15 Real-Life Pirates Who Were Maybe Even Cooler Than Captain Jack Sparrow

On May 26, Pirates of the Caribbean: Dead Men Tell No Tales will hit theaters as the fifth installment of Disney’s swashbuckling film series. While audiences are excited to see Johnny Depp, Geoffrey Rush and even Paul McCartney on the big screen - surrounded by the water, sword fights and booty - pirate fanatics should also be aware of the 15 real-life buccaneers listed below. These men and women went to extreme measures to overtake vessels, burnt prisoners alive, dreamed of making it home to their lovers and wore wooden peg legs (One really did - the first person ever to do so, apparently!)...We don’t want to give too much away, so keep on reading to learn about these brave, nasty, cool pirates who would give Captain Jack Sparrow a run for his money.

15 Ching Shih: From Prostitute To The Most Successful Pirate

After starting out as a prostitute, Ching Shih ended up commanding over 1,800 ships and 200,000 pirates, making her one of the most successful pirates of all time. She also is one of the few pirates to actually retire.

As a younger woman she became a prostitute on a floating brothel in Canton but was noticed for her beauty, which led to her ending up with a pirate named Zhèng Yi, who commanded the Red Flag Fleet in 1801. She then controlled the infamous fleet and ran a tight ship, focusing on business and military strategy and even forming an “ad hoc” government to protect her pirates with laws and taxes. Those who went against Ching Shih and her rules received harsh capital punishment, such as being hunted down, flogged, trapped in irons and even having their ears cut off.

14 François l’Olonnais: From Slave to Torturing Pirate

Via YouTube

Jean-David Nau - better known as François l'Olonnais - was a French pirate active in the Caribbean during the 1660s, but he first arrived in the area as an indentured servant in the 1650s. After fulfilling his servitude, he wandered through the islands as a buccaneer. Once, he shipwrecked near Campeche in Mexico where Spanish soldiers attacked him and his party. L'Olonnais survived by covering himself in the blood of others and hiding amongst the dead. From there, he made his way to Tortuga, held a town hostage, demanded ransom from a Spanish ruler and became an expert torturer. He would slice portions of flesh off victims with a sword, burn them alive and tie knotted rope around their heads until their eyes were forced out. Eventually, most of the area was raped, pillaged and burned by l’Olonnais and his men.

13 Thomas Tew: Holding On For Dear Life

Another famous pirate was Thomas Tew, who ruled the Red Sea in the 1690s, and was dubbed a “wicked and ill-disposed person” by King William III, who mentioned him in his Royal Warrant issued to Captain Kidd. He served as a privateer on English ships during conflicts with France and was elected as a captain of Amity Venture. He was supposed to join the Royal African Company and attack a French factory but abandoned the plan and decided to become a pirate.

One of his most notable victories came after he crossed an Indian ship with more than three hundred soldiers, a battle that he won. In 1695, he attacked another ship, this one belonging to the Great Mogul, and there, he was shot in the belly; he apparently held his bowels with his hands for a while before dying.

12 Barbarossa: Honored To This Day

Barbarossa Hayreddin Pasha was an Ottoman admiral during the mid-16th century. “Hayreddin”, which means “goodness”, was a name given to him by Sultan Suleiman the Magnificent, and “Barbarossa” (meaning “Redbeard” in Italian) was a name he inherited after his brother, Oruc Reis (a man with a red beard) was killed in battle.

Barbarossa conquered almost all of North Africa by 1529, and his conquests led to top honors within the Ottoman Empire, such as the right to sit on the Imperial Council and help run the government.

He died, surrounded by luxury, at the age of 68, as the most successful Islamic naval commander, and Barbarossa now has a mausoleum in Istanbul, which Turkish seamen salute with a cannon shot before leaving the port.

11 Sayyida al Hurra: Prominent Pirate

Via Pinterest

Sayyida al Hurra was forced to flee her home in 1492, and as the daughter of a prominent Muslim family, she became governor of Tetouan in 1515. She then married the King of Morocco, but despite all the wealth and power she had in her life, all she could think of were the Christians who had forced her from her home as a child.

In the midst of seeking revenge, she actually met up with Barbarossa and decided to become a pirate. She took over Christian ships – so many that she soon became a queen with power over the Mediterranean Sea and the main negotiator with the Spanish and Portuguese governments. In 1542, though, she was overthrown by her son-in-law, and to this day, her fate is unknown.

10 Jacquotte Delahaye: Back From The Dead Red

Another famous female pirate, Jacquotte Delahaye, did not have the luxurious life Sayyida al Hurra had; she was born in Haiti to a French father and a Haitian mother, who died giving birth to her brother. Then, her father was killed, and she did not have many resources with which to care for her brother and herself. Therefore, she turned to piracy. She was active in the 1660s, in the Caribbean, and even faked her own death to escape the government, which was hunting down this redheaded beauty.

After this, she lived in hiding as a man and became known as Back from the Dead Red. She’s a true legend, having led hundreds of pirates and overtaking a small Caribbean island in 1656, which was called a “freebooter republic”. She died in a shootout while defending it.

9 Henry Every: Faking His Fancy Life

Henry Every is thought to have been born in 1653, in Plymouth, England, and started his sea career on unlicensed slave ships. In 1694, he went aboard Charles II, a Spanish ship set to attack French smugglers, organized mutiny and was appointed captain. He renamed the ship Fancy and ruled over pirates such as Thomas Tew and William May. His five ships were a tough match, especially to Gang-i-Sawai, part of Grand Moghul’s convoy of ships, which was forced to surrender after a two-hour resistance.

The hours of hiding and fighting back were only the beginning for Gang-i-Sawai, though; survivors were tortured and raped, and 600,000 pounds of treasures were stolen. Every’s pirates each received 1,000 pounds - which would have taken them 80 years of working at sea to acquire.

After this, Every changed his name (to either John Avery, Long Ben or Benjamin Bridgeman), sailed to Ireland and vanished. Some say that he married Grand Moghul's daughter. Others think that he died soon after his retirement as a poor sailor on the streets of London. These are just some of the tales that are now passed along in books and plays, such as The Successful Pyrate.

8 Mary Read: Going To Extreme Male-sures

Mary Read’s father died before she was born, and her half-brother, Mark, passed away soon after that. Therefore, her paternal grandmother supported Mary and her mother…because she thought Mary was her grandson. To keep Mark’s death a secret, Mary was raised a boy.

Even after her grandmother died when Mary was 13, Mary still dressed and acted like a boy. She even became a footboy for a wealthy French woman but escaped and joined the army, where she met a man, fell in love, revealed her true identity and married/opened an inn with this man.

A couple of months later, though, her husband died, so Mary joined the army again. While aboard a Dutch ship, Mary was forced into piracy after the ship was attacked by Calico Jack. However, she ended up liking the pirate life and befriended another female pirate, Anne Bonny. In 1720, the ship was captured, and the pirates were found guilty of piracy; Mary and Anne were spared, though, because they claimed to be with child. Mary died with her unborn child, in prison, from fever and was buried at St. Catherine’s parish in Jamaica.

7 Samuel Bellamy: The Wealthiest – And Most Romantic! - Pirate

In 1984, the first pirate ship to ever be recovered from the sea was found - Samuel Bellamy’s Whydah. Inside, 140 dreams were found, including Bellamy’s: He just wanted to return home to his wife, Maria Hallett.

As part of the British navy, Bellamy sailed to the coast of Florida to look for sunken Spanish treasure, and along the way, he met 15-year-old Maria. Her parents liked him but wanted more for their daughter than just a sailor, so Bellamy said he was going on a new treasure hunt expedition and promised he would return with the greatest ship the world had ever seen. After he left, though, Maria gave birth to his child, who died soon after, and the scandal landed her in jail and forced her out of town.

All the while, Bellamy was unsuccessfully searching for treasure and ended up joining Benjamin Hornigold’s pirate crew. He eventually took over, and in one year, he robbed more than fifty ships and became known as Black Bellamy; his crew called him Pirate Robin Hood, since he showed mercy to those he captured, as he swept in goodies that earned him the title of wealthiest pirate in recorded history – all before his death at the age of 28.

In 1717, Bellamy captured Whydah – full of treasure that added up to a sailor’s 20-year pay. Bellamy was excited to rush home to Maria, but the ship was hit by a storm, causing a crash that only eight survived; six of them were hanged, and only two lived to tell the story, including a Welsh carpenter, Thomas Davis, who passed on information of Bellamy’s reign.

6 Awilda: A Tale Of Teen Rebellion

Awilda was the daughter of a 5th-century Scandinavian king and was set to marry Alf, the prince of Denmark. However, being against the idea, Awilda and some of her female friends dressed like sailors, commandeered a ship and came across a pirate ship. Awilda ended up being named the new captain of this ship, so the King of Denmark sent his son and a navy ship to battle with the pirates. As Prince Alf boarded Awilda’s ship, he immediately took control, which impressed Awilda. She revealed her identity and agreed to marry Alf after all. They married on the ship and lived happily ever after as King and Queen of Denmark.

5 Magister Wigbold: The Smart Pirate

Magister Wigbold was a German pirate who belonged to the famous Likedeeler pirates of Klaus Störtebeker, active in the North and Baltic seas; Störtebeker was the representative of privateers known as the Victual Brothers, who were hired during a war between Denmark and Sweden to fight the Danish and supply the Swedish capital with provisions, so they dubbed themselves Likedeelers (which translates into “equal sharers”).

After being involved in all of this equal sharing, it’s thought that Wigbold entered a monastery yet was expelled and possibly went on to Oxford. While his history is not clearly known, he was often described as the brains behind the pirate band; many pirates sought out battles, but Wigbold preferred to negotiate, surrender and reduce casualties. Apparently, though, while robbing ships on the North Sea, a sizeable military force attacked, and while Wigbold used his wits to escape, he was eventually captured and executed in Hamburg.

4 Cornelis Jol: The OG Pegleg

Via Wikipedia

More of a pirate than an admiral, Cornelis Corneliszoon Jol was nicknamed Pegleg in the 17th century. He ruled over the Dutch West India Company during the Eight Year’s War and was active in the Caribbean during the 1630s and 40s. He raided many Spanish and Portuguese ships for large amounts of loot and ended up losing a leg, becoming one of the earliest documented pirates to use a wooden peg leg. He overtook Santiago de Cuba in August 1635, where he flew the Spanish flag and disguised his crew members, using trickery to enter the harbor. Two days later, he sailed away with his booty, which he enjoyed until being killed in 1641. He is to thank for the traditional wooden stump, though, which stands out more than his raids and riches!

3 William Dampier: Going Down In History

Via Alchetron

The first Englishman to explore Australia AND the first person to circumnavigate the world three times was William Dampier. He was involved in many trading and privateering ventures, which led to him joining a group of buccaneers bound for the Pacific by way of Cape Horn in 1683. A couple of years later, he set out upon his first crossing of the Pacific and wrote a book, A New Voyage Round the World, which earned him command of a Royal Navy ship. During this time, he made important discoveries in Western Australia, before being court-martialled for cruelty. Nevertheless, he rescued Alexander Selkirk – who may have inspired Daniel Defoe’s Robinson Crusoe ­– influenced people like James Cook and Charles Darwin and has gone down in history as an infamous pirate. He died in London in 1715.

2 Miguel Enríquez: Puerto Rican Pirate And Pauper

Via Wikipedia

After starting as a shoemaker and working his way up to defend Puerto Rico and command a small fleet of ships, Miguel Enríquez received a letter of marque and reprisal from the Spanish Crown, a special permit that granted him the privileges of a privateer. Enríquez became the most successful and influential Puerto Rican of his time but was never able to be truly accepted by higher social classes – since he was, after all, a pirate.

Still, he remained close to the Spanish Monarchy and sent out urgent messages to the West Indies. Between 1702 and 1713, he owned a fleet of more than thirty vessels – and over 300 by the end of his career. Under the order of King Philip V, he was awarded The Gold Medal of the Royal Effigy and was granted a Royal Auxiliary Identification Document. At one point, he was wanted for smuggling, but his powerful connections kept him safe, and he died as a pauper in the Catholic Church.

1 Calico Jack: Designer, Trendsetter And Lover

John “Jack” Rackham was an English pirate in the early 18th century – the Golden Age of Piracy. Since he wore calico clothing, he is best known as Calico Jack. He is also known for his design of the Jolly Roger flag (a skull with crossed swords) and for having two female crew members: Mary Read and his alleged lover, Anne Bonny. He met Anne while on a hiatus from pirating but soon returned, in 1720, with his lady by his side. After a short run, though, Jack was captured by Royal Navy pirate hunter Jonathan Barnet; Jack tried to strike a deal through which he would surrender himself if clemency was given to Anne and Mary Read. Despite his efforts, he and his crew members were found guilty of piracy and were hanged the next day, in Port Royal, Jamaica in 1720.

More in Pop Culture