We all want Charlie as our best friend
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John is a bounty hunter and has dragged the boys around behind him. Omega Dean has pretty much raised Alpha Sam. John isn't abusive per se, but rather traditional (omegas are the homemakers, caregivers, weak). Sam and John have always butted heads, so Sam happily runs away to college, not really thinking about Dean. Now that his alpha son is raised John thinks it's too dangerous and too much worry to have Dean around, and thinks the best thing he can do is mate off Dean to one of his work pals. He doesn't intend to give Dean a choice, and Dean rather objects to this. He steals the Impala, some cash and hits the road.
He travels so many roads and they all lead straight to Benny.
- Part 1 of 20,000 Roads