Everyone thinks Cas only one who had free will because chuck wasn't controlling him but it was basically just Cas transferring his loyalty and devotation to Dean instead of God and heaven. Like he went from I serve my father and heaven, I will die for my father and heaven to I serve Dean and I will die for Dean.
And Dean just like God and heaven expected him to be a tool, to give him one hundred percent loyalty and follow orders without question.
And just like with heaven if he questioned orders or done anything for himself he was punished. Except with Dean the punishment wasn't quite as harsh as heaven. Dean's punishments were hurtful words like no one cares your broken or your dead to me and the silent treatment and orders to go to hell and abandonment once in hell which wasn't quite as harsh as literal torture or mind programming.
So because Dean was slightly less harsh on him Cas thought his new God was the most selfless loving caring person he ever knew. Once upon a time he had the same complete awe and faith in Chuck.
Like even his "we are real" scene. Cas desperately needed something to be real. For there to be some divine righteous being for him to serve because as much as free will was talked about Cas never had it.
He never got out of the mindset he had to serve someone, he had to be useful to have a meaning, his whole perceived purpose of himself was to be a sacrifice when the right time came.
He never learnt he mattered or he could be his own person. We came close in s15 ep03 he stood up for himself he left but then he came back because he had to serve had to be useful in the fight.
And his death scene wasn't really free will it was him giving up his life for this new God that Dean had become in his mind. Like that speech made Dean into some kind of God no one on this earth is the most selfless the most caring the most loving person that has never done anything wrong and has no faults unless you view them in some unrealistic Godlike pedestal. He paid his undying love and worship to his new God before laying down his life.
And I think Chuck knew this and was mocking it. He watched Dean and Cas and he pulled Cas on his self loathing and how he never done what he told because he knew Cas would hang himself on the metaphoric rope. The rope being Dean.
It wasn't that Chuck by blindsided or didn't notice Cas. Why bother with someone you know is going to do your own dirty work for you. Cas was going to doom himself completely on his own.
Chuck likely helped it along by nudging events to happen like Dean's prayer. The prayer was very likely Chuck's doing because at the time Chuck was trying to break Sam by telling him that him and Dean needed others that Dean would give up without others and him and Sam alone wasn't enough for Dean.
Chuck showed Sam a future where Dean gives up because Cas is in box and their other friends die whilst Chuck is forcing a situation where Dean is crying over Cas and not by Sam's side.
Two birds with one stone, try to weaken one target (Sam's) faith while strengthening the other targets faith (Cas) in the rope (Dean) that Cas is going to hang himself on.
If anything Cas was the one who Chuck got most satisfaction with. He let the story write itself apart from directing a few scenes with Dean and he got his tragic twisted story. The self loathing angel who longed to serve to be useful sacrificed himself for the man he had transferred all his loyalty to.
It was his happiness moment just saying he loved him and dooming himself into the empty a place worse than hell while the object of his affection had no reaction, didn't care and instantly forgot he had ever existed.
Chuck would of seen it as some type of mix between tragic storytelling of unrequited love and revenge on Cas for worshipping a fake God.
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