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[4] Anne Bonny: The Firebrand of the Caribbean

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  Anne Bonny was not your average 18th-century woman. Raised in Ireland and later South Carolina, she ditched her life of privilege for the pirate’s life. She teamed up with Calico Jack Rackham , became one of the few female pirates in history, and fought alongside men, proving she was just as ruthless. Bonny was fierce in battle , reportedly cursing at her fellow pirates when they surrendered instead of fighting to the death. She and Rackham were eventually captured in 1720 , but she avoided execution by "pleading the belly" —claiming she was pregnant. Her fate remains a mystery. Some say she was quietly released, others believe she returned to a respectable life , and a few claim she resumed piracy. Final Thought: Anne Bonny was the original “ride or die” —except if you were too cowardly to fight, then she had zero sympathy for you . Pirate log book entry [PtF]
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[3] Bartholomew Roberts: The Dapper Desperado

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  Bartholomew Roberts, also known as Black Bart , wasn’t just one of the most successful pirates—he was arguably the most profitable . Operating in the early 18th century, he captured over 400 ships in his career, making other pirates look like amateurs. Unlike the stereotypical rum-soaked, chaotic pirate, Roberts ran a disciplined operation. He even preferred tea over alcohol —which is either the classiest pirate fact ever or the biggest betrayal to pirate culture. His personal code was strict, forbidding gambling and drunken disorder (so basically, no fun). His career ended in 1722 , when the Royal Navy caught up with him. True to his legend, he died in battle, shot in the throat. His crew, following his last wishes, threw his body overboard , ensuring he wouldn’t suffer the indignity of being hanged. Final Thought: Black Bart was the corporate executive of piracy —efficient, no-nonsense, and probably the guy who would reply to emails at 2 AM. Pirate log book entry [Xyd]
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[2] Charles Vane: The Pirate Who Just Wouldn’t Die

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Charles Vane was one of the most violent and unpredictable pirates of the Golden Age. While some pirates accepted pardons, Vane refused, preferring to keep raiding and being an absolute menace to the British Navy. His downfall came when his crew mutinied and left him stranded on a deserted island (which is pirate-speak for "We’re done with your nonsense"). He eventually got rescued but was recognized, arrested, and hanged in 1721. Final Thought: Vane was that one coworker who refuses to do team-building exercises and gets fired for "not aligning with company values."  Pirate log book entry [uuj]
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[1] Mary Read: The Pirate Who Took No Nonsense

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Mary Read’s story reads like an adventure novel . Raised as a boy in disguise, she joined the military before eventually becoming a pirate with Anne Bonny and Calico Jack. She was known for her fearless combat skills , reportedly challenging men who questioned her abilities to duels—and winning. Unlike many pirates, Read didn’t get captured easily; when the authorities raided their ship, she fought to the last moment while the men surrendered like cowards. Like Bonny, she escaped execution by claiming pregnancy, but she died in prison soon after—though some legends say she escaped and vanished into history . Final Thought: Mary Read was basically the pirate version of an action movie hero , except she didn’t need special effects to be a total badass. Pirate log book entry [NXt]
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