Caribbean Beat Magazine

Caribbean Pirates: Low Life on the High Seas

The sordid truth behind the romance: what did those scurvy pirates really get up to?

  • Illustration by Sally Davies
  • Illustration by Sally Davies
  • Illustration by Sally Davies
  • Illustration by Sally A. Davies
  • The last straw- finding that the ruthless pirate with the smoking pistol was a woman. Illustration by Sally A. Davies

Every day, in more Caribbean islands than you can aim a swivel gun at, mock pirate boats set sail laden with partying tourists eager to leap from the poop deck and swing from the yardarm. After dusk, the flambeaux and the barbecues light up palm-fringed beaches as pulsating music and gallons of rum punch let loose a flood of buccaneer bashes and freebooter fetes.

Noticeably absent from the revelry are the flashing blades that once cleaved a bloody swath along these very coves and bays. Not for these merrymakers, either, the cruelly pointed pikes, the primitive grenades and stinkpots, the muskets and culverins so aptly referred to as “Murdering Pieces”, far less the enemy fire, the grim spectre of the surgeon sawing away in his cockpit, and the awful shadow of the hangman’s noose.

But the Caribbean, littered as it is with landmark reminders from Dead Chest Cay in the Virgin Islands to the infamous Port Royal in Jamaica, can be forgiven for romanticising its pirates. The enigmatic Brethren of the Coast have long supplied grist for imagination’s mill, not to mention inspiration for countless immortal works recasting these hordes of scruffy cutthroats as swashbuckling heroes.

Separating fact from fiction is no picnic. Three hundred years separate the swaggering figures who roamed the Spanish Main in Tudor times to the last rum-befuddled wrecks cowering in the coves of the Mosquito Coast. Debate still rages over who merits the name “pirate” anyway. Hawkins and his cousin Drake were commissioned by the Queen and eventually knighted, but to their Spanish victims it made little difference whether they were Her Majesty’s Pirates or merely freelancers.

The tide of Caribbean piracy began to rise soon after the discovery of the New World. Spain claimed ownership of the entire region, but others begged to differ. First the French, later the English and the Dutch, dispatched ships to despoil Spanish settlements and capture their vessels. Most, like the celebrated cousins from Plymouth, hail the blessing of their governments and carried Letters of Marque authorising hostilities against Spain, both national and personal. Such ships were not technically pirate vessels, but ersatz naval auxiliaries known as privateers.

In time, however, the distinction between privateers and freelancers operating for their own gain became blurred. The lure of the great Spanish treasure convoys was irresistible to everyone, and conditions were ideal. There were two thousand miles of islands where ships could be careened and refitted to strike from hidden harbours; the prey was slow and clumsy. Bolstered by convenient notions of patriotism, a ruthless breed of predators transformed the Caribbean paradise into a department of hell.

Greed was undoubtedly the prime motivation for these seafaring thugs who risked life and limb at every turn. Yet however fraught with peril, dogged by disease and prey to the dismal hazards of life without women, theirs was a methodical type of madness. Some were indentured servants, escaping from backbreaking toil in the blistering sun; others remembered the starvation and the poxes of the city slums. Yet others knew what life was like aboard the King’s ships: the rotten rations, the appalling pay and the threat of the crippling lash. Small wonder the risk was worth taking.

Among the most successful pirates were the original Brethren of the Coast, the buccaneers who once made the tiny island of Tortuga the most feared outlaw stronghold in the New World. Mostly French colonists and deserters, named for their practice of smoking meat over boucans, or ovens, their numbers included Francis L’Olonnois, a sadistic killer who fittingly met his maker in the bowels of indignant Amerindians. His tastes, matched only by the demonic Edward Low, ran to chomping merrily on victims’ hearts, and he constantly boasted that he never spared a prisoner’s life.

The question of prisoners was generally a ticklish one, and individual fortunes varied with the temper of the victors or the severity of the defence. Many captives were offered the option of joining the pirates, and useful specialists like gunners and sailmakers stood little chance of going free. A woman’s lot in a seized ship was usually somewhat less attractive than death and rarely smacked of romance on the high seas.

Some women, like the prototype bra-burners Anne Bonney and Mary Read, were made of sterner stuff. Anne, whose youthful pranks had included slaughtering her maid with a case-knife, met the flamboyant Captain “Calico Jack” Rackham in dockside Charleston. Jack’s approaches to courting a woman and taking a ship were essentially the same — straight up alongside, every gun brought to play and the prize hoarded without delay. Anne was soon at his side, murdering and pillaging with the best of them.

Mary, meanwhile, spent most of her life in drag, apparently to improve her chances of eliminating men in large numbers. She vigorously pursued this hobby on board a man-o’-war, as an infantryman, and in a regiment of horse, before shipping out as a sailor to the West Indies. Her transvestitism no doubt saved her neck, or some tenderer part of her anatomy, when the ship was captured by Rackham, whereupon she gleefully signed the pirate articles and got back to work. Her continued ability to conceal her sex spoke volumes about the dearth of shipboard ablutions.

These two charming wenches made a desperate last stand against the arresting forces of the Governor of Jamaica while the rest of the crew skulked manfully below decks. Their ultimate fate is unclear, but Anne’s final sweet nothings, whispered at her lover’s execution, are well recorded: “If you had fought like a man, you need not have been hang’d like a dog.”

Jamaica was the site of Port Royal, the “wickedest city in Christendom” and longtime lair of Henry Morgan. This Welshman, who at one time led a veritable army of cutthroats, is credited with sacking innumerable Spanish settlements and stands out for his shameless dishonesty in the distribution of spoils. He nevertheless graciously accepted both a knighthood and an appointment as Lieutenant-Governor of Jamaica.

One of history’s most celebrated turncoats, he devoted the rest of his life to suppressing piracy as ruthlessly as he had previously practised it, and it must have seemed like divine retribution when, four years after his death, his former stronghold and burial place were toppled into the sea by a massive earthquake.

A more honest villain was Blackbeard, whose ferocious attacks were equalled only by his fearsome appearance. Whereas most pirates intimidated their victims with macabre flags, Blackbeard braided his huge beard with ribbons and strapped a small armoury about his body. Most bizarre of all was a smouldering war bonnet of slow-burning fuses anchored beneath the brim of his hat. Not surprisingly, many of his thunderstruck opponents (if they didn’t die laughing first) surrendered without resistance.

But not all did. The famous, heavily accessorised head made its final journey swinging from the bowsprit of an armed sloop commissioned by the Governor of Virginia.

Violent death was the norm amongst these bandits of the sea, and few lived long enough to reap the benefits of their spoils. Even the legends of buried treasure are doubtful, with only a rare group of pirates, Captain William Kidd among them, ever leaving anything behind. Who had time or inclination to dig furtive holes and draw mysterious maps? Expenses tended to run high. The innkeepers of the island hideouts, the whores, pimps and go-betweens, and the merchants who outfitted the pirates at enormous cost, bagged the greatest share of the loot.

Ill-fated major players like Blackbeard, together with countless small-leaguers like the splendidly named Benjamin Hornigold, Charles Vane, George Lowther and John Evans, marked the golden age of Caribbean piracy. Even relative amateurs, like the Barbadian planter Stede Bonnet, who is said to have come up with the idea of walking the plank, could join in the reign of terror in the Caribbean Sea. But when England tried to mend fences with Spain, the buccaneering days were numbered and even the best became an embarrassment to the European states and a burden on the colonies.

By this time the pirates’ main base had moved to the Bahamas and other dens had been established further east in the Virgin, Leeward and Windward Islands. But the heat was on; there was increased pressure from interfering navies and fearless new Governors committed to extermination. The purge was remarkably effective; by the late 1720s only a scattering of diehards remained.

One final piratical fling erupted a hundred years later when the end of the Napoleonic Wars and the American War of Independence threw thousands of privateers on the breadline. The old profession was resurrected and raids were launched from bases in Puerto Rico and Cuba on the cargo traffic between America and Europe. But a special West India squadron was commissioned as part of the American Navy, and the latter day pirates were eradicated by the 1830s.

The great age of Caribbean piracy thus ended with more of a whimper than a bang. Yet in their heyday, the Brethren of the Coast created an enduring legend and a compelling mystique. Were they indeed towering dreadnoughts with their own code of honour, living life to the full? Or were they the scum of the earth and the scourge of the seas, pitiful rum-sodden villains with neither scruples nor remorse?

Most likely they were both. Victims of circumstance who hid despair beneath the bravado and a sense of tragedy behind the fancy clothing, the fine Cordoba boots and the heavy gold ear loops. Men who learned to swagger through scenes of horrendous carnage, sometimes holding on to the last vestiges of decency, to whom the dream of going home with a sackful of doubloons grew dimmer with each voyage. Filthy, befouled, pathetic, rum-soaked wretches.

Of all the seafaring rogues, perhaps none displayed these contradictions more eloquently than Bartholomew Roberts. A notoriously brutal and spectacularly successful pirate, he nevertheless insisted on keeping the Sabbath and was a strict teetotaller. Gambling and women were forbidden on his ship, but should a woman be taken prisoner, guards were posted to ensure her safety. He drew up, and adhered to, a lengthy set of articles specifying how booty was to be shared and fixing generous compensations for various injuries.

All this might well suggest a raving case of schizophrenia. But Roberts’s head was clear when he made the following statement: “In an honest service there is thin commons, low wages and hard labour. In this, plenty and satiety, pleasure and ease, liberty and power. And who would not balance creditor on this side, when all the hazard that is run for it, at worst, is only a sour look or two at choking! No, a merry life and a short one shall be my motto.”

Short it was. Captain Roberts, with a cross of stolen diamonds about his neck, died in action at the age of forty. Who can tell how merry he was?