1. Old Chummy
The old pirate in the red striped shirt, always with a concertina, or a dirty bottle of pirate rum, Old Chummy is always willing to help the new lads learn the ropes and knows the Pirate code down to the letters. Old Chummy stands by his captain, and makes sure that the rest of the men do to.
2. Peg Legs
Not all aspects of a pirate’s life is rum and booty. There is often a price to be paid, and Davy Jones will take his payment in arms and legs. Peg Legs lost both of his legs below the knees to a cannon shot, and since then plonks around with a cane and two wooden legs.
3. The Bosun
A second in command, this pirate stands with the officers of the ship, or rather behind them. If a pirate is ratted out to the captain, it is usually done by the Bosun. This pirate is vital to the function of the ship, but no one would miss him if he were pitched overboard.
4. The Deserter
Formerly part of the Royal Navy, this ne’er do well has given up the King’s colors to fly under a pirate flag. He has his own reasons, but the Deserter is not a trusted pirate, even by his own shipmates. He’s jumped ship once, who’s not to say he won’t do it again?
5. The Maori
Tall and commanding, this pirate comes from a distant land and is likely to carry an imposing tribal weapon as well as being decked out in piercings, strange tattoos and trinkets of good luck and protection against whatever ails the giant.
6. Failed Merchant
Surrounded by debt and hearing the clank of debtor’s prison, this man fled his home country, forsaking land and obligation to take up a new life on the sea. Somewhere he has a family and many people who would like to see him hang for the money he owes them.
7. The Criminal
Unlike the failed merchant, this pirate comes from a black background and has a number of murders that have been tacked to him. Unlike the merchant, the criminal is proud of escaping the hangman’s noose and has adopted a suitable seadog name. Some examples might be Two-Stab Tom, Cut-Throat Bill, or something suitably colorful.
8. Cannon Man
This pirate is seen with slow matches tucked into his hat and his hands and face show burns from powder charges. Instead of a cutlass, the cannon man has two braces of pistols and can man anything from a 12 pounder long cannon to a deck mounted pot-de-fers.
9. Old John Belaying Pin
Big and tall, handy in a fight, Old John has been sailing for years and knows that the best weapon is the one closest at hand. He is known for his skillful use of a belaying pin rather than a pistol of cutlass. Old John is a close friend of Old Chummy.
10. Cookie John
The ship’s cook and resident historian and storyteller. He has seen plenty of action and after loosing a hand and an eye he found a place below decks. He also keeps a run on the mess and the crew, an unofficial third man in charge after the captain and bosun.
11. Bill the Hook
This macabre pirate lost his hand in a boarding action and has since had is replaced with a hook. He has taken the time to make the hook into a weapon rather than a tool. The point is sharp, and the inner edge is keen as a razor, his preferred method of fighting being to disarm a for with the cutlass and then lay into the man with his hook.
12. False Colors
This pirate is not what he seems. In startling fashion this pirate is an agent of crown seeking to bring the current crew of pirates into custody or to pass along information on their workings. False colors works hard to look like a good honest pirate, but finds a way to avoid combat with the ships of his kingdom.
13. The Strangler
Never a good looser, this pirate is a giant of a man with a temper to match. He is the sergeant at arms and the whipsman of the captain. In combat with other crews or victims, this brutal giant likes to crush men’s throats with his bare hands.
Long in the tooth and grey-headed, Swabby has been on pirate ships since he was boy. He spends most of his time as an assistant or simply swabbing the decks to avoid getting the harder work that often falls on younger pirates tossing dice. Swabby is a good pirate, but doesn’t trust the Cookie John.
15. The Cabin Boy
FResh from the shore, this youth has yet to see his first boarding action, take his first wound, or kill his first man. For that matter he’s yet to take his first wench. One day he might make a good pirate, until then he has to bow to all of the other crewmen and do anything he’s told.
16. The Privateer
A professional pirate, this man was formerly endorsed by a king or crown to hunt the ships of a rival power. He and his ship eventually fell out of favor and were in their eyes, betrayed by the crown. Instead of being heroes, they became the worst of criminals and could only find refuge scattered aboard true pirate ships.
17. The Buccaneer
Why be a pirate? Because it’s fun. When the blood is spilling, cannons blasting, wenches in yer lap and rum in your blood. It’s a jolly good time being a good pirate, and if you have to do a few things that you don’t like…well that’s better than plowing a field, isn’t it?
18. The Swashbuckler
Clad in tight pants and white billowing shirt, this dashing pirate looks more like something out of a ballad. He is good with a sword, but holds very tight to the maritime codes and chivalry rather than true piracy. His actions are motivated by a desire to fight an ignoble ruling power, rather than to be a naughty good pirate.
Why is the rum always gone? The best answer is that Drunky got into the ship’s larder and no one noticed. Considered a fair to useless pirate, Drunky validates himself with his drunken style of sword fighting and blind rage when he is tossed onto another ship without a bottle of rum.
20. Friend to Birds
This pirate can whistle to the birds and for some reason, the birds take notice. He often has a parrot or some other bird close at hand, and has a limited ability to communicate with them. Obviously this long timer of the crow’s nest refuses to eat his feathered friends.
21. Mermaid’s Husband
This pirate has some sort of odd trinket he claims came from his mermaid wife. It is likely a ring of shell or some other trinket or bauble. Oddly, this pirate is able to stay underwater far longer than he should. The trinket gives him the ability to breath underwater so long as he is true to his aquatic wife.
This is an unlucky pirate, fresh from the shore who leans to close to the rails. When the kraken attacks, or the sirens call, he is the first in the water, screaming as he falls.
Known as the dirtiest pirate alive, Grubby is short, fat, bald pirate with the temper of a wild boar and the eyesight to match. He swings a heavy club and has quite a collection of kill notches on it’s handle. First ashore, Grubby can drink like a fish and wench like a stud horse.
As a poor pirate Stubby was cursed with small fingers, his ability to tie rope is laughable and his stature with a sword is mocked, though this midget is able to cause wicked problems for larger pirates with his throwing knives and small size.
Knubby ain’t got no fingers on his right hand, lost em in a pistol explosion. This hasn’t stopped his game any, this pirate can juggle coins across his ruined knuckles, toss bones with skill and is a fair shot with a knife or a pistol.
The worst of pirates, this man is a bottomless well of insults, degrading comments, and rude gestures. He has an opinion on everything, though most often said comment is ‘screw it blind and give me more rum’. Malcontents will rally around the Heckler, but most are fooled, not knowing that he is one of the captain’s best men, and plays at the loyal opposition ro prevent mutinies.
27. The Mutineer
This pirate has a secret, he plans on taking over the ship and becoming the new captain. He has few supporters and most everyone knows of his ambition. The captain knows too, and does a good job of keeping the would be mutineer busy with either vital jobs, or doing things that keep him isolated from others who might follow him.
28. The Lady
A Mad Lass, this lady pirate hold her own with cutlass and pistols to earn her place aboard a ship. No wench to be bounced on a knee, she demands her share of the loot, the rum, and has been seen wenching with the other pirates. Rather than unlucky, the crew considers her to be a lucky piece.
29. The Scallywag
This pirate scratches and has many sores. Perhaps he’s caught some bit of creepy-crawly from a dirty whore, or his hygiene is so bad he’s rotting from the outside. Regardless he smells as bad as Grubby and always has a runny nose or is spitting up bloody saliva.
30. The Seadog
some pirates live for the sea, and could not find a life as a fisherman or a merchant. These are the backbone of the pirate crews, salty seadogs who’ve seen their fair share of battles and can hold their rum.