25 Most Feared Pirates To Ever Set Sail

Posted by on May 31, 2013

When most people think of piracy they probably think of skull and crossbones, eye patches, and wooden legs. While these would all certainly be true to some extent; at its core, piracy has always been about the plunder. If there were nothing to steal there would be no pirates. As it is, however, from centuries past to this very day pirates are alive and well on the high seas. These are the 25 most feared pirates to ever set sail.


William Kidd

William “Captain” Kidd was a Scottish sailor who was tried and executed for piracy after returning from a voyage to the Indian Ocean. Some modern historians deem his piratical reputation unjust, as there is evidence that Kidd acted only as a privateer. Kidd’s fame springs largely from the sensational circumstances of his questioning before the English Parliament and the ensuing trial. His actual depredations on the high seas, whether piratical or not, were both less destructive and less lucrative than those of many other contemporary pirates and privateers.


Peter Easton

Peter Easton was a pirate in the early 17th century who operated along the Newfoundland coastline between Harbour Grace and Ferryland from 1611 to 1614. Perhaps one of the most successful of all pirates he controlled such seapower that no sovereign or state could afford to ignore him and he was never overtaken or captured by any fleet commissioned to hunt him down.


Edward Teach

Edward Teach, better known as Blackbeard, was a notorious English pirate who operated around the West Indies and the eastern coast of the American colonies. Although little is known about his early life, he was likely born in Bristol, England. A shrewd and calculating leader, Teach spurned the use of force, relying instead on his fearsome image to elicit the response he desired from those he robbed. Contrary to the modern-day picture of the traditional tyrannical pirate, he commanded his vessels with the permission of their crews and there is no known account of his ever having harmed or murdered those he held captive. He was romanticised after his death and became the inspiration for a number of pirate-themed works of fiction across a range of genres.


Francois L’Ollonais

L’Olonnais first arrived in the Caribbean as an indentured servant during the 1650s. By 1660, his servitude was complete and he began to wander the various islands, before finally arriving in Saint-Domingue and becoming a buccaneer. A year or two into his piratical career he was shipwrecked near Campeche in Mexico. A party of Spanish soldiers attacked his crew, killing most of them. L’Ollonnais himself survived by covering himself in the blood of others and hiding amongst the dead. He managed to escape and made his way to Tortuga where he held an entire town hostage, demanding a ransom from its Spanish rulers. The governor of Havana sent a ship to kill him, but l’Olonnais captured and beheaded the entire raiding crew save one, whom he spared so that a message could be delivered to Havana: “I shall never henceforward give quarter to any Spaniard whatsoever.”


Edward Lowe

Known for being a hoodlum-turned-pirate, Edward Lowe spent his childhood pick pocketing and beating up people for money. As he approached adolescence, he became a ship rigger and went in with a sloop sailing to Honduras where he had his first experience of piracy. It has been said that he often tortured his captives as he sailed around the Azores and teamed up with other notorious pirates who practiced sadism just as he did.


Bartholomew Roberts

A Welsh pirate, Bartholomew Roberts, more commonly known as “Black Bart”, is often considered the most notorious pirate of his day. He took to sea at a very young age and grew up as a highly competent sailor. In the 17th century, people would dread sailing off the coast of South America because of his notoriety.


Thomas Tew

Referred to by King William III as a “wicked and ill-disposed person,” Tew was one of the most feared pirates of the Red Sea in the 17th century. His piracy began when the Governor of Bermuda sanctioned him to attack all the French ships and colonies he could find along the African Coast. Fearless as he was, he attacked a widely celebrated Indian ship manned by about 300 soldiers in Madagascar and still managed to win. He died, however, after obtaining a mortal wound and the rest of his crew was executed following his death.


Edward England

Born Edward Seegar, England’s career as a pirate began when he was enlisted as a first mate on a ship that was eventually taken by a pirate named Captain Winter. As a captive, he won the confidence of the crew of Captain Winter and became one of them. He sailed throughout the Caribbean and African seas and succeeded in robbing and taking several ships there, the most popular of which was a ship from Bristol named Cadogan. He tortured and killed the captain of the ship before bringing his reign of terror to Madagascar where he attacked several Dutch ships and enlisted even more seafarers into piracy.


Cheng I Sao

A feared female Chinese pirate who married another notorious pirate in 1801, I Sao took over the fleet of her husband when he died and developed a code of laws that steered over 1,500 ships and 80,000 sailors. She became the most infamous pirate in Asia but the murder, looting, and other crimes that she masterminded led to her eventual downfall when she was captured and executed by Portuguese and British bounty hunters.


Sir Francis Drake

Originally a politician of the Elizabethan era in England, Sir Francis Drake was the man behind the second circumnavigation of the world and was notoriously known for his successful attacks on San Juan, one of the largest ports of Puerto Rico.


Calico Jack

Born John Rackham, Calico Jack  proved his ruthlessness and ferociousness as a pirate when he captured the largest Spanish war ship in the Caribbean, killing numerous sailors, and even stabbing many of his closest compatriots in the back.


Stede Bonnet

Born in 1688 to a well-heeled family of landowners, Stede Bonnet, then referred to as “The Gentleman Pirate,” first turned to a life of piracy when he purchased a ten-gun sloop named Revenge. He had the local authorities in England believe that he was a pirate hunter and privateer, when all he did was attack, plunder and burn ships along the Eastern coast and wage battles against Spanish sailors.


Admiral Sir Henry Morgan

Sir Henry Morgan first built his reputation as a pirate when he plundered Santiago De Cuba and Campeche, Mexico shortly after sailing in the buccaneer fleets employed by England to attack Spanish settlements in the 16th century. Later in his life as a pirate, he was commissioned by Jamaican governor Modyford to wage a battle against Spanish sailors in the Caribbean, where he ultimately emerged as the victor and solidified his fearsome reputation.


Henry Avery

Henry Every, also Evory or Avery, sometimes erroneously given as John Avery, was an English pirate who operated in the Atlantic and Indian Oceans in the mid-1690s. He likely used several aliases throughout his career, including Henry Bridgeman, and was known as Long Ben to his crewmen and associates. Dubbed “The Arch Pirate” and “The King of Pirates” by contemporaries, Every was the most notorious pirate of his time; he earned his infamy by becoming one of the few major pirate captains to retire with his loot without being arrested or killed in battle.


Charles Vane

Charles Vane was an English pirate who first arrived in Port Royal during the War of Spanish Succession in the 17th century. Following the rejection of the King to grant him and his fellow pirates an honourable retirement from piracy, he took revenge by utilizing his small ships to spread terror throughout North Carolina where he captured about twelve ships and cruelly tormented sailors who failed to help him locate the treasures on board.