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Famous Pirates in History: Stories from the Golden Age of Piracy

The Jolly Roger Flag: Symbol of The Golden Age of Piracy
The Jolly Roger Flag: Symbol of The Golden Age of Piracy

Real Pirates of the Caribbean

Some of the most famous pirates in history lived during the Golden Age of Piracy, and their stories have served as the basis of pirate myth and lore. Caribbean piracy is famous today as a colorful and adventurous episode in world history, packed full of wild characters and thrilling adventure.

It was a time when free-spirited and courageous people could still disappear in the world, simply by boarding a ship and pointing it toward the horizon. Especially in contrast to our fast-paced lives of today, the pirate life seems awfully appealing.

But historians don’t agree with this idealized depiction, and paint the careers of famous pirates as extremely harsh, cruel and quick. Real pirates were fairly nasty characters, and many died in battle or at the end of hangman’s rope. Piracy was a menace to world governments, and impacted trade and commerce as well as overseas travel to the New World.

If one chose to live the life of a pirate, they were accepting a life on the wrong side of the law.

The Golden Age of Piracy lasted from around 1650 to around 1730. Piracy has existed likely since the first seagoing ships carried trade goods, but this time period is often what we think of upon hearing the word pirate.

What follows are the tales of some of the most amazing characters from this unforgettable historical period.

The Story of Calico Jack Rackham

Calico Jack was a flamboyant pirate with an amazing life story.
Calico Jack was a flamboyant pirate with an amazing life story. | Source

Throughout the Golden Age of Piracy there were few captains more flamboyant that Jack Rackham. Called “Calico Jack” due to his flashy dress, his short career was marked with daring and bravery. Unfortunately for Rackham and those who served under him, the quality of his decision making did not always live up to his larger-than-life persona. He burned bright and faded fast, and left us with one of the most intriguing pirate tales of the period.

Calico Jack served under Charles Vane in 1718. Vane was an Englishman like Rackham, a feared pirate and captain of a ship called the Ranger. When the Ranger encountered a massive French warship outside of New York harbor, Rackham rallied the crew, hoping to take the ship and its cargo. Vane refused and fled the fight.

Later, the crew would vote Vane out of his captaincy for his cowardice, and place Rackham in command. Captain Calico Jack Rackham was born.

Rackham’s plundering yielded few successes, mainly focusing on small towns along the coast. Eventually working his way to the Caribbean, Rackham boldly took a large merchant ship called the Kingston and sailed off with the greatest prize of his young captaincy. But even this turned out to be a poor choice. Unfortunately for Rackham, the merchants he had stolen from were none too happy about his misdeed, and hired a group of privateers to hunt him down.

While Calico Jack and his crew were camped ashore on an island near Cuba, the privateers retook the Kingston. Rackham and his crew escaped deeper into the island with their lives, but they were now left without a ship.

Crammed into a small boat, Rackham and his remaining crew began the three-month sail from Cuba back to Nassau, where he hoped to set himself on the straight and narrow.

In the Bahamas Rackham sought a pardon from Governor Woodes Rogers, claiming that Vane had forced him into piracy against his will. His pardon granted, Calico Jack began a new life as an honest man, taking a commission as a privateer. But it wouldn't be long before trouble found him again.

Calico Jack Meets Ann Bonny

Ann Bonny and Mary Read were female pirates who dressed as men.
Ann Bonny and Mary Read were female pirates who dressed as men. | Source

While in Nassau, Jack fell in love with Anne Bonny, the wife of James Bonny, one of the Governor’s men. When the affair was revealed Rackham offered to pay off James Bonny in a divorce by purchase, much to the chagrin of Anne who would have none of it. The Governor ordered her whipped for her adultery, leaving Rackham and his new love no choice but to steal a ship and escape the island.

With his pardon voided by his actions, Calico Jack recruited a new crew and once again set sail for plunder, this time with Bonny beside him disguised as a man. During one of their attacks, Rackham captured the crew of a merchant ship and took on a sailor with an interesting secret of her own. Mary Read had lived and worked dressed as a man from the time she was a teenager. She struck up a friendship with Bonny, and when Rackham became jealous she revealed the truth.

Thus, Calico Jack Rackham became the only known pirate captain with two cross-dressing women on his crew. It might seem like this trick would have been hard to pull off, but apparently Bonny and Read were pretty tough ladies, able to fight and scrap with the best of them.

Like most pirates, Rackham’s story did not end well. Following a short period of mayhem where once again he accomplished very little, Calico Jack was overtaken by famous pirate hunter Jonathan Barnet while drunk ashore with his crew. Rackham was taken back to Jamaica to stand trial for his deeds, and there would be no pardon this time. He was hanged for his crimes on November 18, 1720.

Before his death Bonny is alleged to have said, “If you had fought like a man you would not hang like a dog!” Talk about your touching goodbyes!

Read and Bonny were found guilty as well, but claimed they were pregnant and escaped the noose until their children were born. Read died in prison, but Bonny disappeared into history, never to be seen again. The body of Calico Jack Rackham was displayed at the entrance to Port Royal as a warning to all would-be pirates.

Throughout his short time of operation Calico Jack Rackham was one of the most feared pirates of the Caribbean, though perhaps one of the most blundering as well. He’s believed to be the original creator of the Jolly Roger flag we are familiar with today, with a skull and two crossed swords or bones. But it may be the characters of Anne Bonny and Mary Read that have cemented Rackham’s place in history. It’s a story almost too amazing to believe, but then again tales like these are what has led many to romanticize the Golden Age of Piracy.

The Sad Tale of Captain Kidd

Did Captain Kidd leave buried treasure that is still out there today?
Did Captain Kidd leave buried treasure that is still out there today? | Source

William Kidd was a Scottish privateer operating under commission granted by the English governor of the colony of New York. Assigned to hunt pirates and harass the French, Kidd apparently got bored and turned to piracy when he attacked an Indian treasure ship in 1697.

Kidd saw this as within his charter, but the crown did not agree. When Kidd sailed to the Caribbean he found out he was a wanted man. Believing friends in the Colonies could help clear his name, he set sail for New York. Kidd was arrested upon arrival, taken to England and tried as a pirate.

During the trial Kidd pleaded his innocence. When details of his exploits came out, including his violence towards prisoners and his own crew, and his interaction with known pirate Robert Culliford, Kidd found few sympathizers. He was deemed guilty and hanged on May 23, 1701.

Short and somewhat sad, Kidd’s tale would be quite mundane if not for one very interesting footnote: Before turning himself over to authorities in New York, Kidd buried treasure on Gardiners Island off the coast of Long Island. Though this is believed a common practice among pirates of the day, Kidd is one of the few documented to have done so. Upon arrest Kidd explained where he had hidden his stash, and the items were recovered.

Before his execution, Kidd taunted his captors by letting them know there was still treasure to be had, and only he knew the location. His words went ignored, but some today believe there may be secrets still out there, buried and awaiting discovery.

The Search for Captain Kidd's Treasure

In 1929 Hubert and Guy Palmer, two brothers who owned a pirate museum, happened upon a cryptic map stashed in a secret compartment of a piece of furniture once owned by William Kidd. The map showed an island with an “X” which the Palmer brothers presumed marked the location of Kidd’s treasure. They set about hunting down more of Kidd’s antique furniture, and sure enough found three more maps. The final and most detailed map labeled the location of the island as in the “China Sea”.

In the time since the original maps were discovered they have disappeared from public record, and only copies remain. Several expeditions have searched for the island, and some claim to have found it, but needless to say nobody has recovered Kidd’s lost treasure.

Oak Island, Nova Scotia, has long been a candidate for the resting place of Kidd’s loot. The whole idea started in 1795 when a man investigating the island found a depression in the earth and a tackle block installed in a nearby tree. Upon further excavation of the pit the man and his friends discovered a layer of flagstones, and then a layer of logs every few feet. They gave up the dig after 30 feet, but clearly something had been buried in what came to be known as the “Money Pit”.

Many expeditions have put a great deal of effort into discovering the secrets of the money pit, only to come up short. Could this be the final resting place of Captain Kidd’s treasure?

People are still studying Kidd’s maps, found by the Palmer brothers so many years ago. Alleged sites of Kidd’s island range from near Hong Kong, to the Caribbean, to the Indian Ocean. And excavation is still going on at Oak Island, managed by Oak Island Tours. The treasure in both cases remains unfound.

But one lost artifact of Kidd’s that has turned up is his treasure ship. In 2007 the remains of the Quedagh Merchant, the ship Kidd had commandeered in the Indian Ocean heavy with treasure, were found off the coast of Catalina Island in the Dominican Republic. One account says Kidd’s own crew looted and burned the ship while Kidd was imprisoned in New York. Another says the pirate Robert Culliford overwhelmed Kidd and his men, looted and destroyed the ship.

The story of William Kidd is a sad one, filled with mysteries and truths lost to time. Kidd may have been an innocent man, or he may have been the rogue pirate the English government made him out to be. Either way, he took his secrets with him on the day he was hanged, over 300 years ago.

The Legend of Blackbeard

Blackbeard may have been the most terrifying pirate to ever live.
Blackbeard may have been the most terrifying pirate to ever live. | Source

He was a wildman in battle, tall and ferocious with burning fuses tucked beneath his hat. Edward Teach, the notorious Blackbeard, was perhaps the most feared pirate in history, and he ravaged the east coast of colonial America and the Caribbean from 1716-1718. At the helm of the Queen Ann’s Revenge, a refitted merchant ship, he led a fleet that grew with each conquest. In truth he likely did not harm his captives, excepting those he killed battle of course, and he treated his own crew fairly in most cases. But his fearsome reputation made him well known in the new world.

Blackbeard’s most infamous deed was probably his blockade of Charles Town (Charleston), South Carolina. For several days in May of 1718 Teach and his fleet of pirates overtook any ship that attempted to enter or leave the harbor. When he captured a group of wealthy English citizens he held them for ransom until the government agreed to furnish his crew with medical supplies.

Soon after his exploits outside of Charles Town, Teach ran the Queen Ann’s Revenge aground off the coast of North Carolina. Some confusion exists as to how this exactly happened. In one account Teach was attempting to careen the ship for repairs when he accidently ran her aground and destroyed her. In another, Teach intentionally ran the Queen Ann’s Revenge aground in an attempt to reduce the number of hands in the fleet.

Whatever the true circumstances, the Revenge was lost and Teach went on his way in a small sloop with a much-reduced crew. The rest of the men he marooned on a nearby island.

Blackbeard accepted a pardon in June of 1718, deeming it a prudent decision in the light of a possible war approaching. For a brief period he lived the honest life in North Carolina, and sought commission as a privateer. But within a few months he was back at sea and on the wrong side of the crown.

Blackbeard's Demise

Blackbeard met up with fellow pirate Charles Vane, the man from whom Calico Jack Rackham would later wrestle command, and several other legendary pirate captains of the day. Alarmed by this allegiance, authorities in the Colonies sent pirate hunters to bring in Teach and his cohorts, but they would come up empty in their efforts.

Blackbeard continued to operate out of North Carolina, which enraged Virginia Governor Alexander Spotswood. Virginia had been hit especially hard by Teach’s activities in the past, and despite the lack of support from North Carolina Spotswood decided to make it his mission to bring down Teach. Spotswood sent pirate hunters off after Teach, promising a reward from the coffers of the Virginia Colonial Government on top of their royal reward.

Lieutenant James Maynard of the HMS Pearl would be the man to catch up with Blackbeard off the coast of North Carolina. Maynard surprised the pirates at sunrise, and a brutal fight erupted. Many on both sides were left dead or wounded from the initial cannon exchange alone, and by the time ship-to-ship fighting ensued the pirates had the clear advantage.

But Maynard had one more surprise up his sleeve. He’d hidden a large contingent of his force below deck, and as the pirates boarded what they thought was an undermanned ship Maynard’s men charged. The pirates were soon overpowered, and Teach was killed in single combat with Maynard. The life of a man who would be known as one of history’s most infamous pirates had come to an end.

But history sometimes has a way of making itself heard again after hundreds of years. A wreck believed to be the Queen Ann’s Revenge was discovered in 1996, and recovery is ongoing. In August of 2011 the wreckage was confirmed as Blackbeard’s ship. Though Blackbeard is one of the most famous of the Caribbean pirates, few know the true story behind his exploits. His ship, which he ran aground before accepting his pardon in 1718, may hold some of those secrets.

Black Bart: The Greatest Pirate of All

Bartholomew Roberts was a very successful pirate, and among the last of his kind.
Bartholomew Roberts was a very successful pirate, and among the last of his kind. | Source

Ironically, the death of one of the most effective pirates in history would also signal the demise of the pirate lifestyle. History knows him as Black Bart, and he was perhaps the greatest pirate who ever lived. His career lasted from 1719-1722, a short three years, but in that time he captured more ships and caused more havoc than any pirate before or since.

Bartholomew Roberts, known only posthumously as Black Bart, is said to have captured some 470 ships in his career. Though he was of Welsh heritage, he showed no particular allegiance, and no adversity to any challenge. Roberts pillaged ships from the Colonies to Africa to South America. Fearless, ruthless and smart, he had no equal on the high seas.

Roberts came to piracy somewhat against his will when the trade vessel he served on was captured by pirate captain Howell Davis. Davis, a Welshman like Roberts, forced Roberts to join the crew. But Roberts soon found the pirate life to his liking, with far better pay and privileges that his earlier positions aboard merchant ships. When Davis was killed six weeks later, Roberts found himself the surprise winner of the crew’s vote for a new captain.

Roberts raided countless ships from the coast of South America to Newfoundland and Nova Scotia, taking on fleets and single ships alike. At the time, the Royal Navy had established control in the Caribbean, but that didn’t stop Black Bart.

He sailed where he wanted, leaving a trail of destruction in his wake. Along the coast of the Colonies, through the Caribbean, and into the West Indies, Roberts took ship after ship. By the height of his career he had effectively halted all trade in the West Indies.

The End of an Era

Back Bart had become a nightmare for the British Navy, public enemy number one, but at the same time he was somewhat of a hero to the common folk. With every conquest his legend grew, and even his adversaries could not help but admire his bravery and cunning. Roberts was invincible, a ghost on the sea who would never be caught.

Though he was widely feared, he also had a reputation for fairness among his crew. Roberts established rules to ensure professionalism and fair treatment on-ship, and even a system for compensating pirates who were wounded in battle.

He eliminated gambling aboard ship, despised shipboard drunkenness, created a system for settling disputes by duel, laid out standardized punishments should any pirate turn against his shipmates or abandon his post in battle, and even established a time for “lights out” below deck.

Roberts would eventually meet his end off the coast of Africa in combat with the Royal Navy in 1722. Having just plundered a merchant vessel, and with one of his ships already captured by the British, Roberts attempted to escape and took on broadside fire which killed him where he stood.

Stunned, his men lost the ensuing battle and were taken prisoner. Two hundred and seventy-two men under Roberts’s command were captured, and 52 of them eventually hanged during a two-week period. Roberts’s body was never found, believed to have been weighted and buried at sea by his crew during the fight.

The death of Black Bart Roberts, the pirate once thought invincible by the Royal Navy and fellow pirates alike, was a heavy blow for pirates everywhere. Indeed, the end of Black Bart may have sounded the death knell for the Golden Age of Piracy.

The Age of Pirates

Though we have since romanticized the Golden Age of Piracy in movies and books, doubtless travel by sea would have been quite intimidating back then. If we lived during the time, we may have looked upon news of pirate activities in the same way we do terrorists and hijackers today. Pirates were hunted and despised, enemies of every government with few places to hide. Most had short careers with few successes, and most died far before their time.

Nevertheless, men (and a couple of ladies) of varied backgrounds, creeds and nationalities took to the seas dreaming of riches, even though most of their brethren ended up at the end of a hangman's noose. For them, it was far better to live the exciting but shortened pirate’s life than endure the mundane existence of a common man.

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Comments 2 comments

Blond Logic profile image

Blond Logic 3 weeks ago from Brazil

How interesting. Even now there are pirates around the coast of Africa, now they seem to strike only at ships and not towns. It must have been a frightening time when you saw their ship coming toward you or your town.

I reckon Ann Bonny was not just 'hard' but also clever to have escaped.


EricDockett profile image

EricDockett 3 weeks ago from USA Author

@Blond Logic: I suspect citizens back then looked at pirates much in the same way we look at modern pirates. Pirates were criminals then just like today.

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