25 Most Feared Pirates To Ever Set Sail

Posted by , Updated on April 24, 2024

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.”


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.


Calico Jack

rackhamSource: http://www.thewayofthepirates.com/famous-pirates/calico-rackham-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.


Turgut Reis

2reisSource: http://www.thewayofthepirates.com/famous-pirates/turgut-reis/

Reis was a notorious Turkish admiral and privateer who terrorized the Mediterranean and Black Sea and was among the most influential men to pave the way for Turkish expansion into Northern Africa. He led a good number of naval battles against the Venetians and gained full control of some of the most advanced naval ships and war equipment of his century. He was also appointed as the naval commander of the Ottoman Empire and raided a number of cities along the coasts of Europe.


Anne Bonny

6bonnySource: http://www.thewayofthepirates.com/famous-pirates/anne-bonny/

Born Anne Cormac of County Cork, Ireland, Anne Bonny sailed across the Atlantic at a very young age. As young as a teenager, she settled for a life of adventure by marrying a renegade seaman and turning to the pirate haven of Nassau. When she got involved in a romantic relationship with notorious pirate Calico Jack, she further solidified her bloodthirsty reputation.


Charles Vane

11vaneSource: http://www.thewayofthepirates.com/famous-pirates/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.


Cheung Po Tsai

Cheung Po TsaiSource: http://www.thewayofthepirates.com/famous-pirates/cheung-po-tsai/

A Chinese pirate, Cheung Po Tsai rose to infamy because of the legend of the hidden treasure in the Cheung Po Tsai Cave in China. History has it that he harassed the Guangdong Coastal area during the reign of the Qing Dynasty, commanding more than 20,000 pirates and hundreds of ships. He is believed to have hoarded vast treasures in a hideout on a barely accessible island somewhere in the South China Sea.


Sir Henry Morgan

13morganSource: http://www.thewayofthepirates.com/famous-buccaneers/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.


Samuel Bellamy

bellamySource: http://www.thewayofthepirates.com/famous-pirates/samuel-bellamy/

Then referred to as “Black Sam” of the Caribbean Sea, Samuel Bellamy was an English pirate captain who terrorized the Caribbean when he captured the giant slave ship Wydah, which carried a valuable cargo of both gold and rum. After mounting 28 cannons into Wydah and turning it into his flagship, Bellamy went toe-to-toe with several royal navy ships. He captured numerous other pirate ships and sailors as he sailed through the Caribbean before he and his crew headed off to New England to plunder more lucrative shipping lanes.


Howell Davis

7davisSource: http://www.thewayofthepirates.com/famous-pirates/howell-davis/

Born in Milford Haven, Pembrokeshire, Wales, Davis started out in piracy on 11 July 1718 when the slave ship Cadogan, on which he was serving as a mate, was captured by the pirate Edward England. He had a short but intense career that lasted just 11 months before he was ambushed and killed. In that short time, however, he managed to leave a legacy of bloodshed and deception.


Mary Read

3 readSource: http://www.thewayofthepirates.com/famous-pirates/mary-read/

Triggered by her harsh childhood, the pirating career of Mary Read began when she joined the navy to find an escape from her miserable life. As part of the naval army, Read would sail to the Caribbean Sea on a Dutch ship, where she would encounter the infamous privateer Calico Jack who captured and plundered their ship. Read started to live a pirate way of life soon after their capture, becoming friends with Anne Bonny and joining her in her conquests across the Caribbean waters.


Henry Every

12 everySource: http://www.thewayofthepirates.com/famous-pirates/henry-every/

Henry Every, often mistakenly remembered as Jack or 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.


The Barbarossa Brothers

9barbarossaSource: http://caldwellgenealogy.com/the-myths-legends/barbarossa-pirates/

Aruj and Hayreddin, jointly known as the Barbarossa Brothers of Greece, began their career as pirates attacking Aegean ships from the island of Lesbos. In 1505, they raided the base of Djerba and ransacked merchant and war ships in the Mediterranean Sea. Aruj killed the Algerian Sultan, took the reins and controlled a big portion of the North African Sea where they built several fortresses to defend their territories and attack the European powers.


Bartholomew Roberts

20robertsSource: http://www.thewayofthepirates.com/famous-pirates/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.


Christopher Myngs

1myngsSource: http://www.thewayofthepirates.com/famous-buccaneers/christopher-myngs/

Myngs joined the British Royal Army and began to sail with the buccaneers in the 17th century. He would eventually get his own ship and become one of the most successful captains of the Caribbean, plundering Spanish prize ships and attacking naval forces surrounding Port Royal. His later conquests would eventually extended to South America where he plundered numerous wealthy coastal towns and villages.


Edward Teach

teachSource: http://www.thewayofthepirates.com/famous-pirates/blackbeard/

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 romanticized after his death and became the inspiration for a number of pirate-themed works of fiction across a range of genres.


Ching Shih

17shihSource: http://www.thewayofthepirates.com/famous-pirates/ching-shih/

Ching Shih was a Chinese prostitute working in a floating brothel in Canton when she was kidnapped in a pirate raid and taken as a wife by the pirate commander Zhèng Yi. Shih didn’t skip a beat while settling into her new role of pirate lord’s wife, however, and when her husband passed away she took control of his fleet herself. In only a matter of years she expanded her pirate empire tenfold, with over 1,500 ships and over 180,000 individual pirates who acted out her every command. Although she may not have the name recognition of pirates like Edward Teach, she was not only the most notorious pirate in Asia, but also the most successful and feared pirate lord to have ever lived.

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