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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

6. A Stellar Start to a Piratical Career

A colorized 1724 depiction of Black Bart at Ouidah, now in Benin, West Africa, with his ship and captured merchantmen in the background. Owlcation

Black Bart kicked off his pirate captain career by sailing to South America, where he came upon a Portuguese treasure fleet assembling in a bay in northern Brazil. Pretending to be one of the convoy, he slipped into the fleet, a wolf in sheep’s clothing. That night, he quietly seized one ship, forced its captain to point out the fleet’s richest vessel, then captured it and fled before the escorting Portuguese warships realized 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 piratical career struck a chord and made him famous. He sailed north into the Caribbean, and other pirates flocked to his side. Black Bart put them to good use, and at the height of his career, he commanded a fleet of four pirate ships and over 500 pirates.

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.