From the Age of Sail to the end of the Colonial Era, pirates were a force to be reckoned with on the high seas. The most famous pirates came from every corner of the globe, but they all carried a greed and ambition that propelled them into the history books. But success breeds resentment, and when it comes to pirates, that usually means a mutiny or a fight to the end. Many pirates were sure to change allegiances many times over the course of their careers - unless, of course, they were the captain and earned enough respect to plunder until they could retire comfortably.
Of course, few pirates passed peacefully in their old age. Most were either slain by their own kind, taken down by the authorities, or claimed by an angry sea. The most deadly and ruthless of them still live on in infamy to this day, so if you’re curious to know who they are, check out this list of the deadliest pirates in history.
François l'Olonnais was a pirate and naval surgeon who arrived in the Caribbean as an indentured servant. After getting shipwrecked, L'Olonnais avoided capture from the Spanish by covering himself in blood and sand and playing possum.
He then went on pirating, holding up a Spanish town for ransom with his new crew, then capturing the Spanish soldiers who were sent to stop him. He beheaded all but one of the rescuers, whom he sent to give a message to the governor of Havana: “I shall never henceforward give quarter to any Spaniard whatsoever.”
L’Olonnais continued his pirating career, gathering a fleet of eight ships and 600 pirates. In every city he plundered, he’d torment the residents to find their wealth. They sacked the fortified settlement of Gibraltar, taking only 70 casualties compared to the 500 Spanish casualties they inflicted. When he raided San Pedro, he captured Spanish soldiers and tortured one of them by cutting open his chest and pulling out his heart. Then, he ate the heart. The rest of the soldiers told him anything he wanted to know.
According to Cindy Vallar:
L’Olonnais was a master torturer. Not only did he burn his victims or cut out their tongues, but when he began cutting them to pieces, he started with a slice of flesh, progressed to a hand, then an arm, and finally a leg. He favored the practice of 'woolding,' where he tied a cord around his victim’s eyes and tightened the cord by twisting it with a stick until the man’s eyes popped out of his head.
Eventually, L’Olonnais was captured by the Indians of Darien, who tore him apart and threw him into a fire.
Blackbeard (who may have been named Edward Teach) originally served as an apprentice to the famous pirate Benjamin Hornigold before ascending to his own captaincy. He captured a French ship and named it the Queen Anne’s Revenge. He increased the ship’s guns from 26 to 40 and used it as a flagship to create his very own pirate fleet.
Blackbeard gained a fearsome reputation, in part due to his long dark beard (which he tied up into pigtails with colorful ribbons) and enough pistols and blades on his person to stop an army. In 1724, Captain Charles Johnson wrote that Blackbeard "had often distinguished himself for his uncommon boldness and personal courage." Before a fight, he’d light smoking fuses tucked under his hat to scare his enemies. He gained infamy not only for his cruel tactics but his blockade of Charleston.
As the Golden Age of Piracy was nearing its close, Blackbeard tried to secure a pardon but was attacked by the British. He perished during a famous duel with the British Lieutenant Robert Maynard, who ordered his men to decapitate Blackbeard and suspend his body from two vessels. The crew disposed of the rest of Blackbeard's body.
In 1801, the Chinese pirate captain Cheng married a sex worker known only as Cheng I Sao. She agreed to marry him only if she could share power and wealth with him, and he agreed. It turns out Cheng I Sao was a pirate prodigy, quickly growing their piracy business into a formidable empire. Even after her husband passed, she led his men into combat to expand her enterprise. Soon, she became in charge of all piracy in the region. She also made inroads on land, creating a network of spies and farmers that kept her organization well-informed and well-fed.
Cheng ruled her empire with an iron fist, beheading unruly pirates and slaying those who cheated on the brides they purchased. But her success garnered the attention of the authorities, and it wasn't long before the Chinese Navy along with foreign bounty hunters were pursuing her across the sea.
After unsuccessfully trying to capture her, the Chinese government offered her a full pardon in exchange for a peaceful resolution to her piracy. She accepted, then retired with her riches to land where she opened a gambling establishment. She passed peacefully as a grandmother at 69, which is pretty impressive for 1844.
While there isn’t much concrete information on her, it’s been said that Anne Bonny rejected her father’s choice of husband and instead married a sailor. She moved with him to the Bahamas, but she quickly grew unhappy with the marriage and became involved with John “Calico Jack” Rackham. She abandoned her husband and commandeered a ship with Rackham. The two began pirating ships off the Jamaican coast.
Always tough, Bonny disguised herself as a man during pirating raids, though her real identity was known to her crew.
After a few months, however, the crew was captured and put on trial. Bonny and her female companion, Mary Read (who also dressed as a man), were both discovered to be pregnant, which earned them stays of execution. Read passed in prison, but Bonny was released. She later married and lived out the rest of her life with her family.
A Welsh sailor aboard the slave ship Princess when it was captured by the pirate Howell Davis, Bartholomew Roberts (known as "Black Bart") was forced to join the pirate’s crew. However, only six weeks later, Davis was slain and Black Bart was voted to become the new captain. Black Bart took to his new position with zeal, plundering a treasure fleet and making off with their richest ship. However, a mutiny led to some of his men taking that ship and its plunder.
Black Bart continued to plunder, battling pirate hunters off Barbados and sinking 21 ships docked in Newfoundland harbor. Soon, Black Bart had his own fleet, and he promoted himself to “Admiral of the Leeward Islands.” He then plundered Africa, where he amassed an even greater fortune and a ruthless reputation - when the captain of a slave ship refused to pay a ransom, Black Bart set fire to the ship without first releasing the enslaved people.
Black Bart was the most successful pirate from the Golden Age of Piracy, looting more ships than any other. Eventually, however, pirate hunters caught up with him. He was hit with grapeshot during the fight, and his men threw his body overboard.
Little is known about Henry Every’s early years, though we know he was a slave trader. He later became the first mate of a privateering vessel, the Charles II. He led the Charles II’s crew in a mutiny, became the captain, renamed the ship The Fancy, and set course for Africa to plunder shipping lanes. They captured several French and Danish ships and expanded their ranks until they had reached 150 strong. With their newfound strength, they targeted Indian flotillas.
Every became tremendously wealthy, successfully capturing heavily armored ships full of hundreds of thousands of British pounds' worth of riches. In 1695, he set his sights on a Mughal flotilla filled with Indian treasure, and launched a bloody strike on the Mughal flagship, the Ganj-i-Sawai. A ferocious fight followed, and the Indian soldiers backed down while their captain abandoned them, and soon Every had control of the ship. His notoriously vicious crew tormented the men on board and raped the women, leading some women to take their own lives to evade the marauders. The jewels, gold, and silver taken during the attack were worth the equivalent of tens of millions of dollars today.
After dividing the spoils among themselves, Every's men set course for the Bahamas to relax. Though the British tried to hunt down Every and his men, they scattered throughout the world and retired with their wealth. Only a few were ever found and executed.
