Building a Pirate Captain

[Delicious Taffy]

After watching all four seasons of Black Sails, I'm in the mood to make a Pirate. Not just a stereotypical "Yar, mateys!", mangled Oirish, Jolly Roger-flying cartoon Pirate, but a proper hardened Devil of a Pirate.

I'm thinking somewhere between the show's portrayal of Charles Vane and the theatrics of good ol' Blackbeard. He needs to be able to stare down a whole fleet and make them believe they're the ones who are outmatched. In a melee, he should be capable of taking on said fleet and coming out on top. His name and reputation should spread like a wildfire. I'm not after a fair and balanced hero, here, I'm after a legend.

For race, I'm considering Fire Genasi, but I'm definitely open to better ideas, if they exist. I just really like Genasi. Class-wise, I'm mostly interested in whatever gives good incentive to use brute force and intimidation, especially if it can do both. Don't hold back for balance's sake.

[Sception]

Conquest pally dexadin with sailor[pirate] background and the mariner fighting style from UA. Be the literal terror of the high seas.

[Delicious Taffy]

Conquest pally dexadin with sailor[pirate] background and the mariner fighting style from UA. Be the literal terror of the high seas.

...I understand the background part, but what's that other stuff? I'm not up on the shorthand lingo.

[Trask]

Just a dexterity fighter or swashbuckler rogue would be thematic. You definitely dont want to use metal armor in case you fall into the sea.

Being a pirate is more of an attitude than a build. Ruthless, greedy, and violent is the name of the game here.

[Fredaintdead]

...I understand the background part, but what's that other stuff? I'm not up on the shorthand lingo.

Conquest Pally = Paladin with the Oath of Conquest (Fear-based Paladin from Xanathar's Guide to Everything)
Dexadin = A Paladin who uses Dexterity over Strength to accommodate lighter armour and more acrobatic swashbuckling endeavours.
Mariner Fighting Style = A Fighting Style in Unearthed Arcana (UA). "As long as you are not wearing heavy armor or using a shield, you have a swimming speed and a climbing speed equal to your normal speed, and you gain a +1 bonus to AC. "

[Mortis_Elrod]

Conquest pally dexadin with sailor[pirate] background and the mariner fighting style from UA. Be the literal terror of the high seas.

I agree with this with adding 3 levels of swashbuckler maybe more.

Might even recommend taking martial adept feat for some maneuvers.


For race I would suggest Triton. It’s a Volo’s guide to monsters race that’s basically aquaman. Or if you want Dex at 16 from start with point buy, use Tabaxi as your race. From same book, they are leopard/jaguar people, call yourself Captain Blackspots or stripes.

Edit : Tony the pirate

[Delicious Taffy]

Paladin is an interesting suggestion for class, and not one I would have expected. I'm not entirely sure about it, based on the divine aspect. Maybe a god of greed or bloodlust would work, thematically. I definitely like the Mariner fighting style, so that's definitely going in there. Volo's Guide races are generally sort of creepy or a little too alien-minded for my taste, though.

[CTurbo]

I vote some kind of Battle Master Fighter/ Swashbuckler Rogue split build.

You'd take the Mariner Fighting Style, and would at least take 5 levels for 2 attacks. For maneuvers, Commander's Strike, Maneuvering Attack, Rally, and Riposte would be my top 4 choices.

You could technically even make it str based if you wanted. Just use a Short Sword, Scimitar, or Cutlass(reskinned Rapier).

You would probably want at least 5 levels of Rogue for Uncanny Dodge but you could technically stick with 3 if you had to.

You'd want a decent Cha of probably at least 16 which will be easy.

For Str builds, Minotaur, Dragonborn, Bugbear, Half-Elf, or Vhuman would be my top choices.

For Dex builds, Bugbear, Half-Elf, Vhuman, Tabaxi(ironic I know), or any Elf.

For feats-
Menacing is mandatory. I'd take it at level 1 if vhuman. It adds +1 to Cha also so plan accordingly with an odd Cha score if not taken at level 1.
Inspiring Leader is also great. You may even want to bump Cha again if you take this. I'd want my attack stat maxed first though.
Magic Initiate for Booming Blade(especially if you only took 3 Fighter levels and lack a second attack), probably a ranged attack cantrip from Sorc or Walock(or Vicious Mockery), and Find Familiar to have a Parrot(owl reskinned)
Dragon Fear is a flavorful choice if you go with Dragonborn. It also adds +1 to Str, Con, or Cha so plan accordingly.

So more Rogue or more Fighter? Well that depends on how you want to play.

More Fighter gets you more hp, extra feat/ASI, more maneuvers, bigger Superiority dice, a 3rd attack, and better self healing
More Rogue gets you more Sneak Attack dice, more Expertise, Evasion, Panache, and Reliable talent.

As easy as it is to use Sneak Attack with a Swashbuckler, I think I'd go mostly Rogue with only 5 or 6 levels of Fighter.

[Honest Tiefling]

Paladin is an interesting suggestion for class, and not one I would have expected. I'm not entirely sure about it, based on the divine aspect. Maybe a god of greed or bloodlust would work, thematically.

How do you NOT have a god of oceans or piracy in your campaign? A god of conquest, plain ol' murder or revenge could do the job very nicely. If you somehow lack all of those things, we need to work on your pantheon.

[Naanomi]

I’ve run two pirate characters; one Lore Bard and one Ranger (only the former fancied themselves an actual ‘pirate captain’ in the traditional sense)

[Vogie]

Warlock 5 / Valor Bard 3 / Swashbuckler Rogue X

In addition to your Swave stabbing, you also have a Sentinel Raven Parrot that keeps you apprised of the situation, and the inspiration to keep your crew alive through the mightiest gales.

Yarr.

[Mortis_Elrod]

Paladin is an interesting suggestion for class, and not one I would have expected. I'm not entirely sure about it, based on the divine aspect. Maybe a god of greed or bloodlust would work, thematically. I definitely like the Mariner fighting style, so that's definitely going in there. Volo's Guide races are generally sort of creepy or a little too alien-minded for my taste, though.

couple notes

1. Paladins don't need gods. They are strong independent oath-bound warriors who don''t need any entity to tell them what to do or how to do it.
2. If you must have a god, Gods of Seas, Winds, Storms, Trade, Travel, Thievery also work. Not having any of these is a bit odd for any pantheon.
3. Krakens are powerful enough to entice worship. This is also an option.
4. For Races Triton and Tabaxi are both very familiar perspectives. Tabaxi are very much like impulsive humans and halflings with lots of curiosity, and maybe cat like aloofness. Tritons are very similar to classical arrogant high elves, with alot of pride for their people and culture. They are usually new to the surface as well.

[Kane0]

Conquest pally dexadin with sailor[pirate] background and the mariner fighting style from UA. Be the literal terror of the high seas.

Having played exactly this, I can thoroughly recommend it. I chose to be a Hobgoblin, which was extra fun. His personal code was 'The Chain o' Command', but he also gave plenty of lip service to Umberlee on the side, primarily because his Navigator was a Storm Sorcerer with the Acolyte background and quite devout.

[8wGremlin]

Paladin is an interesting suggestion for class, and not one I would have expected. I'm not entirely sure about it, based on the divine aspect. Maybe a god of greed or bloodlust would work, thematically. I definitely like the Mariner fighting style, so that's definitely going in there. Volo's Guide races are generally sort of creepy or a little too alien-minded for my taste, though.

Paladins are no longer god mongers, they are oath followers. This is a big change and people forget it.
the Oath can be sworn to protect the followers of a god, or a coven, or anything.

[Finback]

How do you NOT have a god of oceans or piracy in your campaign? A god of conquest, plain ol' murder or revenge could do the job very nicely. If you somehow lack all of those things, we need to work on your pantheon.

The land crumbles into the sea. The lakes and rivers seek her out. The sun aims to settle within her. Everything belongs to the sea. The paladin's role is to simple help that along.

[Finback]

For race I would suggest Triton. It’s a Volo’s guide to monsters race that’s basically aquaman. Or if you want Dex at 16 from start with point buy, use Tabaxi as your race. From same book, they are leopard/jaguar people, call yourself Captain Blackspots or stripes.



Capt. Blackfurred.
Catico Jack.
Bartholemeow Roberts.
William Kitt

[Unoriginal]

Paladin is an interesting suggestion for class, and not one I would have expected. I'm not entirely sure about it, based on the divine aspect. Maybe a god of greed or bloodlust would work, thematically. I definitely like the Mariner fighting style, so that's definitely going in there. Volo's Guide races are generally sort of creepy or a little too alien-minded for my taste, though.

5e Paladins don't need gods. It's about determination, not divinity.

[Sception]

5e paladins are powered by their own force of will, and the conviction they pour into their oath. The Oath of Conquest is all about the paladin swearing to dominate everything around them, to seize control of the world and force it to conform to their desires - whether those desires be benevolent or malign. Such an attitude can absolutely fit with a pirate captain.

The ability set is great too. Cha focus makes you an influential leader. The conquest paladin's spells and features based on the frighten condition make them a terror to face in battle, as their opponents are left frozen in fear, cowering before them, unable to fight effectively and unable to flee. A conquest pally swinging onto the deck of an enemy ship can completely destroy their ability to function effectively or respond to the threat posed by the rest of your crew.

In addition to all the fear-based conquest stuff, you also have paladin stuff that make you a strong maritime leader in general. healing to fix yourself up after tanking attacks in battle, or to keep your favored ship mates alive. purify spoiled food & drink so your stores never run bad. Your very presence makes your crew more resistant to disease. At later levels you and your nearby mates are as fearless as your opponents are terrified.

You rule your ship through intimidation, you rule the seas through intimidation, you control every battle your participate in through fear and force of arms. Your terrifying reputation precedes you wherever you go, which by the way perfectly fits the variant background benefit for sailor[pirate]. The bit of dark divine magic drawn either from your personal force of will or from whoever your setting's gods of seas and storms are only all the better fits for a pirate king in a magical setting. All of this fits a pirate captain perfectly.

What fits less is the paladin's default gear and stats. In general, Conquest Paladin is a control/tanking build that favors charisma over their strength to better assert their will through harder-to-resist frightening spells and abilities, and relies on heavy armor to provide maximum AC with minimum stat investment, usually carrying a shield because as a tanking subclass they value extra AC over the extra damage they could otherwise get from dual wielding or a two handed weapon.

That doesn't so much fit the image of a typical pirate, where light or medium armor better fits the aesthetic than heavy armor, and where shields don't seem to fit at all - though I suppose one could manage with a buckler.

However, 5e is a pretty flexible system, and paladin, along with most weapon using classes, can easily go for light or medium armor with finesse weapons.

Conquest paladin does face some unique hangups though, in that, again, they prefer to prioritize their casting stat over their attack stat, but the balance on that gets trickier if your attack stat is also your AC stat. Medium armor mostly fixes this. You can start with a 16 dexterity and light armor, raise charisma before dexterity, and just switch to medium armor when the best medium armor you can afford has a better AC than light armor with 16 dex. In later levels, when you do add dex, you can switch back to light armor.

The shield's a bit more of an issue. Aesthetically, you want a one handed weapon plus an open hand for climbing and swimming, maybe drawing a dagger or short sword to dual wield in melee, or maybe carrying a hand crossbow (or pistol, setting dependent) in the off hand for some ranged attacking.

That works fine, but combined with not going heavy armor it will leave your AC somewhat lower than is optimal for a tank build. You can still make it work, though. Just something to be aware of as an issue.

Another problem for the typical pirate type character regardless of class is that they tend to go high dex, low strength, but they also need a good athletics score for climbing and swimming. If they do break type to favor strength over dex, then they still want a high acrobatics score for balancing on swaying boats and narrow boarding planks and the like. For a dex based character, the mariner fighting style handles this by giving you climb and swim speeds, no skill checks necessary, plus it gives you half the shield bonus back. But it's playtest material, and old, probably abandoned playtest material at that, so many GMs won't allow it.


Multiclassing is a problem unique to dex-based (ie, light armor) or dex-leaning (medium armor) paladins, because while a single classed paladin doesn't need any strength at all to be a fully contributing character, a multiclass paladin requires a minimum of 13 strength, always, just to be allowed to multiclass at all, which puts a lot of extra pressure on your stats. Again, you can run this character concept entirely without multiclassing, in which case this isn't a problem at all. Conquest paladin has no dead levels, even some of the regular paladin abilities that other paladins consider just ribbons, like aura of courage, the conquest paladin actually likes and makes good use of. However, if you do want to multiclass, whether for style, or to pick up particular skills or abilities, or just to round out your repertoire, then the strength requirement puts a considerable extra strain on you, because you'll still need a top-of-the-line charisma, a pretty good constitution, and you don't really want to settle for less than 16 in your weapon attack stat for more than a few levels.


So if you ARE multiclassing, then I think a single level in warlock (hexblade patron) is something you'll want. Adds to the dark magic / sea witch flavor of paladin, think Skarre Ravenmane from the Iron Kingdoms, and lets you use charisma to attack with. Plus you get the shield spell, which can help make up for the fact that you aren't carrying an actual shield by deflecting particularly nasty blows. Plus a short rest spell slot is nice for paladins given that most of their resources are on long rest cooldowns. Plus hexblade's curse is a good ability, and cursing enemies again fits with that dark magic flair that works in the conquest paladins favor as a pirate captain in a magical setting. And you pick up some cantrips, in particular a strong ranged fallback.

Single classed, the minimum stats you should aim for are S10 (don't want a penalty on athletics), d16, c14, i8, w10 (don't want a penalty on perception), h16.

If multiclass, the minimum post-racial stats you should aim for at 1st level are s13, d14, c14, i8, w8, h16. The lower dex here strongly incentivizes at least a one level dip into hexblade.


In terms of other multiclasses, I'd skip swashbuckler, it sounds thematic but doesn't do much for you specifically. More than one level of warlock can work, any hexblade/conquest multiclass with at least 8 or 9 levels of paladin works fine.

3 or more levels of hexblade to pick up a familiar (via the chain boon or the book boon with the ritual invocation to grab find familiar) for the iconic parrot or monkey on your shoulder would be fluffy. Just keep in mind that the three level stretch from paladin 5 to paladin 7 are big deals for you, and paladin levels 4, 8, and 9 are no slouches either, so delaying or interrupting that progression for aesthetic considerations like a familiar will come with a cost in terms of combat optimization until you catch up. Paladin 8 and 9 can be skipped if you're going to take at least 5 levels of warlock, and eventually will pay big dividends when you can cast Fear as a warlock spell, but until Paladin 7 Warlock 5 (ie, character level 12, something many campaigns don't even see), your fear effects will be well behind what a single classed conquest paladin, or one with only a single level dip in hexblade, would be doing.

It's worth noting that a normal conquest/hexblade multiclass is under heavy pressure to pick up the warcaster feat early in order to cast their warlock spells while fighting with sword & board, but you're already eschewing the use of a shield and mainly going around with a sword and an open hand to climb and swing with, so that's not a problem for you.

Also worth noting that, while a 3+ level trip into warlock can start to wear on your primary class progression, a mere second level of warlock can let you pick up deception and persuasion as skill proficiencies via an invocation, and the build can be somewhat starved in that regard (see below).

.........

One or two levels of fighter can be great. A second fighting style (mariner + defense effectively buys back that shield you gave up for aesthetics), second wind for more self healing (not much if you're only dipping, but as a party tank every little bit helps), and of course action surge is a premier ability that any character would enjoy.

..........

Any number of levels in bard (any type) works very well as a multiclass for any cha based leader concept. From a conquest paladin's perspective you're looking at accelerated spellcasting progression, an extra skill proficiency, and inspiring presence. Inspiring presence is a particularly nice and thematic ability for a captain, as you simultaneously shout orders to your crew and give them bonuses to carrying them out.

The extra skill proficiency is welcome, since this build tends to need more than you get by default. Athletics and Acrobatics are desired just to get around the ship. Athletics can be skipped if you pick up mariner, but even then conquest paladins love the shove maneuver in melee (once they have their conquest aura, frightened enemies they knock over cannot stand up), so athletics is still worth the proficiency slot. Beyond that, Intimidate is how you keep your crew in line and bully others into letting you have your way. Perception is great for seeing ships on the horizon. Knowlegde: nature helps you navigate by the stars, read the mood of the waters, and recognize beasts of the sea. That's already one skill more than you get by default, and you haven't even considered deception, persuasion, insight, and so on.

...........

Otherwise, sorcerer famously multiclasses well with paladin (if admittedly better for other subclasses than conquest), thanks to accelerated spellcasting progression and especially metamagic. Sorcerer even has a storm based subclass which is pretty on theme, if admittedly not the strongest subclass sorcerer has to offer. But subclass is really a secondary consideration there after metamagic, so that's not a big concern.

..........

Again, you can absolutely go single classed paladin all the way with this concept, but hexblade warlock 1, conquest paladin 19; or hex 4, pal 7, hex+2, pal+1, hex+6; or hex 1, pal 8, hex+1, pal+10; or hex1, bard1, pal 18; or hex1, bard1, pal8, bard +10; or hex 1, paladin 9, sorcerer (divine or storm for theme) 10; all that works fine.

Really anything that hits hexblade one, conquest 7, can cast the Fear, has 20 charisma, and finishes out with hexblade, paladin, bard, fighter, or sorcerer levels works just fine. Just be sure to hit those big milestones (hex warrior, aura of conquest, the Fear spell, charisma 20) as early as you can reasonably manage given whatever else you want to fit into the build.

.....................

race-wise, Triton is a great fit for conquest pally stats and maritime based abilities generally. The swim speed might be a bit wasted after the first couple levels if your DM allows mariner, but again many won't, and triton has a lot else going for it regardless. Variant Human is a perennial favorite, especially given how asi starved conquest paladins are in general. Inspiring Leader at first level would be a particularly useful and fluffy feat, though warcaster (if warlock at first level), resilient constitution, medium armor master (if single classed 16 dex wearing medium armor long term), shield master (if you can justify a shield aesthetically - maybe call it a buckler?), or sentinel are all fantastic options as well. Or you can just grab magic initiate [wizard] for that familiar.

Beyond that, Fallen Aasimar and Half Elves make fantastic conquest paladins, and really anything with a charisma bonus can work for you.

[Delicious Taffy]

[...] The Oath of Conquest

[...] Cha focus [...] spells and features based on the frighten condition [...] opponents are left frozen in fear, cowering before them, unable to fight effectively and unable to flee. [...] completely destroy their ability to function effectively [...]

[...]healing [...] purify spoiled food & drink [...]presence makes your crew more resistant to disease.

[...] sailor[pirate] [...]
Conquest Paladin is a control/tanking build that favors charisma [...]frightening spells and abilities [...]

[...] light or medium armor

[...] finesse weapons.

[...]start with a 16 dexterity and light armor, raise charisma before dexterity, and just switch to medium armor when the best medium armor you can afford has a better AC than light armor with 16 dex. In later levels, when you do add dex, you can switch back to light armor.

[...] a one handed weapon plus an open hand

[...] AC somewhat lower than is optimal for a tank build.

[...]good athletics score for climbing and swimming. [...] high acrobatics score [...] mariner fighting style handles this by giving you climb and swim speeds, no skill checks necessary, [...] half the shield bonus back.

[...]a multiclass paladin requires a minimum of 13 strength[...] aura of courage[...] top-of-the-line charisma, a pretty good constitution, and you don't really want to settle for less than 16 in your weapon attack stat for more than a few levels.

[...]single level in warlock (hexblade patron) [...] lets you use charisma to attack with. [...]shield spell, [...] short rest spell slot [...] hexblade's curse [...] And you pick up some cantrips, in particular a strong ranged fallback.

[...]If multiclass, the minimum post-racial stats you should aim for at 1st level are s13, d14, c14, i8, w8, h16. [...] one level dip into hexblade.

[...] hexblade/conquest multiclass with at least 8 or 9 levels of paladin works fine.

[...] delaying or interrupting that progression for aesthetic considerations like a familiar will come with a cost in terms of combat optimization

[...] second level of warlock can let you pick up deception and persuasion as skill proficiencies [...]

.........

One or two levels of fighter [...] mariner + defense [...] second wind [...] action surge

..........

Any number of levels in bard (any type) [...] accelerated spellcasting progression, an extra skill proficiency, and inspiring presence.

[...] extra skill proficiency [...] Acrobatics [...] mariner [...] shove maneuver in melee (once they have their conquest aura, frightened enemies they knock over cannot stand up), [...] Intimidate [...]Perception [...] Knowledge: nature [...]

...........

[...] sorcerer [...] accelerated spellcasting progression [...] metamagic [...] storm based subclass [...]

..........

[...] hexblade one, conquest 7[...] hex warrior, aura of conquest, the Fear spell, charisma 20 [...]
.....................

race-wise, Triton [...] swim speed might be a bit wasted after the first couple levels if your DM allows mariner,

[...] Vuman [...] Inspiring Leader at first level [...] warcaster (if warlock at first level), resilient constitution, medium armor master (if single classed 16 dex wearing medium armor long term), [...] or sentinel are all fantastic options as well.

*Snipped for brevity

Thank ya much. This is a lot to think about, and it gives me plenty of leeway. I'll toy around with these suggestions, see how I like them.

[smcmike]

Ship-to-ship combat calls for extreme long range Eldritch Blasts, with Spell Sniper, Repelling Blast, Eldritch Spear, and Distant Spell. Knock em overboard before they can do anything about it...

[JakOfAllTirades]

One thing the greatest Pirate Captains all had in common was that they were a good deal smarter than their crews.

I'd go with a Wizard, and pick a specialty with lots of storm/water spells. Or just pick War Wizard. MC into Swashbuckler for some weapons, armor, skills, and general skullduggery.

A Pirate Captain who can sink a ship just by casting a spell would be the terror of the high seas.

[Fayd]

In one of my settings, the most feared pirate captain on the seas is a Chaos Magic Sorcerer.

Fire on ships. Woo.