Pete has taken Dean from the police station and driven out to the woods, intending to kill him. Scarlett, Sam and Diana track the car via its lo-jack and arrive just as Pete has a gun to Dean's head. He admits that he killed Claire because she was going to turn him in, and then killed Tony who had been involved in laundering the money and was getting nervous, and Karen because he suspected she knew too much.

Pete tries to convince Diana that he can pin the crimes on Dean, but as he is about to shoot Dean, Diana shoots and wounds him. Pete disarms her, but the ghost of Claire appears and distracts him long enough for Diana to draw her backup gun and kill him. Diana agrees to let the siblings go, telling them she will feel safer knowing they are out there fighting the supernatural.

Ep. 8 - In Rosedale, Mississippi, in 1930, Robert Johnson makes a deal with a demon at the crossroads, asking to be the greatest blues guitarist that ever lived. The deal is sealed with a kiss.

In Greenwood, Mississippi, in August 1938, Robert Johnson is playing blues guitar at Lloyd's Bar. There is a sound outside and he leaves, running as he hears dogs chasing him until he takes refuge in a house. Soon after he is found dying, mumbling about the black dogs that are after him.

In the present day, Scarlett, Sam and Dean are researching the case of an architect, Sean Boyden, who jumped to his death from a building he designed. He had previously reported seeing a dog in the building. Thinking this may be a supernatural black dog, the siblings decide to investigate and under the guise of writers from Architectural Digest, interview Sean's partner. They discover he had been working as a bartender at a bar called Lloyd's ten years ago, when suddenly he'd shown great talent and became an overnight success.

The Winchester siblings start tracking all the complaints about black dogs in the area recently. At the house of Dr. Silvia Pearlman, who has risen to be Chief of Surgery at a young age, her maid confirms the report, and adds that the doctor left unexpectedly a couple of days before. Dean finds a photo of the doctor at Lloyd's. In a hotel room, Dr. Pearlman screams as she is attacked by an invisible dog.

Scarlett, Sam and Dean go to Lloyd's Bar, which is situated near a crossroads. The intersection is surrounded by yarrow, a plant used in summoning rituals, and at its center they dig up a tin containing a vial of graveyard dirt, black cat bones, and the photo of George Darrow. They realize that the black dogs are actually hellhounds which are collecting souls due in payment for deals with a demon.

The Winchester siblings visit George Darrow, a painter, who admits to having summoned a demon ten years ago and made a deal for artistic talent. After the deal, however, the demon stayed at Lloyd's Bar for a week and made deals with Sean Boyden, Silvia Growman, and a man named Evan Hudson. George is resigned to dying and the siblings leave him to his fate.

At Evan Hudson's house, he admits to Scarlett, Sam and Dean that he made a deal with the demon to save his wife from dying of cancer.

Scarlett suggests she go and summon the crossroads demon and try and exorcise it, while Dean and Sam protects Evan. Dean and Sam don't like the idea but as they hear the howling of the hellhounds, they agrees to go along with the plan.

Scarlett summons the crossroads demon and tries to lure her into the Impala, which is parked over a devil's trap. When she realizes the trap she begins to taunt Scarlett about how much she has suffered since John's death. She offers to bring John back, in exchange for Scarlett's soul to be claimed in ten years' time. Just as it appears Scarlett may make the deal, the crossroads demon realizes she is under a devil's trap painted on the water tower she is standing beneath. Meanwhile Dean, Sam and Evan stand inside a protective circle as the hellhounds approach.

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