This Actually Makes A Ton More Sense That The Original Explanation - Tumblr Posts

I know in canon (in 'Bad Boys' 9x07) it says that Dean gambled away the money that John gave them and not that John didn't give them enough but I was wondering how plausible you think it is that this the whole truth? I know Dean was a kid and kids do a lot of reckless things but gambling away food and rent money seems reckless even for a teenager, it would be more plausible to me that there were limited resources and the gambling was an attempt to increase those resources. Though obviously that's all speculation on my part, not to mention I'm not much of a fan of any of the flashback episodes tbh.

I agree. We know Dean had his “rebellious” moments growing up (10.09, 14.12) and that those moments were harshly punished (14.12) but the Dean we meet in “Bad Boys” doesn’t seem to be in that stage of life. He certainly indicates that he resents the burdens placed on him and wants to escape, but his dialogue highlights weariness more than rebellious energy, and the episode over all highlights the importance Dean placed on sheltering Sam above everything, so the idea of him putting their funds at risk needlessly just doesn’t seem to fit imo. It seems much more reasonable to me to conclude that because John was often gone longer than anticipated (1.01, 3.08, 5.13), Dean looked for a way to increase their funds. Poker was an obvious and familiar choice. What my mind always comes back to is the bruises on his wrists. Sonny asks if John was responsible and Dean says it happened on a hunt, but those bruises looked fresh, and Dean had been on babysitting duty and John was away. Meaning they didn’t come from a hunt and they didn’t come from John.