I love love love the idea that Cas was the first ever character that got away from Chuck. He sets everything up, his story is running smoothly, and he vanishes. But there’s one little angel that keeps breaking rank and is fascinated by humans.

But it’s only the policing of the other angels following Chuck’s story structure that pull him back into line. Chuck isn’t seeing this. I don’t think Chuck foretold Cas being the one to lift Dean. I think that was an act on his own. Free will. He got there first.

When Dean convinces Cas not to follow Chuck’s script, it’s the first time Cas has support in this break from the story. It’s the first time someone sees him and encourages his free will. Chuck does not see this. “You’re not supposed to be in this story.”

The Winchesters take Cas in as family based on trust and free will. It is them, love and choice, versus the angels, Chuck’s structured story. Chuck does not understand Cas’ significance and how he shaped the Winchesters.

The issue here is that Cas does not trust his place either. He also can’t see the effect he has. He has trouble believing he’s a part of the family. I think his blindness and Chuck’s are parallel. Chuck’s inability to see Cas as a man character and influencer is his downfall.

This stands to reason that Cas’ ending /has/ to be the realization of his belonging, of the place he has in the Winchester’s /choice/ not their story. They /chose/ him. He chose them.

Cas has started pushing back on Dean’s belief his entire life has been planned. He says that their relationship is real. That family is what matters. Dean, who taught this to Cas a decade ago, is struggling after learning what Chuck has done.

Dean is willing to fall into a structured, no choice plan that hurts his family because he thinks it’s the only way to have his free will back. And now Cas is here to return the favor and show him that there’s always a choice, and one where they can win.

Cas’ story closes not only at him recognizing his place and importance in the Winchester family, in Chuck overlooking it, but also in him convincing Dean that there is a choice, and that the choice is born out of love for the family you create.