The thing is I believe that the worst deaths for Dean are John [as a bastard as he was, he was still his father and he wouldn't be working with JDM for a while], Bobby big time because that man was his dad and Charlie because that girl was his sister that he never asked for
I believe Jensens words were Deans biggest REGRET was not saving Cas.
As much as Widower Arc Dean kills me every time I watch, Charlie's death and revenge is the worst for me. That's when he really let go with the mark
Not everything that affects Dean emotional wise is linked to Castiel even though we did watch the show
Why are people so fixated on Jensen answering questions that are destiel coded??? When they actually aren't???
Id be asking him who would he have liked to come back instead of Mary or something like that then asking Misha would he like to have aeen Castiel be treated like the cute little brother he is and have more time with his big bad archangel trickster brother