Sam is actually the one who owns Dean's soul, he just doesn't realize it until too late.
Oh, hell yes! Angst will, of course, inevitably ensue. Because that is the central ingredient in Show of late.

So I'm inevitably going to be crap at keeping up with fandom for the next month and a half, but! Friend anyway? *waggles eyebrows in an enticing fashion*

(p.s. that icon is awesome. I heart Sam's expression, which is all communicative and yet I can't quite read it)