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Summary
"You ran away on my watch. I looked everywhere for you. I thought you were dead. And when Dad came home…"
Flagstaff, Arizona, 1998: Fifteen-year-old Sam has taken off, and John blames Dean, banishing him until John can find Sam.
So Dean does what he does best: Uses his brain and body to survive on the street. At just nineteen, though, he ends up meeting with people smarter and stronger than him, and if not for some divine intervention from a time-traveling angel, he might be in some deep trouble.
In this story, Castiel travels back in time to one of Dean's darkest memories and tries to make things right for his friend. Along the way, he discovers that their relationship transcends time.
Because we have so little information on what actually happened in Flagstaff (or even when it happened), I've taken a lot of liberties with this story canon-wise.