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History's Most Infamous Pirates

There’s more to pirates than peg legs, parrots, buried treasure and amusing ways of saying “arrr” as this swashbuckling list reveals. Read on to discover which English county produced history’s two-highest earning bucaneers and which woman beats them both to the top spot as history’s most infamous pirate

 5. Sir Francis Drake (1540-96)

It seems unlikely to happen in the modern world that someone could combine being the mayor of Plymouth and an MP with a career as a pirate. But such was the life of Sir Francis Drake, England’s leading bucaneer of the Elizabethan Age.

Drake, born around 1540 in Tavistock, Devon, is generally remembered as something of a national hero for his role in defeating the Spanish Armada and because he was the first Englishman to circumnavigate the globe. But he was also a slave trader and a pirate, albeit one with royal approval (Queen Eizabeth I called him “my pirate”). 

Drake specialised in raiding Spanish ships laden with treasures they’d plundered from the Americas. During the course of his career he made an estimated $115 million in today’s money, placing him second on Forbes magazine’s list of history’s top-earning pirates. His career came to end in 1596 when he died of dystentry off the coast of Panama where he was buried at sea. 

4. Sir Henry Morgan (1635-88)

The Welshman who went on to become Governor of Jamaica is one of the most well-known pirates in the world, and not just because of the rum that bears his name. Like Drake, Morgan was a state-sponsored pirate, plundering Spanish ships and towns all around the Caribbean in the second half of the seventeenth century.

Morgan was lauded as a hero back home and knighted by Charles II, but one of his former crewmen wrote a book about him accusing him of torture and excessive cruelty (even by pirate standards). He’s said to have used nuns as a human shield when attacking a town in Panama. What’s certain is that he was a slave owner, accumulating a fortune from plantations in Jamaica.

Appropriately enough for a man with a brand of rum named after him, Morgan was a heavy drinker. This contributed to the deterioration of his health and his death in 1688. He was given a state funeral and an amnesty was declared for pirates so that they could attend to pay their respects.

Although Morgan was buried on land his body was eventually claimed by the sea. An earthquake in Jamaica in 1692 caused his grave to fall into the Caribbean, from where it has never been recovered. 

3. Samuel “Black Sam” Bellamy (1689-1717)

Born in 1689 in the village of Hittisleigh in Devon, just 25 miles from Francis Drake’s home, Samuel “Black Sam” Bellamy surpassed even his more famous neighbour in terms of loot captured. Forbes magazine rated him as the highest-earning pirate of all-time, having helped himself to bounty worth an astonishing $120 million in today’s money.

What’s even more remarkable is that he did this in a career as a pirate captain that lasted less than one year. Bellamy started as a pirate under the command of Benjamin Hornigold and Blackbeard. But when that notorious pair were voted out of command, Black Sam, who dubbed himself the “Robin Hood of pirates”, took charge.

His capture of the Whydah Gally, a slave ship full of gold on its way back to England, brought him his enormous fortune. He also swapped the Whydah Gally for his own ship, but disaster was to strike soon afterwards.

It’s said that Bellamy was taking the Whydah Gally on a journey to see his girlfriend Goody Hallet, known as the Witch of Wellfleet. But the massive ship got into trouble on a stormy night off Cape Cod in 1717, and Black Sam sank with his fortune to the bottom of the Atlantic.  

 2. Blackbeard (1680-1718)

Relative to Black Sam the earnings of Bristolian Edward Teach, better known as Blackbeard, were pitifully small - a mere $12.5 million in today’s money. But there’s no doubt which of the men was the more infamous pirate.

Blackbeard created the modern image of the pirate with his long plaited beard and terrifying appearance. He is said to have lit slow-burning matches under his hat to create a cloud of smoke around himself when boarding ships. The 1724 book “A General History of the Robberies and Murders of the most notorious Pyrates” described him as "such a figure that imagination cannot form an idea of a fury from hell to look more frightful”.

In 1717 he captured a French slaving ship off the coast of St. Vincent, which he filled with pirates and cannons and renamed Queen Anne’s Revenge. He then proceeded to terrorise the Caribbean and the eastern coast of America, but his career was brought to a bloody end in November 1718, when he was killed in combat by British forces led by Lieutenant Robert Maynard.

Blackbeard did not go down without an almighty struggle. It’s said that it took five shots and twenty sword blows to finish him off. Legends have grown up around the treasure of Blackbeard which he said was hidden in a location “known only to the devil and me”, it remains unfound. 

1. Madame Cheng (1775-1844)

We’ve met some pretty ferocious men on this list but all of them would have quaked in their boots had they have faced the most powerful pirate of them all - Madame Cheng.

Born in Guangzhou in 1775, Cheng’s rise to swashbuckling superstardom began when she married Cheng I, the leader of a family with over one hundred years of piratical experience across the South China Seas. Cheng I had already established an enormous pirate confederation, consisting of over 400 ships and 70,000 men. But, after his death Madame Cheng took over and made it even bigger, commanding over 1,800 ships and 80,000 pirates.

As leader Madame Cheng had a distinctly no nonsense approach to discipline, with a strict code of rules and beheading the preferred punishment. Her mighty pirate fleet fought successfully against the Chinese navy and against British and Portuguese bounty hunters.

Eventually defeated by the force of the Portuguese navy in 1810, Madame Cheng escaped punishment by accepting a Chinese government amnesty. This allowed her to retire, aged just 35, with the booty she’d accumulated from her career in piracy.

Although she never sailed as a pirate again she did act as a naval adviser to the Chinese government in the 1839 war against the British, who were fighting for their right to sell opium to China. Unlike all the other pirates on our list she died peacefully in her bed, at the relatively ripe old age of 69.