Toying with a pirate idea

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I'm thinking either an RP-modified ranger, or a hybrid rogue/warlord.

I'm figuring him to be a swashbuckling rogue with good leadership.

Any help?
The Skald class (found in Heroes of the Feywild) might be worth a look for this idea. It's a melee focused Bard who fights more with physical prowess than magical. It uses Charisma and Dexterity for its main stats, so the swashbuckling and leadership areas are covered without trying to make a mishmash of multiclass/hybrid classes work together.

Bear in mind that unlike conventional Bards, you don't get to be Multiclass McGee, so you'll only be able to poach feats and powers from one other class. That being said, all of the Bards powers are at your disposal, so there are other melee power options for you aside from those listed in the Heroes of the Feywild book that you can use too. They can even work as ranged fighters if you want to add some ranged attacks to your arsenal. As a leader, Bard is sure to have no shortage of powers that allow you to help your allies as well.

Hope this helps. Happy Gaming
I'm currently running a 4e pirate game and we've re-fluffed a bit for some of the classes.

One player is playing a Skald and it fits perfectly. She is the captain of the vessel (won fairly through dueling) and is quite effective. And something about it just fits and screams Pirate!

Another player is playing an Assaulting Swordmage as a Defender. We both think that this seems like a magical pirate-type. Teleporting onto a vessel to board it, chase down enemies, etc.

One player is a Monk, but that's neither here nor there. Could easily be said to be a brawler type character if you go Stone Fist and drop the Asiatic feel to it.

Lastly, we have a two-weapon Ranger (specifically the Scout) that fits the duelist archetype quite nicely.

I guess what I'm trying to say is, anything can be re-fluffed to fit what you are looking for. Of the classes and examples I've listed I see three of them fitting a different type of that pirate mold.

Good luck and happy gaming!