[3.P] Gangplank - the Saltwater Scourge

[ImperatorK]

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Gangplank is a champion in League of Legends, a pirate captain fighting with a sword and pistol. Now, despite what you might think, I'm not actually trying to stat up Gangplank, I'm just making a character that's inspired by him, at least in some respects. It's the Min/Max It! subforum, so lets focus on the mechanical part.
It's a 20th level gestalt build (but classes no higher than T3).
I'd like him to be decent at combat and be a versatile fighter. For that I'm going to be focusing on maneuvers, with Dirty Trick on the front. I think I'll go with Fighter (Dirty Fighter archetype) on the first gestalt side, he'll definitely need a lot of feats to do everything I want him to.
Damage-wise I want him to wield a cutlass or a scimitar one-handed and be crit focused. Generally he can two-hand his sword for more damage, but due to his fighting style he'll one-hand it more often than not. He'll need his other hand to be free to use his pistol and maneuvers or for other stuff.
I also want to squeeze explosions in there somewhere.

I have to go to work and might not have the time to write more or respond for a day or two because I'll be busy. I hope I wrote enough details that you'll have no problems with suggesting ideas.
And please, do not worry about the concept being unoptimal, just help me make it as good as possible.

[ketaro]

Dread Pirate.
Not a great class, but it fills the role of GP quite well and if its ever a PrC that's called for, this would be it.
Maybe just a light dip into Swashbuckler simply to snag Weapon Finesse for free.

Dread Pirate's Two Weapon Fighting free feat can certainly still work the same even in the instance of dual wielding a sword and pistol. And gawd knows its always better to avoid actually having to spend a feat on anything in the TWF tree if you can get it for free for any reason.

Combo the Scourge of the Seas ability, an AoE Intimidate check, with Imperious Command and cower everything within 30ft of you for a round. Cause fightin' dirty 

Freakin' Pirate King.

Lookit' you, you're makin' me wanna do this now. 

[ImperatorK]

Wasn't actually planning on TWFing, but I won't complain about a free feat.

So the build right now would look something like this (at least race- and class-wise):
NE male half-orc
Fighter (Dirty Fighter; Zhentarim Fighter) 20
//
Swashbuckler 1 / Alchemist 9 / Dread Pirate 10

Just FYI, in our games Fighter is combined with Warblade and Barbarian, as well as gets a feat every level (instead of just every other level), so those 20 levels actually give much more than you'd think. Also, Swash is combined with Factotum and Rogue, so taking more than just a 1 level dip might be worth it.
We already have an AoE Intimmidate, but now I'll need some way to make the demoralization give the frightened or even panicked condition on the enemies, if possible.

[ketaro]

Well your AoE Intimidate would stack with the other partymate's you say the group already got and make stuff frightened anyways if you don't go for Imperious Command for cowering. Wait right forgot Intimidate doesn't do shaken haha. But to clarify, Imperious Command would make enemies Cower for 1 round, and then be Shaken for the next round when you use Intimidate's Demoralize ability on them. With the Frightful Presence feat (which, admittedly also feels appropriate for GP to have, haha) the targets could potentially be Frightened for that round after the Cower wears off. Kinda a nice image too, no? Scare some one so bad they freeze on the spot, then the second they recover they turn and run as fast as they can 

Otherwise, that's looking rather nice. And I understand the alchemist bit there too. Yeah. Nothing spectacularly overpowered, fairly manageable lookin'.

[ImperatorK]

Well your AoE Intimidate would stack with the other partymate's you say the group already got and make stuff frightened anyways if you don't go for Imperious Command for cowering.

Err, there's no other partymate with Intimidate, I meant the AoE Intimidate that I'll have from Dread Pirate.

Wait right forgot Intimidate doesn't do shaken haha.

It does in PF.

[Vladeshi]

Wait right forgot Intimidate doesn't do shaken haha.

It does in PF.

It also does in 3.5 as per the PH and the SRD

Demoralize Opponent
You can also use Intimidate to weaken an opponent’s resolve in combat. To do so, make an Intimidate check opposed by the target’s modified level check (see above). If you win, the target becomes shaken for 1 round. A shaken character takes a -2 penalty on attack rolls, ability checks, and saving throws. You can intimidate only an opponent that you threaten in melee combat and that can see you.

[ketaro]

Well, I goofed a teeny bit. None the less! This build looks nice~