Chapter 13 – Raid on Portobello

Attack on the Castillo de San Jeronimo, Porto Bello
John Esquemelin, 1684. The Buccaneers of America, etc.

Admiral Morgan remained at the Point only long enough to do any necessary refitting and resupply basics only available at Port Royal. While there, Captain Jackman joined him, bringing his fleet to nine vessels and 500 men. In May 1668, Morgan ordered his privateers to set sail once again for the South Cays. There they could replenish food supplies at a far lower price than would be possible at the Point. However, knowing how vitally important it was to maintain the element of surprise on such ventures, the admiral did not divulge their final destination—not to his captains, not even to his mentor Governor Modyford—for Spain had spies everywhere.

In fact, Admiral Morgan’s next target was the heavily fortified city of Portobello^[1] on the Isthmus of Panama. Why he chose this city is anybody’s guess, for its fortifications were so massive and well-built, some thought them impregnable.

^[1]Various spellings include Puerto Bello, Portobelo and Puerto Velo.

Portobello lies some 20 miles northeast of Colón in present-day Panamá. It is one of the oldest Spanish settlements on the Caribbean coast and was at the heart of the Spanish Main. Portobello did not have a large permanent population, as its main purpose was to serve as a port from which precious metals and gems from the Americas could be shipped to Spain. 

From ore mined in Cerro Rico (rich mountain), Spain minted bars of silver and pieces of eight and other coins at the city of Potosí in present-day Bolivia (then known as “Upper Peru”) which came under the Viceroy of Lima’s authority. Potosí was the largest city in the New World and the location of Spain’s colonial mint. From Potosí, in the south-west of Bolivia, the Spaniards used heavily guarded llama and mule trains to transport the freshly minted silver and coin to the Pacific coast, from which they shipped their precious cargo north to Panama City. Back on land, they again used mule trains to haul it across the Isthmus of Panama to Portobello on the Caribbean side. At Portobello, it was loaded onto ships of the flota, Spanish treasure fleet, and shipped to Spain. Also passing through the town were gold from various sources, large quantities of emeralds from Colombia, and pearls from the Archipiélago de las Perlas in the Gulf of Panamá.

The town of Portobello was famous for its annual fairs, which lasted for forty days. During these, goods of all sorts from Spain were exchanged for colonial South American products by merchants in booths and tents they erected in the square facing the Customs House. With the flota came merchant ships escorted by Spanish men-of-war and hordes of soldiers, sailors, merchants, clerks, porters, buyers of all nationalities, and the usual onlookers and hangers-on, filling the port to overflowing.

In the 75 or so years before Morgan decided to attempt Portobello and before its defences had been strengthened, two attempts had been made on the town by English privateers. In 1596, Sir Francis Drake had died during his attempt—though he died of dysentery, not of battle wounds. Five years later, the English privateer William Parker succeeded in capturing the city and held it for about 24 hours before withdrawing with 10,000 ducats from the treasury and the considerable “spoil of the town, in money, plate, and merchandise.” That was then. 

Morgan concurred with the conventional wisdom of the Point: Portobello was one of the best-fortified ports in Spanish America, with only Havana and Cartagena more strongly defended. Three hundred artillerymen and infantry normally garrisoned the port. And, should reinforcements be needed, an additional 900 militiamen could be quickly assembled. Besides, every ship entering Portobello’s harbour had to run under the guns of three formidable fortresses: 

• San Felipe de Todo Fierro (known as the Iron Fort), at the entrance to the bay and on a ship’s port side when entering the harbour; 
• Santiago de la Gloria on the opposite side of the harbour and closer to the town; and
• San Gerónimo, which was further in towards land and partially under construction.

However, as we know, Harry Morgan had faced similar challenges before and had always devised the means to overcome defences and surprise his enemies. In this instance, most chroniclers believe he had obtained inside knowledge regarding some weakness he could exploit.

Present-day ruins of Santiago de la Gloria

The small fleet lingered in the cays in Cuban waters for about a month so the privateers could further refit and provision their ships with dried and salted meat and a fresh supply of wood and water. Then it sailed south-west toward Cabo Gracias a Dios on the Mosquito Coast of Central America. And, after dealing with unobliging winds, the fleet arrived off the coast of Panamá near the end of June 1668 and anchored at Bocas del Toro, which is in Panamá near the border of present-day Costa Rica.

Here, Morgan identified their target as Portobello. This did not sit well with many, especially among the French contingent. After rejecting Morgan’s proposal, they split off and probably headed for Tortuga. This left Morgan in command of nearly 500 men and somewhere between nine and twelve vessels of various sizes, which was still a formidable force and a testament to Morgan’s reputation and leadership skills. He had successfully convinced hundreds of independent-minded skeptical men to follow him in what most would have believed was a venture of the highest risk.

Morgan had already decided against a frontal attack on the port. Instead, he chose to approach the town in piraguas. Many buccaneers were experts in using these canoes, for they often used them in coastal waters. Each boat could carry about 20 well-armed men. Some carried two or three of their deadly long-barreled muskets. Many also armed themselves with a brace of pistols, shot, the power that they were careful to keep dry, a razor-sharp cutlass, and a knife. Most also carried one or more grenades.

After assigning skeleton crews to the larger vessels he had hidden at Bocas del Toro, Morgan transferred his men into 23 canoes and set out using paddle and sail on the 150-mile journey to Portobello. One Indian and an Englishman, who had apparently been a prisoner in Portobello, acted as guides. Along the way, Morgan obtained updates from local Indians, giving him the status of the town’s defences. These reports provided encouragement, for he learned that not only were Portobello’s three castles undermanned, but they were poorly maintained and otherwise not in sound fighting condition.  

Morgan’s canoes made their way eastward along the coast, carefully avoiding detection from the many armed settlements on the mainland. Many lurid tales are told about Morgan’s methods of extracting intelligence from local sources. However, it’s unlikely the Indians of Panamá needed much encouragement to betray the Spaniards, for they had suffered greatly under Spain’s rule and were never too far from open rebellion against their overlords.

Over 400 of Morgan’s privateers landed three miles from the city and marched overland to attack Portobello on 10 Jul 1668. As one eyewitness reported, they fired “off their guns at everything alive, whites, blacks, even dogs, in order to spread terror.” [Source: Archivo General de Indias, Panama 81, Evidence of Alonso Sánchez Randoli, and Marley, Pirates and Privateers of the Americas, p. 264.] The invaders lost little time in taking the town, which had no walls to protect it. There was some initial resistance from the partially built San Gerónimo fortress, but it too soon fell to the privateers.

Illustration by Geo. Alfred Williams

As to the two great forts that protected the harbour, the first to fall to the privateers’ onslaught was the Santiago de la Gloria. There had been no time to spare as the news of the attack would soon reach Panamá, and a relief column would certainly be dispatched. So Morgan had ordered a selection of Portobello’s prominent citizens to be rounded up. They reportedly included the alcalde mayor, two friars, several women and nuns and several old men. The privateers then forced those unfortunate souls to march at gunpoint to Santiago de la Gloria's main gate. The privateers carrying axes and flaming torches followed, using the hostages as shields. Then, when close, they rushed forward and assaulted the gate. 

The defenders fired at least one cannon loaded with chain shot, wounding two friars and killing a privateer. Morgan’s invaders went to work on the main gate with their axes and torches. Despite its “30 pieces of artillery,” after only “three or four hours of hard fighting,” Morgan’s men were masters of the garrison. Several of the Spanish defenders refused to surrender and “were either killed, wounded, or cut to pieces.” Next to submit was the fortress across the harbour, San Felipe de Todo Fierro, the Iron Fort, which was armed with 12 pieces of artillery. It surrendered on the following day “after fighting three or four hours.” ^[2]

^[2]Calendar of State Papers, America and West Indies, No. 1899, i, Statement of John Doglar annexed to the memorial of the Spanish ambassador, 7-17th January, 1669. This was probably John Douglas, Morgan’s Commissary-General. Several other sources also, including Esquemeling and Morgan’s personal report to Modyford.

English flags were raised over the forts, and Morgan’s fleet of twelve ships, after sailing from Bocas del Toro and waiting outside the harbour, now sailed in. With his full force of privateers entrenched in the town and in its fortresses, and with his fleet’s added guns, Admiral Harry Morgan was truly master of Portobello.

It did not take long for a Spanish horseman to cross the isthmus and report what was happening to Don Agustin de Bracamonte, who had been appointed interim president of Panamá. But despite the president’s initial haste to send a relief army from the capital, help arrived too late, and he was forced to enter negotiations with Admiral Morgan. The admiral demanded 350,000 pieces of eight to leave Portobello in peace. He added the threat that, should the ransom not be paid, he would garrison the Spanish forts and hold the town indefinitely, or depart and set it aflame.

Prolonged negotiations ensued, during which several members of both armies fell ill with fever. Evidently, Morgan reasoned that manpower shortages would soon force him to withdraw and concluded that 100,000 pieces of eight were better than none. So the admiral accepted the offer presented on behalf of President Bracamonte. According to a Spanish source^[3] noted in Peter Earle’s, The Sack of Panamá, (1981), the ransom comprised 27 bars of silver valued at 43,000 pesos,^[4] 13,000 pesos worth of silver plate, 4,000 pesos in gold coins and 40,000 pesos in silver coins.

^[3]Archivo General de Indias, Panamá 81, 1669( III), fo. 46: Inventory of treasure.

^[4]A peso or Spanish dollar was equal to 8 reales and was also known as “pieces of eight.” It is the model on which the US & Canadian dollar is based, thus we get “two bits” meaning 25 cents.

Morgan had taken Portobello at the cost of eighteen killed and thirty-two wounded. In the month they spent there, the privateers and buccaneers are said to have raped, pillaged and tortured. However, John Esquemeling’s The Buccaneers of America was the primary English source of these reports, in which were several known exaggerations. For example, the fort he reported as being blown up while filled with Spanish prisoners was still in place and in good repair ten years later when another English force visited Portobello. Harry Morgan disputed other parts of Esquemeling’s account when it appeared in print and successfully sued Esquemeling’s English publishers, who issued retractions as part of their settlements. 

Morgan excused his privateers’ behaviour by describing the deplorable conditions in which he had found eleven Englishmen who had been captured in the Spanish reconquest of Old Providence Island two years earlier. These unfortunates were found chained in a dungeon of unspeakable filth. Nearly starved to death and covered with soars, they were the remnants of the English colony that had been established after Edward Mansfield had captured the island. Among the colonists—though not among the rescued prisoners—had been the very popular Sir Thomas Whetstone and former shipmates of the privateers. The Spanish had imprisoned them in contravention of their terms of surrender. This treachery so incensed the buccaneers it undoubtedly led, at least in part, to excesses. Besides, the presence of José Sánchez Jiménez as commander of Portobello’s defences had further enflamed passions. He had led the recapture of Old Providence and so treacherously ignored the colonists’ surrender terms.

Official booty from Portobello included cannon, silks, silver plate, and gold and silver coin with an estimated worth of 250,000 pieces of eight [Edward Long, History of Jamaica, 1774]. As Admiral, Harry Morgan got five men’s shares of the Portobello official and unofficial booty, according to Peter Earle’s The Sack of Panamá. He may also have received more as an investor and/or owner of one or more of the venture’s ships.

Continued …