Date: 2013-10-23 08:16 pm (UTC)
So, if he has a shady agenda of his own, what does he gain by keeping Dean on his good side through manipulation?

Who knows maybe a bit like Crowley after seeing the opponents the brothers have beaten over the years he's a bit wary of having Dean fully against him until he's fully ready?

Hm, I think that is debatable. If Dean hadn't sold his soul for Sam's life, the apocalypse would never have happened.

Well that is true, but has Dean ever expressed regret or guilt for selling his soul for Sam's life? I know he has definitely expressed guilt for his actions under Alastair's tutelage but I can't recall him feeling guilt for that. And even if objectively it is a mistake on the same level if Dean himself does not see it that way then it doesn't mean much in terms of his ability to relate to Sam and his mistakes prior to his recent decisions.
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