2Sir Francis Drake – $115 million
Sir Francis Drake is best known as being the second captain to navigate the globe.
Nicknamed ‘El Draque’, the English captain, privateer and slaver was also a politician of the Elizabethan era.
Drake’s exploits were legendary, making him a hero to the English. And a pirate to the Spaniards. It is rumored that King Philip II offered about $6.5 million reward for his head on a plate.
After defeating the Armada, El Draque continued to make havoc, and eventually he managed to collect huge bounty, becoming one of the richest pirates in the world.