His name strikes fear into the hearts of merchant captains everywhere. A pirate lord whose cruelty is only whispered of, and whose thirst for blood is matched only by his rapacious hunger for treasure. The black mask beneath black sails, the monster at the helm of Revenge is a true terror to all who would sail the high seas. The man known only as the Dread Pirate Roberts.
Of course, we all know that the man who made that name so feared has been retired for years, living like a king off his plunder. But who would want to read a character conversion guide for the Dread Pirate Wesley?
If you'd like to capture the essence of the infamous Man in Black for your Pathfinder game, this guide should get you started. And if you'd like to check out similar guides covering characters as diverse as the Avengers, the Game of Thrones cast, and some of DC's most noted vigilantes, check out the Character Conversions page over on Improved Initiative.
Attributes, Race, and Traits
Westley grew up a simple farm boy, and as far as we know there was nothing overly special about him except his quick wits, determination, and desire to learn. So he's going to be a human, and if you want to capture his time in the story's introduction, you could give him the Heart of The Fields alternative racial trait. The ability to ignore effects that would render him fatigued or exhausted once per day would explain some measure of his determination. Additionally, while he is charismatic, you should also pay attention to his dexterity and constitution, as those are the attributes he relies on more than others.
When it comes to his background traits, the obvious choice is fencer (+1 trait bonus on attacks of opportunity with weapons appropriate for fencing, like the rapier), however, you might also find the trait threatening defender (when you use Combat Expertise, reduce the negative to your attack by 1) to be equally helpful. Criminal is a useful second trait (+1 trait bonus to Disable Device, Intimidate, or Sleight of Hand), though the bonus should go either toward Intimidate or Sleight of Hand for Westley.
Classes and Class Features
Westley is a man of many talents by the time he returns for the woman he loves, clad in black and captaining an infamous pirate ship. While deadly in combat, he also seems to have a trick up his sleeve for nearly every situation. So it's going to take more than one class to bring all of his disparate abilities together.
First, his swordplay. Westley was taught to fight by those who made their living on the high seas, and such warriors have no use for heavy weapons, or heavier armor. Westley himself tends to favor loose, simple clothing whenever we see him take the field, which makes the obvious choice for his prowess the Swashbuckler. You get the benefits of a full base attack bonus, solid saves, and a slew of deeds that allow you to be mobile around the battlefield.
However, the Swashbuckler alone wouldn't explain Westley's variety of skills, and other unusual abilities. But it would dovetail nicely with the Rogue. Four levels of Rogue would give you evasion, sneak attack, and two rogue tricks, like Developed Poison Immunity (automatically save against a poison you've successfully saved against in the past, to explain Westley's tolerance of iocaine powder) and Climbing Stunt (take a -10 on a Climb check in order to climb at your base speed, which would explain how he was able to catch up to Fezzik at the Cliffs of Insanity). And since we don't see Westley disabling any devices, or dodging any traps, you could choose to take the Rogue archetype Swashbuckler (which would grant Westley a minor bonus on saves against fear, and on Acrobatics checks), or Survivalist (which would allow Westley to go for longer without eating or drinking before taking penalties, and give him the ability to be comfortable in nearly any environment... like the Fire Swamp).
Skills and Feats
Between Rogue and Swashbuckler, Westley has a lot of skill points to throw around. On the other hand, we see that he's quite proficient in a lot of different areas. Acrobatics in his fights, Climb for the cliffs, and Survival to track fleeing men and their hostage through the wilderness. Bluff to disguise his true identity, Intimidate to terrify the prince, Stealth to sneak unseen through the castle, and Sleight of Hand to hide where he put the poison. And you should probably throw in Diplomacy, Disguise, Sense Motive, and Perception if you have the points leftover.
When it comes to feats, Westley has an embarrassment of riches. A bonus feat for being human, two bonus feats from Swashbuckler (assuming you have an eight-to-four mix with Rogue), and the typical feat every odd level. While there are a lot of feats that will work in your favor, some suggestions include:
- Weapon Focus (rapier): Gain a +1 bonus on all attack rolls made with a rapier
- Fencing Grace: When making 1-handed attack rolls with a rapier, you may add your Dexterity modifier to the damage instead of your Strength. You also gain a +2 bonus to your CMD against attempts to disarm you if you have at least 1 panache point left.
- Agile Maneuvers: Add your Dexterity modifier to your base attack bonus and size modifiers when determining your Combat Maneuver Bonus. Fezzik remarks that being quick is one of the only things that saves Westley in their fight.
- Combat Expertise: Take a negative to your attacks, but gain a bonus to your armor class. A necessary feat for anyone fighting in his shirtsleeves.
- Improved Feint: This allows you to make a Bluff check to feint in combat as a move action. This means Westley can get his sneak attack in on a flat-footed opponent, but it would also let him grapple someone without provoking attacks of opportunity.
- Piranha Strike: Take a negative to your attacks for a bonus on damage.
- Greater Weapon Focus (rapier): Gain an additional +1 bonus to all attacks made with your rapier. If you're taking negatives for using other feats, that bonus needs to be as big as possible
- Combat Reflexes: Take an additional number of attacks of opportunity equal to your Dexterity modifier every turn. This gives you multiple parrying opportunities, as long as your panache holds out.
- True Love: It goes without saying that Westley would have this feat. Grants a +2 bonus on attack rolls, saving throws, and skill checks when you are below one-quarter of your health. Also, gain a +2 bonus on Sense Motive checks, or a +4 if you have 10 or more ranks in Sense Motive.
Gear and Story
Unlike other fantasy heroes, Westley never acquires mystical armor, or a magic sword. Inigo's weapon is likely the finest in the whole tale, and it was a masterwork weapon crafted by purely mortal hands. With that said, a dueling weapon would be exceedingly useful for Westley to have, in addition to enchanted armor that's light enough he could conceal it beneath his clothes. Gauntlets of Dueling wouldn't go amiss either, but these are meta concerns for keeping up with CR in-game, as opposed to anything we see in the book or film.
Lastly, there's the story. Who is your Dread Pirate Roberts? Are they the founder of a legacy, doing what they have to in order to survive before returning to the one they love once they've amassed a fortune to care for them? Or are they merely the latest to carry the mantle, yearning for a life away from the swelling seas and bloody decks, where they can be who they truly are, instead of wearing their reputation like a black cloak?
That is up to you... just make it a story worth the hearing.