When you think of a pirate, you probably think of Captain Jack Sparrow the star in the Pirates of the Caribbean movies. In this list we don’t look at fantasy pirates, but pirates that really lived and ruled the seas.

10. William Kidd

Jean Leon Gerome Ferris

William Kidd was certainly tried for piracy and is either a black-hearted villain or an unjustly maligned privateer! Initially, Kidd worked with the Navy, defending against the French with whom the English were at war. He got into trouble, through no real fault of his own, when an American colonial governor asked him to attack various people suspected of piracy as well as some French ships. Refusal would have been akin to treason, so Kidd provisioned his ship and set off on the task that had been given to him. As they sailed off, Kidd’s vessel passed a Navy vessel and did not, for some unknown reason, salute it as respect dictated that they should have done. The Naval shop fired a shot, demanding the courtesy due to it, only for Kidd’s men to turn and slap their backsides in that direction! This impudence saw the captain of the Navy ship demanding a number of Kidd’s crew to be pressed into his service instead, a demand that Kidd responded to by sailing away before any of his crew could be taken. The Navy captain responded by declaring Kidd a pirate almost as soon as his voyage began, and Kidd’s crew did little to help this situation, being singularly violent and feloniously minded. The crew refused to return a captured ship to its English owner, despite Kidd urging them to do so stating that it was an Algerian ship, with French passes and therefore could be counted as a legal capture. A short time later, Kidd wanted to capture Robert Culliford, a pirate with whom Kidd had a history, having lost a ship to him earlier in his career, but his crew refused, siding with Culliford and threatening to shoot Kidd. Kidd returned to America and only then became aware that he had been declared a pirate. He held the French passes of the captured ship and was sent to England for questioning by Parliament. Kidd refused to name any names of his backers, hoping that these benefactors would speak up for him: they did not and he was hanged on five counts of piracy and one of murder, the latter for the accidental killing of one of his crew… (There was another pirate of the same name, although different spelling (William Kyd) who operated along the English coast from 1430 to 1450 under the protection of corrupt officials…)

9. Edward England

Born Edward Seegar and said to be a well-educated man, Edward England took the name when he became a pirate. England is also responsible for the ‘traditional’ pirate flag, the Jolly Roger, which features a skull and two crossed femurs. As a young man he made his way to Jamaica, initially serving as a privateer (which, to put it frankly, was just a form of legal piracy!). He was captured by pirate captain Christopher Winter who took him to the notorious pirate ‘head-quarters’ on the Bahamian island of Nassau. England seems to have accepted his fate and worked his way up the pirate hierarchy, becoming quartermaster to Charles Vane, on his way to becoming pirate captain in his own right. While under Vane, England, along with his crew-mates, was captured by the Royal Navy, but they were released in a bid to induce the other Nassau pirates to accept the King’s pardon. (The King’s pardon was a pledge to abandon their piratical ways in exchange for an expunging of their records to that time.) England chose not to accept the King’s pardon and was awarded his own ship by Vane. England sailed off to the African coast where he operated successfully for several years. He was a kindly man, relatively speaking, and would not keep captives imprisoned for long once it was clear that they would not sign up to be pirates themselves. This ‘softness’ was rewarded by England and three loyal crewmen after England insisted on sparing the life (and release) of one James McCrae, a captain of an East Indiaman captured by the pirates. (One of the three crewmen was described as being ‘a man with a terrible pair of whiskers and a wooden leg, being stuck around with pistols’, a description that formed the basis of that most famous fictional pirate, Long John Silver.) England died in 1721, allegedly from ‘severe strings of conscience’, but more likely from a misunderstood tropical disease, leaving behind a legacy of being a kindly man despite his blood-thirsty and violent profession.

8. Piet Hein

Jan Damen Cool

Piet Hein is technically not a pirate, having never illegally captured a ship, but he deserves his place on this list for capturing an incredibly rich treasure; remarkably, achieving this feat without any bloodshed. Hein was born to a sea captain father and became a sailor himself, while still in his teens. He was captured by the Spanish while in his 20s and served as a galley slave for some four years (between 1598 and 1602). On gaining his freedom, he joined the Dutch East India Company and worked his way up to captain. He married and even dabbled in local politics in Rotterdam. Promotion continued to follow him and a vice-admiralcy was quickly followed by becoming a full Admiral. It was while he held this rank that he captured a number of Spanish vessels, gaining 11,509,524 guilder’s worth of gold, silver and other cargo. They did not take any prisoners, turning their Spanish captives out with sufficient supplies and good directions to get them to Havana. Hein was able to issue these instructions in fluent Spanish, a legacy of his many years in Spanish custody. He went on to become Lieutenant-Admiral (or, essentially, supreme commander of the Dutch fleet) in 1629, but died later that same year when he deliberately moved his ship in between two enemy vessels in order to offer them both broadsides simultaneously. He was struck in the shoulder by a cannonball and killed instantly. Even today, Hein is a hero in his homeland, with a ship and a tunnel named for him. One of his direct descendants also found fame, but as a mathematician, poet and physicist, rather than as a privateer or pirate. A song, commemorating his rich capture was penned in the 1800s and is still sung in schools and by choirs in the Netherlands.

7. Ching Shih

Ching Shih

The first woman on this list was something of an impressive character, commanding 300 junks and between 20,000 and 40,000 crewmen (other estimates put those figures as high as 1,800 vessels and 80,000 men). Ching Shih, born in 1775, started life as a lowly prostitute and could hardly have found life to be worsened when she was captured by pirates. In 1801 she married the notorious pirate captain, Zheng Yi. Her husband’s family were something of a Who’s Who of Chinese piracy and with his ancestral skills and his new bride’s astonishing determination, they soon persuaded other pirates to form a coalition, creating a powerful pirate fleet, known as the Red Flag Fleet. When her husband died, Ching Shih immediately manoeuvred herself into a position of power; playing politics with those who could help her establish and then retain her position of power over the immense fleet. She made good use of her husband’s nephew, a man called Chang Pao who would, with time, become first her lover and then her husband and the father of her late-born son (she was 38 when she gave birth). Ching Shih worked on a code of practise for her pirate army and any flouting of her commands were dealt with harshly, instant decapitation being a common punishment for transgressions. (She dealt harshly with those who raped any female prisoners, but was equally harsh with both offenders if the sex was consensual, beheading the male and throwing the female prisoner overboard with cannonballs tied to her ankles to weigh her down… Pirates could keep female companions, as long as they married them and stayed faithful to them, however. Ugly female prisoners were often released or ransomed…) Ching Shih was a most successful pirate and the combined navies of Britain, Portugal and China could not defeat her. She negotiated her own retirement in 1810, when a blanket amnesty was offered to all pirates, and managed to keep her large fortune and evade all official punishment. Her husband, Chang Pao died suddenly, shortly after they retired from their life on the high seas, and Ching Shih returned to her homeland in Canton, with her young son, and opened a gambling house. She died, some 34 years later, at the respectable age of 69.

6. Anne Bonny & Mary Read

Anne Bonny & Mary Rea

Anne Bonney and Mary Read individually are fascinating characters, but it is when they are put together that they become somewhat greater than the sum of their parts.

Anne Bonney did not have the best start in life, being the illegitimate daughter of a lawyer and his housemaid. The couple took their young daughter to America and she grew up fiercely independent and headstrong. She ran away to marry her pirate lover, James Bonney, and they lived in Nassau on the Bahamas. When her husband accepted the King’s pardon and turned informant on his former colleagues, Anne was disgusted and soon left him for a pirate captain, Jack Rackham. Anne disguised herself as a man and joined the crew of his ship, only leaving the vessel for long enough to have his child and leave it with friends in Cuba.

Mary Read was also illegitimate, born to the wife of a sailor who had not been heard of for a long time. Her legitimate half-brother died, shortly before her birth, a fact used by Mary’s mother after many years of waiting for her husband to return. Mary’s mother, knowing her mother-in-law to spurn daughters and only want sons, disguised the young Mary as a boy, before visiting, cap in hand to ask for financial assistance. The older woman was fooled and offered help to the small family in the form of a crown a week. Mary enjoyed the freedom offered by wearing boys’ clothes and continued to do so, even after her purported grandmother passed away and the financial assistance stopped. Initially working as a ‘footboy’ to a French lady, Mary soon tired of this and signed up on a man-o-war. This stint was followed by a period as a foot soldier and then in a horse regiment, in both of which jobs she performed well. She fell in love with one of her fellow soldiers and revealed her true gender, marrying him and settling down to run an inn together. Sadly, he died, and she reverted to her practise of dressing as a man, and went back to sea. The ship was seized by pirates and eventually came under the control of Captain Jack Rackham.

Anne and Mary quickly spotted each other’s secrets and the girls became close friends. Mary took a lover on board and is said to have saved his life by duelling his opponent to defeat. The two women made a fierce team, and their fellow crew members said that no-one fought with more passion than the two in the heat of the battle. While Jack Rackham was a well-known pirate, is name is mainly known today because of his having the two women on his crew. Known as Calico Jack, for his love of clothing, he ceded his vessel to the Royal Navy, hiding beneath the decks with many of his crew, while the two women fought off the attack as best they could, trying to encourage their fellow pirates with such cries as ‘come up, you cowards, and fight like men’. The women were eventually overcome by force of naval numbers and the entire crew was taken into custody. Anne visited her erstwhile lover in prison, but instead of speaking sympathetically to Calico Jack, she told him, ‘had you fought like a man, you need not be hang’d like a dog.’

The two women were tried as pirates also, and found guilty, but their executions were stayed as both women were pregnant and the killing of an unborn child was illegal under British law. Mary died of a fever before her pregnancy was complete (although, some say she feigned her death and escaped prison), and Anne seems to have vanished from the record books altogether, with no record of here execution being found. Some people believed that her wealthy father arranged for her release and she went off to raise her child in peaceful tranquillity. Still others prefer the legend that the two women escaped together and went off to raise their children together.

5. Francis Drake

Francis Drake
Marcus Gheeraerts the Younger

Francis Drake is a name familiar to many and he is best known for his good relationship with Queen Elizabeth I. Once again, he was not technically a pirate, operating under his ruler’s command and bringing home the spoils for her, rather than keeping them for himself. He is on this list for capturing immensely valuable treasure ships and bringing home vast amounts of Spanish gold. One ship alone brought in the equivalent of £7 million pounds in today’s money. So successful was Drake that he occasionally had to bury some of his loot, rather than risk his ships foundering under the weight of it all! In 1580, when Drake returned home, the queen’s half share in his loot was so immense that it outstripped the rest of her income for that entire year. He was also hailed for circumnavigating the globe, a great achievement for that time. Drake settled down shortly after this, moving into politics and leading a more sedentary and quiet existence, but was pressed back to sea in 1585, staying in service until his mid-fifties. He died from dysentery, having survived a cannonball flying into his cabin, and was buried at sea in a lead-lined coffin. Divers often spend time looking for his watery grave, but none have, to date, found him.

4. Henry Morgan

Henry Morgan
Alexandre Exquemelin

Henry Morgan was one of the greatest and most successful pirates in history, and one of the most bloodthirsty too. Born the son of a Welsh famer, Morgan had two famous sea-faring uncles. Once he was of an age, Morgan set out to sea, but little is known of him before 1655. He worked with the English against the Spanish, being very good at privateering and capturing a number of rich ships. While Morgan was never technically a pirate, holding licences to attack ships as a privateer, he soon gathered around him a band of pirates, corsairs and other less than savoury characters around him. This group was known as The Brethren of the Coast. Morgan’s last raid was piracy as England and Spain had signed a peace treaty before the attack took place, but Morgan claimed ignorance of the peace (whether truthfully or not, no-one can be sure) and instead of being punished, was knighted and feted as a great hero!

3. Black Bart

Black Bart
Benjamin Cole

Black Bart was one Bartholomew Roberts and he never used the name during his lifetime. He is often confused with the American outlaw of the same name (Black Bart), but he was perhaps the most successful pirate in history when taken in terms of captured ships: he took 470 ships during his career. Roberts (originally called John, it is believed that he took the name Bartholomew after another famous buccaneer with than first name) went to sea, and soon discovered that his supposedly legal ship was in fact a pirate vessel. Reluctant at first, Black Bart soon took to the pirate’s life and was quickly made captain after their previous captain was shot dead. He was chosen by his comrades, despite his very young age, because he an excellent navigator and a confident speaker. His first act was to revenge themselves on their former captain’s killers and they slaughtered a great number of the residents of the island, looting anything of any value along the way. Roberts was betrayed by one of his men, who sailed off with a good number of the crew and a great deal of treasure. This led him to draw up a number of rules, known as the ‘pirate code’ with his remaining men. He then began a lengthy period of piracy which lasted for many years until Roberts was killed in a fierce battle. His death shocked both his fellow pirates and his opponents, as many of them saw him as a figure of legend, invincible and unkillable by that time.

2. Jack Rackham

Jack Rackham

Like Edward English, Jack Rackham was quartermaster under Charles Vane, before gaining his own command, which he did by mutinying against Vane, declaring him a coward and taking his place. He worked in the Jamaica area, capturing many ships and building a good reputation (pirate-wise) some of which was due to having those two female warriors (Anne Bonney and Mary Read) under his command. He was captured and hanged in November 1820, with his gibbet standing in a place known today as Rackham’s Cay.

1 Black Beard

Black Beard
Jean Leon Gerome Ferris –

Edward Teach, known as the fearsome Black Beard, was a pirate and also a man who understood the importance of image, unusual for those days. Despite his imposing and blood-thirsty appearance and tales of brutality that seemed to follow him, he was actually never known to harm those that he captured, often taking over ships with the permission of their crews, rather than by force. Little is known about where he came from, and it is highly unlikely that Edward Teach was his real name, as pirates often changed their names to protect their identities or those of their families. With so little known about him, it is unlikely that his real identity will ever be known… After his death, he became a romantic and popular figure, becoming the basis of many tales, anecdotes and stories of piracy, love and death on the high seas! He died in a fierce battle in 1719, during which he took no less than five bullets and received at least twenty injuries from a sword or other bladed weapon.

John, hailing from the bustling streets of London, is an avid movie buff and comic book enthusiast. With a keen eye for cinematic detail and a deep appreciation for the art of storytelling,

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