The term Pirate comes from the Greek word “Peirates”, which means “One who attacks ships” and the Latin word “Pirata”, which means “sea robber.”
As long as there have been people floating on the water with something worth stealing there has been someone trying to steal it.

The earliest documented case of pirates was in the 14th century B.C. when a group of pirates known as the Lukkans terrorized Egypt and the Mediterranean. In 75 B.C. Cilician pirates were the most powerful naval force in the Mediterranean, which didn’t sit well with the Romans. Cilician pirates kidnapped Julius Caesar and demanded a ransom of 20 Talents ($600,000). Caesar was like, “Bitch, I’m worth at least 50 Talents.” So, the Cilicians went and collected 50 Talents for his release. During which time, Caesar earned his captor’s respect by bullying them and calling them savages. He would also regularly say he was going to kill the lot of them after he got released. Turns out he wasn’t joking. As soon as Caesar got off the boat he went and got a few boats of his own. The pirates were still parked where Cesar left them counting their money. Cesar captured the pirates, took all their shit (and his 50 Talents) and crucified them. That’s not a metaphor. He nailed them to a fucking cross.

In the 1800’s one of the most successful pirates of all time was a Cantonese prostitute named Ching Shih, who commanded over 1,800 ships and went to war with China and England. After amassing a fortune, Shih retired and opened a gambling house and brothel where she died peacefully in her sleep at the age of 69.

Most of what we associate with pirates comes from what is known as the Golden Age of Pirates that took place in the Caribbean from 1620-1720.
The iconic skull and cross bone flag known as The Jolly Roger was actually used by pirates, although many of them just flew a black flag. Although there is some debate, it is widely believed the term Jolly Rodger came from the French Term “Joli Rogue” which means “Pretty Red.” During sea battles, flying a red flag meant you would show no mercy and take no prisoners. Joli Rogue became synonymous with being cutthroat, yada yada, we get Jolly Roger. Although, flying a red flag was pretty fucking stupid because that meant your enemy was going to fight you like their life depended on it. That is what the military calls “Escalation of Violence” which should be avoided if you can. It turns out Pirates were smart because their preferred mode of operation was to sail up in small, fast boats filled to the brim with pirates and swarm onto merchant ships. They’d steal all the goods and leave everyone alive if they didn’t put up a fight. This led to most merchants surrendering, and in many cases asking the pirates if they could fill out a job application.

"Reality"

Most pirates around this time were government sanctioned thieves called Privateers and Buccaneers who conducted economic warfare on behalf of their country. So, say you worked for England, the British Royal Navy would leave you alone and even help you out. You robbed everyone but the British, the crown got a cut of your spoils and if you were captured the crown would pretend they didn’t know you and you’d be executed for piracy. The pirates obviously got the short end of the stick as far as risk/reward went, but at least they had one less navy chasing them.

It was pretty common for pirates to be ex-military considering being a pirate payed better than government service. Flogging was a regular form of punishment on military ships, and for that reason, was frowned upon by pirates who were sick of their boss getting to beat them with straps of leather. Before you became a pirate, you had to sign a document that stayed posted on the ship called, The Articles of Agreement, which laid out the democratically elected hierarchy of the boat, as well as pay scales, and other rules. The rules were fair, especially considering working conditions at most jobs back then. When you’re stuck on a boat full of armed killers, you want to avoid grumpiness. They even had their own version of worker’s compensation that guaranteed pay if you lost a limb or suffered other injuries.

Sneaking a female on board was punishable by death. Some historians say pirates believed women’s period’s attracted sharks, but it’s probably because having women run around gossiping all day is bad for morale when you’re stuck on a boat for three months. Pirates were ok with dudes banging each other though. They even had their own form of gay marriage called “Matelotage.” If a pirate walked up behind you in 1700 and said, “Ahoy Matey!” it probably meant he wanted to plunder your booty with his One-Eyed Willy, if you know what I mean…

…It’s butt sex. I’m talking about butt sex.

Fighting was not allowed on the boat, which is another reason they didn’t want women on board, because women love starting a fight over absolutely nothing. "Oh god, I left my blunderbuss on the floor. Here we go again with this bullshit. I guess this is what we're doing the rest of the day now, Karen." If you wanted to fight a crewmate you had to wait until you were on dry land. This is actually still a rule on ocean vessels. If you are out at sea and you punch a dude, it’s an automatic felony and you get blacklisted from working offshore. Historians disagree about whether or not pirates actually made people walk the plank. Actually, the disagreement is between “nobody ever did that shit,” to “one or two guys might have.” If they were going to kill you, they’d just do it the old-fashioned way. However, if you really pissed someone the fuck off, they had something much worse than plank walking called keelhauling. That’s where they tie one end of a rope around you and the other end to the back of the ship and dragged you in the ocean until you died.

Pirating didn’t revolve around gold coins as much as movies lead us to believe. Pirates were more likely to be stealing a shipment of lumber or silk than doubloons. If a pirate had a parrot sitting on his shoulder it was because they stole a shipment of exotic pets that were gonna get traded for booze and hookers the second they landed in Tortuga. The holy grail of pirate booty was actually medicine. Infamous pirate Edward Teach aka Blackbeard once blockaded the port of Charlestown in South Carolina and held several prominent townsfolk hostage and demanded medical supplies as ransom. Pirates also didn’t bury treasure, because burying a shipment of lumber would be stupid. Most pirate treasure wound up at brothels and gambling halls.

Random Facts

The famous walls around Vatican City were built by Pope Leo IV after being attacked by Saracen pirates.

The word Plagiarism comes from ancient Mediterranean pirates called the Plagiarri who stole people’s children. If you steal someone’s work, you have stolen their “Brain child” much like the Plagiarri stole people’s “Real Child.” Apparently ancient Mediterranean teachers really, really, cared about people citing their sources.

Pirates didn’t talk how we think they do. That’s all thanks to actor Robert Newman who played Long John Silver in the 1950 version of Treasure Island, and then Blackbeard in 1952.

Pirate’s favorite drink was a mixture of rum, lemon juice, water, and sugar called grog, which led to pirates on every ship being sick and tired of that one guy who keeps saying, “I’m not an alcoholic. I’m just warding off scurvy. Har har har!”

If you’ve noticed any similarity between the super awesome 1990 video game The Secret of Monkey Island and Pirates of the Caribbean, it is because script writer Ted Elliot was hired by Steven Spielberg to write the script for a Monkey Island movie that never got made. Years later Elliot would go to write Pirates of the Caribbean. So, Pirates of the Caribbean is the Monkey Island movie, just with unfortunately less monkeys and no Stan’s previously owned vessels.