Real Pirates of the Caribbean

The 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.