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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

18. From Privateer to Pirate

An eighteenth century depiction of John Avery’s Fancy capturing the Mughal Fleet. Associated Press

The real life inspiration behind the fictional protagonist of The Successful Pyrate was born in Plymouth, England, and went to sea at an early age. By 1694, John Aery was First Mate in the Charles II, a privateer that served the king of Spain, when he led its disgruntled crew in a mutiny that seized the ship. Avery was elected by his fellow mutineers to captain the seized the ship, which was renamed the Fancy. He then made the jump from privateer – semi-official pirates authorized by governments to prey on enemy ships – to outright pirate. He issued a proclamation to assure English vessels that they had nothing to fear from him, and that he would only attack foreign ships. The proclamation was not the worth the paper it was written on: Avery’s first act of piracy was to plunder provisions and supplies from three English merchantmen.

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.