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→14.20 Moriah
As a distressed Castiel waits in a cemetery, Jack teleports in and the two hug. They walk through the cemetery and Jack explains to Castiel that he thought he could make the world a better place if no one could lie, but he recognizes that it really didn't work. He also details his visit with his grandmother. Jack admits after accidentally killing Mary, he was manipulated by [[Dumah]] and then tried to do the right thing on his own, but none of it went right. Jack is disturbed by the fact that his every attempt to be good has failed and says he no longer feels anything no matter how much he wants to.
When Dean arrives with [[the Equalizer]] to kill Jack, Jack refuses to run and flings Castiel aside so that he won't get hurt. Jack kneels on the ground before Dean and expresses understanding for what Dean is about to do, stating that he knows what he has done and that Dean has been right all along and Jack is a monster. However, Dean can't bring himself to kill Jack and instead throws away the gun. [[Chuck]] demands that Dean kill Jack and Sam realizes that Chuck has been playing them all along. Even though Chuck offers to bring back Mary if Dean kills Jack, Dean refuses, knowing that Mary would never want that. With the Winchesters continuing to refuse to cooperate, Chuck snaps his fingers and [[smiting|smites]] Jack, leaving Jack with his eyes burned out and surrounded by the imprint of his wings. Sam shoots Chuck with [[the Equalizer]]. Devastated, Sam, Dean, and Castiel stand over Jack's body before Chuck raises the [[soul]]s of [[Hell]], along with [[zombie]]s, to attack them.
After being killed, Jack awakens in [[the Empty]]. He is greeted there by the [[Cosmic Entity]], who appears to Jack in the form of a black, viscous humanoid. The entity forms a smile on its face at the sight of Jack, who asks what had happened. [[Billie]] appears behind Jack and tells him that they should talk about that.
