In Elizabethtown, Ohio, a nun walks into a nearly empty church. The head priest, Father Gil, walks her out to the car but a man, Andy, steps out onto the balcony above them. He tells them that God has abandoned them and then shoots himself.
Dean and Bobby are working on the damaged Colt while Sam finds the story on the suicide of Andy and another man in Elizabethtown. Bobby keeps working on the gun while Dean and Sam drive to the town and talk to Father Gil. Father Gil notes that Andy was a fine upstanding churchgoer until two months ago, and then he and the other suicide started acting as if they were possessed. Also, a lot of other people in town have turned to vice and sin. The brothers note that the Devil’s Gate opened two months ago and figure the situation is connected to it.
At the hotel, Dean runs into an old friend, Richie, who is meeting with a prostitute, Cheryl. After Cheryl leaves, Richie plays up how he and Dean have worked together in the past. Richie notes that Trotter seems to be the man making the most money from the recent wave of drinking, gambling, and prostitution. Dean and Sam go there and find a big crowd. Father Gil is also there, drinking, and admits he goes where his flock is. As he leaves, another man, Reggie, comes in. Reggie complains that he isn’t feeling well, and then takes out a gun and shoots down his friend. Dean tackles Reggie and Sam tests him with holy water, but there’s no indication of demonic possession. Reggie tells them that the murdered man slept with his wife.
As the police take Reggie away, the sheriff asks the brothers to stick around for a photo opportunity because of their heroic actions. The brothers quickly leave but notice that Richie has disappeared. Richie has left with the attractive bartender, Casey. She takes him to the basement of the old house where she lives. As they go downstairs, Casey casually says that he’s a hunter. Richie tries to kill her but Casey reveals she’s a demon and quickly disposes of him.
Bobby finishes assembling the Colt. As he test fires it, Ruby shows up. He shoots it at her but it has no effect. Ruby offers to help him fix the Colt so it works.
Sam is trailing Trotter at the bar and calls Dean. Dean arrives at the bar and flirts with Casey, who is back behind the counter. She says she doesn’t know Casey but invites him to come back to place. Dean accepts and leaves with her. Meanwhile, Sam breaks into Trotter’s office but Trotter and his man arrive. They threaten to call the police but Sam struggles with them, gets their guns, and sprays holy water on Trotter. Nothing happens and Sam apologetically takes the bullets, gives them back their guns, and exits.
At Casey’s home, Dean reveals that Richie was his friend, and he tracked his GPS signal. He’s already been in the basement and found Richie’s buried corpse. Casey tries to attack him but discovers that Dean also inscribed a devil’s trap beneath the rug. Dean pulls out a book to perform an exorcism, but Casey summons a gust of wind to scatter the pages. She then brings the ceiling down, sealing Dean in with her. Dean tries to perform the exorcism ritual by memory but he isn’t very good at it. Dean figures Sam will come investigating, but Casey admits she has a partner as well, and they settle down to see which partner will arrive first.
Sam goes back to the bar and discovers that Dean has gone missing. He bribes the bartender to find out that he left with Casey, and what address Casey lives at. He goes there and finds traces of sulfur, but it’s not the house Casey uses for her victims. He calls Bobby and then goes to Father Gil for help. He convinces the priest to help him find Casey and Dean… unaware that Father Gil is possessed by a demon.
As they wait, Casey and Dean argue about God vs. Lucifer. Casey warns that the demons are preparing a warm welcome for him in Hell when his year is up. She admits that she admits him for sacrificing himself to save Dean. When Dean wonders what the big plan was, she explains that the Yellow-Eyed Demon, Azazel, was the one with a plan: Sam was supposed to lead the demon armies.
Sam and Father Gil find the address and enter. Dean tries to warn Sam by cell phone, but Father Gil gets the drop on them. However, Bobby arrives due to Sam’s call. He tries to shoot the demon-possessed priest with the Colt but misses. Father Gil knocks them both down and goes inside to free Casey. Ruby arrives and tells Sam to go help his brother.
Father Gil clears the wreckage and smashes aside Dean. He breaks the devil’s trap from the outside and then kisses Casey. She tells him to leave Dean alone but he insists on killing the Winchester. He starts to choke Dean but Sam arrives and shoots Father Gil with the Colt. Dean tries to honor his deal with Casey but Sam brutally shoots her as well before Dean can stop him.
As Dean and Bobby prepare to leave town, Dean wonders if they’ve done any good: Elizabethtown is just as corrupt as ever. He also notes that Sam gunned down Casey without a second’s hesitation. He wonders if Sam might have been changed when he came back, but Bobby thinks he’s okay.
At the hotel, Ruby visits Sam. She insists they can save Dean but refuses to explain why. Sam threatens her with the Colt but Ruby isn’t concerned. With no other choice, Sam accepts her offer but Ruby warns it won’t be easy for him.
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