The 10 Most Successful Real-Life Pirates

A list of real-life historical pirates. When the word pirate is mentioned, images of Johnny Depp as Captain Jack Sparrow instantly come to mind. Real pirates, however, were (and are) a lot more intimidating. These marauders and swashbucklers have roamed the seas for hundreds of years, raining terror and mayhem down on poor unsuspecting souls. These are the most successful and/or terrifying pirates to ever sail the ocean blue.

Who is the most successful pirate? This list of real life pirates will befuddle, maybe even bewilder you, knowing that these men of the high seas actually pulled off heists worthy of the movies. 

  • Ching Shih
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    It may be hard to believe, but the most notorious pirate to ever live was a former prostitute named Ching Shih, the wife of pirate Zheng Yi and later the wife of the couple's adopted son Cheun Po Tsai. Sounds twisted, right? Ching Shih terrorized coastal villages from Macau to Canton in the People's Republic of China until she eventually gave up her pirating ways, living out her 69 years running a casino and brothel.

    [In the "Pirates" movies, she's depicted as "Mistress Ching," one of the members of the Brethren Court.]

    • Age: Dec. at 59 (1785-1844)
  • Cheung Po Tsai is one of the pirates depicted in the movie "Pirates of the Caribbean: At World's End." He was the adopted son-turned-husband of the most noteworthy female pirate, Ching Shih. With a fleet of 20,000 men and several hundred ships, Cheung Po Tsai was able to wreak considerable havoc along the Guangdong coastline. After his eventual capture by the Chinese government, he was enlisted as a captain in the Qing Imperial Navy.
    • Age: Dec. at 39 (1783-1822)
    • Birthplace: Xinhui District, China
  • François l'Olonnais
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    Franois l'Ollonais was a sadistic French pirate believed to have eaten the bloody heart of a Spanish solider during his bloodthirsty reign. His most notable plundering expedition involved the town of Maracaibo, Venezuela, where he left a path of destruction in his wake after raping, pillaging and burning much of the city. His treasures from that attack included gemstones, cacao beans and over 200,000 Spanish Dollars.

    Pursued by the Spanish, l'Olonnais eventually ran aground in Panama, where he was captured and, yes, devoured by the native tribes.
    • Age: Dec. at 33 (1635-1668)
    • Birthplace: Les Sables-d'Olonne, France
  • Blackbeard, or Edward Teach, as he was once known, was one of the most terrifying pirates to ever sail the Atlantic Ocean and Caribbean Sea. Though his reign of terror only lasted two years, during that time he managed to amass a vast supply of booty, ranging from grains, to alcohol, jewelry and much, much more. He was eventually overtaken and beheaded after a fierce battle against Lieutenant Robert Maynard of the Royal Navy in 1718. (His head was later palced on a stake near Virginia's Hampton River as a warning to other pirates.) Legends about the infamous pirate still circulate today, and he is portrayed by Ian McShane in "Pirates of the Caribbean: On Stranger Tides." (The film is based on the novel "On Stranger Tides" by Tim Powers.)
  • Henry Every
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    Henry Every was an British pirate known by many different aliases over the course of his pirating career, making him a bit difficult to track. One of Every's most notorious looting escapades involved the capture of the Gang-i-Sawai and the subsequent torture and rape of the women on board the ship. If that's not terrifying, what is? So desperate was the East India Company to get rid of him, they offered a 1,000 pound bounty (a neat sum in 17th Century terms), setting off what is considered to be among the first worldwide manhunts in history. He was never captured, however, and is thought to have died after settling on some unknown tropical island.
    • Birthplace: Newton Ferrers, United Kingdom
  • Bartholomew Roberts
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    Captain John 'Bartholomew' Roberts has the distinction of being the most notable ship plunderer to ever exist. It's rumored that he pillaged approximately 400 ships over the course of his pirating days, one of which included 80 slaves, whom he burned alive at sea. Roberts was notable for his pride and boastful nature, and he famously dressed in his finest clothes before a battle.

    Roberts was killed in 1722, while battling the Royal Navy's HMS Swallow, after he was shot in the neck. He came to be known as "Black Bart," though this nickname is also associated with American outlaw Charles Earl Bowles.
    • Age: Dec. at 39 (1682-1722)
    • Birthplace: Pembrokeshire, United Kingdom