Is it possible to capture the entire Caribbean with a pirate force? It didn’t happen in history. But one man came close. His name was Henry Morgan, and he was captain of the ship Satisfaction. That’s right. The guy on the rum bottle, he was real.
It’s a matter of debate if Morgan was really a pirate. He held an English privateering license, and is considered a national hero by the British. But if anyone had looked closely at what Morgan was up to, they would have seen that what he had permission to do and what he was up to were two entirely different things. Having permission to spy on Cuba does not mean that you can sack Panama City.
In 1688, Jamaica was under threat of attack by the Spanish. The governor of the island needed ships and men, so he issued a proclamation making Captain Morgan Admiral of the Fleet. Morgan was happy to have the honor, but it didn’t come with either ships or men; Jamaica had no navy at all.
What it did have was privateers, like himself, and outright pirates, who were welcome at the time. Knowing how vastly undermanned and underfunded the Royal Navy was at the time, authorities in Jamaica had opened up the island to pirates. They figured, rightly, that a large number of English-built ships carrying guns would keep the Spanish at bay, no matter who actually owned or operated the ships.
As a result, Port Royal had become the “wickedest city on earth.” That’s right. Not Tortuga, and not even Nassau. Port Royal had been an “open city” for years. One in every three buildings housed a tavern, and women came from as far as London to work the city’s streets. After all, this was a place where men paid with gold what sold for copper in lawful towns.
When Morgan was made admiral, he needed to raise his own fleet from the men and ships of the most lawless place on earth. He responded by putting on his best red coat (just like the one in the pictures) and hitting every tavern in town in a single night. He climbed onto tables and made speeches about patriotism—and gold. By the time the sun rose, he had inspired 1,500 men to join him and bring their ships.
By the standards of the time, this was an extremely impressive force. But instead of defending the island by sailing or exercising guns in the nearby waters, Mogan used his force to attack two Spanish cities, one after the other, until his men had acquired enough treasure to satisfy them.
Morgan’s attack in the city of Porto Bello is a famous example of good tactics. The city was a gathering point for treasure before it was shipped to Spain. It was an important enough venue to merit two castles defending it from the sea.
Morgan landed three miles away, marched his pirates inland, and attacked from the rear. His men, though untrained and not well supplied, defeated the Spanish soldiers. It’s a tribute to Morgan’s planning and the motivation of men who want to get rich.
This is the strength of pirates.
Historically, the pirates of Nassau did not carve out their own kingdom; when they had the first major meeting of captains, everyone showed up drunk. Pirates were defeated by the easy living and rum that their success gave them.
Morgan made other raids, varying his tactics, using fire ships in sea battles, and going around Spanish negotiators to extort money from the terrified citizens. When actual war between England and Spain broke out (largely because of Morgan’s efforts) Morgan was given an actual fleet, but he still relied primarily on his privateers.
Black Sails has been the best pirate show ever on TV, but it’s the exploits of men like Henry Morgan that show what pirates could actually accomplish.
It’s true that the rank-and-file peasants of the 18th century weren’t very bright. But the people who became pirates were not the norm. They were more motivated, perhaps more imaginative than most. And having been pirates—or privateers with an eye on making money the quickest way possible—they had been given a taste of the good life.
Morgan was eventually recalled to England to face the fact that he had been far exceeding his orders, to the point of piracy. But by the time he had successfully made the journey, the military situation had changed once again. Morgan’s military genius was needed more than the spectacle of his hanging.
Instead of facing a trial, Morgan was knighted by King Charles II (English kings were often fond of pirates). He was also made Lieutenant Governor of Jamaica, a far more important post because there was no actual governor at the time. When he returned to Jamaica, where he took part in politics, he continued to fight the Spanish and to support the pirates and privateers of the island.
It was his friendship with these men that eventually led to his death. Drinking in dockside taverns night after night, Morgan told the tales of his adventures to appreciative ears—and also drank himself to death. The man on the rum bottle died of liver failure.
So, in real life, one of the islands of the Caribbean was in fact ruled by a pirate, though under control of the English government. Maybe we’ll see a little of that on Black Sails before its finale, too.