Dean had one year to live before he was dragged off to Hell. Of course, Castiel knew about Lillith, with how the angels talked. He figured Dean was a part of it somehow.
Then Ruby came into the picture. She seemed to want to help the two, but Castiel knew better. He WAS an angel, after all.
Castiel looked away as Dean was ripped to shreds by the Hellhounds. He remembered, with pain, how he'd seen his brothers and sisters, the other angels, howl in pain from their injuries until someone, usually another angel, put them out of their misery.
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Sastiel Through the Seasons
FanfictionCastiel had been observing Sam for years, even before the angels came to Earth. Seeing the boy was one thing, meeting him was another.
