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Buccaneering Eras > Sack of Portobello (1668)

Sack of Portobello (1668)


The Sack of Portobello in 1668 was a famous buccaneer raid on the Spanish city of Portobello located in the Viceroyalty of Peru led by the English buccaneer named Henry Morgan. The buccaneers had previously sacked Puerto Principe and were looking for new targets. On 10 July 1668 attack and sacked the city of Portobello and held the city ransom for weeks until the Governor of Panama agreed to pay the buccaneers a heavy ransom.

PortobeloPortobelo was a sleepy little town on the so-called "Spanish Main," which referred to the northeastern part of South America and Panama.Usually there were very few people there, as the primary purpose of the town was to serve as a shipping point for Spanish gold from Peru. Every year or two, gold, silver and other treasures would be sent down from Peru to the west coast of South America, where it was sent to Panama City. Then it was carried by mules overland to Portobelo, where it was loaded onto a massive, heavily armed treasure fleet to be shipped back to Spain.During these times, Portobelo was bustling, but otherwise it was a dull place with only a couple hundred regular inhabitants.The Defenses of PortobeloIn spite of the fact that it was a dull backwater most of the time, Portobelo had decent defenses on account of the occasional presence of great treasure. There were three castles to contend with. At the entrance to the Bay stood the castle of San Felipe, with 12 cannons and a garrison of 100 men. On one side of Portobelo Harbor was Santiago Castle, with 200 men and 32 guns covering the harbor and the road into the city. On the other side of the harbor was the unfinished fortress of San Gerónimo. These fortifications would be manned even though the treasure fleet was not expected for another year or so.Portobelo UnawaresSuch were the defenses on paper, anyway. Because of the castles, the people of Portobelo had known years of peace and were not ready for an attack in July of 1668. The castles were seriously undermanned: there were 50 men out of 100 in San Felipe, 75 men out of 200 in Santiago, and only eight in the unfinished castle of San Gerónimo. There were a handful of soldiers in town as well on the night of July 10. Although the soldiers had good small arms including pistols and muskets, the cannons in the castles were in bad repair and there was a shortage of grenades. There were also insufficient gunners to man the cannons if needed.Morgan Moves Into PositionMorgan knew the city was unsuspecting, but did not know the castles were so undermanned. He decided on a land assault. He took his fleet down the coast and unloaded his men - some 500 in all - using long canoes he had brought along for that purpose. The men paddled the canoes for four days, sneaking past the fortress of San Lorenzo at night. One ship remained with them, a little further out to sea. This escort ship was eventually spotted by the Spanish, but caused no alarm: what damage could one ship do? The buccaneers made a fortuitous capture as well: a local fisherman who was pressured into guiding them. On the night of July 10, they were at Orange Island, ready to begin the assault.Morgan Attacks!Late at night, Morgan ordered an attack. The canoes moved swiftly and landed at a lookout post some three miles from Portobelo. A Spanish canoe that had been sent to observe the strange ship saw them and raced back to the city to sound the alarm. Morgan's men had to move quickly. They had captured a guard at the lookout post and they bound his hands, making him lead the way into town.When they reached the approach to the city as dawn broke, they paused: there stood Santiago Castle guarding the entrance. But their guide assured them that the castle was in disarray and the pirates rushed across the open ground to the town. The cannon gunners in Santiago only got off one shot, which sailed harmlessly over the attackers' heads.Morgan's men rushed into town as dawn broke on July 11, 1668, firing at anything that moved. As the defenders frantically struggled to get organized, Morgan ordered sharpshooters to the top of a nearby hill which was actually higher than Santiago Castle. From their vantage point, the skilled buccaneers picked off any defender foolish enough to raise his head, effectively neutralizing the threat posed by the castle.Fall of San Gerónimo CastleThere were some defenders in unfinished San Gerónimo castle, located in the harbor and surrounded by water. They fought for a while, but there were too few of them. Once some freed English prisoners (who had been forced to work on the construction of the castle) showed the buccaneers that the water between the town and fort was only knee-deep, a force of invaders rushed the castle, where the garrison of approximately eight men begged for quarter.The prisoners were bound and put in the church.Fall of Santiago CastleOnce the city and San Gerónimo had been secured and all of the prisoners under guard in the church, Morgan turned his attention to Santiago castle. He sent more sharpshooters to the hill and put riflemen in the houses nearest the church.The castle defenders were in a bind: their cannons were in poor shape and they were reluctant to fire into the city anyway.When a frontal assault was driven back, Morgan got creative. He took some important prisoners including the mayor, some friars and nuns and some old men and women and marched them towards the castle, his own men behind them. One cannon fired, injuring two Spanish friars and killing one pirate, but no more. When they reached the gates, the pirates began hacking at them with axes.Meanwhile, a second force of buccaneers had found some ladders and scaled the wall on the other side of the castle. There was some desperate fighting, but by 10:00 am the castle had fallen. More than half of the defenders had been killed and most of the others were wounded. The officer in charge of the cannons was ashamed of his own incompetence and begged the pirates to kill him: one happily obliged with a pistol-shot.Fall of San Felipe CastleMorgan controlled the town and the fort of Santiago, but he still could not get his fleet into the harbor while there were enemies in San Felipe castle on the other side of the bay. There were some 50 well-armed defenders there, but they had no food. It turns out that food was sent over daily from the town, and the castle had no stores. Still, young Castellan Alexandro Manuel Pau y Rocaberti decided to fight.The buccaneers took their canoes across the bay and got into position for an assault. When some of them made it to the base of the wall and began trying to burn down the gates, young Castellan Pau panicked and invited invading captains into the castle for a parley to determine terms of surrender, much to the shock and chagrin of the other Spanish in the castle who wanted to fight. Still, once the pirates were inside there was no going back.Under the terms of surrender, the soldiers were allowed to take the road to Panama and keep their swords. Castellan Pau was himself made prisoner, and drank poison that night, ashamed of his cowardice. Had San Felipe held out, the results of Morgan's attack might have been very different.The Sack of PortobeloMorgan ran up the English flag on the three forts, giving his ships the sign they had been waiting for. As the fleet arrived, the jubilant invaders set about sacking the town, looking for loot and alcohol. All of the loot was brought together: under the strict code of the privateers, any man who withheld treasure was severely punished. Prisoners were tortured to get them to reveal the whereabouts of any hidden treasure.Captain Morgan ordered the forts manned. With the pirates in charge, Portobelo did indeed become a formidable target: Morgan had twice as many able soldiers as had been there when he arrived.The Ransom of PortobeloMeanwhile, the Governor of Panama, Don Agustín de Bracamonte, had heard of the attack on Portobello and swiftly organized a relief column to march to the aid of the city, some 70 miles away.He had 800 men and they marched quickly, hoping to catch the pirates before they could secure their victory. When they met up with the soldiers from San Felipe who had been allowed to leave, their spirits sank. It would be next to impossible to take the city back with only 800 men if Morgan was expecting them. They tried to assault the city a couple times but were quickly driven back by Morgan's sharpshooters.Morgan sent a letter to Bracamonte demanding 350,000 pesos as a ransom for Portobelo. If Bracamonte did not pay, Morgan claimed, he would burn the town to the ground and take the prisoners away, where they would get the same treatment as the English prisoners that Morgan had liberated (which was forced labor).Bracamonte replied that he would never deal with a corsair, and Morgan dared him to re-take the city.When the Spanish heard a rumor (incorrect, as it turns out) that the whole Portobelo attack was simply a diversion for Morgan's French allies to attack an unguarded Panama, they hurried back. Bracamonte left behind a representative to negotiate: eventually Morgan agreed to 100,000 pesos for the city.The ransom was brought by mules in the first week of August: 27 bars of silver worth 43,000 pesos, silver plate worth 13,000 pesos, and 44,000 pesos worth of gold and silver coins: 100,000 pesos in total. Morgan kept his promise: he loaded the treasure (plus what had been found in the city), freed the prisoners and set sail, leaving the city and forts intact (or at least not damaging them any further). One of the greatest raids of the Age of Piracy was in the books.


The raid on Portobello would have significant consequences throughout the New World and Europe. The Spanish were furious at the British and despite their peace agreement at the time the Queen of Spain allowed the issuance of letters of marque to Spanish privateers to begin attacking settlements on British Jamaica. These Spanish captains managed to attack a few small settlements on Jamaica which prompted the subsequent sack of Maracaibo and Gibraltar along with the sack of Panama in 1670.

Morgan himself would settle down and invest his money on the island of Jamaica.

However, he soon would come out retirement toWhen news spread of the attack, Spain at first sent reinforcements, but Morgan was long gone before anyone got there. The privateers once again disbanded, with individuals finding work elsewhere: the Spanish could not have their revenge.In Jamaica, Morgan was hailed as a hero. The raid was hugely successful: each privateer made more than he could have doing honest work in a year, and the taverns and brothels of Port Royal did booming business for a while. With each telling, the Spaniards grew tougher, the castles stronger and the loot more valuable, and the legend of the attack grew quickly.Morgan settled down and invested his money in land in Jamaica, but he soon came out of retirement, first to attack Maracaibo in 1669 and then Panama itself in 1671. On each occasion, when it was learned that Captain Morgan himself was leading the raid, hundreds of privateers, pirates and other rogues flocked to his banner. For his assault on Panama he had over 2,000 men, an unheard of number at the time. Although these other raids were successful, Portobello would always remain Morgan's biggest score in terms of loot.Spanish power in the New World was weakening, and Portobelo made them admit it. They could no longer be in denial that the English (and the Portuguese, French and Dutch) had established bases in the Caribbean and that they would continue to steal from the Spanish as long as they could get away with it, European treaties notwithstanding.

Buccaneer Raids


Primary Sources

Secondary Sources

Cordingly, David. Under the Black Flag New York: Random House Trade Paperbacks, 1996

Earle, Peter.The Sack of Panama New York: St. Martin's Press, 1981.

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