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I've been playing catch-up with my timeline of S9 (which only lives on my harddrive until the end of the season, because it has a tendency to fluctuate while episodes are still airing).
Anyway, I just got around to timelining 9x07 Bad Boys.
Sidenote: I know there are some fans who prefer the original concept of Dean being 14 in this episode, but I'm going to stick with what the writers decided was better and keep Dean 16 for the purposes of the timeline, because that's now the official canon.
So, I was updating the pre-series part of my Timeline and was pretty intrigued with what it looked like after I was done:
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1995 - Sam wins a division championship soccer trophy (Bad Day at Black Rock)
- While Sam waits in the car, Dean kills something (most likely a werewolf) with a silver-arrow to the heart while on a hunt with his father and "embraces the life" of a hunter.(Bloodlust) (Note: Although Dean shows up at Sonny’s in the spring of 1995 with bruises left by a werewolf, I think character-wise, this hunt most likely happened in the summer of 1995. Sam also references a werewolf hunt “last summer” in After School Special, which takes place in Nov. 1997. So it might be safe to assume that as kids, Sam and Dean went on a disproportionately high number of werewolf hunts.)
~March-May, 1995 – While John is on a hunt (Rugaru), Dean loses his and Sam’s food money in a card game. He is subsequently caught stealing bread and peanut butter from a store. He is sent to a boy’s home in Hurleyville, NY, for two months by the local authorities, when John decides not to bail him out as punishment. Sam is told that Dean got “lost on a hunt” and spent the months at Bobby’s until John collected him and then went and picked up Dean. (Bad Boys)
- April 20th, 1995 - Dean is Champion in an “All States Sports Meet” in Wrestling-135lbs weight class.
- I thought early-March to early-May made the most sense for Dean to be at Sonny’s, based on the fact that we know that after one month he had joined the wrestling team, but Sonny made no mention at their celebratory “one month” dinner that Dean had already won the championship.
-May 16th, 1995 - William (Bill) Anthony Harvelle is killed while on a hunt with John. (Hunters Log - S2 DVD special features)
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So, to me, it looks likely that the "job" that John was heading to when he picked Dean up from Sonny's was the same job that got Bill Harvelle killed.
Anyway, I thought it was interesting... also, I momentarily wondered why there weren't more Teen Wolf crossovers set when Sam and Dean were kids (ie: their werewolf hunting days) and then it occurred to me that all the characters in Teen Wolf would be 2 years old. :P ....though I'm sure kid werewolf Derek Hale would be super adorable.