The Real Pirates of the Caribbean

Pirates illustration by Howard PyleOn a sweltering afternoon in June of 1719, the Princess, a 140-ton ship out of London, was sitting at anchor off  Anomabu, a steamy West African slave port, waiting to take on a load of slaves for the plantations in the West Indies, when a strange vessel materialized out of the heat haze along the horizon. It came on fast, and full of purpose, its decks bristling with heavily armed men, and hoisting a black flag as it approached.

They were pirates, a rough crew under the command of the notorious Howell Davis. The sailors aboard the Princess knew better than to resist; it would only enrage the attackers and turn what might otherwise be simple armed robbery into a murderous bloodbath. The Princess struck its colors and prepared to be boarded. The pirates ransacked their prize—looking not just for gold but basic shipboard necessities: guns, powder, clothing, sails, carpentry tools, rope, compasses, whatever might come in handy since they weren’t welcome in many ports and couldn’t readily shop for their needs.

They wanted men as well, new recruits. While some of the riff -raff  aboard the Princess  were more than happy to sign on, and swap the low-paying drudgery of life before the mast for the gaudy lawlessness of a pirate, others were far less enthusiastic.

One who definitely didn’t care to turn pirate was the third mate, a tall, dour, abstemious 37-year-old Welshman who begged, pleaded, argued, and reasoned with Davis’s men to pick somebody else—to no avail. They had need of an experienced navigator, and like it or not, he was it. He was dragged aboard to begin a new life as a pirate.

Which turned to be not quite so bad as he’d imagined. In fact, the buccaneering life rather agreed with him. So much so that within six weeks he’d become the captain, Howell Davis having been killed in a raid. He was better than good at it, he was a natural, discovering in mid-life his true calling as a leader of men and a daring rogue in the Sir Francis Drake mold, to say nothing of getting in touch with his larcenous side.

By the time a piece of grapeshot from a Royal Navy cannon ended his meteoric second career, less than three years later, Captain Bartholomew Roberts—also known as Black Bart—had become the most successful pirate in history, capturing more than 400 prizes, from Portuguese treasure ships off  the coast of Brazil, to fishing smacks in the icy waters of Newfoundland, to Royal African Company slavers in the Gulf of Guinea. At his height he commanded a fleet of four ships and more than 500 men.

He did so with arrogance and style. His personal standard, which flew from his flagship, Royal Fortune, was a black silken flag with a skeleton standing triumphantly on skulls representing Barbados and Martinique, mocking the islands whose authorities had had the audacity to try to capture him. But he was no fool. He knew this could only end one way. Having made up his mind to go a-pirating, he no longer gave a damn: “In honest service there is thin commons, low wages and hard labour; in this plenty and satiety, pleasure and ease, liberty and power…No, a merry life and a short one shall be my motto.”

There’s the spirit. Everybody admires a cavalier rogue, particularly from a distance, and with the exception of Robin Hood and some Wild West gunmen, few characters in fact or fiction ever captured our imaginations quite like the pirates of old. Much of what is known about them comes from just two books—The Buccaneers of America, published in 1678 and written by Alexander Exquemelin, a French adventurer who sailed with Henry Morgan, and A General History of the Pirates published in 1724 and written by a certain Captain Charles Johnson, about whom almost nothing is known, other than he appears to have been uncannily well informed about his subjects, clearly spent many years at sea, and may possibly have been a pirate himself. Book books were immediate best-sellers and have provided a wealth of inspiration ever since, both for the modern screenwriters of Disney’s Pirates of the Caribbean and for Robert Louis Stevenson in his classic Treasure Island.

“It was a master surgeon, him that ampytated me—out of college and all, Latin by the bucket, and what not; but he was hanged like a dog and sun-dried like the rest at Corso Castle,” Long John Silver tells his listeners around the apple barrel about his old pirating days and how he lost his leg. “That was Roberts’ men, that was….”

The marvel of it, as you read the old accounts, both of which are still in print, is how life and art imitate each other where pirates are concerned. They really did fly the Jolly Roger, keep parrots as pets, drink rum, and sing lusty sea chanteys. They marooned people on desert islands, knocked the tops off their brandy bottles with blows of their cutlasses, and they blasphemed mightily. If you ventured below decks, into the galley, it wouldn’t be at all unusual to find a tough old one-legged veteran like Long John Silver slinging hash; pirates looked after their own, and if one of their number became incapacitated, he could always stay on as cook.

They even looked the part, dressing like the Jacobean dandies you see in those old color plates by Howard Pyle and N.C. Wyeth. Of course, they never had to pay for their brocaded finery. Instead they looted it from the officers and gentlemen passengers they found aboard their prey. Likewise their weapons—only the best would do. “In this they were extravagantly nice, endeavouring to outdo one another in the beauty and richness of their arms,” Captain Johnson writes. They would vie for the choicest pistols, which they then tricked-out with bright silken ribbons to hang over their shoulders, a foppishness “in which they took great delight.”

It wasn’t all Disney, of course. They meandered off script in places. For one thing, they didn’t make captives walk the plank. That baroque mode of dispatch was popularized by Peter Pan author J.M. Barrie for Captain Hook to employ on Wendy and the Lost Boys, mindful perhaps that real-life pirate amusements such as the strappado and the hideous torture of  “woolting,” where a cord is tightened around a victim’s forehead until his eyes “bulged out like eggs,” could be a little harrowing for his younger readers.

Nor, alas, did pirates bury treasure. If they had it, they spent it, in wild drunken sprees in places like Jamaica’s Port Royal, home port of Henry Morgan and said to be the wickedest place on Earth back in the roaring 1660s. “I have seen a man give 500 pieces of eight to a whore just to see her naked,” writes Alexander Exquemelin. “Three months later he was sold for his debts.”

Exquemelin tells of drunken pirates breaking open barrels of wine in the streets and forcing passersby, at pistol point, to join in the drinking; of another who bought a cask of butter and amused himself by hurling gobs of it at people on the street. They threw their money away until there was nothing left  but empty pockets and hangovers.Then off  they’d go again to sea, primed and loaded and looking for trouble.

Like school bullies with perfect attendance records, pirates tended to be healthier than their before-the-mast counterparts. Their diets were better since they all shared and shared alike in the officers’ provisions they found aboard their prizes. They worked less and were better rested, since pirate ships carried large crews for fighting and thus could spread the workload around. And since they were almost constantly swilling rum punch, of which limejuice was a key ingredient, they seldom suffered scurvy.

Roberts might have been the most successful pirate in history in terms of ships taken—his tally is roughly five times that of Blackbeard’s—but starting his career on the tail end of the Golden Age of Piracy, he missed out on the really rich pickings and social cachet his predecessors enjoyed. Had he been born 50 years earlier, he could have operated as Morgan did, as a privateer, and roved the Caribbean with the King’s commission to ravage and plunder His Majesty’s enemies abroad—chieflythe Spanish. Today we’d call that sort of thing state-sponsored terrorism, but back then it was an expedient way of having a naval strike force on the cheap: freelance adventurers financed with the booty they stole.

Morgan stole plenty—capturing not just Spanish galleons but entire Spanish towns, leading fleets of pirate ships all around the Caribbean, from Cuba to the Spanish Main. Nor did he stop there. In 1671, clearly feeling his oats, he led an army of 2,000 cutthroats across the Isthmus of Panama and sacked the fabled treasure port of Panamá, destroying the city in a month-long orgy of looting, torture, pillage, and fire. Through it all, thanks to his Letter of Marque sanctioning his activities as a privateer, Admiral Henry Morgan remained a respectable citizen of Jamaica, a man who invested his plunder wisely and, when he wasn’t at sea, led the life of a gentleman planter.

Coming along 50 years later, Roberts could only have looked back and shaken his head in wonder. The wide-open frontier days and the opportunities that came with them were gone. In the shrinking seas of the 18th century, Roberts and his ilk were nothing but pirates, the “common enemy” of all mankind according to maritime law, and running out of places to hide in a rapidly changing world.

When he set his final course for West Africa, in April 1721, the handwriting was on the wall. Blackbeard was dead by then, killed in a ferocious sea battle off  North Carolina in 1718; Kidd had been hanged years before; Morgan was ancient history. Gibbeted pirates were decorating waterfronts all around the Atlantic. Others had accepted amnesties, or quit the sea while they were ahead and vanished into obscurity. Indeed when Captain Johnson’s General History of the Pirates appeared in 1724, its author was already referring to the reign of “these desperadoes” in the past tense. Roberts was among the last of the legends still afloat. His career ended in high operatic drama in February 1722: in a massive tropical thunderstorm off  Cape Lopez, the doomed hero at the helm of the Royal Fortune, attempting a desperate end-run around the British warship Swallow that had boxed him in, and whose gunners, he could see, were preparing a broadside.

There was little hope of escape, and Roberts knew it. His short merry life had reached its end, but he met it with style, dressed, as Captain Johnson informs us, “in a rich crimson damask waistcoat and breeches, a red feather in his hat, a gold chain around his neck with a diamond cross hanging to it, a sword in his hand and two pairs of pistols at the end of a silk sling…. He ordered his men to arms without any show of timidity, dropping a first-rate oath that it was a bite, but at the same time resolved, like a gallant rogue, to get clear or die.”

He did not get clear. Instead, moments later, a Royal Navy cannonade brought down the curtain on Roberts and the Golden Age of Piracy.