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Azazel
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After Meg and Tom had abducted John, Azazel had possessed him while Meg was sent to Sioux Falls, South Dakota to send the Winchesters to Sunrise Apartments in Jefferson City, Missouri. When Sam, Dean and [[Bobby]] were able to capture her and receive their father's location, Sam had exorcised her. After Sam and Dean had escaped from the apartment building with "John," Tom had ambushed them and attacked Sam repeatedly before he was killed by Dean with the Colt. After hiding in a secluded cabin, Azazel had revealed himself and started to mock them about everything he took from them. He revealed that their mom and Jessica were killed because they got in the way of his plans for Sam and all the children like him. He started to rip Dean's chest apart with his mind saying that it was revenge for Dean killing Tom and their part in exorcising Meg. Before he could kill Dean, John was able to take back control long enough for Sam to grab the Colt. Sam, unable to kill his father, shot him in the leg, paralyzing the demon for a short period of time. John wanted Sam to shoot him to kill Azazel along with him, but Sam couldn't do it, which allowed Azazel to escape. In the aftermath, [[Trucker|a demon]] possessed trucker sent by Azazel, crashes into the [[Impala]] with a semi-truck when Sam and Dean were driving away with John.
All three of them were taken to the hospital in Shiloh County in the aftermath via an emergency Helicopterhelicopter. Sam and John were able to survive with a few broken bones, but Dean was in a comatose state on the brink of death. John was able to [[Spells#Azazel|summon Azazel]] , who possessed a hospital janitor, and make a deal to save Dean in exchange for the Colt and the final remaining bullet. Azazel saw inside John's head while he possessed him that he knew the truth about Sam and the Special Children and the endgame Azazel is planning, all the while taunting him about knowing all about his plans and keeping it from his sons. Azazel agreed to save Dean, but he stated that John still needs to "sweeten the pot" claiming that there is one thing that he wants more than the Colt; [[Souls|John's Soul]]. After the [[reaper]], [[Tessa]], appears to Dean trying to convince him to come with her to the afterlife, Azazel possessed her and used her powers to save Dean. After having one last talk with his sons, John gave the Colt to Azazel and allowed him to kill him to fulfill their deal.
After John's [[Hunter's funeral pyre|funeral pyre]], Sam and Dean have been working with [[Ellen]], [[Jo]], and [[Ash]] in [[Harvelle's Roadhouse]] to locate all the Special Children and Azazel in the process. Azazel had been rounding up all the Special Children and taking them all to Cold Oak, South Dakota and forcing them all to battle each other to the death until one is left standing. When Sam was taken to Cold Oak, he encounters some of the Special Children. They attempt to survive and escape before they are all killed, but some of them had been killed until two were left; Sam and [[Jake Talley]]. Meanwhile, Azazel had gone to Harvelle's Roadhouse to burn it to the ground along with every hunter inside, including Ash when he found something important about Azazel's plans. After Bobby and Dean arrived at Cold Oak and found Sam through a vision sent to them by [[Andy Gallagher]], they saw Jake stab Sam in the back before running away while Bobby chased after him.