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D&D 5E Help me build a badass Pirate (probably Warlock/Rogue)

faria

First Post
I was thinking of multiclassing Rogue (for both flavor and Assassinate at level 3) with a thunder/lightning caster class (calling storms at sea, controlling the direction of the wind, smiting enemies with lightning, sinking enemy ships with thunder and Shatter).

The problem is: to utilize Assassinate's autocrit, the spell needs to be a melee/ranged spell attack roll. Not a lot of thunder/lightning spells require attack rolls!!! They're all frickin' DEX saves for half damage. The only real spells I see that would work are Witch Bolt and Chromatic Orb (correct me if I missed something though).

Tempest Cleric was my first idea. It would be awesome to stack Channel Divinity with Assassinate, right? Well, actually, that can't happen. Tempest Clerics don't seem to get ANY thunder/lightning attack roll spells! They get other nice things like armor and heal spells and whatever, but Tempest Cleric wouldn't be optimal compared to other choices below...

Lightning dragon Sorcerer could work because they have access to several lightning attack roll spells. Sorcery points would give some significant buffs to spells and Elemental Affinity will help a little too. Sorc17/Rogue3 seems like a solid choice if I wanted to be a caster. At Sorc14, I'd even grow a pair of wings and can picture my character summoning lightning bolts from above while flying around. Kinda badass.

Wizard could work because of access to useful spells, but it just doesn't fit the pirate idea. No idea which school would be best for this character. Evoker Overchannel does seem nice though and would stack with Assassinate for a hell of a burst! Sucks having to wait so many levels to get Overchannel though. Ideas for other schools?

Warlock is an option that's less "stormy" but genuinely interesting. I'm actually leaning toward Warlock, but don't know enough about it. A drowning pirate captain trading his soul to The Great Old One of the Sea for a chance at revenge (tracking down and killing his mutinous crew) would be awesome. Not sure which pacts or class level breakdowns are best though since I've never built a Warlock before.

Pact of the Blade would be great because I could actually utilize the Sneak Attack dice (while casters can't use them with spells)! Would it be better to go Lock17 or Rogue17 with this pact? Is there another level breakdown that seems appealing here?

Pact of the Chain for a parrot familiar or monkey or whatever would fit the pirate theme well. This pact seems more versatile too because you can go either caster or melee. As a caster, I would spam Eldritch Blast ("A beam of crackling energy" sounds lightning bolt-y enough to fit the theme). As a melee, I would get Sneak Attacks on stuff because the Familiar can flank enemies and Help gives advantage with skill checks. What level breakdowns seem best for this pact for casters vs melee?

Pact of the Tome would be cool if the Tome can double as a treasure map! Not a clue how to build this though.

Yeah, I need a lot of help with Warlock. Not even sure if The Great Old One is the way to go here.
 
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