(1) So I had an idea for a mob!boss au a while back. Winchester and Novak are rival families. John Winchester has decided that uniting the two gangs will be beneficial to the family business. The best way to bring the rivals together is a marriage. He's mostly gotten Naomi Novak to agree. The numbers add up and profits will sky rocket and she can't say no to that. But the problem is Sam is too young to marry and Dean has already declared he wants nothing to do with this life.
(2) so john stages a "hit" thats supposed to look like the novaks targeting Dean. The plan is to take out Deans driver and then convince Dean that marrying the Novak son is the only way to bring peace and save lives. The problem is no one realized Dean has Sammy with him. Sam gets badly hurt which definitely wasn't Johns plan, but Sammy lives and it ends up being plenty of incentive to get Dean to agree to the marriage if only to protect Sammy. (3) Cas has been amicable to the marriage proposal from the beginning. He hears about the shooting of course but assumes it's lower level criminals trying to get in good with someone. Dean and Cas get married. Cas views it as a business transaction of course. Completely professional even if Dean is particularly attractive he's determined to view the situation unemotionally. Dean of course while going along with things could never forgive the people who got Sammy hurt.(4) and he of course includes himself in that group of people. As the months tick by and Cas and Dean get to know each other they both find themselves begrudgingly becoming attached to their husbands. Cas knows feelings complicate things especially in his line of work but he's grown rather fond of the stubborn snarky Winchester who gives off so much warmth without even realizing it.(5) And Dean is determined to hate Cas but finds himself a little more infatuated every day with the scruffy, beheaded, slightly socially inept guy who's surprisingly dorky for a mobster. Dean is still trying to keep his nose clean and let's Cas handle all the family business. Cas comes across the shooter who injured Sammy and after some. . . Questioning finds out that it was John who hired him. Cas brings this information to Naomie, he's furious but unsure how to move forward.(6) Naomi already knows of course and tells Cas it's of little importance. They've already put plans into place to remove john and Sammy anyway. Then they'll have complete control of the looked assets from the merge. "And don't worry we've already set up to remove you're problem as well." She tells Cas. They're planning on using Dean as bait to get John Winchester out in the open. John's no fool. They may have merged families but he's still been keeping himself safe. So Dean will lure him out.(I think I'm on 6?) "And once those two are out of the picture all that's left is the one who already as a bullet hole in him." And after that here comes Cas in a flying rage first rescuing Dean and then bringing his own mother down from the top of her regime. He tells Dean everything, which allows Dean to finally admit his feelings for Cas without any guilt. They show John his new place at the bottom of the ladder as well.(7) And together as the hottest power couple in existence they lead the most powerful crime family in the US. Sidenotes: this ended up being way longer than I meant it to be? Also I tried for a bit to see if I could avoid asshole John cause that always breaks my heart for Sam and Dean but I just could not avoid it here.
AAHHH
