Dean Winchester had always been close to his father even when he was a boy Dean and his brother Sam were always very close to his dad who taught the boys everything he knew about this world. So when Dean got involved in the life of crime, Dean was the one who drug his father and brother Sam into this thing of ours. Dean was the one who got his own crew under Godfather Chairman Luis Patangeli, after that Deans Right Hand Mr. Kuyza was killed in a war and Dean knew no one he could trust other than his father John. So his father stepped up and filled the role of Right Hand helping Dean Winchester run his operation The Red Right Hand at the time.

After Dean and his father were well established his brother then got involved in the family, Sam he was always the odd one out but he was still family. The boys and their old man finally got sent out to Chicago. Dean was given the nod to go run the city himself, once he got out there things went smoothly. But after a while Sam got an inkling that he wanted to run off again, maybe go back out west where he went to college. So when it was announced Los Angeles was open to business to anyone with the stones to go out there his brother left the family in the windy city to go out and run his own operation.

After the family was split, John went into a depression and was seen around the family less and less. Dean though had a responsibility to the city and knew he needed to replace his father with someone who would be around more and help the family. He called on an old friend Addie Moretti, once the old man was replaced he started going down a bad road. He frequented the strip club more and was always seen doing a line and drinking. After a week or so of this behavior the old man disappeared. 

It was later found out that the old man killed himself, a single bullet to the head. The reason was never learned but after this it changed Dean. He was less caring and didn't feel the need to make nice with people any longer. People could tell this was a real turning point for the young man. Would this make him go ruthless or would it make him care more about life... well time would only tell.