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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

5. Black Bart’s Cruelty

Piracy - Black Bart's flag, showing him and Death holding an hourglass — Black Bart’s flag, showing him and Death holding an hourglass. Pinterest

Black Bart owed much of his success to organizational and leadership abilities, combined with charisma and daring that inspired and encouraged his men. In only four years, he captured and looted over 470 ships. He was cruel and sadistic, and relied on terror and a frightening reputation to ensure 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 shackled slaves aboard. A bloodthirsty man, Black Bart’s end was appropriately bloody: in 1722, he decided to fight it out with a Royal Navy ship, 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 they surrendered.

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.