Pirate Captain Advice: What ARRRRRRRR your thoughts?

[JoyfulJester]

Hi everyone!

I'm looking to play up a pirate captain and could use some advice. RP-wise my character ideally gets others to do his dirty work (he's a captain for crying out loud!). I want to structure my character around this idea of being a leader and either intimidating or persuading others to get what he wants. So here's my idea...

Human Variant with inspiring leadership feat. Point buy 27 with

Str: 8, Dex: 16, Con: 14, Int: 8, Wis: 10, Cha :16

My DM is going to let me use a pistol with hand crossbow stats just for flavor.

lvl 1 Fighter 1: Proficiency in con for spells later on, fighting style in archery, second wind, leather armor, and shield when I need it.

lvl 2 Bard 1: Spellcasting and Bardic Inspiration. I want to pick up spells and B.I. to help my team members from the back line and have some utility outside combat as well.

lvl 3 Fighter 2: Action Surge

lvl 4 Fighter 3: Battle Master. I want to concentrate on commanding strike, getting my comrades to attack for me and commanding them to do so seems like a pirate captain to me. I can also use distracting strike to give advantage on attacks and suggest that maybe they attack that guy over here, and rally to keep them fighting for me.

lvl 5 Fighter 4: Crossbow Expert so I can attack multiple times with my pistol

lvl 6 Fighter 5: Extra attack for multiple maneuvers and more options during combat.

After this I was thinking I would continue on with Bard lvls to get more spells and utility or get lvl 6 for an ASI. I was just curious to know if you think it fits the flavor of my character and/or if you think there's a more representative idea I haven't thought of.

[Aett_Thorn]

Well, I'm kind of curious about the whole "Gets others to do his dirty work", and then focusing so much on attacking yourself. Going Fighter to me screams that you are the one doing the dirty work.

For others to do your dirty work, I would think that this Captain would be focused on buffs and heals for his crew, and not so much attacking himself (although he'd have that ability, because he is a Pirate). As such, I would think that a Blades/Valor Bard, or some sort of Cleric with some buff spells would be a better fit here.

[JoyfulJester]

Well, I'm kind of curious about the whole "Gets others to do his dirty work", and then focusing so much on attacking yourself. Going Fighter to me screams that you are the one doing the dirty work.

For others to do your dirty work, I would think that this Captain would be focused on buffs and heals for his crew, and not so much attacking himself (although he'd have that ability, because he is a Pirate). As such, I would think that a Blades/Valor Bard, or some sort of Cleric with some buff spells would be a better fit here.

The "getting others to do my dirty work" thing was using commanding strike whenever possible, so others are attacking during my turn with bonus damage. I can see what you're saying though because I'd only be able to do that once per turn, you're suggesting I concentrate on spellcasting more? College of Blades seems more like being in the fray, going straight valor though is a thought. What about adding in the mastermind archetype from rogue?

[Crgaston]

Don’t forget that as a pirate captain, you have to be able to personally kick some ass as well.

I think your plan is solid.

Except you need a familiar ASAP.
:)

[Bahamut7]

Talk to your DM about porting over Warlord from 4e. He could be setup to not attack at all but to command his "crew." In fact here are some abilities:

Commander's Strike: One ally of yours makes a Basic Attack. You could make this a mage using a cantrip or martial doing their main attack.

Hammer and Anvil: You attack and an ally adjacent also gets to attack. This is normally recharged on a short rest and the ally's attack is a free action. I would make it use their Reaction instead.

There are more of course and would need a little work but there is a reason the Warlord could be made to be called the Lazy Warlord. The class is found in the 1st Player's handbook.

[JoyfulJester]

Don’t forget that as a pirate captain, you have to be able to personally kick some ass as well.

I think your plan is solid.

Except you need a familiar ASAP.
:)

I really wanted to figure in a parrot or monkey, would be fun 🤣

Talk to your DM about porting over Warlord from 4e. He could be setup to not attack at all but to command his "crew." In fact here are some abilities:

Commander's Strike: One ally of yours makes a Basic Attack. You could make this a mage using a cantrip or martial doing their main attack.

Hammer and Anvil: You attack and an ally adjacent also gets to attack. This is normally recharged on a short rest and the ally's attack is a free action. I would make it use their Reaction instead.

There are more of course and would need a little work but there is a reason the Warlord could be made to be called the Lazy Warlord. The class is found in the 1st Player's handbook.

Ohhhh I didn't consider pulling in warlord. I'll have to have a conversation with my DM about that.

[CantigThimble]

Another option would be Mastermind Rogue/Bard. Shout orders to your crew every turn as a bonus action to give them advantage. Though if you go with this build I might go lore bard because you'll always have a good use for your bonus action, so being able to spend inspiration as a reaction would be better. (Unless you hand it out before combat of course.)

[Unoriginal]

Why have INT so low? You're the captain, if you're dumb you won't last long.

Another option would be Mastermind Rogue/Bard. Shout orders to your crew every turn as a bonus action to give them advantage. Though if you go with this build I might go lore bard because you'll always have a good use for your bonus action, so being able to spend inspiration as a reaction would be better. (Unless you hand it out before combat of course.)

Mastermind Rogue would be good, the ranged Help action would fit OP's concept well.

[Kane0]

I made a Dex based hobgoblin Conquest pally pirate captain once. Now that was damn fun to play.

[JellyPooga]

First off; as Captain, you need to not have weakness; being Charismatic will take you far, but being thick as a plank and physically weak will get you thrown overboard by someone smarter or stronger than you.

Second; Fighter and Bard don't blend that well. They MC ok, but not great. I'd suggest either Battlemaster Fighter/Mastermind Rogue, if you want to go down the martial path, or something like Ranger/Bard or Paladin/Bard if you want to go magical. Considering that you want to grab Archery FS, Ranger/Bard makes sense (bit will be MAD, especially considering my 1st point). Taking Natural Explorer : Coast would be nice and fluffy too.

[Harrysonford]

What about a pact of the blade, hexblade warlock? If you grab Improved Pact weapon, you can use a bow.

This covers a lot without a need for multi classing.

CHA is your spell casting ability, so that’s covered.
DEX doesn’t have to be built as much, because of the hex warrior feature letting you use CHA for your Pact weapon.
That gives you more room for INT and STR, Which others mentioned were important. Plus you have some dark magic to keep people in check.

[JoyfulJester]

Another option would be Mastermind Rogue/Bard. Shout orders to your crew every turn as a bonus action to give them advantage. Though if you go with this build I might go lore bard because you'll always have a good use for your bonus action, so being able to spend inspiration as a reaction would be better. (Unless you hand it out before combat of course.)

I like that. It would give me an excuse to talk like a pirate more of you know what I mean. 😆

I made a Dex based hobgoblin Conquest pally pirate captain once. Now that was damn fun to play.

That sounds awesome. Did you recruit people into your crew after dominating them?

[Kane0]

That sounds awesome. Did you recruit people into your crew after dominating them?

There was a civil war happening at the time but before I lost my ship we had 'acquired' some goblin riggers/runners, some water genasi navigators and even a minotaur that was our best boarder.

[Avigor]

Hybridize the sailer/pirate background and the caravan master background from adventurer's league.

Then, go Mastermind Rogue / Purple Dragon Knight Fighter and have fun.

[Dudewithknives]

I guess it comes down to whether you want to be the beloved captain that everyone respects a d the crew is like a family.

Or

The captain who rules because he has the most power and people work for him because he is successful but they don't particularly like him.

If beloved captain: I would go with College or Swords Bard, oddly their blde four is he's do not specify melee weapon so you could use the handcrossbow. Or a straight swashbuckler rogue.

If power and fear, conquest paladin or maybe even a storm sorcerer. People follow you based on the charisma and your storm powers could be great for a pirate.

[Kane0]

Storm Sorcs actually make the best helmsmen/navigators. Their level 6 ribbon is phenomenal when you're on a ship a lot of the time.

Full sailor party:
Mage: Storm Sorc
Priest: Coast circle druid or tempest cleric
Thief: Swashbuckler Rogue (expertise in all things to do with seamanship and ropes)
Warrior: Conquest paladin (mariner fighting style, aquatic summoned mount)
5th Wheel: Gunificer

[Harrysonford]

Storm sorcerer can work for either style of captain.

“Fear me, I control the storm,”

Or

“I’ll keep you safe from the storm so stay with me.”

[JoyfulJester]

First off; as Captain, you need to not have weakness; being Charismatic will take you far, but being thick as a plank and physically weak will get you thrown overboard by someone smarter or stronger than you.

Second; Fighter and Bard don't blend that well. They MC ok, but not great. I'd suggest either Battlemaster Fighter/Mastermind Rogue, if you want to go down the martial path, or something like Ranger/Bard or Paladin/Bard if you want to go magical. Considering that you want to grab Archery FS, Ranger/Bard makes sense (bit will be MAD, especially considering my 1st point). Taking Natural Explorer : Coast would be nice and fluffy too.

I had planned to write off my weaknesses as him being an older captain where time has caught up with him, giving him lower strength and being a pirate I didn't think he'd be very book smart giving him lower int. So I want him to rely on his experience and influence and this led to him being a battlefield controller.

I guess it comes down to whether you want to be the beloved captain that everyone respects a d the crew is like a family.

Or

The captain who rules because he has the most power and people work for him because he is successful but they don't particularly like him.

If beloved captain: I would go with College or Swords Bard, oddly their blde four is he's do not specify melee weapon so you could use the handcrossbow. Or a straight swashbuckler rogue.

If power and fear, conquest paladin or maybe even a storm sorcerer. People follow you based on the charisma and your storm powers could be great for a pirate.

I guess the image I have is a snarky and intimidating, using his influence to get what he wants. Fear plays a role, but so does playing up a person's desires. I'm not sure conquest paladin would fit and sword Bard doesn't feel controlling enough.

I like the idea of Mastermind/valor Bard because I was worried about my bonus action being taken up by too many things.

The storm sorcerer does fit a pirate quite well but I'm not sure it controls enough. Perhaps if I could move enemies and allies around on a regular basis?

[Waffle_Iron]

Just spitballing here, pirate background, ranger 3 beastmaster gets you a parrot companion and all the nautical experience you need, plus archery, and a small number of heals, then mastermind rogue makes you “helpy” and makes your pistol do sneak attack damage, plus expertise in intimidate and persuade.

Might be cool.

[PopeLinus1]

In the game don’t make pirate puns.

Seriously, your party will hate you by the third session.

[Vogie]

you need a familiar ASAP.
:)

What about a pact of the blade, hexblade warlock? If you grab Improved Pact weapon, you can use a bow.
This covers a lot without a need for multi classing.
CHA is your spell casting ability, so that’s covered.
DEX doesn’t have to be built as much, because of the hex warrior feature letting you use CHA for your Pact weapon.
That gives you more room for INT and STR, Which others mentioned were important. Plus you have some dark magic to keep people in check.

One level of Raven Queen Warlock will give you a Sentinel Raven faux-miliar which will also give darkvision. As long as it's w/in 100 ft of you, you can see through its eyes, so you can literally man your own crow's nest while on deck. Repelling Blast allows you knock people off the boat with that single level as well if you go a second level dip (whoops).

If your pistol-crossbow is a magic weapon, I would still suggest Pact of the Blade so you can store it in hammerspace, while solving all other proficiencies.

If not, Chronicle of the Raven Queen with Pact of the Tome seems like a fantastically pirate-y thing to do... the question would always be "Where is your treasure buried?"

[Bahamut7]

In the game don’t make pirate puns.

Seriously, your party will hate you by the third session.

Pirate Puns 100% at the table until the character is dead.

[JoyfulJester]

Just spitballing here, pirate background, ranger 3 beastmaster gets you a parrot companion and all the nautical experience you need, plus archery, and a small number of heals, then mastermind rogue makes you “helpy” and makes your pistol do sneak attack damage, plus expertise in intimidate and persuade.
Might be cool.

I thought about beastmaster, it just seems too underwhelming to take 3 levels in =\

In the game don’t make pirate puns.

Seriously, your party will hate you by the third session.

Did you even read the topic of this thread? Sorry but I'll have to agree with Bahamut with this one. Pirate puns 100% of the way. If not what's the point really? 🤣

One level of Raven Queen Warlock will give you a Sentinel Raven faux-miliar which will also give darkvision. As long as it's w/in 100 ft of you, you can see through its eyes, so you can literally man your own crow's nest while on deck. Repelling Blast allows you knock people off the boat with that single level as well

If not, Chronicle of the Raven Queen with Pact of the Tome seems like a fantastically pirate-y thing to do... the question would always be "Where is your treasure buried?"

Crow's nest...love it! Pirate puns ftw. I like that where is my buried treasure, my character is getting on in age. Hard to remember things like specific locations. I'll pick up proficiency in drawing or something and make maps.

[Blacky the Blackball]

If you want to be a persuasive pirate captain who gets others to do their dirty work, be a Chain Pact GOO Warlock who is pledged to some great undersea gribbly (the Kraken or Cthulhu or something).

Then make your special familiar an imp and persuade the DM that it should be able to turn into a parrot rather than a raven.

You'll then be the charismatic yet slightly sinister captain with magical powers that (if you choose the right spells) can be used to persuade and intimidate, and your parrot can spy for you and keep an eye on the crew (and you can use it to relay orders, since it's intelligent).

Besides, it's worth it just for Vicious Mockery ("You fight like a cow!")

[JoyfulJester]

Besides, it's worth it just for Vicious Mockery ("You fight like a cow!")

Seacow*

I think I've decided to go with battle master and swashbuckler for a couple of reasons. People have mentioned that my character as a pirate Captain should still be able to kick butt himself and I agree. Keeping to the pirate theme I'll pick up swashbuckler. I still want to make other people attack during my turn so I'll pick up battle master and commanding strike and play it out like this: when a fight starts I'll use commanding strike to get others to attack for me. As the fight goes on if my crew can't kill the enemy (when superiority dice run out) that's when I'll step in and show them how it's done. Using my years of experience sword fighting I'll dart in, use disarming strike and twf at times or find chances to use my sneak attack. I can keep my Dex at 16 and drop my cha to 14 for more points and balance my stats. Furthermore I won't need the feat first lvl and can take +1 to all stats instead. I'll lose spellcasting but I think having a well rounded character feels nice.

[Vogie]

Crow's nest...love it! Pirate puns ftw. I like that where is my buried treasure, my character is getting on in age. Hard to remember things like specific locations. I'll pick up proficiency in drawing or something and make maps.

Not your buried treasure - THEIRS.
The Chronicle of the Raven queen allows you to ask a question of a recently-dead person, place their hand on your Tome, and the answer is written in their blood on the tome. The idea of a pirate sails the seas with a book of treasure maps penned in the blood of their enemies, a pirate who can *literally* shoot first and ask questions later... that's pretty awesome.

[JoyfulJester]

Not your buried treasure - THEIRS.
The Chronicle of the Raven queen allows you to ask a question of a recently-dead person, place their hand on your Tome, and the answer is written in their blood on the tome. The idea of a pirate sails the seas with a book of treasure maps penned in the blood of their enemies, a pirate who can *literally* shoot first and ask questions later... that's pretty awesome.

Ohhhhhhh! Apologies, I did not read up on that invocation. That's a sweet idea! Then I could walk around saying "dead men do tell tales" 😁

[Sception]

Repelling Blast allows you knock people off the boat with that single level as well

Not to object to the idea, I'm a big fan of raven queen warlock for this, but repelling blast will require a second dip level, as repelling blast is an invocation, and warlocks don't get any of those until second level.


Otherwise, I think at least a few levels of mastermind rogue really is obligatory here, so you can be yelling out orders in your pirate voice in the thick of battle.

Also also, even if you dump strength, don't skimp on athletics, and if you take a few levels of rogue make that one of your expertise skills. You want to be able to climb the rigging and swing from ropes and actually swim if you ever fall overboard.

[PopeLinus1]

Pirate Puns 100% at the table until the character is dead.

Just going from experience. I actually got left to die by the rest of my party.

[Joe the Rat]

Not to object to the idea, I'm a big fan of raven queen warlock for this, but repelling blast will require a second dip level, as repelling blast is an invocation, and warlocks don't get any of those until second level.

I'd take it to 3 for the Chronicle invocation. Since you're tome already, you can skip Grasp of Hadar and get Thorn Whip as your pulling cantrip - good for yanking people overboard. but at this point we're deeply fighter/'lock or rogue/'lock (or bard/'lock). it's probably best to decide if you want to be a lazy pirate captain (martial-driven), or a spooky pirate captain (magic-driven).