Piracy in the Caribbean: 5 Famous Real-life Pirates

Caribbean piracy is famous today as a colorful and adventurous footnote in world history, but the truth is far removed from the whimsy invented for movies and amusement parks. Real pirates of the Caribbean were fairly nasty characters, and struck terror in the the hearts and minds of seafarers during the 17th and early-18th centuries. Piracy has existed likely since the first seagoing ships carried trade goods, but this so-called “Golden Age” is often what we think of upon hearing the word pirate. Historians don’t agree with this idealized depiction of pirate life, and paint the careers of famous pirates as extremely harsh, and very short.

Nevertheless, men (and some ladies) of varied backgrounds, creeds and nationalities took to the seas dreaming of riches, even though many of their brethren ended up at the end of a hangman's noose. What was the allure of this lifestyle, and did anyone really sail off into the sunset with their gold, and their head? What follows is a brief glimpse into the careers of 5 real-life pirates of the Caribbean.

Jack Rackam was an English pirate who earned his nickname from the color of his favorite clothes. He first became captain of a sloop called The Ranger, a vessel he had served on under pirate Captain Charles Vane. When Vane balked at attacking a much larger vessel, Rackam accused him of being a coward, swinging the hearts of the crew in his own favor. Pirate ships of the time were operated under democracy, and Calico Jack used the opportunity to send Vane on his way. Captain Rackam then began to plunder the coastline, eventually taking over a ship called the Kingston.

After a brief attempt at going straight in 1719, Rackam returned to the sea and his life of piracy in 1720, this time with a pair of women as part of his crew: His lover Ann Bonny and a woman named Mary Read. Both ladies dressed as men and served as sailors aboard his ship, hiding their true sex from the rest of the crew. Following a short period of mayhem, Rackam and his crew were captured by famous pirate hunter Jonathan Barnet. Jack Rackam was hanged for his crimes in November of 1720 in Port Royal, Jamaica.

Throughout his short time of operation, Calico Jack Rackam was one of the most feared pirates of the Caribbean. His corpse was displayed at the entrance to Port Royal as a warning to other pirates who may think about plundering British ships. 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.

Edward Teach, known as Blackbeard for his wild facial hair, ravaged the east coast of colonial America and the Caribbean from 1716-1718. History describes him as tall, lean and menacing, and he would often burn fuses in his beard or under his hat to frighten his adversaries during battle. Blackbeard, at the helm of the Queen Ann’s Revenge, led a fleet of ships that grew with each conquest. His most infamous deed came when he successfully blockaded Charles Town (Charleston), South Carolina, for six days, taking nine ships in the process.

Blackbeard, too, experimented with the honest life, accepting a pardon in 1718. Not long after, he would resume his life of piracy, taking several vessels in the Caribbean from the helm of his new ship, the Adventure.

Blackbeard would cross paths with fellow pirate Charles Vane, the same man from whom Calico Jack would later wrestle command. Alarmed by this allegiance, authorities in the Colonies sent pirate hunters to bring in the pair, to no avail. But the Royal Navy eventually caught up with Teach. In a bloody last fight, Lieutenant James Maynard would get the best of Blackbeard, and kill him in hand-to-hand combat off the coast of North Carolina.

Blackbeard is one of the most famous of the Caribbean pirates, though few know the true story behind his exploits. His ship Queen Ann’s Revenge, which he ran aground before accepting his pardon in 1718, was found in 1996 and recovery is ongoing.

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. Suddenly an outlaw operating beyond his charter, Kidd went on to attack a Moorish ship allegedly sailing under French authorization. He divided the spoils among his crew, in true pirate fashion.

It didn’t take long for England to learn of the pillaging, and 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 might be unremarkable 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. But some believe Kidd may have secrets still out there, buried and awaiting discovery. Alleged locations of buried treasure range from Oak Island, Nova Scotia to Long Island, NY, to the Thimble Islands in Connecticut to Grand Manan in Canada, but nothing has been found to date.

Yup, this is the guy they named the rum after. Captain Morgan, too, started out as a privateer and made the jump to piracy. Commissioned to stalk Spanish ships in the 1660s, Morgan made a reputation for himself as a good privateer and seaman. He was a floating nightmare for Spaniards in the New World, sacking cities and capturing ships along the Spanish Main. England was happy with him, the Spanish feared him, and he was becoming rich from his conquests.

In 1670 Morgan attacked and demolished Panama City, an act that violated the new peace between England and Spain. Morgan was arrested and taken to England for trial, where he claimed to have no knowledge of the peace at the time of his assault. Due to certain family connections, instead of a conviction Morgan was set free, knighted and returned to Jamaica as Lieutenant Governor.

Though operating under the charter of a privateer, to the Spanish there was likely no difference between Morgan and any other pirate. His ruthless style and bold military planning made him feared throughout the Caribbean. Morgan is also one of the few pirate captains of the time to live beyond his career. He retired to his plantation in Jamaica where he passed away at the age of 53.

Bartholomew Roberts, known as Black Bart, is said to have captured some 400 ships in his 4-year career, making him the most successful pirate in history. Showing no particular allegiance, nor adversity to challenges, Black Bart pillaged ships from the Colonies to Africa to South American. Fearless, ruthless and smart, Black Bart had no equal on the high seas. At the time, the Royal Navy has 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.

Though he was widely feared by adversaries, 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.

Roberts would meet his end in combat with the Royal Navy in 1722. In an attempt to escape, Roberts’s ship took on broadside fire which killed Roberts where he stood. Stunned, his crew lost the fight and was taken prisoner. Two hundred and seventy-two men 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, sent shockwaves through the pirate ranks. Indeed, the end of Black Bart may have sounded the death knell for the Golden Age of Piracy.

Though we have since romanticized the Golden Age of Piracy in movies and books, doubtless travel by sea back then would have been quite intimidating. 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. But a soiled reputation wasn't enough to stop thousands of men from going to sea to test their mettle, and maybe find their fortune. For those of us who enjoy travel and cruising, it’s definately a good thing that piracy in the Caribbean died out along with the famous pirate Black Bart!