He was not like all the rest of them, with their stiff, business like appearances. They chose their vessels poorly, picking Wall Street refugees and tight-assed lawyers instead of real holy men and women. They stood uncomfortably in their borrowed skin, being human for those few moments on the earthly plane nothing more than an insurmountable chore. Castiel was also uncomfortable in his own skin, but it was not for a lack of having the right vessel. Jimmy Novak had done all that he asked even when he knew his family would become nothing more than an intangible memory. No, it was more of programmed character flaw. Angels had been coming down to earth for ages but their people skills hadn't got any better. Hell, look at Jacob. He had to get into fisticuffs with one, and his reward was a limp and a new name.
What a failure.
Castiel sat with his dark hair bowed, a mixture of shame and confusion in the motion. His eyes, usually so piercing, hidden behind drooping lids. Keeping up with the Winchesters and their band of merry men was so tiring. Yet, he couldn't stop. Clearly, this was another character flaw. He was so dedicated to the brothers he felt like their very DNA was intertwined with his. Heavenly orders were easy to ignore if he mentally detached himself from them. He bet, no, he knew, that Jimmy hadn't signed up to take in this disaster. He had signed up to do God's work, to be part of missions that were greater than himself. And now, here he was with an angel that was straddling the line between good and...something.
It was easy to stand up and proclaim your freedom, but it was a whole different thing to allow yourself to be splattered through the atmosphere with just the simple snap of borrowed fingers. That showed some real dedication.
Then why did he feel (God was he feeling?) like helping stop Heaven and Hell's greatest battle, the war to end all wars, was wrong?
Questioning your judgment was a very human exercise. And this time, he didn't think Jimmy was to blame.