2. Captain Henry Morgan
You guessed it, he’s that character on the rum bottle. Old Captain Morgan wasn’t your average pirate, though: he was paid to do the work of pirates as a privateer. He began his career working for the English as they plundered the New World from coast to coast and then went rogue launching attacks on the Spanish–using Port Royal, the now-sleepy Jamaican fishing village that was known as the world’s wickedest place before an earthquake destroyed two-thirds of the place in 1692, as his homebase–for a commission.