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.
At the end of the fight, Blackbeard had been stabbed twenty times and suffered at least five gunshot wounds, before bleeding to death while trying to reload his pistol to keep the party going. Maynard then cut Blackbeard's head off and hung it from the bow of his sloop, partly for effect but mostly because he needed the head to collect his reward. He was paid 100 pounds for his trouble, the modern equivalent of about $18,000 or a 2006 Buick Rainier.
Go ahead. You've earned it.
Why He Had to Go
Escobar was the head of the Medellin Drug Cartel, a Colombian drug empire that moved 80 percent of the world's cocaine (the remaining 20 percent was trafficking its way through Dennis Hopper). In 1989, Forbes magazine famously named Pablo Escobar the seventh richest man in the world with an estimated worth of $25 billion. He was immediately rocketed to prominence in the world of rap lyrics and airbrushed t-shirts.
Not pictured: historical context.
Escobar was personally responsible for over 4,000 deaths, which is roughly 100 times more people than you will ever meet. He ordered the assassination of a Colombian presidential candidate who supported an extradition treaty with the United States. Then he blew up a commercial airliner to kill a man that wound up not even being on the plane, and leveled several city blocks in the bombing of a government building in Bogota.
He routinely murdered judges and politicians, and had a standing public bounty on police officers. He ordered two to three car bombings a day, enough that we're surprised people didn't just start walking to work.