Avast Ye - The Pirate Build
I'm currently playing in a PF2 pirate campaign, and it got me thinking about the best build for a pirate in D&D. There are several good builds on the internet, each with its strengths and weaknesses. I aimed to build my vision of the best classic pirate I could be. Going rogue was a no-brainer since the swashbuckler is the OG pirate build. It definitely works, but there are many ways to improve it.
The swashbuckler can be portrayed as brave and daring, but being pirates, they must also be scoundrels. Pirates also need a certain flair while willing to do whatever sneaky and dirty deeds are required to kill their foes. For this build, we accomplish this by multiclassing into the fighter class so we can acquire the battle master subclass. Gunslinger was my first choice, but it is unofficial content. So let's get building!
Quick note. I'll use the "classic" racial bonuses and point buy regarding our Pirate Captain's stats. OneD&D is coming soon, and the UA looks interesting, but for now, let's stick to the 5th edition Legacy races.
The Pirate Captain
Swashbuckler Rogue/Battle Master Fighter
Race - Bugbear
The bugbear is one of my favorite races, and the legacy bugbear is the perfect race, in my opinion. The +2 to Strength allows us to save 2 points, and +1 to Dexterity is an added bonus. Bugbears believe in ruling through fear and strength, and a pirate captain isn't going to be a warm and cuddly type regarding their crew. This doesn't mean a pirate captain wouldn't consider their crew their family, but an overbearing and cruel patriarch/matriarch runs many dysfunctional families. Your racial traits include the following:
Darkvision: I despise having to carry around torches to see at night.
Long-limbed: This trait is such a massive advantage in sneak attack situations.
Powerful Build: Makes it easier to carry the overflowing treasure chest back to the ship.
Stealth Proficiency: What a bonus! This allows you to grab another skill without worrying about taking Stealth, a must-have for any rogue.
Sneak Attack: It's too bad the racial and class sneak attack doesn't stack, but that's me being greedy.
Stats - Str. 13, Dex. 16, Con. 13, Int. 8, Wis. 11, Cha. 14.
I've said it before; there never seem to be enough points to spread around. We'll need a Strength of 13 to multiclass. I hate having a negative modifier, but since your Saving Throws are Dexterity and Intelligence, you'll still have a +1 to Intelligence saves. This allows you to put the extra points in Charisma. We're playing a mean pirate; the higher of Intimidation modifier, the better. You could also bump your Constitution score to 14 if you value hit points more.
Skill Proficiencies - Acrobatics, Athletics, Deception, Intimidation, Perception, Sleight of Hand, and Stealth. You've got to love the rogue and their four proficiencies right out of the gate. Add to that the racial Stealth proficiency and Athletics and Sleight of Hand because of the pirate background (see below), and you've got proficiency in a whopping seven skills at 1st level.
Background - Pirate, of course. Tool proficiency in water vehicles and navigator tools is absolutely required. Add to that your Bad Reputation feature, and the crowds will part when you walk down the street.
Armor/Weapons - Leather armor, a couple of daggers, a rapier, a short bow, thieves' tools, and a burglar pack. Your Armor Class may seem lower when compared to the party's fighter, but an AC 14 is about as good as it gets for a rogue right now.
Our character sheet is filled out. Let's start leveling up our character.
Rogue 1
Expertise - Stealth and Intimidation. We give ourselves the extra boost every person who plays a rogue takes, and we play into our take-no-bullshit pirate personality.
Sneak Attack - I know we already have a sneak attack, but if you've never played a rogue, here's what makes the class so strong at first level. Once per turn, you can deal an extra 1d6 damage to one creature you hit with an attack if you have advantage on the attack roll. The Attack must use a finesse or a ranged weapon, hence why we have a rapier and a short bow. You don't need advantage on the attack roll if an ally is within 5 feet of it, so wait until the barbarian charges forward. Finally, if your enemy isn't incapacitated and you don't have disadvantage on the attack roll, you can also use your sneak Attack. In short, it's painful for them and glorious for you.
Thieves Cant - Flavor ability. It's been around since the beginning of D&D; if I had to guess, it will forever.
Rogue 2
Not much is going on when you get to the 2nd level. You can't complain, given everything you get at 1st level and everything that awaits you at 3rd.
Cunning Action - An actual use for your bonus action! Sure, you can "only" use it to Dash, Disengage, or Hide, but you'll be trying to Sneak Attack at every opportunity, and these bonus actions, are all exceptionally helpful. Disengaging prevents attacks of opportunity, which our target will undoubtedly take after you've stabbed them in the back. Hiding and Sneak Attack go hand in hand, and never be too proud to run away when all else fails.
Rogue 3
Swashbuckler - Now we can start calling ourselves real pirates. Initially found in the Sword Coast Adventurer's Guide and republished in Xanathar's Guide to Everything, the swashbuckler was the 5th edition's answer to being a pirate. Don't worry; we'll make being a pirate even better soon.
Fancy Footwork -No need to waste that bonus action to disengage now. If you make a melee attack against a creature during your turn, you don't need to worry about those pesky opportunity attacks for the rest of your turn. You won't even need to use it to Hide because of …
Rakish Audacity - One more reason for putting those points into Charisma at 1st level. Your initiative rolls receive a bonus equal to your Charisma modifier. Going earlier is always better for a rogue. This ability is even more potent in its ties into your sneak attack ability. Now you don't need advantage on the attack roll to use your Sneak Attack against a creature if you are within 5 feet of it, no other creatures are within 5 feet of you, and you don't have disadvantage on the attack roll.
Sneak Attack - Damage increased to 2d6.
Rogue 3/Fighter 1
It's time to rush fighter until we get to the 3rd level. You should have enough gold to buy some additional items. Pick up a pistol, another rapier if you haven't got a finesse or light magical weapon yet, and new armor. Studded leather or chain shirt gives you an AC 15, or a breastplate gives you an AC 16. Personally, I'd stick with the studded leather.
Fighting Style, Two-Weapon Fighting - The Sneak Attack followed up with an additional attack is no joke. Dueling isn't a bad option since you have to hit before you can do all that tasty damage, but this is 5e. Hitting your target is easier than ever and gets even easier as you progress in levels.
Second Wind - You may only be able to use it once per short or long rest, but it's one more bonus action, and bonus actions are good. You regain hit points equal to 1d10 + your fighter level. The more hit points, the better.
Rogue 3/Fighter 2
Action Surge - An extra action on a turn once per short or long rest. There's no doubling up on a sneak attack since the wording states it's only once per turn. Still, I'll take an extra attack whenever possible.
Rogue 3/Fighter 3
Martial Archetype - Battlemaster. We're now a real pirate captain who can do devious pirate stuff.
Student of War - Let's get this out of the way. Ships are made of wood, and carpenters build stuff out of wood. We'll gain proficiency in Carpenter's tools.
Combat Superiority - We start off with 4 Superiority dice and a Maneuver save DC 14. Speaking of maneuvers, let's get to the juicy stuff that makes us badass pirates.
Menacing Attack - Part of being a pirate captain is not only scaring your crew but also enemies. After you hit a target, roll one superiority die, add it to the damage, and the target must make a Wisdom saving throw. Failure and they won't be coming any closer.
Riposte - A use for your Reaction! How dare you try to hit the pirate captain. You can be damn sure they'll regret their life choices when you expend one superiority die to strike back.
Sweeping Attack - Here's another time your extra 5 feet of reach comes up big. Per the rules, when you hit a creature with a melee weapon attack, you try to hit an adjacent target for the same amount of damage. You choose another creature within 5 feet of the original target and within your reach. How much fun will it be to slice through the monster in front of you AND its friend standing behind them? Bet they didn't see that coming.
Rogue 4/Fighter 4
We'll want to get both classes to level 4, taking a Feat with one and ASI with the other. It doesn't make much difference which order you level up.
ASI - +1 Dexterity, +1 Constitution. More hit points are always better, and we'll soon have a +4 modifier in Dexterity.
Feat - Gunner. Gunslinger may not be official material, but the Gunner feat is. A +1 to your Dexterity score now gives us the +4 modifier we just discussed. As a ranged weapon, a pistol isn't the best, but it perfectly fits our pirate captain. A sword in one hand, a gun in the other, taking a shot as you walk forward. As you get closer, drop the pistol and pull your second sword with a dramatic flourish. Slashing away, you'll look like a combination of Errol Flynn and Blackbeard.
Rogue 7/Fighter 4
Let's rush to our rogue half to the 7th level.
Uncanny Dodge - At the 5th level, we get another use for our Reaction. You can halve the Attack's damage against you. Reactions are underrated and often forgotten about until it's too late. I use a sticky a to remember, but I'm old.
Expertise - At the 6th level, we gain Expertise in Deception and Perception. You can always take Acrobatics instead of Perception, but without any modifier through our stats to Wisdom, doubling our Proficiency bonus is very helpful.
Evasion - At the 7th level, when you are subjected to an effect that allows you to make a Dexterity saving throw to take only half damage, you instead take no damage if you succeed on the saving throw and only half damage if you fail. Less damage is obviously better.
Rogue 7/Fighter 11
Extra attacks, higher hitpoints, and more archetype abilities are all things that make us the most feared pirate sailing the seas.
Extra Attack (5th level) - You get another attack. Two Attacks are better than one.
Sneak Attack (5th level) - Sneak attack damage increases to 3d6.
ASI (6th level) - We increase our Constitution to 16.
Superior Dice (7th level) - Increase to five d8s.
Indomitable (9th level) - Once per long rest, we can re-roll a Saving Throw. I'm sure you'll be the target of many a spellcaster, so this will come in handy.
Sneak Attack (9th level) - Damage increases to 4d6.
Martial Archetypes - 7th &10th levels
7th level - Commander Strike, Maneuvering Attack. One allows you to act more like a captain and help the crew. One ally may use their Reaction to attack. The other can give you Advantage via Flanking if you use those rules or provide a meat shield. You're the captain. Better a crew member dies in battle than you. Otherwise, who would lead this bunch of scallywags?
10th level - Rally, Trip Attack. Again, you act like a captain, inspiring your crew. What a great guy you are! You can also trip a foe. It's a dick move, but there's no such thing as fighting fair.
Extra Attack (11th level) - We're up to three attacks!
Rogue 9/Fighter 11
Our final levels go into rogue, but you can always put them into fighter if you're focused on being a front-line fighter.
ASI (8th level) - If, for some odd reason, you don't have a magic item that increases your Dexterity to 20 or more, put both points in Dexterity. Otherwise, both should go into Charisma.
Rogue Archetype, Panache (9th level) - Your crew can find you charming when you want them to, but you'll often bestow disadvantage upon an enemy.
Sneak Attack (9th level) - Damage increases to 5d6. Ouch.
Welp, there it is, my build for the Pirate Captain. If you'd like to share your thoughts or a pirate build of your own, please do in the comment section below.
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