pirates The 10 Most Successful Real-Life Pirates  

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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 is listed (or ranked) 1 on the list The 10 Most Successful Real-Life Pirates
Photo: Freebase/Public domain

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: Died at 59 (1785-1844)

Profession: Pirate

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Cheung Po Tsai is listed (or ranked) 2 on the list The 10 Most Successful Real-Life Pirates
Photo: Freebase/GNU Free Documentation License
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: Died at 39 (1783-1822)

Birthplace: Xinhui District, China

Profession: Pirate

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François l'Olonnais is listed (or ranked) 3 on the list The 10 Most Successful Real-Life Pirates
Photo: Freebase/Public domain

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: Died at 33 (1635-1668)

Birthplace: Les Sables-d'Olonne, France

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Blackbeard is listed (or ranked) 4 on the list The 10 Most Successful Real-Life Pirates
Photo: Freebase/Public domain
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.)

Profession: Pirate

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