I think one of John’s greatest regrets is how he raised Dean and you can see that in Sam and Adam. Like Dean never had a chance. From the moment Mary died, Dean was in it just as much as John. Dean even mentioned he was six when John started teaching him how to use weapons, Sam says Dean was younger than nine when he started hunting. Dean was learning about all of it along with John because Dean had to be Sam’s protector when John couldn’t. Dean had to be adult, despite being a small child. And I don’t remember who it was on this site that said that when John started looking at Dean different after the shtriga attack it was because he realized Dean wasn’t an adult warrior but a ten year old kid, but I find myself agreeing with that. John didn’t look at Dean the same because up to that point he was viewing Dean more and more like his soldier and not the small ten year old child that he was. After that it was kind of a reminder that while Dean was forced to mature far too quickly and grow far too fast, he was still a child.
And for that reason of how much he regretted pushing Dean that far, he didn’t want Sam to know. Dean had said John would kick their asses if he found out that Sam had his journal as well as telling Sam he can’t tell John that Dean told him a thing. That shows that John was very insistent with Dean many times (not that he had to be because I’m sure Dean was just as insistent) that Sam CANNOT know about any of it. He wanted at least one child to have peace of mind, to not know what was really out in the world. And had Sam not gotten frustrated at being left out, at never being given a truthful answer, who knows when or if they would have ever told him. I’m leading more towards they weren’t going to tell him. And after Sam did find out, Sam had actually wanted to get involved. As we see in the episode with Sully, Sam had begged to be included, to be allowed to join in on the hunts and it was John who way saying no. Dean was asking for Sam, but his heart wasn’t in it because Dean didn’t want Sam involved either. However John changed his mind, and Sam very quickly changed his mind too. Sam hated hunting almost from the minute he got involved. Part of that is because he wasn’t raised up doing it like Dean.
But John had never wanted this for his sons. He had tried to keep Sam out of it, but Sam ended up in the middle of it anyway. And John, bless that man, had no idea how to be both a Soldier and a father, so he took over as a commander, and left the balancing act to Dean. Dean had to be the care taker and the soldier an John saw how much it hurt Dean, how much hunting hurt Sam. And then Sam went off alone, and all the other two see is the that, that he’s alone.
Then Adam comes along and John decides that he’s going to do this one right. He keeps anything related to hunting, including Dean, as far away from Adam as possible. He doens’t want anything related to hunting anywhere near Adam because he’ll be damned if he screwed up all three kids lives. Dean never had a chance, and he tried with Sam but Sam was far too close to hunting. So he wanted to keep Adam isolated so that nothing could ever approach him….and sadly that is the kid who died without a chance.
People can say what they want about how John raised his sons, but at the end of the day, Sam and Dean are still alive (albit they’ve been brought back many times) and I guarantee that if they had never been involved in hunting John would have been the type of father that told his kids that he doesn’t give a shit what they want, they are going to go to college and get an education. Then again, I don’t think Dean would have ever gone to college. I see him more interested in going to a trade school.
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