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Real-Life Pirates of the Caribbean

The Men and Women who Terrorized the Seas


We've all seen the Pirates of the Caribbean movies, gone on the ride at Disneyland and dressed like a pirate for Halloween. Therefore, we know all about pirates, right? They were jolly fellows who had pet parrots and went looking for adventure, saying funny things like "Avast ye, scurvy dog!" Not quite. The REAL Pirates of the Caribbean were violent, desperate thieves who thought nothing of murder, torture and mayhem. Meet some of the men and women behind the legends.

1. Edward "Blackbeard" Teach

Frank E. Schoonover, 1922

Edward "Blackbeard" Teach was by far the most famous pirate of his generation, if not the most successful. He was famous for putting lit fuses into his hair and beard, which gave off smoke and made him look like a demon in battle. He terrorized Atlantic shipping in 1717-1718 before he was killed in battle with pirate hunters in November of 1718.

2. Bartholomew "Black Bart" Roberts

Engraving by Benjamin Cole (1695-1766)

"Black Bart" Roberts was the most successful pirate of his generation, capturing and looting hundreds of ships in a three-year career from 1719-1722. He was at first a reluctant pirate and had to be forced to join the crew, but he quickly earned the respect of his shipmates and was made captain, famously saying that if he must be a pirate, it was better "being a commander than a common man."

3. Captain William Kidd

Illustration by Howard Pyle (circa 1900)

The infamous Captain Kidd started out as a pirate hunter, not a pirate. He sailed from England in 1696 with orders to attack pirates and the French wherever he could find them. He soon had to give in to pressure from his crew to commit acts of piracy. He returned to clear his name and was instead jailed and eventually hanged...some say because his secret financial backers wished to remain hidden.

4. Captain Henry Morgan, Greatest of the Privateers

Getty Images / Hulton Archive

Depending on who you ask, the famous Captain Morgan wasn't a pirate at all. To the English, he was a privateer and a hero, a charismatic captain who had orders to attack the Spanish wherever and whenever he wished. If you ask the Spanish, however, he was most definitely a pirate and corsair. With the help of the famous buccanneers, he launched three raids from 1668-1671 along the Spanish main, sacking Spanish ports and ships and making himself wealthy and famous.

5. John "Calico Jack" Rackham

18th Century Woodcut, Artist Unknown

Jack Rackham was known for his personal flair - the bright clothes he wore gave him the name "Calico Jack" - and the fact that he had not one, but TWO female pirates serving on board his ship: Anne Bonny and Mary Read. He was captured, tried and hanged in 1720.

6. Anne Bonny

Artist Unknown

Anne Bonny was the lover of Captain Jack Rackham, and one of his best pirates. Bonny could fight, cuss and work a ship as well as any of the male pirates under Rackham's command. When Rackham was captured and sentenced to death, she allegedly said to him "If you had fought like a man, you need not have hanged like a dog."

7. Mary Read

Artist Unknown

Like Anne Bonny, Mary Read served with "Calico Jack" Rackham, and like Bonny, she was tough and deadly. allegedly, she once challenged a veteran pirate to a personal duel and won, just to save a handsome young man she had her eye on. At her trial, she declared that she was pregnant, and although this spared her a trip to the noose she died in prison.

8. Henry Avery, the Pirate who kept his Loot

Artist Unknown

Henry Avery was the inspiration for a whole generation of pirates. He mutinied on board a ship of Englishmen fighting for Spain, went pirate, sailed halfway around the world and then made one of the biggest scores ever: the treasure ship of the Grand Mughal of India.

9. Charles Vane

Artist Unknown

Charles Vane was a particularly unrepentant pirate who repeatedly refused royal amnesties (or accepted them and returned to a life of piracy anyway) and had little regard for authority. He once even fired on a Royal Navy frigate sent to re-take Nassau from the pirates!

10. Howell Davis, the Clever Pirate

Artist Unknown

Howell Davis was a clever pirate who preferred stealth and trickery to combat. He was also responsible for launching the piracy career of "Black Bart" Roberts.

11. Biography of Pirate “Black Sam” Bellamy

Howard Pyle (1853-1911)
"Black Sam" Bellamy had a short but distinguished pirate career from 1716-1717. According to an old legend, he became a pirate when he could not have the woman he loved!


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