Raskolnikov? He would be too paranoid. He discovers that he ISN'T a Napolean, remember. Razumikhin might be alright though

What about Edmund Blackadder from Blackadder III. He is forever plotting and schemeing and his put downs would be olympic class

Elric

ahh kerrigan, I thought someone would mention her.

oh, how about jarlaxle?
he is absolutly perfect!
the best no doubt

I think Winston Churchill (who is not, as far as I know, a fictional character) would be undisputed world diplomacy champion. He wasn't one of the Machiavellian realpolitik masters like Bismarck, but he had an uncanny ability to reason with people, showing them how cooperating with him was in their own best interests. It is borne out by the historical record that those who disagreed with him ended up regretting it.

Castruccio Castracani Of Lucca?
I'm not sure if he actually existed or was just a figment of Machievelli's imagination, which is what I understood. If the later, I propose him. His life story is at the end of 'The Prince'.
Oh, and how about Napoleon the pig from animal farm.
Not sure if those two are allowed as both were written to point out how impressive the correct use of diplomacy and force can be.
Another idea from me, again not from the modern fiction all the other idea's given seem to come from: The Pied Piper of Hamelin. Anyone who can get a whole village to follow him just by playing music would be awesome at the game.
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This thread got me thinking of the lord of the rings in terms of diplomacy. I think it would be quite a funny story if rewritten in diplomacy terms...

LotR diplomacy? That's funny.
Saruman: A Orthanc-Rohan, A Westfold Sup Ort-Roh
Merry: A Fangorn-Ort
Saruman: You don't have an army there!
Merry: I roused an army of walking trees ;0)

however LOTR was a bipolar world. good and evil. the lotr pc game had a few factions and you could play it like Total War Rome but it was poorly thought out game structure.

Cersei Lancaster from a Game of thrones would have been good.

What about Wormtongue in LOTR? Very tricky...

And of course Sauron when he could still chnage shape.

Kirk from Star Trek?

Richard Sharpe from bernard Cornwells series might suck at the whole diplomacy, but he'd squish everyone!

wombat what book are you up to? in feast of crows cersei is up shit creek with a paddle bigtime. i think the dwarf is a better diplomacy player, crafty but with a heart! (and a taste of tasty tail)

wormtongue? gandalf soon saw to him but.

"Keep your forked tongue behind your teeth. I have not passed through fire and death to bandy crooked words with a witless worm"

kirk? picard would run rings around him. sure kirk would be alright in a straight fight, brave, willing to bluff, bold when he needs to be and all that but the man has little guile or craftiness.

Harry Potter...his sheer luck brings him through. :P
Robin Hood...the sheriff never gets him, so we can assume that we can't get him either.
Master Yoda...well you own if you can predict your opponents.

I've played as Porfiry Petrovich from Crime and Punishment (he seemed more cunning than the others) and Peter Wiggin. from the Ender series. True, he's not as much of a tactician as Ender or Bean, but he has the desire to take over the world.

i nominate Arc Angel Michael, was in charge of commanding gods armies. and for those of you who think angels are real i guess ill pick Neo as a backup. Aside from his otherworldly fighting skills i think he could transfer his 'chosen' status to any aspect of life.

neo might go from crushing self doubt to overwhelming confidence with one mov.... er game.

@peterwiggin - yes, he certainly has ambition

oh...someone here loves Shogun (James Clavell) too.......great book great character....

Henry Rollins. He wins everything.

Fine- Tyrion then, Sean...

For Wormtongue, I assume no magical powers or wizards are involved in the talking stage of diplomacy (take my suggestion of Sauron in his fair form)

I disagree with you on Kirk- Picard is a diplomat, yes, but Kirk's got a style and energy for taking risks that puts him up there- at least people will talk to him

Major _______ de Coverly anyone?

A bunch of characters from the Foundation Novels..

Obviously the Mule, First Speaker, perhaps the mayor at the first story.. maybe Seldon as well too..

@Gunzo, I'm actually reading that book right now. I'm absolutely hating it. Nothing ever seems to happen. I guess I'm just not a big fan of the randomness genre. I don't really like anything by Tim O'Brian or Kurt Vonnegut all that much either.

The 'randomness genre' - love the categorisation! I'm sorry you are not enjoying it (it's my favourite book) but can understand why. It took me 6 months to read the first time. Even if you struggle with every word I urge you to finish it as they say the world is divided into three categories:

Those who have read Catch-22
Those who have yet to try
Those who gave up reading it!

The next book he wrote, 'Something Happened' is slightly longer and much, much less happens in it. Reading it is like pulling teeth. As Douglas Adams said, it's '...an altogether terser work, for masochists.'

Anlari: great call with the Foundation. I agree entirely and would like to say that the Mule and First Speaker(s) may not fare well in an internet-based game but would obviously kick-ass in face-to-face. I would expect Salvor Hardin and Hober Mallow to perform well in any version of the game...

what about those who havent heard of it?

General Tacticus, Ankh-Morporks infamous General.
The words:AB HOC POSSUM VIDERE DOMUM TUUM, or "I can see your house from here" decorated the front of his castle.
He was the military leader of Ankh-Morpork, and introduced innovative ideas in the art of war.

On the Kirk-Picard debate:
Kirk is the only one to pass the Kobayoshi Maru test, by changing the environment of the test. That test was an otherwise impossible situation, which clearly shows a string of thinking outside the box at indirect options that would help him in Diplomacy. Picard however, is overly conscerned with doing the "right thing" and following all the directives. I don't think that Picard would have the guts to backstab an otherwise helpful neighbor. Without that, you don't win.

thats true churchill. picard wouldn't make a good stabber. worf would be next to useless.

Lol General Sean, although i think that Havelok, the patrician could well be far better. Or perhaps Granny weatherwax.

If you haven't read Catch-22 then you have defintiely missed out.

The character Milo Minderbinder would be pretty handy I reckon.... pretty shady fellow, but somehow manages to get everyone to trust him repeatedly. i think his catch phrase was something "What is good for Milo is good for your country"

Being contracted by both Germany and the US in Orvieta would be akin to having both France and Germany support your English fleet into Belgium in Aut '01. He was also ruthless enough to use US bombers to attack their own base at Paniosa.... which has got to be up their with the biggest stabs of all time.