the wall; and while they were about it, there happened a very remarkable accident, which occasioned their victory.  One of the pirates being wounded with an arrow in his back, which pierced his body through, he pulled it out boldly at the side of his breast, and winding a little cotton about it, he put it into his musket, and shot it back to the castle; but the cotton being kindled by the powder, fired two or three houses in the castle, being thatched with palm-leaves, which the Spaniards perceived not so soon as was necessary; for this fire meeting with a parcel of powder, blew it up, thereby causing great ruin, and no less consternation to the Spaniards, who were not able to put a stop to it, not having seen it time enough.” (Esquemeling, 189-190)

“The pirates perceiving the effect of the arrow, and the misfortunes of the Spaniards, were infinitely glad; and while they were busied in quenching the fire, which caused a great confusion for want of water, the pirates took this opportunity, setting fire likewise to the palisades.  The fire thus seen at once in several parts about the castle, gave them great advantage against the Spaniards, many breaches being made by the fire among the pales, great heaps of earth falling into the  ditch. Then the pirates climbing up, got over into the castle, though those Spaniards, who were not busy about the fire, cast down many flaming pots full of combustible matter, and odious smells, which destroyed many of the English.” (Esquemeling, 190)

“The Spaniards, with all their resistance, could not hinder the palisades from being burnt down before midnight. Meanwhile the pirates continued in their intention of taking the castle; and though the fire was very great, they would creep on the ground, as near as they could, and shoot amidst the flames against the Spaniards on the other side, and thus killed many from the walls. When day was come, they observed all the movable earth, that lay betwixt the pales, to be fallen into the ditch; so that now those within the castle lay equally exposed to them without, as had been on the contrary before; whereupon the pirates continued shooting very furiously, and killed many Spaniards; for the governor had charged them to make good those posts, answering to the heaps of earth fallen into the ditch, and caused the artillery to be transported to the breaches.” (Equemeling, 191)

“The fire within the castle still continuing, the pirates from abroad did what they could to hinder its progress, by shooting incessantly against it; one party of them was employed only for this, while another watched all the motions of the Spaniards. About noon the English gained a breach, which the governor himself defended with twenty-five soldiers.  Here was made a very courageous resistance by the Spaniards, with muskets, pikes, stones and swords; but through all these the pirates fought their way, till they gained the castle. The Spaniards, who remained alive, cast themselves down from the castle into the sea, choosing rather to die thus (few or none surviving the fall) than to ask quarter for their lives. The governor himself retreated to the corps du gard, before which were placed two pieces of cannon: here he still defended himself, not demanding any quarter, till he was killed with a musket-shot in the head.” (Esquemeling, 191)

Morgan arrives

On January 12, Morgan and 33 ships arrived from Santa Catalina.  They sighted the English flag flying and their comrades lining the walls of the fort and began cheering.  The crew on Morgan’s flagship, the Satisfaction, were so enthusiastic that they did not notice the shallow Laja Reef lying at the entrance to the mouth of the Chagres River.  The Satisfaction ran right up onto the reef, and, like some slow-motion freeway pileup, four more ships followed.  The most feared pirates in the region were soon frantically trying to recover from their own self-destruction.  All five ships were a total loss, but the crew and most of their provisions were saved. 

Morgan immediately prepared to sail further up the Chagres River.  He left Captain Richard Norman in charge of 300 men to guard his rear flank at San Lorenzo.  On January 19, 1671, Morgan sailed with more than 1,400 men in seven small ships and 36 boats and canoes.  They planned to follow the Chagres to the Las Cruces Trail to Panama City.  But they did not know the start of dry season triggered a drop in the river’s water level.  Soon the shallow water forced them to abandon the ships and rely on small boats to carry the equipment while the men marched along the banks.

Panama prepares for the attack

Word of the attack on San Lorenzo had reached Panama City within 24 hours.  The unlucky Governor Guzmán was bedridden with a terrible fever, but rallied and began organizing the city’s defense.  He sent Francisco Gonzalez Salado and 400 men out to ambush Morgan along the Chagres.  Gonzalez and his men prepared four defense sites along the banks of the river at Barbacoas, Caño Quebrada, Tornomarcos and Barro Colorado.  Most of his men were blacks, half-castes and Indians who were well-suited for ambush assaults because of their jungle knowledge.

Up the Chagres to the Las Cruces Trail

Gonzalez was waiting at an advance post at Dos Brazos when they heard cannons firing at San Lorenzo.  When the wounded deserters began filtering upriver, however, Gonzalez faltered and retreated further upriver to the nearest fortification at Barro Colorado.  When he heard next of the castle’s fall, he left Captain Luis de Castillo in command and retreated as he sent all of his men from the other stations to Barro Colorado.  Castillo himself cowered at Barbacoas, the fortification furthest from the approaching privateers.

At this point, the Spanish still though Morgan’s force numbered only about 400 men.  When the first group of advance Spanish scouts saw the huge flotilla coming up the river, they were so surprised that they kept hidden.  Instead of attacking, the two companies of about 300 men tried to retreat to a lookout further upstream.  On the way, they conveniently “got lost” for the remainder of the altercation.

For the privateers, following the river was difficult, since water levels were low.  When Morgan reached Barro Colorado, some of his men made a sneak attack on the site’s fortification, only to find that Castillo and his men had abandoned the fort and burned it and any food that they could not carry away.  After the disappearance of the 300 advance scouts, Castillo had just 216 remaining men at Barro Colorado when he learned of the true size of Morgan’s army.  The Spanish had lost their nerve and retreated even further upriver.

Starving the enemy

 Morgan proceeded unopposed by men, but nature in the form of fallen trees and other debris blocked his progress on the river bank.  The privateers took to land, carrying their weapons but leaving their food behind.  They assumed they would be able to shoot game and steal food from the Spanish and native villages as they made their way across the isthmus.

But everyone fleeing in their path systematically carried away or hid their food supplies, and the game retreated in front of their noisy progress.  Hunger began to weaken the more than 1,000 men.  At one point, they came upon some empty leather pouches.  In desperation, they cut them up into pieces and boiled and ate them.  Then they found a barn full of dried corn that they devoured raw.

On Sunday, January 25, they had been marching three days without food when they finally reached the beginning of the Las Cruces Trail to Panama.  Here they expected to meet resistance, but again Gonzalez and Castillo had burned the village of Cruces, taken all the food and retreated.  If only they had known how weakened Morgan’s men were from hunger, they could have successfully ambushed them and turned them back at this point.

At the Cruces settlement, the privateers found a few unfortunate dogs that were immediately turned into meals and 16 jars of Peruvian wine.  After drinking the wine, the majority of the men became ill and declared that the Spaniards had poisoned it.  Most likely, however, the revolting combination of leather, raw corn and wine in their stomachs was the real cause of distress.

Las Cruces Trail

Now the attackers had the Las Cruces road to march on.  As they progressed, they were ambushes several times, but suffered only light casualties.  Most of their attackers were arrow-wielding Indians who were loyal to the Spanish.  Fortunately, the arrows were not tipped with the potent poison commonly used in the area.

On the fifth day of their march without food, the privateers caught their first sight of the Pacific Ocean and entered a field of cattle and horses that they immediately proceeded to butcher and eat only half cooked.  The Spaniards’ careless oversight of this food source greatly contributed to their eventual downfall, as the abundant meat soon restored the privateers’ energy and resolve.  

Panama’s secret defense

Meanwhile in the city, Governor Guzman’s health had deteriorated, but he continued to rally the 800 or so remaining defenses.  The Spanish pitched camp at Guayabal, about 16 miles from Panama City.  But when news arrived that over 1,000 hungry, bloodthirsty pirates were on their way, two-thirds of the men deserted.  Guzman was forced to retreat to the city, and he set his forces up on a cleared area just outside of town.

Desperate, Guzman devised a secret weapon – a herd of 2,000 wild bulls held in a corral.  The plan was to stampede them toward the enemy.  As the attack began, the Spanish infantry horses bogged down in the mud and Morgan’s men decimated their riders.  The wild bulls were released and began running toward the attackers.  Morgan’s trumpeters turned and commenced blasting on their horns, and the racket frightened the animals into turning in another direction.

Seeing that the enemy was gaining the upper hand, the Spanish retreated.  As the privateers advanced on the city, the citizens and clergy gathered up many of their valuables and sailed away in several ships.  Those left behind felt the wrath of the attackers.

Control of the city

Earle reports that the Spanish themselves set fire to the city before leaving, but Esquemeling (208) reports that Morgan ordered the fires set.  At any rate, most of the city burned, destroying much of the remaining valuables and food.  Instead of commandeering a ship and following the escapees, Morgan’s men began to open the wine stores and revel in their victory.  They had finally sacked Panama City!

When they did come to their senses, they sailed about looking for the escaped ships, but were never able to locate the one that held the king’s treasure and gold ornaments from the church.  As a result, the booty collected from the city was small in comparison with the great effort and sacrifice made to obtain it.  Morgan and his men remained in Panama City for a month, torturing citizens to extract every last hiding place for their valuables.

Return to San Lorenzo

Meanwhile at San Lorenzo, the privateers patrolled nearby waters looking for ships carrying supplies.  They chased a Spanish ship into the Chagres harbor and happily unloaded its food supply.  On February 24, Morgan’s group left Panama with 275 mules and about 600 prisoners.  They followed the trail back to Cruces and sailed down the Chagres to San Lorenzo.  But before reaching the fort, Morgan had every privateer, including himself, searched for hidden valuables.  None were found, but his privateers were offended by the show of mistrust.

Morgan’s fate

Back at the fort, Morgan sent the prisoners to Portobelo with a ransom note for 100,000 pieces of eight, which the governor refused to pay.  Morgan let the prisoners free anyway and prepared to leave.  However, since his men were unhappy about the small amount of loot taken, Morgan secretly loaded up his own ships with all the food and the best of the valuables and sailed away, leaving most of his followers behind. (Esquemeling, Minter)  Although their ships were intact, those remaining at San Lorenzo could not leave for quite a while before they could amass enough food to sustain them on a long journey.

Morgan returned to Jamaica, only to be sent to England in chains.  However, when he sent King Charles II a large amount of treasure taken from Panama, Morgan recovered his good standing.  The king knighted Morgan and appointed him lieutenant governor of Jamaica, where Morgan returned to live out his final days in luxury.  He died in 1688.

England pressures Spain

Despite Spain’s monopoly on ships allowed to trade in Panama, English and French smugglers established a black market cleverly timed to coincide with the Portobelo fair.  The smuggler ships would anchor in hidden coves between San Lorenzo and San Felipe and sell slaves and goods without charging Spanish taxes.  Generous gifts to local officials ensured they reported that the coast remained smuggler-free.  However, when illicit trade outstripped Portobelo fair revenue by an estimated five to one in 1624, Spain finally reacted by adding smuggling and accepting smuggler’s bribes to the list of Spanish Inquisition sins.  By 1700, English frustration contributed to the War of the Spanish Succession, which ended in 1713 with a treaty giving the English an exclusive contract for slave trade to the Spanish colonies.

The treaty also permitted just one 500-ton British ship to attend the annual Portobelo fair.  The enterprising Brits sent a convoy escort with the fully loaded navio de permiso (authorized ship).   Just outside the harbor, the smaller ships transferred even more goods onto the mother ship, which in turn unloaded all unessential cargo, including most of its sails, crew and its heavy anchor.  A skeleton crew sailed the mother ship under one sail to the Portobelo pier.  But English patience with this token bit of commerce soon wore thin and ended in outright attack.

Edward Vernon

In November 1739, British Admiral Edward Vernon attacked Portobelo with six ships, taking Fort San Felipe.  Vernon then loaded the best of Portobelo’s cannons onto his ships and proceeded to destroy the rest of the fort.  The walls of the fort were so thick (nine feet) that it took 16 to 18 days of blasting to destroy the fort.

Britain reacted to the success that it proclaimed Vernon’s birthday a holiday.  One of Vernon’s aides was Lawrence Washington, from Virginia in the English colonies and brother of George Washington, the future first president of the United States.  The Washington family honored their son’s participation in the destruction of Portobelo by naming their Virginia estate Mount Vernon.

Spurred on by success, Vernon returned to attack the San Lorenzo castle again in March 1740, using the very same cannons he had taken from Portobelo.  For two days and nights he bombarded the fort, but the Spanish refused to surrender.  In the end, Vernon completely decimated the fortress and all defending it.

These two victories broke the Spanish trade monopoly.  Thereafter the merchant mariners of England could acquire licenses to trade in Spanish American ports.  The fair at Portobelo was discontinued, but San Lorenzo was rebuilt stronger than ever to become the new clearing point for ship traffic.  The Chagres River - Las Cruces Trail became the preferred route across the isthmus, and the harbor at San Lorenzo became the Atlantic terminus for trade goods.

Gregor MacGregor

A full 300 years after Spaniards laid claim to Panama, the British were still trying to grab some of its riches.  In 1819, the British filibuster Gregor MacGregor led 500 mercenaries on a successful attack of Portobelo.  London investors backed MacGregor’s expedition, and his plan was to also take Panama City and sell control over the trans-isthmian route to the British government.  But MacGregor was defenseless against Panama’s deadly but invisible ally – mosquito-born fevers that laid the group flat on their backs before they could march out of Portobelo.  While the mercenaries were recovering, Spanish troops arrived from Panama City and literally chased them back onto their ships. (Minter, 189)  Just two years later, Panama gained its independence and Spain lost control over the isthmus.

Fort San Lorenzo

However, Fort San Lorenzo lingered as a Spanish stronghold and may have been occupied by the Spanish until 1840. (Minter, 193)  The San Lorenzo ruins that visitors see today are the remains of the fortress that was rebuilt after Vernon’s attack in 1740. 


A 300-year precedent

As early as 1532, the Spanish began thinking of digging an all-water route across the Americas.  King Charles (Carlos V) ordered the first survey of the best route across Panama isthmus.  A royal cedula signed on March 12, 1532, ordered the governor to clear the Chagres River to its last navigable point and open a road from there to Panama City.  Another cedula signed on February 20, 1534, commanded the governor to send surveyors to study the land between the Chagres River and the Pacific for the possibility of making an all-water route.

The resulting report called such an undertaking impossible and recommended improving the existing Chagres route instead.  Perhaps more importantly, King Charles recognized the value of maintaining the Spanish monopoly on South American trade and access to the Pacific by not opening a canal.  Subsequent monarchs followed the same line of thinking, and no further surveys for building a water route were made until the early part of the nineteenth century.

But the king’s will did not keep others from speculating.  In his memoirs in 1555, Antonio Galvao, a Portuguese governor in the Moluccas (South Pacific islands) writes of meeting Alvaro de Saavedra, a cousin of Hernan Cortez (the conqueror of Mexico).  Saavedra was in the Moluccas searching for cloves and spoke of four possible routes for a canal connecting the Atlantic and Pacific oceans.

Two of his proposed routes crossed Panama, one in the Darien between the gulfs of San Miguel and Urabá and the other on a route between Nombre de Dios and Panama City.  The other two possibilities were across Lake Nicaragua in Nicaragua and across the isthmus of Teohuantapec in Mexico.  (Howarth, 57)  Less than 50 years after the European discovery of the Pacific Ocean, the Spanish had mapped the New World accurately enough to identify four best choices for building a canal across it.  Later surveys would confirm the viability of these four routes.

Alexander Humbolt explored Central America in the early nineteenth century and enthusiastically spoke of the potential for building a canal across Mexico, Nicaragua or Panama.  Inspired, the Spanish monarch passed a decree in 1814 authorizing the construction of a canal across Panama.

Despite this optimism, no action was taken except for a growing resistance to Spain’s dominance.  By 1819, Latin America was rebelling against Spain; by 1823, all of the Spanish colonies had established their independence.  On November 28, 1821, Panama became part of New Granada, which encompassed modern-day Colombia and Ecuador as well.

Several canal route surveys were conducted between 1824 and 1840, but nothing came of them.  In 1838, New Granada granted a concession to a French company to construct a railway or canal with the Pacific terminus at Panama City.  But the wary French forfeited the concession when detailed surveys revealed the magnitude of the job.  In 1848, New Granada signed a treaty for the United States to provide transport across the isthmus under the condition of neutrality for all wishing to use it.  Instead of a water route, the project took the form of railroad tracks that roughly followed the route of historical trails across the isthmus and robbed the Chagres River – Las Cruces Trail route of its importance.




The Privateers, 1625 – 1698. 21

Under the British flag. 22

Division of goods. 22

Privateer’s code. 23

Santa Catalina Island. 23

Panama responds. 23

Sir Henry Morgan attacks, 1666 – 1671. 24

Panama – the prize. 24

Fortifications, 1666. 25

Morgan appointed admiral 25

Morgan’s plan. 25

Under cover of night 26

Attack on Portobelo. 26

Santiago Castle. 27

Torture. 27

San Felipe castle. 28

Panama learns of the attack. 28

Ransom.. 29

Disease strikes. 29

Counter-intelligence. 30

Negotiations. 30

The payoff 31

Panama recovers. 31

Fortifications at Portobelo and San Lorenzo, 1699. 32

The final attack. 32

Fort San Lorenzo. 33

Turn of events. 33

San Lorenzo falls. 34

Morgan arrives. 36

Panama prepares for the attack. 37

Up the Chagres to the Las Cruces Trail 37

Starving the enemy. 38

Las Cruces Trail 39

Panama’s secret defense. 39

Control of the city. 40

Return to San Lorenzo. 40

Morgan’s fate. 41

England pressures Spain. 41

Edward Vernon. 42

Gregor MacGregor 42

Fort San Lorenzo. 43

The search for a water route. 44

King Charles of Spain.. 44

A 300-year precedent 44

Dreamers. 44

Humbolt explorations. 45

End of Spanish rule. 45

Further explorations. 45