June 17, 1791 - Roberto Cofresí
Operating in the Caribbean during a period of regional upheaval, Cofresí built a career of piracy that proved remarkably difficult to suppress — evading the navies of six nations before he was finally caught and executed at thirty-three. His success owed less to force than to tactics: small, fast vessels and lean crews gave him an agility that heavier, well-armed pursuers couldn't match. The instability of the Spanish colonial economy that shaped his early life also shaped the waters he sailed, making him one of the last significant pirates of the Atlantic era.
From Wikipedia
Roberto Cofresí y Ramírez de Arellano (June 17, 1791 – March 29, 1825), also known as El Pirata Cofresí, was a Puerto Rican pirate. He was born into a noble family, but the political and economic difficulties faced by the island as a colony of the Spanish Empire during the regional independence wars against the metropole meant that his household was poor. Cofresí worked at sea from an early age, which familiarized him with the region's geography, but provided him with only a modest salary. He eventually decided to abandon the sailor's life and become a pirate. He had previous links to land-based criminal activities, but the reason for Cofresí's change of vocation is unknown; historians speculate that he may have worked as a privateer aboard El Scipión, a ship owned by one of his cousins.
At the height of his career, Cofresí evaded capture by vessels from Spain, Gran Colombia, the United Kingdom, Denmark, France, and the United States. He commanded several small-draft vessels, the best known a fast six-gun sloop named Anne, and he had a preference for speed and maneuverability over firepower. He manned them with small, rotating crews, which most contemporaneous documents numbered at 10 to 20.
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