Pirates have been an integral part of the maritime culture for centuries, captivating the imaginations of people worldwide with their romanticized image. These seafaring bandits are notorious for their cunning and intrepid deeds on the high seas, with some even achieving legendary status. This article intends to examine the lives of some of history’s most famous pirates, revealing the reality behind the myths that envelop them.
Blackbeard
Blackbeard, although not the most successful and feared sea robber, remains the most prominent pirate in Caribbean history, as well as in the history of piracy in general.
His notorious and fearful reputation was largely due to his long black beard that covered most of his face, which he would often separate into tails tied with different colored ribbons for his own entertainment. In terms of apparel,
Teach, as he was also called, always carried multiple pirate weapons, wearing a sling with three pairs of pistols across his chest, in addition to his cutlass and a few knives fastened on his belt. His mere appearance was enough for many opposing crews to surrender, though there are rumors that he treated his accomplices generously.
Despite being a pirate, he was intelligent and well-educated, capable of reading and writing. Blackbeard was also known for his weakness for women, having had around 14 wives, though his marriage to 14-year-old Mary Ormond was reportedly his only legitimate marriage.
During the War of Spanish Succession, he worked in Jamaica as a privateer. Following the war, Blackbeard relocated to New Providence, Bahamas where he served as an ordinary crewman on Captain Benjamin Hornigold’s pirate ship.
Later, he was granted his vessel along with a small crew by his mentor, and promoted shortly after. Blackbeard built up a fearsome reputation by plundering many ships alongside Hornigold and captured the 300-ton frigate armed with 26 guns, “Concorde”.
When Woodes Rogers, the governor of the Bahamas, extended general amnesty for pirates in the Caribbean, Hornigold accepted it. Edward Teach got control of the fleet upgraded the captured frigate with 40 guns and renamed it “Queen Anne’s Revenge” to continue his pirate career. He achieved significant victories, including an epic sea battle against the formidable warship HMS “Scarborough,” which boosted his reputation even further.
Benjamin Hornigold
Benjamin Hornigold was a Caribbean privateer who turned to piracy after the War of the Spanish Succession had concluded. However, fate provided him with one final mission in his career, which was to become a pirate hunter. He was regarded as a skilled captain who treated prisoners more humanely than other pirates.
Hornigold was most famed for being Blackbeard’s associate. Even though there are no facts about his privateer days, Hornigold was highly successful during this period, which made him an exceptional leader and captain.
After the conclusion of the war, Hornigold sailed from New Providence and became a pirate captain. Among his crew was a group of talented pirates. Samuel Bellamy, among others, later became more famous and successful than Hornigold. The most renowned apprentice under his supervision was Edward Teach, who went by the moniker Blackbeard.
Captain Kidd
Captain William Kidd was a Scottish privateer who became famous for his acts of piracy. He was born in Greenock, Scotland around 1645 and had always dreamed of becoming a sailor, and later a privateer and pirate hunter. In New York, Kidd’s career as a privateer grew rapidly after many successful raids. He even married a wealthy young widow and had two children.
In 1695, Kidd was called to England by the king to be put in charge of the galley warship “Adventure” and hunt pirates on the Red Sea. The mission also involved semi-legal actions that were aimed at bringing a big profit. Kidd was given two commissions, one to capture French ships and the other to be a pirate hunter for the government.
However, upon leaving the Chatham dockyard, almost all of Kidd’s best crewmen left him, forcing him to recruit new members in New York. Unfortunately, these new crewmembers were mostly former smugglers and pirates who intended to attack all ships with no exception.
Later in 1698, Kidd captured his biggest prize, the Quedagh Merchant, a 400-ton ship hired by Armenian merchants and led by an Englishman. The catch was a great success, but it led the revolted East India Company to force the government to brand him a pirate. The backers could not support him anymore, and Kidd became a wanted man.
In April 1700, he sailed to New York for refuge but was arrested and sent back to England. Kidd was tried in May 1701 and sentenced to death for piracy and killing his gunner. His once-promising career as a privateer ended tragically with his execution.
After his death, the pirate Captain Kidd became a subject of romanticism, and his exploits became popular in pirate-themed works of fiction. The legend of his leaving buried treasure contributed substantially to his myth, inspiring numerous treasure hunts throughout history.
Charles Vane
Charles Vane was an exceptionally skilled pirate captain known for his unmatched navigating and ship combat expertise, successfully pillaging numerous vessels. Despite his successes, his difficult relationships with his crew ultimately led to his downfall and the end of his career.
Vane’s pirating began in 1716 as a crewmember under Henry Jennings, raiding the ships and camps of Spanish galleon salvagers on the coast of eastern Florida. In 1718, after Jennings accepted a pardon from Governor Woodes Rogers, Vane became a captain in his own right and quickly gained infamy through capturing vessels and brutally torturing and killing prisoners. He was one of the few pirates who refused to accept the king’s pardon.
Calico Jack
Despite not achieving the same level of wealth and respect as some other well-known Caribbean pirates, John “Jack” Rackham, also known as “Calico Jack,” remains one of the most memorable pirates due to his unique associations and female crew members.
Calico Jack was not known for his fighting skills or naval tactics but instead relied on his cunning mind and tendency to use politics and backstabbing to achieve his goals.
After his death, written publications and the rise of the pirate romanticization movement contributed greatly to his fame and the legend of Calico Jack continued to grow.
One of his significant impacts on the modern image of pirates is his iconic Jolly Roger flag featuring a black background with a white human skull and two white crossed swords beneath it. While many pirate crews used flags with full skeletal depictions using weapons, Calico Jack’s design remains a synonym for piracy on the high seas.
Anne Bonny
Anne Bonny was an exceptional woman who lived way ahead of her time. During the 18th century, men held all the power and made crucial decisions while women were denied basic rights. As a result, Anne Bonny had to work hard at gaining equal status and respect as a crewmember and pirate in this male-dominated world.
Anne was married at an early age but left her spouse and eloped with the charming pirate captain, Calico Jack Rackam, who even proposed to buy her freedom from her husband.
Calico was a low-profile pirate mainly targeting coastal ships and wasn’t overly profitable; however, he possessed a talent for spending money extravagantly. Anne and Calico’s romantic affair was not openly disclosed; however, their ship’s crew was fully aware of Anne being referred to as “the captain’s woman.”
When Ana discovered she was expecting a child, Rackam left her in Cuba to give birth. After some time, Ana rejoined Rackam’s vessel, however, notorious Mary Read had joined the crew by then.
It wasn’t long before the two women formed a close bond and became good friends. Some crew members claimed that Ana and Mary even had a romantic relationship.
Emanuel Wynn
Emanuel Wynn, also known as Emmanuel Wynne and Emanuel Wynne, was a French pirate who operated during the 1700s. Although little is known about him, records indicate that he was active in the late 17th century in the Province of Carolina and later became a threat to Spanish and English ships in the Caribbean.
The only written accounts about Wynn come from the British Admiralty Record which reports his encounter with Captain John Cranby of HMS Poole ship. The two ships engaged in a battle near the Cape Verde Islands, and Wynn fled towards Brava Island with the help of Portuguese Soldiers.
Emanuel Wynn is believed to be the first pirate to fly a Jolly Roger with his flag depicting a variant of the now iconic crossbones motif. However, it featured an hourglass symbolizing that the time for the pirate’s target has ended. Some suggest that the hourglass flag represented the notion that the target can only evade death by surrendering immediately.
Henry Every
Henry Every, who also went by the aliases of John Avery, Long Ben, and Benjamin Bridgeman, was a well-known pirate who was the subject of many books and plays detailing his swashbuckling adventures.
It is believed that he was born near Plymouth, England around 1653 and began his career at sea working on unlicensed slave ships. In 1694, Every served as the first mate on board the “Charles II,” a 46-gun Spanish ship that had been granted permission to attack French smugglers near Martinique.
However, Every instigated a mutiny aboard the vessel and was ultimately chosen by the crew as the new captain. He then renamed the ship “Fancy” and charted a course for the Cape of Good Hope. His ship went on to become one of the most famous pirate ships in history.
The most significant achievement in Henry Every’s career was the capture of “Gang-i-Sawai,” which was part of the Indian Grand Moghul’s fleet. During the attack, they managed to obtain approximately 600,000 pounds worth of loot, consisting of gold, silver, and jewels.
Many pirates on his crew chose to retire, leading to the disbandment of the fleet, with Henry continuing his journey on the Fancy alongside several remaining original crew members.
They sailed towards the Caribbean, where he offered the governor of New Providence a bribe of 7,000 Pounds for protection. Following this transaction, Henry changed his name to Benjamin Bridgeman before sailing off to Ireland, ultimately disappearing into anonymity.
Bartholomew Roberts
Bartholomew Roberts, also known as Black Bart due to his violent activities, is believed to be the most successful pirate in history. According to rumors, he plundered nearly 400 ships – a feat no other pirate could match.
Roberts hailed from South Wales and was originally named John Roberts. He had a long-standing association with ships since his younger days and served as a Third Mate on board the British Slaver “Princess.”
However, while serving the ship near Guinea cost, he was captured and held captive after pirates led by Howell Davis raided it. Initially forced to join his captors, Roberts soon embraced the pirate life and saw it as an ideal career.
Roberts displayed exemplary qualities from the outset and quickly became Davies’ trusted aide. However, in June 1719, Davis and some of his crewmates were killed in an ambush, prompting Roberts to take charge of the remaining crew.
Despite having spent only a brief time with the crew, they unanimously elected him their new captain. Hence, he adopted a new identity, Bartholomew Roberts, and commenced his life as a notorious pirate.
His lasting success can be attributed to his boldness and fearlessness. Despite encountering many superior warships, which other pirates would avoid at all costs, Roberts terrorized every ship he came across in the Caribbean Sea.
Roberts did not choose piracy as a trade by himself, but once he embarked on it, he quickly became a notorious and successful pirate. He was described as a tall and attractive man who loved to wear expensive clothes and jewelry.
Ching Shih
Ching Shih, who was also known as Shi Xianggu, Madame Ching, Zhèng Shì, Jehng Sih, Zheng Yi Sao, and Cheng I Sao, is undoubtedly one of the most exceptional pirate leaders ever.
Born in 1775, she stood out not only because of her gender but also because she personally led more than 300 pirate ships and commanded over 20 thousand pirates. Moreover, she formed an alliance with multiple other pirate leaders, who followed her, creating a naval force that included 1500 ships and 180 thousand pirates.
What sets her apart from other sea pirates in history is that she managed to retire from being a pirate without facing punishment, spending the rest of her days in peace until she passed away from natural causes in 1844.
Samuel Bellamy
Black Bellamy, formerly known as Captain Samuel Bellamy, was a tall and robust man who had impeccable manners. He had a fondness for wearing expensive clothing, particularly his favorite black coats. His preferred weapons were four dueling pistols which he always kept on his sash.
He governed his crew through democratic rules, earning their affection and sometimes even being referred to as “Pirate Robin Hood.”
Aside from his good leadership, Captain Bellamy was also an adept strategist. He usually commanded two ships; one was a powerful flagship equipped with numerous cannons, while the other was swift and light, creating a well-balanced team. With well-coordinated attacks, they could successfully take over other ships without causing unnecessary damage.