12 of History's Most Notorious Pirates Will Make You Want to Stay off the Seven Seas
12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas

12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas

Khalid Elhassan - November 11, 2017

12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas
Black Bart. Owlcation

Bartholomew “Black Bart” Roberts

Considered the most successful pirate of the Caribbean, Bartholomew “Black Bart” Roberts (1682 – 1722) captured and looted more ships during his career than his contemporaries Black Beard, Jack Rackham, Francis Sprigg, and Edward Low put together. His spectacular success as a pirate was ironic because he had never wanted to be a pirate to begin with.

In 1719, Roberts had been an officer aboard a slaver that was captured by pirates, who forced him to join them. Within 6 weeks, he had impressed his new crewmates so much that when their captain was killed, the pirates elected Roberts their new captain. His career as a pirate captain got off to a spectacular start when, sailing to South America, Roberts came upon a Portuguese treasure fleet assembling in a bay in northern Brazil. Pretending to be one of the convoys, Roberts slipped into the fleet, a wolf in sheep’s clothing. That night, he quietly seized one ship and forced its captain to point out the fleet’s richest vessel, then captured it and fled before the Portuguese escort warships caught on to what was happening under their noses. The loot came to over 40,000 gold pieces, plus jewelry commissioned for the king of Portugal.

That daring deed to start off his pirate career struck a chord and made Roberts. Sailing north into the Caribbean, pirates flocked to his side, and he put them to good use. At the height of his career, he commanded a fleet of four pirate ships and over 500 pirates, and much of his success is owed to his organizational and leadership abilities, combined with charisma and daring that inspired and encouraged his crews. During his four-year career as a pirate, Black Bart captured and looted over 470 ships.

He was cruel and sadistic and relied on terror and a frightening reputation to win compliance. In 1722, he captured a slave ship at anchor while her captain was ashore, and sent him a message demanding ransom for the return of his ship. When the captain refused, Roberts burned the ship, with 80 slaves shackled aboard. A bloodthirsty man, his end was appropriately bloody: in 1722, he decided to fight it out with a Royal Navy vessel, only to get his throat torn out by grapeshot in the first broadside. His men honored his standing order that he be buried at sea, and immediately weighed him down and threw him overboard before surrendering.

12 of History’s Most Notorious Pirates Will Make You Want to Stay off the Seven Seas
Cheung Po Tsai. History of Piracy

Cheung Po Tsai

Cheung Po Tsai (1783 – 1822), whose name translates as “Cheung Po, the Kid”, was a poor fisherman’s son who went on to become a notorious Chinese pirate operating in the vicinity of modern Hong Kong. He became legendary because of a treasure he supposedly buried in a cave that bears his name on Cheung Chau island southwest of Hong Kong.

Cheung was kidnapped at age 15 by a pirate who pressed him into his crew. The teenager quickly took to piracy, exhibited a precocious talent for the new career suddenly thrust upon him, and rose swiftly through the ranks. Before long, Cheung had become his kidnapper’s favorite protege and subordinate and ended up getting adopted by him and his wife. After his adoptive father’s untimely death by drowning, his widow and Cheung’s adoptive mother took over his pirate fleet, and Cheung became her right-hand man. The pair soon developed an incestuous affair and married, after which Cheung took charge of the piracy business from his wife/ adoptive mother.

Cheung’s scale of piratical operations far exceeded anything seen in the Caribbean during the Golden Age of Piracy, and at the height of his career, he commanded more than 600 ships and over 50,000 men. With that massive armada, Cheung and his pirates effectively controlled and held for ransom the shipping lanes around southern China.

His massive depredations and the resultant outcry finally compelled the Chinese authorities to launch a commensurately massive campaign to eradicate piracy and restore order. In 1810, seeing the writing on the wall and deciding that discretion was the better part of valor, Cheung accepted a pardon, joined the Chinese navy, and spent the rest of his life as a pirate hunter.