Pirates and Leadership

John Bradley "JJ" Jackson

27 Oct 2025 • 2 min read

I Love the Look

I recently binge-watched the pirate series called Black Sails on Netflix at a friend’s suggestion. I was entertained, but also unexpectedly educated. The show inspired me to dig deeper into the ethics of piracy. Pirates, it turns out, were forward-thinking in surprising and instructive ways. Who knew?

In the heat of an 18th-century summer, a pirate crew spotted a merchant ship off the Virginia coast and attacked. Through the smoke and chaos came their leader, pistols strapped across his chest, black ribbons in his beard. The TV show’s version of Blackbeard is part or mostly legend, but it led me to real-life captains like Bartholomew “Black Bart” Roberts and Samuel “Black Sam” Bellamy, who were equally formidable and surprisingly enlightened (by the way, this sliver of 18th century history is all new to me).

Pirate leadership practices included shared power, ownership, and inclusion offer lessons that still resonate today.

Everyone Has a Voice: Life on merchant ships was often a dictatorship. Captains ruled by fear, punishing dissent as mutiny. Pirates turned that system upside down. They voted on their captain, limited his power, and guaranteed each crew member a say in ship affairs. Roberts’ crew even had written “articles of agreement” that spelled out these rules. If a captain lost the crew’s trust, they could vote to replace him or maroon him. Imagine if modern organizations worked that way. Kind of like term limits.
Shared Ownership Creates Order: Pirate crews operated under ship “articles,” a kind of constitution drafted by unanimous vote before a voyage. The rules set pay, duties, and even injury compensation for battle wounds. If you got hurt, the crew took care of you. Kinda like disability insurance. Because they helped write the rules, every pirate felt personally invested. They weren’t just following orders. They were co-owners of the mission.
Talent Instead of Pedigree: Pirate ships were among the most diverse organizations of their time. Crews had mixed races, religions, genders, and nationalities. On land, slavery was law; at sea, Black sailors could vote, share equally in plunder, and even command ships.

Pirates were bad guys who lived outside the law, but not without order. They practiced democracy, inclusion, and accountability long before these ideas went mainstream. Their success depended less on fear than on fairness and shared purpose.

Leadership lessons can surface in the most unlikely places. Even from the deck of a pirate ship.

Argh.

Source: https://www.thewayofthepirates.com/pirate-life/pirate-code/