mostly brief mentions and it happened in the past and off screen
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Summary
Mary still dies and John still loses his mind. Dean takes the brunt of John's issues and protects Sam in any way he can. Dean will always do whatever is in his power to keep them surviving even at the cost of himself until he no longer can. When he finally falls under the weight of pressure, he finds the people around him will always be rooting for him.
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For all that Dean's street smarts have done for him he can't think of a better option to get money quick. Pickpocketing is good short term and so is hustling but that's not going to get them the money they need before people start catching onto him. Not to mention anyone that would hire a fourteen year old to work isn't the kind of person who would pay well. There's only one kind of job that would pay more for someone his age.