Dean goes to a Chinese grocery and identifies himself to the man at the counter. The man sends him upstairs and buzzes ahead. Dean finds an old friend of the family waiting for him: Dr. Robert, who used to treat John when he was injured. Dr. Robert introduces his assistant, Eva, and tells Dean to get up on the bed. Dean pays up and asks Dr. Robert to mail an envelope to Ben Braden if he dies. When Dr. Robert asks why he isn't leaving anything for Sam, Dean says it won't make a difference if he doesn't come back. Dr. Robert gives an injection and Dean dies.
Dean's spirit leaves his body and walks downstairs. He uses an invocation to summon the Reaper, Tessa, and says that he needs a favor. Dean asks her to summon Death, but she warns that she can't bring him. However, Death appears and tells Dean to talk fast. When Dean tries to bargain using Death's ring, Death informs him that he already knows where it's hidden. Dean asks Death to break Sam's soul out of Lucifer's cage, along with Adam's. Death tells him to pick one, Sam's or Adam's, and Dean immediately picks Sam's. Next, Dean brings up the damage done to Sam's soul, and asks if Death can heal it. Death says that he can't remove the damaged part, but he can wall the memories away. Tessa warns that it isn't permanent, but Dean agrees. Death notes that he hasn't agreed, and offers him a wager. Dean will don Death's ring and be him for one day. If Dean removes the ring, he loses. Dean asks why, and Death starts to explain... and Dr. Robert revives him after Dean has been dead for seven minutes.
Dean tells Sam and Bobby about the bet, but Sam doesn't want to take the risk of being mentally destroyed by the memories of his torture in Hell. Bobby wants to know what Dean has to do, and Dean admits he has no idea what Death wants. Sam steps aside, saying he needs a minute to take in the new information. He walks around the junkyard and finds the hole where Dean buried the ring. It's empty, and Dean and Bobby arrive with the ring. Dean insists that he's not going to let it go wrong, and Sam gives in. As Dean goes, he tells Bobby to watch Sam. As they go inside, Sam asks if Bobby is going to lock him up, and Bobby wonders if he'll have to do so.
Dean puts on the ring and finds himself on a city street. Tessa shows and tells Dean she doesn't like it, and warns that Dean has a habit of messing things up. She tells him that he's to follow the rules and kill everyone on her list, and then she'll reap them.
Sam casts a spell and summons the angel Balthazar. Balthazar wonders why he shouldn't kill him given what happened the last time they met, Sam says that he's desperate and asks if there's something that can keep a soul out. The angel realizes that Sam's soul is still in Hell, Balthazar says he can help, and will do it for free so Balthazar will have him in his debt, and screw over Dean in the process. However, he warns that Sam needs to scar his vessel with the blood of his dead father. Balthazar assures Sam that it doesn't need to be the blood of his father, just someone like a father to him.
As they walk, Tessa warns that people have questions when they die, but she can't help Dean figure out the answers. They go to a grocery store where a robber is holding up the owner and his son. The owner draws a gun and shoots the robber. As the man lies dying, Dean lets him wait in agonizing pain for a minute, and then finally touches him. The robber asks why, and Dean tells him that it's because he's a dick, and wishes him well in Hell. Tessa takes the robber away.
As they walk down the street, Dean notes an overeater and figures he's ready for a heart attack. The man has a heart attack and Dean claims him, and the man asks why. The best Dean can do is lyrics from a Kansas song.
Sam returns to Bobby's place and Bobby offers him a drink.
Tessa takes Dean to a hospital where a 12-year-old girl, Hilary, is scheduled to die. Her father is there with her, while Nurse Jolene tends to the girl. Tessa informs Dean that the father doesn't have any other family. Dean refuses to take her, even though Tessa insists that it's her destiny. Tessa says that he's been okay messing with life and death before, no matter what the results. Undeterred, Dean lets Hilary go.
Sam and Bobby play poker.
Dr. Owens informs Hilary's father that her heart has miraculously healed and he won't have to operate. As Hilary and her father leave, Jolene gets a call from her husband and tells him that her surgery was cancelled and she'll see him soon.
When Bobby goes to get some more beers, Sam tries to attack him but Bobby is ready and knocks him out. However, when Bobby turns his back for a moment, Sam slips away. Bobby hears Sam coming and ducks into a closet, and Sam starts hacking the door down with an axe. When Sam says that Bobby shouldn't have cornered himself, Bobby pulls a lever and dumps Sam into the cellar, and then locks the steel reinforced door. Sam says that he has to do it to keep his damaged soul out, and he has to kill Bobby to keep himself safe. He figures that Dean cares more about his brother than the soulless Sam. Bobby talks through the door and tries to reassure him, but doesn't get an answer. He carefully goes down and discovers that Sam has climbed out through the ventilator shaft in the safe room... and he's injured.
EMTs arrive at the hospital with Jolene, who was caught in a car accident and needs heart surgery. Tessa explains that since Dean spared Hilary, Jolene went home early and was in an accident, and Dr. Owens left early so he can't help her. Tessa tells him to take Jolene or he'll set off further consequences. He reluctantly does so, and Tessa tells Jolene's spirit that she was supposed to live for decades, until Dean screwed up. As Tessa takes her away, Dean tries to apologize. Jolene's husband Scott arrives and cries over his wife's body.
Tessa and Dean go back to Hilary's room, and Tessa says that he has to kill Hilary. She's disrupting the natural order by living, and chaos will follow her for the rest of her life. Dean looks out the window and sees Scott living, and tells Tessa that he needs a minute.
Bobby follows Sam's blood trail to the shed and goes inside, and Sam ambushes him.
Scott is drinking and driving, and Dean appears in the car beside him. He tries to get Scott to stop, but is still a spirit. Scott speeds up and Dean takes off the ring. Once he materializes, he grabs the wheel and drives the car off the curb into a wreck. They both survive, but Dean realizes that he's lost the bet. He gets out and calls for Tessa, and realizes that she can't hear him until he puts the ring back on. Tessa says that they're done, but Dean goes back to the hospital. When Tessa points out that Hilary skated by, Dean figures that no one skates by. He whispers to Hilary's father to say goodbye and then takes Hilary. She asks Dean why, and all he can say that there's a natural order to thing. They both agree that the natural order is stupid. Tessa takes Hilary away
Bobby tries to get through to Sam, but Sam prepares to cut his throat inside of an enchanted circle. Dean arrives just in time and knocks him out.
Once Dean and Bobby lock Sam up in the safe room, Dean wonders what they can do with him now that they know he'll do anything to survive. Dean goes upstairs and finds Death waiting for him, eating a bacon dog from a stand in Los Angeles. He admits that the ring is a heavy burden, and that now Dean understands. Death asks if Dean would have killed Hilary initially, and Dean says he would. In response, Death says that now Dean has a better look at having to clean up when someone wrecks the natural order. He figures that Dean has tossed away his life so many times because he thinks he'll always come back. Now he's learned something about the value of the human soul. Dean accuses him of rigging the game so he'd fail, but Death claims he has no idea what he's talking about. Death then gets up and says he's going to get Sam's soul. When Dean wonders why, Death explains that the Winchesters are an affront to the universe because they keep coming back. However, they're digging at something, and he wants them to keep digging. As Death takes the ring, he says that there's about 75% chance that the soul thing with Sam will work.
Dean and Bobby run to the safe room and find Death with a bag. He opens it, takes out Sam's soul, and tells him not to scratch at the barrier in his mind. Sam begs him to stop, but can only scream in agony as Death puts his soul back in his body.
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