Indeed, I'll bet he does. And Sam knows what he did during the Mystery Spot time-loop, too, and just how far he was willing to push the boundaries to get Dean back that time -- RoboSam from Season Six was a model citizen who hugged puppies and rescued kittens by comparison.

I don't think Dean really gets that about Sam. There's a part of his mind that no evidence can touch that's going to be forever convinced that Sam is still the kid brother who only needs a stern talking-to and maybe a swift kick to set him back on the right path.

Sam knows himself better than that. He knows that once he decides for some reason to take the brakes off, he is capable of doing absolutely anything in pursuit of his chosen goal.