Pirates in the Caribbean
Peg legs, parrots, and an easy-to-imitate “ahoy matey” lexicon: these are requisite elements in any pirate tale, but so are avarice and episodes of unspeakable violence. The combination is clearly compelling. Our fascination with pirates knows no bounds.
The true history of piracy has largely been obscured by competing pop-culture images. On one hand, there is the archetypal opportunist—fearsome, filthy, and foul-mouthed. On the other is the lovable scallywag epitomized by Captain Jack Sparrow in Disney’s Pirates of the Caribbean franchise. Actual pirates, however, usually fell somewhere between these two extremes.
They could be uneducated men with limited life choices or crewmen from legitimate commercial and exploratory vessels left unemployed in the wake of changing political agendas. In either case, the piratical career path offered tempting benefits. Making a fast doubloon was only the beginning. Piracy also promised adventure plus egalitarian camaraderie—a kind of social equality unlikely to be found elsewhere during that class-conscious period.
Life aboard ship was governed by majority, as opposed to autocratic, rule. Pirates, moreover, adhered to the Pirate’s Code (a sort of “honor among thieves” arrangement). On the ships, at least, the common good took precedence.
"X" Marks the Spot
The Caribbean offered easy pickings for pirates because Spanish imperialists had already done the heavy lifting, extracting gems and precious metals from their South American colonies. Pirates from competing powers (namely England and France) could simply grab the spoils as Spanish ships island-hopped homeward.
Jamaica: Calico Jack Rackham, his lover Anne Bonny, and Mary Read were ultimately captured in Bloody Bay near Negril. Reportedly the male crew members were too busy drinking rum to mount a proper defense.
Dominican Republic: The centuries-old Spanish architecture in Santo Domingo’s Zona Colonial is so well-preserved you can almost picture the area populated with tankard-toting buccaneers and corset-clad wenches.
Puerto Rico: Massive fortifications, like Castillo San Felipe del Morro in Old San Juan, show just how far the Spanish were prepared to go to protect their assets from seagoing attackers, whether authorized or otherwise.
British Virgin Islands: Sir Francis Drake Channel, Jost Van Dyke, and Great Thatch Island were named for pirates or privateers. Ditto for Norman Island, which reputedly inspired the setting for R.L. Stevenson’s Treasure Island.
St. Thomas: A strategic location, protected anchorages, plus easy-to-hide‑in inlets made the U.S. Virgin Islands an ideal habitat for plunderers. High points like Drake’s Seat and Blackbeard’s Castle were used to survey the terrain.
Anguilla: Underwater heritage preserves let divers explore vessels that sailed during piracy’s Golden Age. Stoney Ground Marine Park contains a Spanish galleon wrecked in 1772, plus cannons, anchors, and other artifacts.
St. Barthélémy: Logically enough, Frenchman Daniel Montbars used this French island as his home base. Legend has it some of his treasure remains hidden in the beachfront caves around Anse du Gouverneur.
St. Lucia: Now a peaceful national park, Pigeon Island (on St. Lucia’s northern tip) was once the hideout of François Le Clerc. This peg-legged pirate orchestrated attacks from his hilly vantage point in the late 16th century.
Famous Pirates
Sir Francis Drake: Drake was a busy fellow. The first Englishman to circumnavigate the globe, he popularized tobacco, led slave-trading expeditions, helped destroy the Spanish Armada, and still had time to terrorize treasure-laden ships with Queen Elizabeth’s blessing.
Henry Morgan: Captain Morgan led a colorful life before lending his name to a ubiquitous brand of rum. Leaving Wales for the West Indies as a young man, he successfully segued from debauched buccaneer to semi-respectable privateer and, after dodging piracy charges in England, ended up as the Lieutenant Governor of Jamaica.
Blackbeard: Born Edward Teach, Blackbeard was notable for his business savvy (which included making profit-sharing deals with politicos) as well as his fiendish looks. His signature beard was braided and often laced with lit fuses to terrify enemies. Alas, in 1718 Blackbeard’s head was severed in a dramatic showdown with Lt. Robert Maynard of the Royal Navy.
William Kidd: Life was a roller-coaster ride for the legendary Captain Kidd. Kidd was a retired privateer living in New York when he accepted a commission to hunt pirates and then became one himself with the encouragement of a mutinous crew. He was executed in London in 1701, but hopefuls still hunt for the treasure he supposedly left buried.
Black Bart Roberts: Though not the most famous pirate, he is often considered the most successful. He racked up impressive credits, plundering some 400 ships between 1719 and 1722. A snappy dresser who was fashionably attired even in battle, he was also a strict disciplinarian.
Daniel Montbars: Montbars proved Brits didn’t hold a monopoly on bad behavior. French lineage aside, he differed from his 17th-century peers in that he was affluent and educated. His manners needed polishing, though. Violent outbursts (disemboweling Spaniards was a favorite sport) earned Montbars the nickname “The Exterminator.”
Calico Jack Rackham: An Englishman who ascended from mate to captain, Rackham secured his legend by adding women to his crew. Workwise, his favorite tactic was attacking small vessels close to shore. Such boldness led to an inglorious end. Rackham was hung then tarred, feathered, and displayed in a cage in Port Royal, Jamaica.
Anne Bonny and Mary Read: Thought to be unlucky, female pirates were rare. Yet the comely Bonny and cross-dressing Read were respected by their shipmates and feared by their victims. Captured together in 1720, they were sentenced to death. Both, however, escaped the noose by claiming to be pregnant.
