Have you ever read A General History of the Pyrates? You should. The Kindle version is like… a dollar, but the entertainment it will give you is priceless. I’ve been obsessed with pirates for as long as I can remember, but you don’t have to be a pirate historian to get a kick out of some of these stories. Because a lot of these guys were dumbasses.
(I’m going to take a moment to interject here that both of the female buccaneers we know about, Anne Bonny and Mary Read, were phenomenal pirates. Coincidence? I VERY DOUBT IT.)
Anyway, there’s nothing more hilarious than dudes trying to be badass and shamelessly failing at it. So without further ado, I give you History’s Dumbest Pirates.
Stede Bonnet, the Gentleman Pirate
Right off the bat, that is not a good name for a pirate. And an even worse Pirate Nickname. “Blackbeard” struck fear into the hearts of sailors, but “the Gentleman Pirate” probably just made them want to get attacked. They’d most likely get a cup of tea and a ride home. There is literally nothing less frightening than that.
Stede Bonnet was a wimpy rich boy who felt his wife was becoming a drag and thought traipsing as a pirate might be a fun lark. Because when I get bored and want to change things up, theft and murder and navigating the treacherous seas seem like the perfect light-hearted funfest I’m looking for.
Needless to say, Bonnet was a really terrible pirate. His first ever voyage (which was literally just getting from Barbados to the pirate republic in Nassau, Bahamas [which I really want to write about, but that’s another blog post]), he ended up critically wounded. Everyone knew Bonnet couldn’t pirate jack shit on his own, so for some reason, Blackbeard actually took Bonnet under his wing and tried to mentor him in the Ways of Piracy. Was it pity? Was it too much rum? I will never know, and that infuriates me. (Blackbeard was actually kind of a really great guy, but THAT’S ANOTHER BLOG POST TOO DAMMIT.)
Bonnet ruined everything he touched, and Blackbeard eventually let him go. I like to imagine copious facepalming and exasperated sighs and “I really tried, man”s here. Bonnet retired from piracy shortly thereafter.
Aaaaand then he started up again and immediately screwed everything up and got captured. He was subsequently hanged. I wanna feel bad for the guy but… Well, if you’re gonna break bad, you gotta be sure to do it right. And to never call yourself “The Gentleman” anything unless it’s obviously a joke.
“Calico Jack” Rackham
Calico Jack did one thing we can all appreciate, and that was design the Jolly Roger which essentially became the 18th century version of a meme.
Calico Jack should have chilled out with the pirate stuff and pursued a career in graphic design.
Rackham was great at one thing besides flag-designing and that was being drunk as hell literally always. Lucky for him, he had two secret weapons on his side and they were Lady Pirate Duo of Awesomeness Mary Read and Anne Bonny. After seducing Anne away from her boring husband, Rackham and Bonny terrorized the seven seas and were actually pretty successful. But that’s because Rackham was basically just a figurehead captain. Bonny ran that ship, and she ran it tight.
I could talk about Anne Bonny for a loooong ass time, but that’s yet another blog post. Suffice it to say, girl was not a great person, but she was a hell of a pirate. And she was devoted to Calico Jack. Which meant he got to stay as drunk as he wanted, knowing his lady friend would take care of everything and he would get all the credit.
When Rackham’s crew picked up Mary Read, things got even better for him. Mary was one of the most capable pirates out there, and her close bond with Anne and Jack made their little ship a force to be reckoned with.
Until Jack’s drinking finally did him in, anyway.
When a privateer ship came upon a partying Rackham and his crew, their job was too easy. Anne and Mary were (of course) the only two crew members sober enough to put up a fight. And they did an unrealistically good job at it. But two against a whole crew just wasn’t enough. Jack and his men were captured and hanged.
Shoulda stuck with the flags, Jackie.
(Did you know there’s a brand of rum named after Calico Jack? Every time I see it I’m like “Do you want me to think your rum is stupid and lazy and bad at its job???”)
Charles “No Cool Pirate Name” Vane
The first thing you need to know about Vane is that he was a dick. “Isn’t that kind of an essential part of being a pirate?” you ask. Well… I guess so, but definitely not to the extent that Vane was. See, Vane was actually the most successful pirate on this list, but he was such an asshole, I had to include him.
This guy tortured rivals, screwed over his shipmates, murdered surrendering sailors, treated women like actual garbage and just generally always picked the violent route when he could’ve gotten what he wanted bloodlessly. This guy suuuuuucked. And everyone else thought so, too. They thought he sucked so much, that they actually mutinied against him and made Calico Jack their new captain. Yeah. The Calico Jack I just told you about was considered the better option.
All alone with nothing but his recent rejection to warm his bed at night, Vane found himself marooned shortly after his deposition. Fun fact: a fellow pirate sailed by the island Vane was on and actually declined to rescue him because, “I shan’t trust you aboard my ship, unless I carry you a prisoner; for I shall have you plotting with my men, knock me on the head and run away with my ship.”
Another pirate who didn’t actually know Vane came by and did rescue him… only to run into the first pirate who promptly told the second pirate just what a scumbag Vane truly was. Vane was immediately turned over to authorities in Jamaica.
You guessed it. He was hanged.
It just goes to show there is nothing dumber than being a dick to literally everyone. That’ll come back to bite ya, and hard.
So if you’ve got any plans to try your hand at piracy, please do your research, drink responsibly and keep the cruelty to a minimum. It might not sound as fun, but you’ll thank me later when you get hanged a good year or two later than all the other pirates.
Tru Detctive 