1. Lale Longarm, the Gentleman Pirate
Lale Longarm is a tall man with blonde hair and a carefully styled goatee. He wears the best and as close to the latest trends in fashion as possible and easily comes across as a dandy or a fop. This is somewhat true in that he is a fashion conscious clotheshorse, but he is also quite skilled with a sword, daggers, and a musket. He is suave, charming, and a ladies man, easily charming most such ladies out of their undergarments. Inside, Lale is cold and dead, and has little interest in anything other than gold, power, and the fear of his rivals. His crew is a good deal cleaner than the average pirate crew, and there is a strong sense of discipline on his ship. This means that when Longarm's men go wild on an enemy ship they are releasing a good deal of pent up hostility and frustration.
2. Aschul Flintspark
Dwarven Pirates are rare, and when they are found they are rightfully feared. Aschul Flintspark is not just an able bodied pirate with a quick temper and a fondness for alcohol, cheating at cards, and wenching. He is also a competent and frightening artificer. He specializes in making pirate hand grenades, explosive shells for the cannons, and even tinkering with firearms of his own devising. Seldom seen above decks in a fight, Aschul works below decks, leading the teams operating heavy cannons. He is a mercenary pirate and spends most of his time living ashore, selling his wares. On occasion he is hired to come out on a ship, where he lends his skill and knowledge to the gunnery crews and keeps the guns in top shape. He can also make less explosive alchemical and apothercaric creations, but he is less skilled in these and takes much less pleasure in making them.
3. Oango the Blood Hand
A bastard hybrid, Oango was born to a human mother and a more fiendish father, giving him a human countenance, but infernal temper and appetites. As a tiefling, Oango has some innate ability with magic, but he has largely not explored this avenue of his ability, as he is more than pleased with his ability to cause harm to others and inspire fear. His ship is known for its bloody red hand pirate flag and for rumors that Oango the Bloody Hand very rarely takes prisoners. While there is certainly some truth to this, Oango has had several raids get out of hand that ended with no survivors he generally likes to leave lots of terrified survivors so that most of his victims survive and are scared pantsless and are more willing to surrender rather than fight out a pointless battle. He maintains his black reputation by having ceremonial executions aboard the ships he captures, hanging dead bodies from the sides of the ship, and so forth. He is infamous for sailing brazenly into port with dozens of prisoners and hostages tied to the rigging and sides of his ship. After collecting a ransom for the hostages he sailed out of the port and cut the hostages free to attempt to swim to safety through the shark infested waters.
4. Pirate Lord Peyard, the Keeper of the Code
Peyard has been a pirate longer than most pirates have been alive, and he has long since hung up the sword. As the keeper of the code and esteemed highly among pirates he has since become the governor of a pirate territory. He keeps the peace through sheer force of reputation and a willingness to act should a pirate cross the code. Frequently seen in a heavy red leather jacket with a battered concertina on his side, he is prone to telling stories, playing music and singing in a rough baritone. He will punctuate his songs and stories by addressing matters in a direct and pointed fashion. This can range from telling a story about mutineers and how they were all hanged and then asking a person who has been considering mutiny how they feel, to pulling a pistol at the end of a song and shooting a potential government/crown man in the face.
5. Lasech, Disciple of Calypso
Lasech would be an attractive woman if not for the scars from some strange disease contracted on a tropical island, the intricate tattoos on her face and arms, or the strange way she stinks. Lasech is a priestess of the pirate/sea goddess Calypso, and as such is an agent of fate, the sea, and chaos in all things. She is valued asset on a ship for her gifts to turn away disease, turn seawater into grog, and calm the sea enough to keep a ship from breaking up in a storm. She is also a burden as she requires the ship to maintain certain observances and rituals to please Calypso that range from typical nautical taboos, to superstition, and so on. As a holy woman, she expects to remain untouched by the crew and has a knife and the skill to remove the bravado of any man who tries to force himself on her. She can also blight a crew will sickness, madness, or incite foul weather to sink the ship should she choose.
6. Captain Zukalris
Born a fisherman's son, Zukalris never dreamed he would be anything more than a man in a small boat fishing. He was raised in a dour and pragmatic household on a rocky stormy coast, where discipline and skill separated the fishermen from the fish food. Zukalris was eventually abducted by pirates in a pressganging raid up the rocky coast. The men of the rocky coast were good sailors, and were not prone to mutiny. Zukalris eventually started rising through the ranks, and eventually ended up the captain of his own small ship. While he still thinks of retiring to a small fishing cove one day, he is currently pleased to be making a steady profit and enjoying the wealth, freedom, and indulgence of the pirate life. He has a fondness for nets and fish hooks, and uses both in combat, and enforcing discipline on his ship.
20. The Esteemed Raleigh Leland Whaler
Raleigh was raised in the lap of luxury, a prominent son of a powerful and wealthy man. Living far from the home country, the Whaler's were independently wealthy and lived as tyrants on their tropical island. That is until they were overthrown by a violent local uprising. It wasn't the tyranny and garden variety decadence that caused the revolt, such things are common in the islands. Rather it was the Whaler clan had gotten its power and influence through unholy and alien deals with eldritch beings. Calling on ancient magic, Raleigh's grandfather Hiram Whaler summoned and bound a starspawn of Cthulhu and created a pact with the being. The Whalers would continue on for several generations as powerful high clergy of Cthulhu, offering sacrifices to the Old One in exchange for madness, and magic. Whaler survived and is a high born aristocrat, but lacks money and land. He is a competent sorcerer, with specializations in summoning sea monsters, polymorphing, and has an affinity for tentacles. He is also a wildly hostile and desperate man as he aches for the trappings of wealth and power, but has naught more than a spot as an officer on a pirate vessel. For now.
23. Rocerack, Disciple of Ma-O
Warlocks are an uncommon sort of magic user, as to become a warlock requires the would me magus to enter into a powerful pact with an otherworldly being. Rocerack, a petty man of petty stature would do just this sort of thing. He spent several years, after failing to become a true mage, studying on how to form a spirit pact. He found that his options were strongly limited by his nature and ability. After almost drowning himself in a ritual, he was able to summon a Shikome, an infernal servant of Ma-O. Through the Shikome, Rocerack forged an infernal pact with the Great Demon of the Ocean and rose from the sea a brine soaked sorcerer. He draws upon the darkest, bloodiest aspects of the sea with Ma-Os poison in his veins, and loosed chaos and hell on Earth. As a pirate, Rocerack is a mercenary sailmage, who sells his service to pirates to keep their ships safe through storms. He will use his power to break enemy ships, elude rival magi, and to send offerings to Ma-O to keep his powers strong. Rocerack is a man with a death mark from the civil government, he is untrusted by his ship mates, and he knows that his time on Earth is only as good as the offers he gives the sea. He is secretly trying to work out a plan where he can escape the dry land and find a refuge in the mountains where he 'thinks' Ma-O cannot reach him.
28. Arceneaux Sparrowhelm
Sparrowhelm is a force of chaos incarnate, able to somehow walk through a battle unscathed, without spilling her drink, or even getting her greatcoat dirty. Equal parts rogue extraordinaire and chaos/probability manipulation mage, Arceneaux has blended her innate arcane talents to flow seamlessly into her scoundrel black arts. Fate and fortune smile upon this irreverent, sometimes nonsensical pirate. Arrows miss, crown's men look the wrong way, and in a swashbuckling adventure, she is able to always grab and cut the right rigging rope to escape a losing fight, pick the cup with the poison in it, and so forth.
29. Syn, Disciple of Leviathan
A tall woman with silver hair and a penchant for wearing as little clothing as possible, there are few foes more dangerous than this black hearted servant of Leviathan. A powerful necromancer and sea sorcerer, most of her crew is dead, and her ship was once a great whale, but is now equal parts warship and reanimated corpse. Syn has two simple objectives, destroy civilization to the best of her ability and protect the domain of Leviathan from those who would defile it. Syn has sailed her ship into many a harbor or port to use the ship itself to smash and destroy ships there before unloaded her payload of zombies and ghouls to rampage through the city. Her parting gift is usually some sort of horrific disease or black curse. She is nominally a pirate, as there is enough value in gold and potential allies among pirates to warrant not destroying them as well.
30. Garrick Half-Face
Garrick is a cold, murderous brutal man who stands out in a profession where being a killer is rather close to the norm. He is tall, and as suggested, half of his face is a tangled mess of scar tissue. Garrick is an assassin by trade, but not the silent stealthy type assassin that sneaks in quietly and does the deed quickly and sneaks back out. Garrick kicks in the door, cuts people down left and right and carves a bloody path between himself and his target and doesn't stop until the job is done. While his work on ships is the usual sort, as a middling officer keeping discipline up, his most common work is ashore, either hunting targets in crown held ports and cities, or playing out his part in pirate lord vendettas.
Additional Ideas (1)
The dwarf Argent Forgescale was once a member of the Grand Order of the Reef, defending the Boshic Sea paddling on his longboard and armed with a shark-toothed oar. An ideological dispute about defending the wider seas caused a rift with his branch of the order, and Sir Argent became a free agent. Still dedicated to his cause, he joined in with a band of pirates, seeing an opportunity to eliminate threats to the natural balance of the seas. He is at home on the water, paddling along his longboard as a scout ahead of the ship. He can disappear beneath the waves and hold his breath like a porpoise. Sir Argent is skilled with his toothed oars, wielding two at once and slicing opponents with the barbed teeth. His companion is a great squid that comes to his aid when summoned, tearing with tentacle and beak.