Tracking the Origins of 7 Pirate Stereotypes

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Ahoy, flossers! Most fictional pirates fit a standard mold: everyone expects them to be eye-patched parrot fans with puffy Seinfeld shirts, swilling from jugs of rum while yo-ho-ho-ing below deck. Between hunting for buried treasure and sailing the seven seas, these caricatures kill time by making scallywags walk the plank. Also, they say “Arr!” a lot for some reason.

Why does everyone buy into this image? As Talk Like a Pirate Day 2015 drops anchor, let’s explore a few buccaneer stereotypes and where they came from. 


A good percentage of the things we all associate with pirates trace back to Robert Louis Stevenson’s Treasure Island. Published as a serial between 1881 and 1882 (and in novel form one year later), it’s been the guiding light for every buccaneer story from On Stranger Tides to Pirates of the Caribbean: Dead Man's Chest.

Treasure Island also made celebrities out of its characters—especially Long John Silver and “Captain Flint,” his faithful parrot. Stevenson hinted that the bird was an homage to Daniel Defoe's Robinson Crusoe (1719). Stranded on a desert island, Defoe’s protagonist goes for over 20 years without human contact and relies on a talking avian for company.

The literary pirate-parrot link has a slight basis in truth. Granted, the food supply was often low on many vessels, making pets a luxury that most buccaneers couldn’t afford. Nevertheless, seamen of the 16th to 18th centuries did frequently capture exotic animals as souvenirs. Since parrots sold for high prices in London’s markets, pirates were known to round them up. Stephen Haynes—a despised pirate captain—bribed high-ranking British officials with live ones.


There’s an ingenious explanation for why pirates might have worn eyepatches. But this doesn’t mean that they actually used them.

Adapting to darkness can take the human eye as long as 25 minutes. During a pirate raid, if you’re walking around in pitch-black gloom below deck, those are 25 minutes that you might not have. Strapping a patch over one eye for an extended period keeps it dark-adjusted and ready for immediate use in low-light conditions. What a brilliant strategy!

Alas, the hypothesis has one fatal flaw. By buccaneer fashion standards, eyepatches were rare accessories. In fact, the only gentleman of fortune who unambiguously wore one was Rahmah ibn Jabir al-Jalahimah, a famous Arabian ruler and pirate. Having lost an eye in combat, he donned a patch.

The whole eyepatch-touting buccaneer concept was likely inspired by a revered non-pirate. At the 1794 siege of Calvi in Corsica, Lord Horatio Nelson sustained a serious facial blow that cost him the use of his right eye. To draw attention to this handicap, artists began painting the naval officer with an eyepatch (something he probably never used). Nelson’s heroic exploits turned him into a living legend and, over time, the public subconsciously started associating eyepatches with acts of nautical bravery.


The foreboding design goes way back: during the bubonic plague outbreak in the Middle Ages, it was used to symbolize death. By the early 1700s, buccaneers had started sewing skulls and crossbones onto black flags (a Caribbean terror named Emanuel Wynn may have kicked off the trend). Believe it or not, these sent a peaceful message. Unfurling a black flag of any sort meant that if a vessel surrendered its goods, the outlaws were willing to spare her crew. No such mercy accompanied a red flag. Sailors utterly dreaded this signal because it warned that the pirates were ready to slaughter every man aboard.

Of course, pirates—unlike, say, the Royal Navy—didn’t follow rigid style guidelines. While black skull and crossbone flags were popular, some captains used very different emblems. Thomas Tew (a.k.a. “the Rhode Island pirate”) went instead with an arm holding a cutlass. And Blackbeard scored extra points for creativity by choosing a horned skeleton that was clutching an hourglass while spearing a big crimson heart.

As far as what we call pirate flags, they were colloquially known as “Jolly Rogers,” but historians aren’t sure why. Some say the term descends from “joli rouge,” French for “red flag.” Others point out that “Old Roger” was the devil’s nickname in 18th century England, so perhaps “Jolly Roger” is a corruption thereof. 


At best, plank-walking deserves to be regarded as a historical footnote. Trustworthy accounts of it actually happening are very scarce. We know that when Caribbean pirates seized the Dutch ship Vhan Fredericka in 1829, her captured sailors did indeed meet this terrible fate. Seven years earlier, the captain of Blessing (a Jamaican sloop) was forced off a plank’s edge and shot before he could swim back.

Still, cases like this are—by a wide margin—the exception rather than the rule. Generally speaking, pirates kept their prisoners alive as hostages. And if a captive needed to be disposed of for some reason, tossing him overboard was a good deal easier.

In the world of Treasure Island, however, walking the plank is more common—Stevenson’s bestseller references the practice twice. Perhaps he’d read about American pirate Stede Bonnet, who was said to have made his prisoners walk the plank, but no extant records back this up. 


The cliché was probably single-handedly (or should we say “single-leggedly?”) cemented by everyone's favorite pirate, Long John Silver, and a famous literary sea captain. But more on that in a second. Stevenson could’ve based the character upon any number of real-life peg-leg owners. Francois Le Clerc, for example, once commanded a fleet of eight huge vessels and 300 seamen. During a spat with English forces in 1549, he lost a leg and seriously damaged an arm. Le Clerc later made a name for himself by stealing from the Spanish, who called him “Pie de Palo” or “peg leg.”

A more likely candidate wasn’t a pirate at all, but one of Stevenson’s close friends. At the tender age of 19, tuberculosis claimed young William Ernest Henly’s left leg. The limb was amputated a bit below the knee and its owner spent the rest of his life with a wooden substitute. An esteemed journalist and poet, Henly is best remembered for writing “Invictus,” which ends with the defiant stanza “It matters not how straight the gate/ How charged with punishments the scroll/ I am the master of my fate/ I am the captain of my soul.”

But weirdly, Long John Silver might not have used a peg leg (at least very often) in the book. He's clearly described as managing a crutch with "wonderful dexterity" under his left arm, and most of the early illustrations show him missing the leg entirely. Which makes sense, as he's described as the one-legged man. The peg leg was probably an addition of certain movie adaptations—possibly influenced by a literary sailor who definitely had a peg leg: Captain Ahab from Moby-Dick, who is described as having an ivory leg.


Pirates weren’t squirrels. When these criminals came into possession of some loot, they did what most criminals do: spend it immediately. Burying treasure together would have been a risky, inconvenient trust exercise to say the least.

Therefore, it’s hardly surprising that—like plank-walking—historical documents about buried treasure are almost nonexistent. We’d probably never link buccaneers with this practice at all if a notorious captain hadn’t stashed some loot underground. His name? William Kidd.

On one occasion, the Scottish pirate buried a sum of gold and other valuable items that were collectively worth about £20,000 (over $1 million in today’s dollars) on Gardiner’s Island—which sits near the forks of Long Island. Following his arrest in 1699, this cache was recovered. Kidd’s execution took place on May 23, 1701, yet the man’s legacy is still very much alive, thanks in no small part to long-lived rumors about an even bigger treasure of his remaining undiscovered somewhere.

Edgar Allan Poe’s short story “The Gold-Bug” (1843) revolves around this notion, with the main characters using a cipher to hunt down Kidd’s lost bounty. Treasure Island blatantly rips off the premise, substituting a map for the cipher. As Stevenson himself admitted, “I broke into the gallery of Mr. Poe.” When all’s said and done, good writers borrow, great writers steal.


In the golden age of piracy, British, French, German, and even Jewish buccaneers terrorized the oceans. So—with apologies to a certain holiday—the belief that they all spoke with a uniform “pirate dialect” is beyond ridiculous.

Treasure Island again deserves the blame here, but this time, we’re talking about Disney’s 1950 movie adaptation. Actor Robert Newton didn’t just give an inspired performance as Long John Silver—he fundamentally changed the way people think about pirates. Over 96 minutes, the man hollers and growls through an overblown West Country English accent. As linguist Molly Babel told the Vancouver Sun, “Speakers of [this] dialect tend to emphasize their r’s… They tend to replace ‘is’ and ‘are’ with ‘be,’ and indeed, use the word ‘arrr’ in place of ‘yes.’”

Newton was subsequently typecast in 1952’s Blackbeard the Pirate and 1954’s Long John Silver. Both performances came with a reprise of his harsh piratical voice, elevating it into a full-blown stereotype that’s still thriving today. If ye be celebrating Talk Like a Pirate day this year, raise yer glass in his honor.

All photos courtesy of iStock