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.


William Kidd

BurdickSource: http://www.thewayofthepirates.com/famous-pirates/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.


Pierre le Grand

24legrandSource: https://www.revolvy.com/page/Pierre-le-Grand-%28pirate%29

Although little is known about the mysterious Pierre le Grand, with some historians doubting his existence altogether, what is known is nothing short of hardcore. With his tiny ship and crew of only 28 men, le Grand was able to take a Spanish treasure ship by surprise and subdue its captain and crew before they even knew they were being raided. According to the legends, le Grand also had a hole cut in the side of his own ship to sink it before the raid, proving to his crew that retreat was not an option and forcing them to fight for their lives.


Black Caesar

Black CaesarSource: https://www.britannica.com/story/black-pirates-and-the-tale-of-black-caesar

Born a slave, for nearly a decade, he raided ships along the Florida Keys and later served as one of Captain Blackbeard’s chief lieutenants aboard the Queen Anne’s Revenge. He was one of the surviving members of Blackbeard’s crew following the captain’s death in 1718 and would eventually captain a ship and crew of his own. Caesar’s Rock, one of three islands located north of Key Largo, is the present-day site of his original headquarters and named in his honor.


Edward Low

BurdickSource: http://www.thewayofthepirates.com/famous-pirates/edward-low/

Known for being a hoodlum-turned-pirate, Edward Low spent his childhood pick pocketing and beating up people for money. As he approached adolescence, he became a ship rigger and signed onto 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, often teaming up with other pirates who shared his brutal ways.


François l'Olonnais

OlonniasSource: http://www.thewayofthepirates.com/famous-buccaneers/francois-lollonais/

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.”

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