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Pirates tend to be reduced to costumes and catchphrases, but the real-life figures were more perceptive, more eccentric, and far more strategic than the myths suggest. Many were skilled navigators, ruthless tacticians, or political opportunists who understood empires better than the empires understood them. Their lives unfolded in port cities, colonial chokepoints, and lawless stretches of water where authority quickly faded. Some sought only profit; others harbored a deep-seated grudge against crowns and companies; and a few managed to do both. Here are 20 pirates who left their mark on entire eras of maritime history through their strength, their sense of opportunity, and their composure.

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