10 Swashbuckling Buccaneers from the Golden Age of Piracy

swashbuckling-buccaneers-golden-age-of-piracy (Image: Jean Leon Gerome Ferris)

Nothing gets our modern pulses racing quite like epic tales of piracy. The danger, the romance of the sea, the old-fashioned swashbuckling nature of it all… it’s tempting to say the Golden Age of Piracy still casts as long a shadow over our culture as the Wild West or the Jazz Age. Especially when you consider the veritable rogues gallery of timber-shivering, treasure hunting ruffians who terrorised the Caribbean at that time. Here are 10 of the most famous pirates and buccaneers of the era.


The scurviest sea dog of them all, Blackbeard (AKA Edward Teach) is today more legend than man. But man he was, and his story is more fascinating than any number of romantic legends.

blackbeard-the-pirate-edward-teach (Image: Jean Leon Gerome Ferris)

Probably born in Bristol some time around 1680, most of Teach’s early life is now lost to the mists of time. Some have speculated he was the son of a wealthy family. Others that he was a common nobody. All we know for certain is that he washed up in the West Indies sometime around 1716, perhaps after fighting in the superbly messy Queen Anne’s War. It would certainly explain the name of his ship. Captured in late 1717, the Queen Anne’s Revenge was a monster of a vessel. Equipped with 40 guns, it was capable of smashing its way through virtually anything that crossed its path.

Despite all this, Teach was a comparatively gentle man. There are no records of him harming or killing anyone his crew had taken prisoner. Instead, he relied on his appearance (helped by his superlative beard) to strike fear into people’s hearts, sticking smoking matches under his hat to emphasise his devilish look. He even ran a fairly democratic ship, allowing his underlings a say in how the Revenge was run.

Most surprisingly of all, his reign of terror really didn’t last very long. The first records we have of Teach date back to 1717. By late 1718, the most-famous pirate in history was dead, less than two years into his career.

Calico Jack Rackham

calico-jack-john-rackham-jolly-roger (Image: Open Clip Art Library)

Born John Rackham in England around 1682, Calico Jack is nowhere near as well remembered as Blackbeard. A relatively minor pirate who terrorized the Bahamas, Jack captured only a few ships, and was caught and executed not long after he took up the mantle of pirate for the second time in 1720. However, there was one contribution he made to the annals of pirate lore that won’t be forgotten. Calico Jack may have flown one of the earliest versions of the Jolly Roger.

There had been Jolly Rogers before Jack, but they tended to be more elaborate; featuring horned devils stabbing hearts or men drinking with death. Jack’s was the first to simply show a skull on a black background, with a pair of swords crossed beneath it. While others would add the notorious crossed bones, it was Calico Jack who flew the first iconic design.

He was also the only pirate captain known to have had women among his crew. Both Anne Bonny and Mary Read (see below) joined his ship – an incredibly progressive move for the early 18th century from a buccaneer whose early life we know very little about. Calico Jack’s reign of piracy came to an end on November, 18 1720, when he was hanged at Port Royal, Jamaica.

Captain Kidd

Although celebrated today as the archetypal pirate, there’s plenty of evidence that William Kidd was a more honest, sober man than his reputation would allow. Originally a privateer given a Royal Commission to attack anyone bothering British ships in the Indian Ocean, Kidd didn’t turn to piracy until mid-1697 – a move that would quickly see him make and lose a fortune.

pirate-captain-william-kidd (Images: Howard Pyle; The Pirate’s Own Book)

By early 1698, the infamous Scottish rogue had already accomplished his most-famous deed, capturing the Armenian vessel Quedagh Merchant. Filled with piles of what can only be called “booty,” the Quedagh would become as legendary as its captain. Scuttled in 1699, it vanished off the face of the Earth, seemingly taking its invaluable treasure with it. In the years that followed, many thousands of men would waste considerable time and money trying to dredge it back up from the ocean floor, each without success.

Interestingly, we still can’t say for certain that Kidd really was a pirate. When his arrest warrant was issued, he sailed directly to the governor of New York and tried to have the charges dropped. The governor instead had him tried and hanged. It’s said evidence in the captain’s favour was supressed during this period, and that he may have gone down simply for being Scottish. Nonetheless, Kidd had the last laugh. The world never again saw a penny of his lost treasure.

Henry Every

Unlike most pirates of his age, Henry Every managed to avoid a violent death. A rogue from Devonshire in southwest England, Every instead managed to work his way to the very top of the pirate game before vanishing completely.

captain-henry-every-pirate (Image: John Ward Dunsmore)

His story begins as many others’ do. Drawn into the Royal Navy, Every spent a few years knocking about from port to port, trying his hand at various trades – including time spent working on a slave ship. By 1694, though, he’d decided to settle into life as a pirate. Joining a Spanish ship, he plotted and carried out a mutiny, installing himself as commander of the rechristened Fancy.

It was the start of an epic career. With undisguised glee, Every plundered ships heading to and from Africa; forging alliances with other pirates until he had an entire fleet under his control. In 1695, he and his fleet sacked a group of Indian Mughal ships, earning him the undying enmity of the East India Company. With a bounty on his head, Every scuttled his ships before sneaking back into England to hide out from the law.

What happened next, no-one knows. It seems Every just vanished, perhaps living out his life on the proceeds of his loot. On the other hand, there are rumours that he was cheated out of his treasure by a group of merchants in Bristol, after which the man once dubbed Long Ben and The Arch Pirate subsequently died in poverty.

Anne Bonny

Of all the pirates on our list, the Irish-American Anne Bonny might be the most-impressive of them all. Not only did she manage to become a fearsome marauder during an age when women were considered bad luck on ships, she also managed to avoid a violent death, living out the rest of her life in relative luxury.

anne-bonny-pirate (Image: via Wikipedia)

A born ruffian, Anne was a force to be reckoned with from the moment she hit the ground. It’s rumoured that as a teenager she beat an attempted rapist so badly he wound up in the hospital. By the age of 22, she’d already surrendered her normal life as the daughter of a lawyer and taken to the high seas in search of adventure.

And find it she did. After hooking up with Calico Jack, the couple began to terrorise ships off the coast of Jamaica. When they boarded enemy vessels, Anne would charge straight into the thick of battle, ready for blood. At the same time, the couple had to elude agents of Anne’s husband – the product of a forced marriage – hunting them across the seas.

Unfortunately for the pirate duo, their adventure couldn’t last. Not long after their first meeting, Calico Jack was caught and hanged, and Anne was sentenced to death. Luckily, her pregnancy got her sentence commuted, giving her lawyer father enough time to extricate her from prison. Anne was taken back to her home in South Carolina, where she lived to a ripe old age as a respectable woman.

Mary Read

A compatriot of Anne Bonny, little is known today about Mary Read. What we do know, though, paints a picture of a an extraordinarily complex woman.

mary-read-pirate (Image: Stephencdickson)

For starters, it’s debatable whether we should be calling her a woman at all. Read spent most of her life, from a very young age, dressing and living as a man. By her late teens, she had enlisted to fight in the British military, serving as a soldier during an intensive war against the French.

However, it’s not as simple as claiming Read was transgender. From what we know, it seems she began living as a woman after the war, only returning to her male guise a few years later when her lover died. It was at this point she decided to turn to piracy.

Still disguised as a man, Read joined up with Calico Jack and Anne Bonny and set off on a short career of plunder and mayhem. Vicious and brutal, Read was a born fighter, allegedly not above killing her own comrades when they refused to enter battle. Like her compatriots’ though, her career was short lived. Read was arrested at the same time as Calico Jack and Anne Bonny and sentenced to death. Although she was given a reprieve due to pregnancy, she later died in prison. There are no records to indicate her child survived.

Stede Bonnet

Born into a wealthy English family on Barbados, Stede Bonnet’s decision to jump into piracy was ill-advised at best, and downright daft at worst. With no sailing experience and no background as a pirate, Bonnet decided to solve his marital problems by setting up a ship, purchasing a crew and heading off to wreak havoc in the summer of 1717.

stede-bonnet-gentleman-pirate (Image: via Wikipedia)

For a while, that’s exactly what he did. Bonnet’s crew plundered and burned vessels along the American coast, taking particular delight in sacking those from his native Barbados. But it wasn’t long though before his lack of training caught up with him. Wounded in a firefight with a Spanish man-of-war in December 1717, Stede was forced to turn control of his ship over to his acquaintance Blackbeard while he recovered. His paid-for crew, perhaps sensing Stede wasn’t exactly up to the job, quickly abandoned him and joined Edward Teach’s Queen Anne’s Revenge.

Now without a crew or ship and wounded to boot, Stede had no choice but to seek a pardon. It was awarded, and the former-pirate turned privateer was put in charge of a ship tasked with attacking Spanish merchant vessels. Within a month or so, Stede had decided to return to piracy. A month or so after that, he was caught and sentenced to hang. The Gentleman Pirate, as he was sometimes known, was executed in December 1718, only a year and half after his ill-thought out adventure began.

Charles Vane

In all the annals of pirate lore, perhaps no buccaneer has been as hated or as feared as Charles Vane. An Englishman who famously refused to be pardoned for his actions, Vane was loathed for his extreme cruelty and willingness to torture anyone he felt like.


(Image: via Wikipedia)

This included his own crew and people who should have been friends. In his brief run as a professional pirate, Vane became known for cheating his own men, slaughtering prisoners, and accepting surrenders only to subsequently torture those who threw down their arms. He also had a terrorist’s sense of spectacle. Twice in his career he jammed a ship full of incendiaries, set it alight and rolled it straight at Navy vessels, causing earth-shattering explosions.

In the end, though, it was his cruelty that undid him. Deposed by his own unhappy crew, he eventually wound up abandoned on a desert island. When help finally came, it was in the form of Vane’s enemies. Dragged back to Jamaica, Charles Vane was tried and executed. It seems few people missed him.

Samuel Bellamy

Of all the rogues who terrorized the Caribbean in those days, perhaps only Samuel Bellamy could qualify for the appellation “lovable.” Young, dashing, kind to his crew and remarkably merciful to his enemies, Bellamy was known as the Robin Hood of the Sea.

samuel-bellamy-pirate-treasure (Image: Theodore Scott; pirate gold recovered from the wreck of the Whydah)

It was a title he only half-deserved. While Bellamy certainly threw out money to those loyal to him with joyful abandon, he was less interested in rewarding the general poor than he was lining his own pockets. In the single year he was active, Bellamy managed to seize at least 53 ships stuffed full of booty, the equivalent of around $120 million in today’s money. In 2008, this was enough to earn him the number one spot in Forbes’s rank of ‘Top-Earning Pirates’.

The buccaneer also consorted with the great and not-so-good of his day. In 1716, the year before he became a fully-fledged pirate, Bellamy sailed under a certain Edward Teach, the man who would later become Blackbeard. More-impressive still, he once managed to snatch a boat from the infamous buccaneer Lawrence Prince with only a single shot fired.

Yet for all his charisma and connections, Bellamy couldn’t escape fate. Less than a year after he assumed control of his first ship, the Robin Hood of the Sea was caught in a storm off the coast of Massachusetts. The vessel, the Whydah Gally, went down with all hands on deck, taking Bellamy’s fledgling career with it.

Bartholomew Roberts

If you thought Bellamy’s tally of 53 captured ships was impressive, wait until you hear about Bartholomew Roberts. A Welsh pirate who terrorized the Caribbean, North America and West Africa for two and a half years, Roberts managed to capture or sink an incredible 400 vessels.

bartholomew-roberts-welsh-pirate (Image: Benjamin Cole)

While his actual takings were less than those of Bellamy, in terms of sheer numbers his career was staggeringly successful. It becomes even-more impressive when you consider his relatively advanced age. While Bellamy was dead by 28, Roberts didn’t even start his career in piracy until the age of 37.

And what a career it was. Roberts blazed a trail all the way up from Barbados to Newfoundland and across the ocean to Ghana. Everywhere he went, vessels burned in his wake. He was considered a god, a monster, an unstoppable killing machine by everyone who crossed his path.

But in the end, Roberts was as mortal as you or I. While charging past the vessel Swallow off the coast of Guinea, Roberts was caught in the throat by a grapeshot. He immediately died, his body consigned to the waves by his grieving crew.

Related – 10 Amazing Lost Treasures That Have Never Been Found


About the author: Morris M



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