User blog comment:Dominic1743/“The Trap” Discussion/@comment-3045936-20200121020056/@comment-108.36.76.116-20200122093223

I think Chuck plays to win, and uses a long game strategy. The Winchesters were born to do lots of things, including let Amara out, and to have Dean get through to her in a way she never saw coming. One might say Chuck had faith in Dean. I don't buy that he really thought he would be killed by her. So he keeps the monsters from running wild? Maybe he also keeps sending them just the right places to make the WInchesters into who they are, prodding them here and there all their lives.