I just can't see Jim or Cochran winning. Jim comes across to me more as someone who is instrumental in the actual direction the game takes, and who might even make the finals, but who has burned too many bridges (and will likely continue to do so) to actually win.
In particular, he's the polar opposite to Coach's game this season. Assuming he and Coach both make the merge, I highly doubt Coach would vote for someone who has proven to be disloyal and a liar and schemer.
As far as Cochran goes, it seems like his struggle to find acceptance and be liked isn't presented as a story arc, but rather just as a character trait. If he somehow managed to get into a Final Three with Jim and Brandon he could definitely win and prove me wrong, but at this point I would be surprised if Dawn wasn't a finalist, and IMO she beats almost everyone (at least for now).
Don't underrate Keith though. He's not Grant!
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Thank you, Eddie Guerrero.
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