20. Queen Elizabeth I’s Favorite Sailor
Sir Francis Drake (circa 1540 – 1596) was many things: a sea captain, naval officer, explorer, politician, slave trader, privateer, and at times, he was also an outright pirate. And not just any pirate, but Queen Elizabeth I’s favorite pirate. He gained her favor for good reason. The Virgin Queen invested in English pirates like modern venture capitalists invest in Silicon Valley startups, and she made out like a bandit from the returns on Drake’s high seas hijinks and predations.
The most celebrated seaman of the Elizabethan Era, Drake led one of history’s more adventurous careers. He first went to sea at an early age. As a teenager, he was enlisted by his relatives, the Hawkinses, a clan of privateers who preyed upon French coastal shipping. By the 1560s, Drake had risen to command his own ship, entered the slave trade, and smuggled shackled captives illegally into Spain’s New World possession. By the time his storied career and life came to an end, Drake had become the greatest pirate of his day.