In Greenwood Mississippi in August, 1938, bluesman Robert Johnson is playing at a roadhouse. In the middle of his song, he hears a dog growling in the distance. The audience members also notice, and Robert tries to go on, but the shadow of a dog passes by the windows. The barking grows louder and Johnson runs outside and into the woods. The growling sounds follow him, and something moves in the brushes. Johnson drops his guitar and runs into a cabin, barring the door behind him. Something slams into it and he bars the door, and then collapses to his knees. Seconds later, Johnson’s lady and two of the audience members who have followed Johnson break down the door, and find the bluesman having convulsions. As they go to get the doctor, the woman asks Johnson what happened. He mutters, "dogs" and then dies.
In the present day, Sam and Dean stop at a diner and Sam confirms that Dean is now in the Federal database. Dean is more amused by the fact that the authorities haven't bothered to list Sam. They discuss their case about Shawn Boyden, an architect who leaped to his death from his own condominium after claiming he was pursued by what he claimed was wild black dogs. No one else saw the dogs, and two days after calling Animal Control, Boyden killed himself. There's plenty of lore on black dogs but nothing specific.
The brothers pose as reporters and interview Boyden's business partner. He's amused at their claim that they want to do a tribute, given that Boyden left his family and partner behind. The partner says that Boyden had a charmed life and had no reason to kill himself, but ten years ago he was lousy at his job. Boyden was working as a bartender at a bar called Lloyd's, and then overnight he got a huge commission designing genius-level buildings. Later, Dean talks to the woman at Animal Control, Carly, and gets a list of all the complaints called in. The brothers end up at the home of a Dr. Sylvia Pearlman, but her maid informs them that her employer has disappeared. She never saw or heard the dog. Dean confirms that Sylvia is the youngest chief of surgeon in medical history, and got the job ten years ago. He finds a photo of Sylvia at a bar and discovers that she was at Lloyd's Bar 10 years ago.
A panicked Sylvia is holed up at a hotel. There's a pounding on the door, but it's only the manager, who wants her to pay. Sylvia opens the door and goes to get her money, but when she turns, the hotel manager's face transforms into a hideous visage. She throws the money at him and locks the door, while the manager smiles in satisfaction.
Dean and Sam drive to Lloyd's Bar, which is in the middle of the countryside at a crossroad. They notice yarrow flowers planted, a type of flower used for summoning rituals. The Winchesters dig at the center of the crossroad and find an old metal box containing a bottle of graveyard dirt and other hoodoo spell components for summoning a demon and making a pact. The "dogs" are hellhounds, sent by the demon to collect. Dean figures that Sylvia is trying to run.
At the hotel, the hounds pound on the door as Sylvia cowers in the corner. The creatures stop and Sylvia eyes the door, and then approaches it. However, a large invisible creature smashes through the window. shreds her leg, and pulls her away.
In Rosedale, Mississippi in 1930, Robert Johnson buries a box at the crossroad. A red-eyed demon in a female host bodies appears and Robert asks her to make him the best bluesman that ever lived. The demon agrees and kisses him to seal the deal, and then disappears.
In the present, the brothers figure that Robert Johnson made a deal and Dean explains that many of his songs contain occult references. He isn't thrilled that they have to save the people who willingly made the deals, but Sam insists and his brother agrees. There's a photo of the summoner inside the hoodoo box, and they go into the bar to see if anyone recognizes it. The brothers identify the man as George Darrow and go to his address. There's nothing fancy about where Darrow lives, and they wonder what kind of a deal he made. They get to his door and discover a barrier of something pepper-like. When Darrow answers the door, Dean asks if he's seen the hellhound yet, and Sam asks for five minutes so they can help. Inside, Darrow identifies the powder as hoodoo goofer dust, used to keep out demons. He gives them a bag of the dust and then says that he's resigned to his fate. Darrow asked for talent as a painter, but he's broke and lonely. Worse of all, the demon didn't leave. It stayed at Lloyd's for a week, making more deals. No one paid attention to his warnings, and Boyden and Pearlman made their deals. There was one more, Evan Hudson. Darrow figures he's going to Hell no matter what, and all he wants is a day or two to finish his last painting. He tells them to get out and help someone who wants help.
Evan Hudson is working at his office when he hears a dog barking outside. His wife Julie comes in and says that she's leaving to see her sister, and Evan says that he'll see her when she gets back. He kisses her and says he has some bills to pay, and she should enjoy herself. Evan tells her that he'll love her forever, surprising her, and then tells her to go. As she goes, Evan sees her face turn into a demonic visage, and then revert to normal as Julie says that she loves him.
Dean and Sam arrive at the house and Evan answers the door. When they ask him about Lloyd's, he slams the door in the face, figuring that they're demons. They break in and follow Evan to his study, and he begs them not to hurt him. Once they explain why they are there, Evan says that he doesn't want to die, and Dean asks what he made his deal for. Evan explains that he made a deal to save his wife from cancer, and he'd do it again. Dean asks if he did it for Julia, or if he did it for himself so he wouldn't have to live without her. He asks how Julia would feel if she knew, but Sam tells him to back off. Outside in the hallway, Sam asks if Dean is all right. Dean insists that he's fine and tells Sam to use the goofer dust to hold the hellhounds off while he goes to the crossroad, summons the demon, and binds it. Sam figures that Dean is on edge because he's realized that John made a deal to save him. Dean admits that he figures John traded his life for his son's. Evan hears the hellhounds outside, and Dean tells Sam to keep him alive as he leaves, ignoring Sam's objections.
At the crossroad, Dean performs the ritual and buries the hoodoo box. The demon appears in a female host body and says it knows all about him. It asks what it can do for him, and he invites her to negotiate in his car.
Sam seals the study with goofer dust and then draws a circle of it around Evan and tells him to stay within it.
Dean asks to release Evan from his contract, but the demon says that it's not negotiable. He offers himself for Evan, and the demon notes that he's just like his father. It admits she didn't negotiate John's deal, but wishes that it had. It starts to get into the Impala, but notices a devil's trap drawn in the dirt below.
Evan hears the hellhounds growling outside. The doors start to shake and Sam steps into the circle with him.
The demon threatens to rip Dean limb from limb, but then says that it's better to watch his misery now that he knows how John sold his soul to save him. As Dean backs away toward a nearby water tower, it says that it could have brought John back, but now it just wishes Dean a long life. As it starts to leave, Dean tells it to wait.
The hellhounds grow quiet and stop trying to break in through the door, but then smash through the vent.
The demon turns back and says that it will negotiate. Dean asks her to bring John back, and the demon says that John will live a long natural life, and Dean will have ten years before she calls his debt due. It steps beneath the water tower with him and ask if it's a deal, and he steps away. The demon looks up and realizes that he drew a devil's trap on the underside of the tower. He tells it to let Evan go in return for its freedom, but it refuses and Dean begins an exorcism.
The invisible hellhounds close in on the circle and pace around the perimeter.
The demon tells Dean to think of John, but he begins the exorcism.
In the study, a wind blows up out of nowhere and the dust forming the circle starts to blow away. Sam grabs Evan and they run out into the hallway. The hellhounds chase them as they barricade themselves in the laundry room.
The demon tells Dean to wait.
The hellhounds stop their assault on the laundry room door.
The demon seals the new deal with a kiss. Evan is free of his deal and he and his wife will live a long life.. When Dean considers sending it back anyway, the demon says that it will escape eventually and skin Evan before coming after Dean. After a moment more, Dean breaks the trap. As the demon leaves, it says that Dean would have negotiated for John's release if he knew his father was, and says John is being tortured in Hell. When Dean threatens to send it back to Hell, it evacuates its host body, leaving a confused woman behind.
Later, Sam and Dean are driving away and Sam suggests that the demon was lying. Dean doesn't believe it, and wonders how John could have done it, His legacy is making a deal with a demon, not going out fighting. Sam insists that John saved plenty of lives, and that his legacy is that they can continue the fight. Dean seems to accept that. Sam asks him if he ever considered making the deal with the demon, but Dean doesn't answer.
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