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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

2. L’Olonnais Was Truly Terrifying

lolonis fight spaniard — Francois L’Olonnais and his men torturing captives. Period Paper Historic Art

An expert torturer, Francois L’Olonnais got up to some pretty macabre stuff. Among other things, he liked to slice off strips of his victims’ flesh, burn them, or tighten ropes around their skulls until their eyeballs popped out of their sockets. Early in his career, he was shipwrecked off Yucatan. A majority of the crew survived and made it to shore, only for most of them to perish soon thereafter when Spanish soldiers found and fell upon them. To survive, L’Olonnais covered himself in blood and viscera, and hid among the corpses. Later, he snuck into a nearby town that was celebrating the deaths of the pirates, and arranged for an escape back to Tortuga. L’Olonnais resumed his depredations against Spain and the Spaniards, and in 1666 he assembled a fleet of eight ships and 440 pirates to attack Maracaibo in modern Venezuela.

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.