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The Golden Age of Piracy’s Most Terrifying Pirates

Khalid Elhassan March 7, 2025 16 min

Piracy - A Tortuga buccaneer — A Tortuga buccaneer. Wikimedia

7. The Caribbean’s Most Successful Pirate?

Bartholomew “Black Bart” Roberts (1682 – 1722) was one of the most successful pirates of the Caribbean. He captured and looted more ships during his career than his famous contemporaries Blackbeard, Jack Rackham, Francis Sprigg, and Edward Low put together. His spectacular success was ironic, because he had never wanted to be a pirate to begin with. In 1719, Black Bart had been an officer aboard a slaver that was captured by pirates, who forced him to join them. Within six weeks, he had impressed his new crewmates so much that when their captain was killed, the pirates elected Bart to replace him. He soon got over any doubts he might have had about his new career, and took to piracy with a will. As seen below, few pirates ever began their career with as big a bang as did Black Bart.

Written by

Khalid Elhassan

A lifelong history buff, I developed a particular passion for WW2 history as a child, when I spent hours listening to my grandfather, enraptured, as he recounted his wartime experiences in the British East African Campaign and with the British 8th Army in North Africa.

I graduated with a history BA from George Mason University, then went on to get a JD from the University of Virginia School of Law. After lawyering for a decade, I moved to sunny Rio de Janeiro and a less demanding career, opening a tourism agency in Copacabana.

A big chunk of my free time is spent blogging (you can follow me on Quora https://www.quora.com/profile/Khalid-Elhassan ) or freelance writing, mostly about my favorite subject, history.