25 Most Feared Pirates To Ever Set Sail

Who were the most feared pirates to ever set sail? Well, we’re here to find out. While today’s culture loves to romanticize pirates as lovable and charismatic rogues who sailed the seas to bravely rebel against the tyrannical and greedy trade companies, it shouldn’t come as too much of a surprise that real pirates weren’t nearly so hip. In their own time, pirates and buccaneers were shunned from society not only because they were often criminals and murderers, but because they were downright terrifying. Whether it was because of their vast success or their extreme cruelty, there’s no denying that these villainous mariners are the 25 most feared pirates to ever set sail.


Thomas Tew

tewSource: http://www.thewayofthepirates.com/famous-pirates/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. He was notoriously fearless, and he once attacked a widely celebrated Indian ship manned by about 300 soldiers in Madagascar and managed to return victorious. He was eventually killed by a cannonball during a raid in Madagascar, with the rest of his crew being executed following his death.


Don Pedro Gilbert

Pedro GilbertSource: https://www.citylifebarcelona.com/fame-in-spain-the-pirate-captain-pedro-gilbert/

Don Pedro Gibert was an early 19th century pirate, who was one of the few remaining pirates continuing to raid shipping on the Atlantic coast. Gilbert held the distinction of taking part in the last recorded act of piracy in Atlantic waters, although the distinction of “last American pirate” belongs to Nathaniel Gordon who was executed in 1862 for attempting to smuggle African slaves in violation of the U.S. Piracy Law of 1820.


Edward England

englandSource: http://www.thewayofthepirates.com/famous-pirates/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. He eventually won the confidence of the crew and joined them in sailing and plundering throughout the Caribbean and African seas. Eventually he received a ship and crew of his own and brought his reign of terror to Madagascar, where he attacked several Dutch ships and enlisted even more seafarers into piracy.


Stede Bonnet

14bonnetSource: http://www.thewayofthepirates.com/famous-pirates/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 was able to convince the local authorities in England 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.


Laurens de Graaf

16degraafSource: http://brethrencoast.com/pirate/Laurens_de_Graff.html

Regarded as one of the best and most respected buccaneers to ever sail, Laurens de Graaf led a number of lucrative pirate raids on Spanish ships and coastal colonies in and around the Gulf of Mexico and Caribbean seas. By the end of the 17th century he had earned so much notoriety that a number of Spaniards began referring to him as the Devil incarnate.

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