In the early summer of 1668, a Welshman of indeterminate origin and an apparently boundless contempt for diplomatic niceties anchored a small fleet at the mouth of the Chagres River. Henry Morgan had with him roughly four hundred and sixty men, twelve canoes purchased or stolen along the Mosquito Coast, and no document from any sovereign authorising what he was about to do. Portobelo, his target, was at that time the third most fortified town in the Indies. It had three castles. It also had, as Morgan had been carefully informed, the treasure of the year sitting in its warehouses awaiting the next galleon to Cadiz.

The conventional narrative — repeated in Esquemeling's Bucaniers of America and then in every drawing-room history since — has Morgan rowing his men ashore three leagues from the town and marching them overland through the night. This much appears to be true. What is rather less often discussed is how completely the operation depended on a single piece of intelligence: that the garrison of San Felipe, the smallest of the three forts, was understrength and demoralised after months without pay.

What Portobelo was

It helps, at this point, to say something about the town itself. Portobelo on the Caribbean coast of Panama was not a city in any meaningful sense. For roughly forty days of the year — the duration of the feria, the annual fair — it became, briefly, one of the richest places in the Americas, as the silver of Peru and the merchandise of Spain met across its waterfront. For the remaining three hundred and twenty-five days it was an unhealthy backwater with perhaps four hundred Spanish inhabitants, a fluctuating population of enslaved Africans and free people of colour, and the unfortunate reputation, well-deserved, of being among the most malarial places on the globe.

Morgan arrived shortly after the previous year's fair had ended. The treasure had not yet been moved inland. This was not luck; this was the work of months of intelligence-gathering by buccaneers who had been quietly watching the town from sloops disguised as turtlers.

The assault

The assault began before dawn on the second of July. Morgan's men, having left the canoes hidden in a creek, came down on the town from the landward side — the direction from which, by the contemporary logic of fortification, no serious attack was possible. The Spanish governor, Don José Sánchez Jiménez, was at that moment asleep in the citadel of San Jerónimo, which faced the harbour. By the time he was woken, the lower town had fallen and the smaller fort of San Felipe — undermanned, as predicted — had been overrun.

It was at San Jerónimo that the assault stalled. Sánchez Jiménez was elderly, in poor health, and, by all accounts including the buccaneers', physically brave. He refused to surrender. His garrison, perhaps a hundred men in fighting condition, held out into a second day. And it is here that the sources begin to behave badly.

The Captaine of the Pirates, perceaving that the Castle could not be subdued without much loss of his men, took ten or twelve of the chief religious of either sex, and prepared scaling ladders. And he commanded them to set the said ladders against the walls... — ESQUEMELING, BUCANIERS OF AMERICA, 1684

The "religious of either sex" — priests and nuns dragged from the town's churches and forced, according to Esquemeling, to climb the scaling ladders ahead of the buccaneers in the hope that the defenders would not fire on them. This is the single most damaging episode in Morgan's career as reported by his own physician-turned-chronicler, and it is the moment that has historically separated those who consider him a brigand from those who consider him a privateer.

Morgan, for what it is worth, denied it. When the English translation of Esquemeling appeared in London in 1684, by which time Morgan was a knight, a sometime Lieutenant Governor of Jamaica, and a sugar planter of some standing, he sued the publishers William Crooke and Thomas Malthus for libel. He won. The English edition was withdrawn and reissued with that section materially softened. Whether this constituted vindication or merely successful litigation is a question on which historians have differed for three and a half centuries; I incline, mildly, toward the second view.

What was taken

The buccaneers held Portobelo for thirty-one days. The ransom eventually paid by the Spanish authorities at Panama — to prevent the town being burnt to the ground — came to one hundred thousand pieces of eight. The plunder taken from the houses and warehouses came to perhaps two hundred and fifty thousand pieces of eight more. Divided among the surviving buccaneers (Morgan had lost roughly eighteen men in the assault, an astonishingly low figure), the per-share payout was on the order of seven hundred pieces of eight, or about a hundred and eighty pounds sterling: rather more than a master shipwright in London would earn in three or four years of steady work.

Morgan kept his captain's portion and various uncounted side-deals; his actual personal take from the raid is impossible to determine with any precision, but later inventories of his Jamaican estate suggest it was in the low thousands of pounds.

The political aftermath

This is the part that almost never appears in popular accounts, and it is the part I find most interesting.

The Treaty of Madrid between England and Spain, which would formally end English raiding on the Spanish Main, was not signed until 1670 — eighteen months after Portobelo. In 1668, when Morgan raided, England and Spain were technically at peace, but the peace was new, vague, and (in the Caribbean, where news arrived months late) not really in force at all. Morgan claimed afterwards that he had been acting under a commission from Sir Thomas Modyford, the Governor of Jamaica, to gather intelligence on a rumoured Spanish attack. He produced the commission in court. It does not survive in the archives, and there is good reason to suspect that the document Morgan flourished in 1668 was not the document Modyford had actually signed.

What is undeniable is that Modyford, when news of the raid reached him, did not arrest Morgan. He wrote to London expressing measured regret, banked his ten-per-cent share of the proceeds as Vice-Admiral of Jamaica, and quietly issued Morgan a new commission for the following year. The Crown, for its part, summoned Morgan to London in 1672 to be examined — at which point Charles II knighted him and sent him back to Jamaica as Lieutenant Governor.

The lesson of Portobelo is therefore not, as it is often presented, a story about piratical daring. It is a story about how seventeenth-century imperial states actually conducted policy in places far from the metropolis: by deniable proxies, by selectively forgotten paperwork, and by the calculated promotion of useful villains. Morgan was less a renegade than a contractor who had grasped, more clearly than most, where the line was, and how often the line moved.

A note on the sources

Anyone wanting to read further should begin with the National Archives at Kew, where the Modyford correspondence in the Colonial Office series (CO 1/22 and CO 1/23) gives the Jamaican government's contemporary account. Esquemeling, for all his unreliability, is indispensable; the 1684 English edition is the one Morgan sued over, but the 1678 Dutch original (De Americaensche Zee-Roovers) is significantly closer to what its author actually wrote. The most recent serious scholarly treatment is Stephen Talty's Empire of Blue Water, which is more popular than academic but takes the sources seriously and is conscientious about flagging where it is speculating. Peter Earle's older study of Henry Morgan remains, in my view, the best single book on the man himself.