The Dread Pirate Gestalt

[The Dread Pirate]

I want to make a character who is as close as possible to the Dread Pirate Roberts from the Princess Bride.

I know one side would likely be Swashbuckler, due to his speed and skill tricks with a blade I could say he is an expert duelist.

But the other side alludes me, I know this would do best with a Cha based class but I am not sure what.

[kestral287]

Rogue, Investigator, or Slayer. He's sneaky, he uses poisons, he's not afraid to lie like mad. Each of those three classes does at least some of those things well.

His Swashbuckler side is Inspired Blade, I'd think.

[The Dread Pirate]

Those classes do well with their cleverness.
And Definitely Inspired Blade is the archetype for the Swashbuckler.

Investigator may work but the Extracts are not something he seems to work with.

[Ms. Pleiades]

Consider the Sleuth archetype for the investigator half.

Sleuth

[The Dread Pirate]

That is a very interesting Archetype, it stacks with Grit, allows for the use of very clever actions.

I was thinking maybe a Mastermind Sleuth which stack.

[Ms. Pleiades]

And you'd be keeping poison immunity, so you really could use the iconic line "I've developed an immunity to iocane powder."

[Imbicatus]

He bested Inigo at Steel, so he would need Swashbuckler training. He also bested Fezzik in Strength, his greatness. He also developed an immunity to iocaine powder, but not necessarily all poisions.

Swashbuckler//Lore Warden Fighter with the Venom Drenched trait.

[The Dread Pirate]

If I went with that build I would tag on Martial Master to show his flexibility in combat.