In modern times we tend to associate the word piracy with dodgy folk downloading from the comfort of their own homes to earn a buck, but we’ve taken a look at 4 of the most popular pirates of all time to see how these guys earned their reputations for being real pirates, in the truest sense of the word.

WORDS by Leticia Nguyen

Bartholomew ‘Black Bart’ Roberts

Englishman Bartholomew ‘Black Bart’ Roberts is arguably one of the most successful pirates during the ‘Golden Age of Piracy’, as he managed to capture 400 ships during his brief career that spanned over 4 years. Originally forced to join the crew aboard Captain Howell Davis’ ship, Royal James, it was only 6 weeks after his arrival when Davis was killed and Roberts was named the new captain by his cohorts, who had been impressed by his leadership and organisational skills. Although he was a reluctant pirate at first, Roberts embraced the role of captain, saying, “It is better to be a commander than a common man.” Despite that he was known for his charms, at times he was equally cruel and in January of 1722, he was sailing near Whydah, a well-known slaving area, when he found a slave ship and ordered it to be burned when the captain refused to pay a ransom. Roberts couldn’t stand to wait for them to release some 80 shackled slaves and in his haste, set the ship alight with the slaves on board. After a bountiful career sweeping across the Bahamas, the Caribbean, Africa and Brazil, Roberts and his crew were eventually pursued by the Royal Navy’s Swallow and rather than surrender, Roberts decided to thrust himself into battle. After donning his fancy threads for battle (crimson silk waistcoat, feather in hat and a gold chain around his neck), he was killed in the first broadside as grapeshot fired from one of the Swallow‘s cannons.

Francois L’Olonnais

Frenchman Francois L’Olonnais left a legacy as one of the most barbaric and ruthless pirates who had a deep-rooted hatred for the Spanish. L’Olonnais was an expert torturer, and he was partial to slicing portions of flesh off the victim with a sword, burning them alive, or ‘woolding’, which involved tying knotted rope around the victim’s head until their eyes popped out. After an attack near Campeche, Mexico, in which L’Olonnais lost almost his entire crew at the hands of Spanish soldiers, L’Olonnais survived by covering himself in the blood of others and hiding amongst the dead. After the Spanish departed, L’Olonnais escaped and made his way to Tortuga where he and his remaining men held a town hostage, demanding a ransom from its Spanish rulers. The governor sent a ship to kill L’Olonnais’ party, but L’Olonnais captured and beheaded the entire raiding crew except one, who was spared so as to send a message that he wasn’t a pushover. During another incident in which he was so frustrated with a Spanish captive he was interrogating, L’Olonnais took out his cutlass and cut open the chest of the Spaniard in question, pulled out his heart and began to gnaw at it, saying “I will serve you all alike, if you show me not another way.” But as the saying goes, ‘he who lives by the sword dies by the sword’ and L’Olonnais was served an equally gruesome death as he had given his victims when he was captured in the Darien, Panama, and eaten by the native Kuna people.

Cheng I Sao

Giving her male counterparts a run for their money, Cheng I Sao, also known as Ching Shih, added a female touch during her reign of terror of the China Sea and was one of the few pirates to retire from piracy. Cheng I was working as a prostitute in a small brothel in Canton when she was snared by pirates and managed to capture the attention of Zheng Yi, who she then married, launching her into the world of piracy. After her husband died in Viet Nam, she quickly took the reigns and made her way to a position of leadership. She was savvy in forming alliances with powerful family members of her late husband and through her business smarts, military strategy, and leadership skills, Cheng I took piracy to a new level. Not content with just pillaging and looting, the ambitious pirate added extortion, spying, kidnapping, and ‘protection’ service. Over the span of her pirate career, Cheng I controlled more than 1500 ships and some 80,000 men. She enforced a strict code on her crew, such as, anyone giving their own orders (ones that did not come down from herself) or disobeying those of a superior were beheaded on the spot. The Chinese navy, along with the navies of Britain and Portugal could not defeat Cheng I. Realising the futility of defeating her, the Chinese government offered amnesty to Cheng I and her crew and she took advantage of it. She ended her career that year after accepting the amnesty offer and ran a casino/brothel after retiring from piracy.


If there were a poster boy of piracy, Edward ‘Blackbeard’ Teach would most probably be the guy. A legendary pirate who has been steeped in popular culture throughout the ages, he was a charismatic chap who earned his name for his black and bushy facial hair. He was all about keeping up appearances and instilled fear through his distinctive flag that featured a white, horned skeleton against a black background, holding a spear that pointed to a red heart. There are blood drops near the heart and the skeleton is toasting the devil with a glass in his hand. He had one of the most formidable pirate ships in history, which he’d equipped with 40 cannons to terrorise the Atlantic and the Caribbean for almost a year before it ran aground. Before battle, he made himself look intimidating by dressing all in black, strapping several pistols to his chest and putting on a large black captain’s hat. Then, he would put slow burning fuses in his hair and beard, that would emit smoke and give him a fearsome, demonic appearance and apparently, his enemies were terrified of him. At one stage, it looked as though he was going to retire from piracy when he accepted a pardon from the Governor of North Carolina. However, old habits die hard and before long he was back in the game until he was eventually captured and decapitated. His head was put on display on the prow of his capturer, Robert Maynard’s ship.

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