The prestige class “Dread Pirate” is from Complete Adventurer and as you are probably thinking is based on the Dread Pirate Roberts from the Princess Bride (or at least I am presuming so). What makes this class interesting, just like the character it is based on, reputation is everything. For all practical purposes alignment doesn’t matter. Many of the class features only reputation matters. An Evil character could have a good reputation and a Good character could have an evil reputation. A good reputation (Avoiding unnecessary bloodshed and honoring truces) would make it more likely for others to negotiate with him and give his allies bonuses to diplomacy and rerolls on failed saves. An evil reputation gives bonuses to intimidate and attack rolls.
Character Personality
The Dread Pirate Simmoines is extremely cruel and takes pleasure in torturing his victims. He is very intelligent and when in battle is tactically and strategically minded. He loves his reputation and uses it to its fullest potential to intimidate his prey and enemies. His crew on the other hand he treats fairly well.
Character Background
The Dread Pirate Simmoines was born to a semi-wealthy family though he doesn’t know much about it. When he was only 8 years old his family was journeying by sea. Their ship was attacked by pirates. All were killed except for the Simmoines who was taken captive by the Captain, the Dread Pirate Charlie. Simmoines was taken because Charlie wanted a cabin boy and another human onboard his ship. From Charlie he learned about seafaring and piracy amongst other things. He worked his way up through the crew to eventually become the second mate of the ship at the age of 16. His cruelty towards those ships preyed upon made Dread Pirate Charlie look tame and merciful. His cruelty made much of the Goblin crew fear and respect him. When he reached the age of 18 he led the crew against the Dread Pirate Charlie and the First Mate. As Captain of the pirate ship Lost Hope, he took piracy to the absolute evil it could be taken. When he attacks a ship he doesn’t just kill its crew and passengers. He tortures them; he rapes women and children before killing them. He quite often keeps one person alive, though mentally scarred for life to tell the tale. He has gone so far as to occasionally sneak into a port at night to secretly deliver the the lone survivors to ensure the tale is told. Because of this he and his ship are the most feared pirates on the sea.
His crew however he treats a little differently. He fears that one day they might mutiny against him. So he ensures that they receive an equal share of the spoils, though keeping the best for himself. However, any crew member who shows sign of weakness, or mutinous actions or thoughts is tortured or killed.
He shuns any type of organization between other pirate ships. He is not for hire and will only consider any type of negotiation if he feels the other party has something truly worth getting. After getting what he wants he kills the one(s) he negotiated with and leaves no survivors.
Advancement
This is a level 16 character so it is already pretty powerful. However, making the Dread Pirate Simmoines more deadly is easily done. Depending on what you need done there are several ways. The simplest method would be to improve his equipment. Gives his weapons additional pluses since they are only +1 items. Add keen to them to increase the critical range from 18 to 17 making it more likely to critically hit. Give him gloves of dexterity to increase his dexterity which would make it more likely to hit his targets and make him nimble thus harder to hit and improve his balance and rope skills.
Adding class levels is obviously a good way to go if you need his CR to be higher. Adding levels of Rogue would give you loads of skill points to make him extremely skillful as well as improve his sneak attack and give him Improved Uncanny Dodge. I would add to those Jump, Tumble, Use rope and Intimidate skills to make him most interesting. Adding levels of fighter would give him extra feats and greatly improve his combat abilities. Adding sorcerer would improve his will saves and add some low level magic to his repertoire. Adding Bard would give him many skill points and limited magical capabilities. Druid could be an interesting choice, especially with the aquatic animal wild shapes. However the druid’s necessity to not have metal would greatly limit him in the long run. Barbarian, cleric, ranger and wizard, though could be interesting really don’t offer anything. Monk and paladin are out of the running.
The most interesting way of improving upon him is to make him a vampire. Now I know what you’re thinking. “But Vampires have problems with traveling on the water and as Captain of a ship he may need to be out in the sun.” Well it is a simple problem to resolve. Give him a magic item or an artifact that allows him to cross water and be in the sun.
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