1. Sir Francis Drake
Mentions – 4
Wealth – 9 ($115 million)
Total – 13 points
Sir Francis Drake was born in 1540 by some records, and he spent his life at sea, as a captain, privateer, navigator, and slaver, while also playing the role of a politician. He is best known for being the second to circumnavigate the world in a single expedition, between 1577 and 1580.
Drake wasn’t the typical pirate, like you see in the movies, mainly because he was fully backed by the English. While the Spanish certainly hated him and called him a pirate after taking over several of their ships and their treasures, he was a hero to the English, with Elizabeth I of England awarding him a knighthood in 1581. In fact, the Spanish hated him so much they put a bounty on his head, one that was never claimed.
As vice-admiral in command of the English fleet, Drake managed to overcome the Spanish Armada trying to invade England back in 1588, going as far as to capture the Spanish galleon Rosario.
Drake’s last big fight ended in defeat as Spanish ships shot a cannonball into his cabin, although he survived that attack. Weeks later, however, he died of dysentery. Drake was feared, famous and successful, putting him at the top of our list of the 10 most successful pirates in history.
