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1995 was an interesting year in Supernatural
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.
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Part of me thinks that John must have known that everything hinged on Sam from fairly early on - because he did isolate them from the hunting community. Most likely, because he knew that there were hunters like Gordon out there, who would hunt Sam just for being connected to evil, even if Sam had never done anything wrong.
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I agree with you about John finding out about Sam's connection to evil early on. I mean, Mary died in Sam's nursery, with the demon there, so John, being John, and human, once the curtain was pulled back for him from Missouri, he had to have questioned why was Mary killed in Sam's nursery. So, that alone, makes me think that John started putting two and two together early on. Plus, like you said, the fact that John isolated the boys from the hunting community, he had to have feared that other hunters would put the pieces together as well and didn't want his boys become targets, which is why I think he also moved them around so much. He didn't want to stay in one place too long for that exact fear of rogue hunters, like Gordon, finding his boys. Plus, he didn't even bring them around to Bill and Ellen, so even though he probably trusted those two, he didn't trust anyone else that Bill and Ellen were surrounded by.
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The other thing that's interesting to remember about John is that he never saw the demon in Sam's room - he saw his son, and he saw his wife on the ceiling above his son... but, for all he knew, they were the only two things in the room that night. We know from Missouri that John had her over to the house and she told him that a great evil had been there - and that she also met Dean and Sam, so would have told John that Sam was innocent, but she also may have sensed the "power" in Sam that she references again in 1x09. So, yeah, John probably knew from the jump that there was SOMETHING going on with Sam, something different about him, something that John had to learn about, and something that he had to hide from other people who might view any human with "power", even latent, as something they needed to kill.
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I hadn't thought of that, but so true that if Missouri could sense Sam's powers in 1x09, could she also have sensed something in baby Sammy as well? Very interesting. That just solidifies in my mind more that John knew something was going on with Sam from the beginning. I can see why John would keep that a secret from both boys. And why he was so strict with Dean to keep a close eye on Sam at all times, and why they moved around so much.