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===[[:Category:Season 7|Season 7]]===
In [[7.01 Meet the New Boss]], [[Castiel]] spares the hunters, but refuses to heal [[Sam]]. As Castiel travels the world, wreaking havoc in his attempt to right the wrongs he sees, Dean despairs. He sees chance of stopping the [[angel]], and instead resorts to drinking, focusing on the broken [[Impala]], and worrying about Sam. As Castiel's actions become more erratic, Dean does come up with an option: binding [[Death]], as [[Lucifer]] did. Dean, Bobby and Sam succeed in putting a spell on Death, but Castiel undoes it in a moment. Death does agree to assist in reopening [[Purgatory]], but it is up to them to get Castiel to release the [[soul]]s. Dean refuses to pray for Castiel to come, thinking there is no hope. Instead Sam prays, and eventually Castiel appears. Cas tries to apologize to Dean, but Dean is not forgiving. Cas returns the souls, and survives, but is taken over by [[Leviathan]]s, which hung on inside him. In [[7.02 Hello, Cruel World]] the leviathans escape in Castiel's body to a reservoir, and let themselves loose on the world. Castiel disappears beneath the water, and Dean finds [[Castiel's
trenchcoat]] at the shore, and takes it with him.
Dean and [[Bobby]] take a disturbed Sam back to [[Bobby's place]], and confront him about the consequences of losing his wall. Sam admits that he is seeing [[Hallucifer|Lucifer]], and cannot tell if he is out of [[Hell]], or still there. Dean worries about Sam as he leaves to investigate the first of the known Leviathan killings. When he returns to Bobby's house, he finds Sam missing, and tracks him by his phone GPS. Sam's hallucinations manifested as Dean, and led him to a warehouse as part of an imaginary hunt. Tormented by his visions, Sam nearly shoots the real Dean when he arrives. Dean, with as much calm as he can manage, grabs Sam's injured hand, and uses the pain of it and his own experiences in Hell to convince his brother that this is the real world. When they return to the salvage yard, they find Bobby's house destroyed, and no sign of the hunter. Dean calls Bobby's phone, and leaves him a desperate, near suicidal, message, pleading for him to be alive.
Back in the Bunker, Dean and Jack are discussing the case. Jack asks him if since Vance is back in his grave, he can't hurt anyone, and Dean says the stake through the heart will keep him there. Jack then asks, "So that's... love?" Dean laughs and says that love can actually get crazier than that, and with Harper still out there it might get crazy yet. He then tells Jack he did good, which Jack uses as evidence that he should be able to go on hunts. Dean tells him it's not about being right, that he'll make mistakes but it's how he handles himself after making them and learning from them. Jack responds "and not beating yourself up about them." Dean smiles and agrees, and says he'll talk to Sam when he returns... but Jack starts coughing violently and collapses on the floor bleeding from his nose and mouth while Dean looks on helplessly.
[[14.07 Unhuman Nature]] picks up with Dean and [[Sam]] waiting in the hall outside [[Jack]]'s room while [[Castiel]] attempts to heal him. Cas tells them he did what he could but he doesn't know what's wrong with him. They hear Jack fall from his bed and rush in, finding him on the ground and foaming at the mouth. They rush him to the hospital where the doctors begin to treat him, as Sam, Cas, and Dean look on, worried. The doctor emerges and tells them that all of the tests they've run on Jack have come back negative but his body is in systemic failure and they don't know why; they need to run more tests. Dean, talking to Sam, wonders how many more tests they can run, and Sam believes there isn't anything else the hospital can do for him -- they've never seen anything like Jack and they obviously can't tell them what he really is. Dean suggests taking him home and finding another way to treat him, like calling [[Rowena]], and Sam says he's already called her. They put Cas'
trenchcoat on Jack and, telling the doctors they're going to get a second opinion, they take him back to the [[Bunker]].
After much convincing from Sam, Rowena attempts to cure Jack while Dean, Sam, and Cas wait in the hall. She tells them because he's a [[Nephilim]], his [[Grace]] is what holds his human and angel sides in balance and without it, his cells are destroying themselves. Cas offers his grace but because Jack is part archangel, Cas' grace isn't strong enough. While Rowena is explaining this, Dean's vision begins to blur and the voices echo, but only for a moment. He recovers in time to hear Rowena say Jack's condition will be the end of him.