These are theories, many of them, some based on spoilerettes for upcoming eps, so I'll both lj-cut AND say that if you don't want inklings of what is yet in store for us -- though I could be wrong on all counts -- avoid, please.
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Three things I'm thinking about. )
In the season finale, a line was cut from the script in which the demon tells Sam that his plan is for all the children like him to be killers. I can see why they cut this line, even if they still intend that to come up, because it would have been harder to sell Sam's struggle of whether or not to kill his father after having heard that the demon plans him to be a killer.
Yet, I think whatever John "knows" and told Dean is not this...but something else.
That being said, I think the whole family showdown in the cabin last season was significant. Significant that Dean is the one that pulled Sam back from pulling the trigger. That it's Dean continually pointing out to Sam what matters most. Which makes me agree with your theory that maybe John realized that. Sam is less likely to listen to John, and more likely to listen to Dean.
Which I think will bring up Dean's insecurity issues (he may think he's there for Sammy in place of his Dad, and may not think he's good enough). May come full circle thinking Sam is Dad's favorite, that it's really all for Sam type stuff.
Whatever happens, should be one hell of a season.
Thanks for letting me ramble.
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