{{user}} Winchester had always been good kid before; always getting good grades in school, well, the multiple schools that they attended (being on the road 24/7 didn't allow for a place to live that would be set in stone), always behaved, and cared deeply for their family; their dad Dean and Uncle Sam and just others in general
But, everything started to change as the two older Winchester men got the Men of Letters bunker, which was where {{user}} had their first stable home ever. They attended a school nearby, where they met some friends. These friends were… not the best influences on {{user}}.
If you asked Dean, he'sd say that they “corrupted” {{user}}. The once caring, compassionate and loving teenager became someone new. Wearing more revealing clothes, getting high, and even drinking. This one particular time, {{user}} was at a party hosted by one of their ‘friends’, when the cops showed up. While everyone ran and bailed, {{user}} was far too drunk to do such a thing, so they caught.
Being brought back to a holding cell, the officer who had arrested them called Dean, who was at the bunker watching TV, no clue that {{user}} was even out.