Sir Francis Drake
Possibly one of the only things more badass than being a professional pirate is the life of a privateer. You get all of the benefits - the pillage, the adventure, the glory, but with a much lesser chance of finding yourself on the wrong end of a noose. As long as you have some sort of government sponsor instead of being considered a criminal and a murderer, you're a goddamned national hero. Sure, you have to give most of your plunder to the crown, but what good is plunder if you have to spend your winters holed up in a dingy cave somewhere instead of kicking back with some fly honeys on your pimp-ass plantation? Privateering is the life, and the most badass of the privateers was Sir Francis Drake.
Drake was just your average boring old British limey sailor delivering goods to the Spanish Main when all of a sudden one day in 1569 he got cocked over by the Spaniards while ashore in San Juan de Ulua. His ship was ambushed and he survived by jumping overboard and swimming to safety, and like any good badass from that day forth he swore he would live for revenge by plundering and pillaging Spanish settlements throughout the Carribean by putting a huge cannon between his legs and cock-slapping Spaniards in the face with it. He led balls-out pirate expeditions up and down the South and Central American coastlines in from 1570 through 1573, with his greatest accomplishment coming in 1573 when he captured the Silver Train - a huge train of pack mules carrying something like eight gajillion tons of silver, fifteen DVD players and a mint-condition Mickey Mantle rookie card. Drake smacked the donkeys, kicked some ass, and ganked all the shit he could carry before heading back home.
Drake's most famous expedition came in 1577 when he set sail to become the first Englishman to circumnavigate the globe. He went down the Eastern coast of South America sacking cities, pillaging ships and robbing liquor stores, then went through the Straits of Magellan before going back up the West Coast and hitting all the unguarded Spanish cities on the coast there. By the time he hit Panama he only had one ship, the Golden Hind, and eighty men left in his crew (some bitch had tried to incite a mutiny so Drake responded by kicking him in the junk and dropping an anchor on his head). He went on to capture the Spanish galleon Cacafuego, which if my Spanish serves me correctly translates to "burning shit", where he recovered thirteen chests full of gold, twenty-six tons of silver and more jewels than you could fit inside a ten gallon hat. By the time he sailed around the world and returned home he only had fifty-nine men left, but for his awesome bitchin'ness he was knighted by the Queen in 1581, declared a national hero, elected mayor of Plymouth and made a Member of Parliament.
A reproduction of H.M.S. Golden Hind.
He wasn't finished whomping jerks yet though. In 1585 he sacked towns in Colombia and the Dominican Republic. Then he faxed King Philip II of Spain a picture of his bare ass, causing a renewal in hostilities between England and Spain. Drake had so badly pissed off Philip that he put together the largest fleet that had ever been assembled - the Spanish Armada, consisting of 150 Spanish galleons, ten Imperial Star Destroyers and a half-dozen trained porpoises with swords attached to their heads. Drake was the assistant commander of the heavily-outgunned British force that opposed the Armada, but even though it looked hopeless he had a fucking plan. He was all like, "dude let's set some motherfucking ships on motherfucking fire and send them right into the Spanish Fleet". So the British did. The entire Spanish fleet caught on fire like a pumpkin filled with gasoline and broke apart in confusion, allowing Drake the chance to personally capture the Admiral of the Spanish Navy and steal his cool Admiral Hat.
After the sweeping victory against the Armada, Drake decided to chill out back at home for a while. He build a sweet mansion like the kind you see on MTV's Cribs, got hitched to some duchess babe with huge cans and walked around downtown Plymouth with a sweet pimp cane made out of gold-plated diamonds. Eventually he got bored of the good life and set sail for the Caribbean in 1595, but after a failed attempt to sack Panama he caught dysentery and was killed by his own explosive diarrhea.
Drake was fucking sweet as hell, because he was not only a badass pirate motherfucker who captured enough gold and silver to bankroll the New York Yankees, but he was also a national hero among Brits for his unequalled ability to beat the crap out of Spanish people. He was tough, daring and incredibly skilled, and was so hatefully remembered by the Spanish that for many years they actually celebrated the anniversary of his death. That's fucking awesome when you can piss off your enemies so badly that they celebrate your death years after it happened. That's the sort of goal that every badass should hope to achieve.
As if he wasn't badass enough in life, Francis Drake is just as fucking tough in death. During all of his adventures, Drake carried with him a custom-made drum that bore his coat of arms. Legend has it that when Mother England is in times of great peril, the drum starts beating like Tommy Lee at a Motley Crue reunion. It happened during the British evacuation of Dunkirk and again during the Falkland Islands War, and rumor has it that if England ever gets into really super-omega deep shit, Drake will actually come sweeping into town like the ghost army from Lord of the Rings, grab the drum and use it to bash the shit out of anything that threatens the well-being of his country, proving that even though he's been dead for four hundred years he's still a goddamned force to be reckoned with.
"The most famous anecdote about Drake relates that, prior to the battle, he was playing a game of bowls on Plymouth Hoe. On being warned of the approach of the Spanish fleet, Drake is said to have remarked that there was plenty of time to finish the game and still beat the Spaniards."
In Drake's Wake
Sir Francis Drake History
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