10 Most Notorious Pirates of All Time

In the waters of the Caribbean and beyond, pirates will always be alive in the hearts and minds of the communities they terrorized. All pirates enjoyed a specific, short-lived period of success in the waters in which they were active. Even though they have been glamorized in films and books, they were feared as much as we fear their modern-day counterparts. Some pirates used deception for plunder, some were bloodthirsty, while others were merely greedy. Few of them were so notorious that their names still instigate fear in people. Check out ten such names of the most notorious pirates.

1. François l’Olonnais, a French pirate who was active during the 1660s, was known to have killed everybody on the ships he plundered. He even cut out a person’s heart who refused to share information and ate it in front of other passengers. Once, he beheaded an entire crew.

Francois Lollonais and pirate ship
Image source: wikimedia, Pixabay

François l’Olonnais’s original name was Jean-David Nau. He first arrived in the Caribbean as an indentured servant in the 1650s. Upon completion of his servitude, he became a buccaneer after arriving in Saint-Domingue. Around two years into his career as a pirate, his ship was wrecked by Spanish soldiers near Campeche in Mexico. Almost the entire crew was killed. L’Olonnais survived by covering himself in the blood of others and hiding among the dead.

After the Spanish soldiers left, L’Olonnais, with the help of few escaped slaves, held a Spanish town hostage and demanded ransom. When the governor of Havana sent a ship to kill L’Olonnais’ crew, L’Olonnais beheaded everybody on the incoming ship except one whom he spared to send a message to Havana: “I shall never henceforward give quarter to any Spaniard whatsoever.”

In 1666, he sailed from Tortuga with a fleet of eight ships and a crew of 440 pirates to sack the city of Maracaibo (present-day Venezuela). When he proceeded to pillage the city, he noticed that most of the residents had fled and hidden their gold. He ordered his crew to track down each of the residents and torture them until they reveal the location of their possessions. Being an expert torturer, he would slice portions of flesh off the victim with a sword and burn them alive. Also, he used to tie knotted “woolding” (rope bound around a ship’s mast to strengthen it) around the victim’s head until their eyes were forced out.

Over the next two months, L’Olonnais’s men raped, pillaged, and eventually burned much of Maracaibo before setting sail to San Antonio de Gibraltar. There they slaughtered 500 soldiers of Gibraltar’s garrison and held the city for ransom even though they were outnumbered. Even after the ransom was paid in full, L’Olonnais continued to sack the city and acquired a total of 260,000 pieces of eight, gems, silverware, silks, as well as a number of slaves. This earned him the nickname “The Bane of Spain.”

For his next expedition to the Central American mainland, 700 pirates signed up with him. In 1667, after pillaging Puerto Cavallo, L’Olonnais’s crew was ambushed by a large force of Spanish soldiers. L’Olonnais barely escaped death but captured two Spaniards. It was one of these Spaniards whose heart L’Olonnais cut out and gnawed it with his teeth. The surviving Spaniard was horrified and showed L’Olonnais a clear route to San Pedro. When they were on the coast of Darién, a province of Panama, they headed inland to find food. There, they were captured by the Kuna tribe which killed and ate L’Olonnais. (source)

2. Cheng I Sao, the Chinese prostitute who became a pirate, commanded 80,000 outlaws and beheaded anyone who disobeyed her. She could not be defeated by the Qing Dynasty Chinese officials or even by the Portuguese and British bounty hunters. She was among very few pirates who actually retired from piracy with her loot.

Cheng I Sao
Image source: harrietdumont, wikimedia

Cheng I Sao was a Cantonese prostitute who worked in a small brothel in Guangzhou. Her brother was captured by pirates led by Zheng Yi. Cheng I Sao then married Zheng Yi and maneuvered her way into the leadership position after the death of her husband. She is known to have issued some of the harshest laws in the history of piracy in order to unite her crew and keep them under control. First, anyone giving their own orders, basically orders that did not directly come from Cheng I Sao or disobeying her orders, were to be beheaded on the spot. Second, it was forbidden to steal from the public fund or any villagers that supplied the pirates. Third, all goods taken as booty had to be presented for group inspection. Fourth, actual money was turned over to the squadron leader who only gave a small amount back to the seizer so the rest could be used to purchase supplies for unsuccessful ships.

She also had a special code of laws for female captives. Even though most of the women were released immediately, some crew members were known to choose the beautiful ones to be their wives. In Cheng’s ship, pirates who raped female captives were put to death. In case a pirate had consensual sex with a female captive, both of them were punished. The man was beheaded and the woman, with cannonballs attached to her legs, was thrown over the side of the boat.

Another one of her strict laws was made towards deserters. Those who leave without official permission had their ears chopped off and then were paraded around their squadron.

She married Cheung Po Tsai, the adopted son of her husband. With his help, she demanded protection money from coastal communities. She also attacked ships in the South China Sea and once even kidnapped Richard Glasspoole, an officer of the East India Company’s ship The Marquis of Ely. Neither the Chinese dynasty nor bounty hunters could defeat her army of outlaws. Finally, in 1810, she was defeated by the Portuguese army. She took an amnesty offered by the Chinese government and retired from piracy with her loot.(source)

3. Black Bart, a Welsh pirate, plundered over 400 ships and once burned an entire ship with 80 live slaves as the ship’s captain refused to pay the ransom. During one takeover of a 52-gun warship, he hung the Governor of Martinique from his own ship and then tortured and killed the Governor’s French crew before taking the ship as his own.

Captain Bartholomew Roberts
Image source: wikimedia

Black Bart, originally Bartholomew Roberts, was the most successful pirate of his time considering the number of vessels he captured. His career started as the third mate on the slave ship Princess under Captain Abraham Plumb. Princess was captured by pirates led by captain Howell Davis.

Upon being captured, Roberts along with several others in the crew were forced into piracy. Roberts’ abilities as a navigator were quickly discovered by captain Davis. He even started to confide information to Roberts in Welsh, as they were both Welshmen.

After the death of Davis, Roberts rose into the post of captaincy within just 6 weeks of his capture. Historians believe he was elected for his navigational abilities and his personality which history reflects was outspoken and opinionated. His first task as captain was to avenge the death of Captain Davis.Davis was killed during an ambush by the Portuguese. Roberts and his crew landed on a Portuguese island at night, killed a large portion of the male population, and stole all items of value that they could carry away.

During one of his raids, he discovered 22 merchant ships. The ships were abandoned by their panic-stricken captains and crews. Black Bart was so angered by this that he forced the captains to attend him on his ship. If anyone failed to do so, he burned their ship.  His depredations brought seaborne trade to a standstill in 1721.

On 5 February 1722, Captain Chaloner Ogle of the HMS Swallow came upon Black Bart’s vessels. The Swallow veered away to make the pirates think that the ship was just a fleeing merchant ship. One of Black Bart’s vessels, the Ranger, took the bait and followed the ship. The Swallow then open fired on the Ranger, under the captaincy of Skyrme, and captured it.

The Swallow returned again on 10 February and found another of Black Bart’s ships.  Upon recognizing the Swallow, the pirates planned to sail past it. The crew was drunk and they were not able to keep the right course. Black Bart was killed by grapeshot which struck him in the throat while he stood on the deck. Before his body could be captured by the Ranger, his wish to be buried at sea was fulfilled by his crew. They weighed his body down and threw it overboard after wrapping it in his ship’s sail. It was never found.(source)

4. Anne Bonney, the lover to the famous pirate Calico Jack, used to dress up as a man to fight alongside the male crew. Once the British Navy came for them. While the male crew headed below deck to hide, she, along with another female pirate Mary Read, took on the British officers by themselves holding them back for a good amount of time on their own.

Anne Bonny
Image credit: Anushka.Holding via wikimedia

Anne Bonney was the illegitimate daughter of servant woman Mary Brennan and Brennan’s employer, lawyer William Cormac. Her father moved to London to get away from his wife’s family and began dressing his daughter as a boy and calling her “Andy.” When discovered, he took Anne and her mother and moved to the Province of Carolina. It is recorded that Anne had red hair and was considered a “good catch,” but may have had a fiery temper. When she was 13, she supposedly stabbed a servant girl with a table knife.

Anne married a poor sailor and small-time pirate named James Bonny. James only married her in hopes that he could win possession of Anne’s father’s estates. But Anne was disowned by her father. She and her husband then moved to Nassau. There she received a pardon from Governor Woodes Rogers and became an informant for the governor.

While in the Bahamas, Anne began mingling with pirates in the local taverns. She met John “Calico Jack” Rackham, captain of the pirate sloop Revenge, who became her lover. She joined Rackham and continued the pirate life having divorced her husband and marrying Rackham while at sea.

She took part in combat alongside the male crew of Calico Jack. She was competent and effective in combat and respected by her shipmates despite being a female. She was named in a “Wanted Pirates” circular by Governor Rogers published in the continent’s only newspaper, The Boston News-Letter. Although she was renowned historically as a Caribbean pirate, she never commanded a ship of her own.

When the British Navy came for them, the male crew was drunk, and they headed below deck to hide. But Anne, along with another female pirate, Mary Read, took on the British officers by themselves holding them back for a good amount of time on their own. They were finally overpowered after some time. Rackham and his crew were taken to Jamaica where they were convicted and sentenced by Governor Lawes to be hanged. Anne and Read were pardoned as they pleaded being pregnant. In accordance with English common law, both women received a temporary stay of execution until they gave birth. Read died in prison, most likely from a fever from childbirth.(source)

5. Hayreddin “Redbeard” Barbarossa, along with his brothers, depopulated the entire Giglio Island of 1,200 people. He deported 1,000 people as slaves and killed the remaining 200. He was exiled from so many countries that he ended up starting his own country (Regency of Algiers) with the blessing of The Ottoman Empire which became present-day Algeria, Tunisia and parts of Morocco.

Hayreddin Barbarossa
Image source: wikimedia, wikimedia

Barbarossa, by the name of Khayr al-Dīn, was a Barbary pirate. He was later appointed the Admiral of the Ottoman fleet. It was through his initiative that Algeria and Tunisia became part of the Ottoman Empire. His attraction to piracy was intensified by hatred for the Spanish and Portuguese who attacked North Africa between 1505 and 1511.

Khayr al-Dīn was one of four sons of a Turk from the island of Lesbos. He and his brother hoped that, with the aid of Turks and Muslim emigrants from Spain, they would be able to wrest an African domain for themselves. They had begun to succeed in that strategy when Arūj was killed by the Spanish in 1518. Now fearing that he would lose his possessions to the Spanish, he offered homage to the Ottoman sultan, and in return was granted the title beylerbey and sent military reinforcements.

In 1533, he was appointed Admiral-in-Chief of the Ottoman Empire. The very next year he conquered the whole of Tunisia for the Turks. The Holy Roman Emperor Charles V led a crusade that captured Tunis and Goletta in 1535, but Barbarossa defeated Charles V’s fleet at the Battle of Preveza (1538). He managed to secure the eastern Mediterranean for the Turks until their defeat at the Battle of Lepanto in 1571.

For three centuries after his death, Mediterranean coastal towns and villages were ravaged by his pirate successors.(source)

6. Blackbeard was an English pirate who often determined an approaching ship’s nationality first and raised the same country’s flag on the pirate ship to appear friendly. Once able to draw close to the unsuspecting ship, Blackbeard would hoist his pirate flag and plunder the ship. Once he conquered a ship that had 455 African slaves on board. Many of the African slaves went on to become pirates.

Edward Teach aka Blackbeard
Image source: wikimedia, wikimedia

Edward Teach, better known as “Blackbeard,” was an English pirate who operated around the West Indies and the eastern coast of Britain’s North American colonies. Not much is known about his former life. It is speculated that he may have been a sailor on privateer ships during Queen Anne’s War. Teach joined the crew of Captain Benjamin Hornigold around 1716.

Teach commanded four ships and had a pirate army of 300 at the height of his career. He defeated the famous warship HMS Scarborough in sea-battle. He captured over 40 merchant ships in the Caribbean and without flinching, killed many prisoners. It was known that he used to shoot or kill members of his own crew from time to time in order to keep fear intact in the hearts of his followers.

Blackbeard and his crew of pirates terrorized sailors in the Atlantic Ocean and the Caribbean Sea from 1716 through 1718. They used to determine an approaching ship’s nationality first and raise that country’s flag on the pirate ship to appear friendly. Once able to draw close to the unsuspecting ship, Blackbeard would hoist his pirate flag and plunder the ship.

Teach deliberately developed a terrifying appearance. He had an enormous black beard (hence the name “Blackbeard”) which he tied up with black ribbons and twisted into braids. According to some accounts, the beard covered his entire face and grew down to his waist. Before going into battle, he tucked pieces of hempen rope soaked in saltpeter into his hair and lit them. The slow-burning chords of rope gave off clouds of thick black smoke that gave him the appearance of the “Devil” himself.

After a fierce battle in which he stood out with candle smoke rising from his beard, he was overtaken by the Royal Navy and beheaded.(source)

7. Edward “Ned” Low once burnt a ship with the cook tied at the mast because he felt the cook was “a greasy fellow” who would sizzle in the fire. In another instance, he slashed off the lips of the captain of a captured Portuguese ship with a cutlass, broiled them, and forced the victim to eat them while still hot.

Edward Ned Low
Image source: wikimedia, wikimedia

Edward Low was an English pirate who operated during the latter days of the Golden Age of Piracy. Low belonged to a very poor family and he took to crime when he was quite young. As he grew older, he took part in numerous of serious crimes. He then decided to leave England and try his luck in the new world. After he arrived in America, he traveled from city to city from 1710 to 1714, finally settling down by marrying his wife Eliza Marble. Eliza died shortly after the birth of Low’s only daughter.

With the death of his wife, Edward once again entered into a life of crime. He worked as a dock worker and shipmate but soon he and his crew mutinied against their captain and took control of the ship. He became a pirate captain and managed to capture several trade ships off the coast of Boston and New York.

As his piracy career progressed, so did his notoriety. He managed to capture 13 fishing vessels off the coast of Nova Scotia. He picked one of the largest fishing vessels to be his new flagship, the Fancy. His exploits in the Caribbean brought the death of many of his prisoners. Tales of his crimes were famous in every nook and corner of the Atlantic. Many surviving victims of his pirate attacks described him as a psychopath who liked to inflict pain on others. He was known to often chain, mutilate, burn, and even force some captives to eat the heart of their captain.

Low and his pirate crews captured at least a 100 ships during his short career, burning most of them. Low kidnapped numerous fishermen and forced them to join his crew. Once such fisherman was Philip Ashton who was able to escape. In his detailed account, he mentioned that he had been beaten, whipped, kept in chains, and threatened with death many times as he refused to sign Low’s articles and become a pirate.

When the Caribbean authorities were no longer able to endure Low’s crimes, they dispatched a force to kill him. Low’s crew faced defeat against English Captain Peter Solgard and his warship HMS Greyhound, but Low managed to escape. Over the next year, his tales of brutality became more fearsome. Finally, his own crew mutinied against him and left him marooned.(source)

8. Charles Vane was one of the few pirates to have turned down a government pardon. He and his crew hacked, murdered, or hung the crew members of the ships they plundered before lighting fire to the ship itself. He was so successful in his conquests that Governor Rogers decided to send out Colonel William Rhett to hunt Vane down.

Charles Vane
Image credit: The Jefferson R. Burdick Collection, Gift of Jefferson R. Burdick via wikimedia

Charles Vane was an English pirate who preyed upon English and French shipping. He was a protégé of the notorious Blackbeard. His career in piracy started in 1716 when he became a crewmember under Henry Jennings. In 1718, Jennings took pardon from the new governor of New Providence, Woodes Rogers. Before taking the pardon, he made Vane the captain of his ship.

He was one of the very few brave pirates who did not accept the king’s pardon. When Vane’s ship was blocked by Woodes Rogers’s fleet, Vane set his own ship on fire. He then set it to sail straight towards Rogers’ ships. While they were trying to avoid the ship in flames, Vane sailed away laughing. He even fired a few shots. As his attacks became constant threats, the governor Spotswood of South Carolina hired many capable pirate hunters to capture him. But none of them were successful.

Vane had very little respect for his crew members. His second-in-command, Yeates, decided to leave Vane’s command because of this. Yeates and his followers took one of the Vane’s ships with part of the plunder, 90 slaves, and fled from him. Other crew members who remained behind were equally dissatisfied.

His downfall started when he tried to capture a powerful French Warship. Vane decided to flee from the battle causing his crew members to accuse him of cowardice. They then elected a new captain.

Even though Vane was successful in putting together another small pirate fleet, his ships were wrecked by a hurricane. Stranded on an island and waiting for rescue, he was identified by the former buccaneer, Captain Holford, who handed him over to the authorities. Vane was hanged at Gallows Point in Port Royal. His corpse was hung in chains at Gun Cay as a warning to other pirates.(source)

9. Henry Every, who operated before the “Golden Age of Piracy,” is famous for the capture of two of the Moghul Emperor of India’s treasure fleet ships. He and his crew then stripped the men of their clothing, tortured them, and finally killed them. Young women passengers were brutally raped. Some of the women committed suicide to avoid this.

Captain Henry Every
Image source: wikimedia, wikimedia

Henry Every was an English pirate who operated in the Atlantic and Indian oceans in the mid-1690s. He earned his fame by becoming one of few major pirate captains to retire with his loot without being arrested or killed in battle.

He started his sea career on board unlicensed slave ships. In 1694, he was a first mate on Charles II, a 46-gun Spanish ship that had a license to attack French smugglers. Every organized a mutiny and was selected to be the new captain. Every renamed the Charles II to Fancy and set course to the Cape of Good Hope.

The biggest catch in Henry Every’s piracy career was the capture of the Gang-i-Sawai. Gang-i-Sawai was part of the convoy ships of the Mughals of India. When the Mughal’s convoy spotted Every’s fleet, they scattered. Every tried to pursue them but night fell and it became difficult for him. In the morning, he could only see two ships.  After a short fight, the small one, Fateh Mohammed, surrendered. But the bigger, 40-gun Gang-i-Sawai resisted for two hours. Every had luck on his side, and one of the cannons exploded on the Gang-i-Sawai heavily damaging the deck. Without strong leadership and with a damaged ship, the crew of Gang-i-Sawai had to surrender.

Survivors were brutally tortured to reveal hidden treasures. Woman passengers were raped. Some of the women committed suicide to avoid this. Brutality in this era was not uncommon especially because of religious and racial differences. Pirates counted about 600,000 pounds of plunder which included gold, silver, and jewels. Each pirate received 1,000 pounds which was worth as 80 years of honest sea pay. The Mughal emperor announced a 500-pound bounty for his head, and he was not welcomed in the Caribbean and the English colonies.

Every was known to change his name to Benjamin Bridgeman and with the remaining crew, sailed to Ireland. Some of them were captured and hanged, but Henry Every escaped and vanished.(source)

10. Henry Morgan was a Welsh privateer empowered by the British government. He later entered into piracy. Once he used Jesuit priests and nuns as human shields while capturing a ship. He was arrested and tried as a pirate but was saved by King Charles II and was even knighted.

Henry Morgan
Image source: wikimedia, wikimedia

Sir Henry Morgan started his career as a Welsh privateer led by Sir Christopher Myngs. He later went on to become the  Lieutenant Governor of Jamaica. He successfully undermined Spanish rule when sanctioned by England.

When Spanish activity increased in Cuba, Morgan was chosen to lead the Jamaican fleet. In January 1668, Henry, along with more than ten ships and over 500 soldiers, sailed to Cuba. Henry easily conquered the City of Puerto Principe without much loss. The problem was that this raid brought to his army only 50,000 pieces of eight. Many disappointed soldiers left Morgan.

Henry planned another attack right away despite his army being halved. The target was a fortified and a well-guarded town, Puerto Bello. The strategy that Morgan used during this conflict was crucial. He anchored his ships away from the city and used canoes to approach the city at night without making any sounds. The attack was quick, the guards were unaware, and two of the three main forts were easily conquered. But the third one was almost impossible to occupy. It is here when he came up with the brilliant idea to use imprisoned monks and nuns as human shields. With that strategy, they succeeded in conquering the last obstacle. The buccaneers captured the town, and the governor of Panama was forced to pay a lot for the slaves. Also, 250,000 pieces of eight were taken from the raid.

Throughout his piracy career, he may have pillaged upwards of 400 ships. His greatest achievement was the capture of the wealthy Panama City with thirty ships and 1,200 men. It was here that he was arrested, but upon being knighted by King Charles II, he was released as deputy governor of Jamaica. There he lived a very well-respected life as a planter until his death.(source)

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