Sir Francis Drake Was Uglier Than His Name Suggests and Also a Professional Troll

We’re talking about Sir Francis Drake today, because imagine sitting still for long enough for Marcus Gheeraerts the Younger to paint a portrait of you and it turning out like this:

That is a bad look, Frank. And a disappointing look. Your name is Sir Francis Drake. You should look like Brad Pitt looked in Moneyball.

To be fair, this may have been the style at the time. Or British people of that day and age might have just been a little ugly. Of all of Gheeraerts’s other work, I think the only portrait where the guy doesn’t look like a total loser because of the painting is his portrait of Robert Devereaux. Devereaux still looks like a loser, but that’s because of how he’s dressed and what he’s holding. What are you up to, Rob? Whatcha got there in your left hand?

We’re talking about Sir Francis Drake today because his portrait sucks, but I also want to talk about him because his job was bonkers. Sir Francis Drake’s job, for most of his life, was to antagonize Spain, raiding and pillaging Spanish outposts in the New World. There’s some disagreement on how much blessing his raiding and pillaging had from the English crown, but he definitely had at least some encouragement. He was a privateer, which has led the Spanish to call him a pirate, which sounds very true. I don’t think there’s a big difference between a privateer and a pirate. If a ship is bearing down on you to steal your treasure, you don’t say, “Hey, wait a second. Are you financed by a recognized government?” That doesn’t make it feel very different. Captain Phillips would have gone very similarly if the line had been, “Look at me. I am the captain now. Also I have a permit to do this and am operating on behalf of the Somali government.”

There are many good parts to Drake’s career, but one is that the man’s circumnavigation of the globe (his was the third expedition to do it) was partly motivated by a desire to fuck with the Spanish. You know how people sometimes go out of their way to see the Grand Canyon when they’re in Las Vegas or Scottsdale for a bachelor party? That was Sir Francis Drake, except instead of a bachelor party he was on the California and Oregon coast to raid the Spaniards and instead of going to see the Grand Canyon he just kept on sailing all the way back to England the long way.

Another is how much Sir Francis Drake hated Spain. He hated, hated, hated Spain. Early in his career—back in the slaving days (Sir Francis Drake, kind of a bad guy, even adjusting for the time)—Spain kicked his butt in a battle down by Mexico, and as Wikipedia puts it:

The bitter end of the fourth voyage turned Drake’s life in a different direction: thereafter he would not pursue trading and slaving but would, instead, dedicate himself to attacking Spanish possessions wherever he found them. Drake’s hostility towards the Spanish is said to have started with the battle and its aftermath.

Sir Francis Drake was a professional hater. Thank goodness this guy wasn’t around at the same time as The Internet. His trolling would have been insufferable.

NIT fan. Joe Kelly expert. Host of Two Dog Special, a podcast. Can be found on Twitter (@nit_stu) and Instagram (@nitstu32).
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