Chester's Role in the Past?

alchemydesign wrote:Yeahhh, crossbow is pretty epic, first time I beat O&S was with a +10 Heavy Crossbow.

Really?

Everytime I've beaten O&S is killing S with an upgraded Uchi with Sunlight blade, and then just bleeding Orn to death.

The only real threat I have in that fight is getting 1-shot at the beginning by Orn, getting caught in S's charge, or mis-timing my dodge and taking Orn's lightning butt to the face.

Ahahaha, yeah, i just hid behind the pillars and plinked away.

All I dare say for certain about Chester is that he is from Carim, judging by his weapon of choice and his untrustworthy attitude. He appears to support the spread of the Abyss rather then the Chosen Undead, and he is even willing to invade the world of the Chosen Undead.
This doesn't seem like he is doing it for an important reason, but rather as form of sport.

Should he defeat you, he doesn't seem surprised or intimidated by your sudden return. He makes it sound like he was counting on it.

Personally, I think Chester is just another Joker. He doesn't have a plan. He is not trying to gain anything specific. He just wants to create havoc and imbalance and laugh at the outcome, however it might turns out.
(Also as a slight side-note: He is a sore loser)

*puts on his best Michael Caine voice* "Some men...just want to watch the world burn..."

Sorry for thread necromancy, but anyone think Chester could be related to the Fat Officials in Demon's Souls?  Body-type aside, they both wear similar-looking clothing (well, hats.  Their outfits don't look a whole lot alike, but neither looks super medieval either, though Chester's get-up looks a tad more modern) and both have sardonic grins.  Just a random thought I had the other night.