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In the early days of the Golden Age of Piracy, he sailed as a privateer and developed a reputation for courage fighting against the Spanish on behalf of the British crown. He was celebrated for his role in Sir Henry Morgan's infamous raid on Panama in 1671.
After retiring from privateering, he settled in Jamaica and entered the slave trade to bolster his wealth. In 1717, his flagship slave galley, The Whydah, was attacked by Black Sam Bellamy, though Prins managed to survive and continue slaving.