crazylolli on DeviantArthttps://www.deviantart.com/crazylolli/art/The-Chicago-Way-278892074crazylolli

Deviation Actions

crazylolli's avatar

The Chicago Way

By
Published:
1.6K Views

Description

In anticipation for this week’s Supernatural, I give you 1944!Cas/Dean/Sam/Jess!!

Dean and Sam Winchester are mid-level enforcers for the Campbell family, a mob syndicate that runs a hefty portion of the gambling and smuggling rings in Chicago. The patriarch of the family, Sam’s namesake, sends the two to deal with a WWII-veteran-turned-private-investigator who’s been hounding one of their gambling operations.

Castiel Novak doesn’t seem like much, unimpressive in stature and limping slightly from the wound that got him sent home early from the war. He’s still managed to almost single-handedly arrest most of the thugs running one of the Campbell’s more lucrative gambling dens, supposedly in pursuit of the one that murdered a friend of his, one Anna Milton. Sam and Dean show up at his door, more than ready to dissuade Castiel from his current activities through any means necessary, but that door happens to be guarded by Castiel’s comely secretary, Miss Jessica “Jess” Moore.

Sam falls head-over-heels for Miss Moore at first sight and he’s reluctant to break the legs of her employer, who also happens to be a distant but dear cousin of hers. Dean, who’s always wanted Sam to find the right girl to settle down with, and maybe even get out of the family business for, strikes up a truce of sorts with Castiel. Castiel agrees to stop targeting the Campbells if the one responsible for Anna’s death is delivered to him.

From then on, the uneasy truce starts getting more easy, Dean accompanying his brother on his daily trips to court Miss Moore. Dean and Cas enjoy the antagonistic friendship of sorts they’ve developed (and possibly more…?) while Sam and Jess enjoy the wonders of new love.

But there’s a new crime syndicate moving into town, brewing up a storm the likes of which hasn’t been seen in Chicago since Prohibition. The Winchesters are going to need all the help they can get, if they plan on surviving much longer…

This verse also features Gabriel Novak, intrepid and sugar-obsessed reporter for the Chicago Herald; Bobby Singer, recalcitrant and surly junkyard owner (and friend to the Winchesters); Ellen and Jo Harvelle, the lovely but hardy owners of a bar the Winchester brothers frequent, and many other familiar faces!

WHO THOUGHT ABOUT THIS A LOT?

THIS CRAZY FANGIRL.
Image size
1275x1650px 1.02 MB
© 2012 - 2024 crazylolli
Comments5
Join the community to add your comment. Already a deviant? Log In
starrsilver's avatar
HEE SAM AND JESS ARE SUCH CLEVER SCHEMERS
also your use of slashes forces me to assume this is a foursome, which in turn leads me to PICS OR IT DIDN'T HAPPEN. :D