After landing in Chicago Dean was told to have his crew begin taking over the city, Dean was grateful he didn't have to do this alone as mobsters from all over the country came to assist The Red Right Hand in clearing out the local "Mob Boss" some asshole who wouldn't play ball with the rest of the country and wouldn't even let them safely travel among his city. Someone like this couldn't be allowed to keep control of a city. The man was Nick "The Dick" Thompson, he was moving in swiftly many though he was from Cleveland, Ohio and moved his crew out there because there was much more money to be made nevertheless this man had to go! Though with the help of the nation they were quickly killed or forced to relocate outside of the city.

With this move Dean started looking toward the future, he knew he would run The Loop it's where the city leaders always lived and operated from but he had a whole other half of the city to think about before now he never had to think on such a large scale Godfather Patangeli did all that for him, he was just told who to grab and when to do it. Who would run South Side he though, well my father could do it.. well no he's too old at this point. I'd rather give it to a young guy like myself working hard for the family and making a name for themselves. Meek! Why hadn't he though about that sooner his Left Hand had always been there working hard to help run the family back in Philly he should be the one to go to South Side and make it his own! So Dean sent Meek Mill out to establish his record label, this city needed some music and he would be the one to give it to them! This was going to be a happy thriving city yet.

Next Dean looked around his headquarters which was no long in the back of a butcher shop, well now this place is still very full. He looked to his new Left Hand who was still getting used to the job Frankie Vizzini, when he knew it was time to send out yet another good friend to expand within the Loop. Dean had him go and start a family based on the same principle that his own family was started on, a Waste Removal service. The trash trucks would run through the city and would collect of anything the families needed collected and either dropped off or disposed of in the proper manner.

Chicago was really coming together under Dean Winchester watchful eye, he had now sent his people out with enough funds to fully protect themselves with trusted and knowledgeable people to help them along the way all there was to do now was to sit back and watch as they continued to build this once great city back to what it was.