Edward Teach a.k.a. Blackbeard
Why He Had to Go
Blackbeard or Edward Teach was a famous English pirate and a massive asshole by all accounts. He had between fourteen and sixteen wives, most of them about a biscuit older than Dakota Fanning. One wife in particular would be routinely forced to run a train with the crew while Blackbeard watched and "buffed his peg leg" so to speak. He burnt hemp beneath his ... um, black beard, to make it look like he was breathing fire, which worked to intimidate his enemies but likely alienated his crew since such a stunt would make an 18th century pirate smell like a snowman made of dogshit.
He'd also occasionally murder his first mate, just to keep everyone on their toes.
"I can't even remember why I was mad at you."
How He Went Down
Blackbeard eventually retired to North Carolina to spend his senior years rolling around in gold coins. But the Governor of Virginia put out a hit on Blackbeard, sending two ships after him, commanded by Robert Maynard.
Rather than running from the two enormous ships sent to kill him, Blackbeard boarded Maynard's ship. Well, first he bombed the deck with an assload of primitive grenades like Jim Brown in The Dirty Dozen. That's when things got all sorts of stabby. Blackbeard nearly severed the fingers on one of Maynard's hands with his sword, and Maynard broke his fucking sword stabbing Blackbeard back.