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http://images4.wikia.nocookie.net/capcomdatabase/images/a/a3/ShinkiroWesker.png

VS.

http://devils-lair.org/gallery/extra/chara/Jester.gif

Wesker because Wesker does not look like an asshat.

Wesker because Jester is has character induced stupidity.
Jester will attempt to play around, appear in front of Wesker, and talk Wesker into a deal, just like what he did with Dante except Wesker will betray Jester just like Excella causing Jester to become another one of Wesker's minions.

Going with Jester. Not sure if Wesker can heal like the fool but more so when you cut him he sprays confetti.. that's a win in my books.

I'd most likely have to say Jester as he seems to be much faster and has a wider variety of attacks as shown when you fight him in DMC3 SE (anyone remember the strawberry attack). also Jester isn't as dumb as he looks so I'm sure he would be able to see through Wesker's plans or at least parts of his plans should they strike a deal.