Leith, Scotland – 1723
A young man, Gavin MacLeod, is packing when a wind blows up in and a light flashes outside. Abaddon walks in and says that she's a friend of the family, and Gavin orders her out. Ignoring his protestations, Abaddon says that he's not going to the colonies after all. Gavin's friend comes in, sees Abaddon, and asks if they're having a party. She telekinetically slams him back on a coat hook and then grabs Gavin and starts chanting, and a sigil on the door glows bright red.
Several friends are chatting at a bar when one of their co-workers, Ezra, comes over and tries to make conversation with them. They ignore him until he says that Metatron handpicked him. Ezra boasts about how Metatron is relying on him to redo Heaven, starting with a chosen few. Afterward, Ezra walks out and heads down an alley, and two angels grab him and drag him off. They take him to a room in a power plant and chain him up, and another angel comes in and says that there are consequences when someone gives away Metatron's plans. A figure walks ominously down the hallway and Ezra stares in terror... as Castiel comes in.
Sam and Dean go to the power plant in response to Castiel's phone call and Benjamin takes them to his "commander." Castiel has set up a command base in the power plant complete with tracking maps and computers, all dedicated to finding Metatron. The angel hugs the Winchesters and explains that the angels insisted on following him. He brings the brothers up to speed on what has happened and how he is now forced to lead the angels, but still hopes to find a diplomatic solution to get rid of Metatron. Castiel insists that the angel-on-angel violence has to end, and he wants them there to question Ezra. Dean eagerly agrees as Sam looks at him suspiciously.
At the Humboldt Hotel in Cleveland, OH, Crowley tells his cadre of advisers to spread the word that he is the king, and the kingdom is on sound footing. None of them speak up, and Abaddon comes in in response to their summons. She knows about the First Blade and the Mark of Cain, and tells Crowley that the Winchesters will come after him once they eliminate her. Abaddon invites Crowley to ally with her to dispose of the Winchesters and then they'll deal with each other. Crowley refuses, pointing out that she has no hold over him. Abaddon brings Gavin in and tells him to say hello to his father, Crowley stares at him in surprise. He points out that he and Gavin loathe each other, but Abaddon says that she knows all about Crowley's problem and the humanity he's been infected with from the human blood he's been taking. Crowley insists that he's clean and there's no humanity in him, and Abaddon starts crushing Gavin's skull. After a few moments of silence, Crowley finally breaks and tells Abaddon to stop.
Ezra tells the Winchesters that he has nothing to say, and Dean prepares to start cutting. Sam calls him back and points out that Ezra won't say anything if he's dead. He also dismisses Ezra as a nobody, pricking the angel's pride. Dean plays along, calling Ezra a wannabe, and Ezra insists that he's been to Heaven since the Fall. He says that he has a private portal and Metatron hides it by moving it from place to place.
Once he cleans up, Gavin insists that Crowley isn't his father, and his father Fergus MacLeod was a tailor and a drunken monster. Crowley explains that he's 291 years in the future and Abaddon shows him the view of the city outside. Gavin figures that they're angels.
Sam and Dean continue mocking Ezra, saying that Metatron doesn't even know he exists. When he insists that he was appointed to a key post as a member of Metatron's ground forces, they wonder why he wasn't there and Ezra admits that he was just a finalist. Ezra starts to have second thoughts, and Sam suggests that he doesn't know what mission he was considered for. The brothers leave, wondering what Metatron has in mind.
Crowley explains how he sold his soul and eventually got a new body, and now he's the King of Hell. Gavin doesn't believe it.
One of Castiel's angels goes to check on Ezra and finds him dead. When they get word of the murder, Sam and Dean meet with Castiel and suggest that there's a mole. Dean goes to do some nosing around, but Castiel asks Sam to stay back. He asks him about the time when Gadreel possessed him and Sam explains that he was still himself. Castiel asks if Sam felt threatened, and Sam explains that Gadreel felt that he had unfinished business and was misunderstood. He admits that Gadreel didn't feel hostile, but figures that he was wrong because Gadreel killed Kevin.
Crowley defends his actions, saying he didn't have any role models. When Gavin complains that he never learned how to read, Crowley touches his forehead and gives him literacy. Gavin realizes that he would be a prince, and Crowley could keep him from burning in Hell no matter his sins. Crowley is impressed that his son is negotiating with him, and Gavin figures that it could work out... once he goes back to his own time and travels to the New World. Crowley starts to explain about the ship and then says that it isn't important, and summons Abaddon.
Castiel has one of his angels summon Gadreel and they meet in a quiet spot in the forest. Gadreel respects Castiel's reputation for honor, and insists that what happened in the Garden wasn't his doing. Castiel figures that he feels he's misunderstood, but warns that he's placed his faith in the wrong master. He tells Gadreel to re-swear his loyalty to their original mission, and Gadreel insists that he is. As they argue, two of Metatron's angels charge out and try to kill Castiel. Castiel kills the first attacker while the second one kills Castiel's lieutenant, and Castiel kills him.
Dean sits alone and remembers Magnus giving him the First Blade. He looks at the Mark of Cain on his arm as Sam comes in and points out that his cell phone is ringing. It's Crowley, who says that he's found Abaddon. He agrees to tell them where to find the First Blade, and then he'll give them Abaddon's location and they can kill her. As he talks, Crowley glances over at Abaddon.
The Winchesters drive to a graveyard and dig up a coffin. Crowley has hidden the blade in a corpse and as Dean prepares to remove it, they hear hellhounds growling nearby. The brothers run for it as the invisible hound chases them into a mausoleum. Dean calls Crowley and tells him what is going on, while Sam tries to keep the gate closed. Crowley has them put him on speaker and tells the hellhound, Juliet, to stand down.
Once it's apparently safe, Sam and Dean go back to the coffin and Dean starts to reach into the corpse. Sam suggests that he do it, and Dean says that it's safe for him to grab it. Despite that, Sam reaches in and takes it out, and they go to find Crowley.
Crowley tries to convince Gavin not to go to the New World once he goes back. His son storms off, just as Dean calls to say that they have the First Blade. Crowley tells him where he is and that he'll draw Abaddon out so they can kill her. Before he hangs up, Crowley says that they have to leave Poughkeepsie right away. As he hangs up, Dean suspects that something is wrong.
At the hotel, Abaddon points out that Crowley has been plotting with the Winchesters for some time. She wonders if he might have second thoughts, takes out a gun, and shoots Crowley in the shoulder. The bullet has a devil's trap carved on the bullet, rendering Crowley powerless.
Castiel meets with Gadreel again in a different location. Gadreel insists that he had nothing to do with it and insists that there has to be honor, even in war. Castiel points out that Metatron doesn't believe that way, and Gadreel's trust will bring him down again. However, he tells Gadreel to stay where he is and report to him about what Metatron has planned. When Gadreel objects, Castiel points out that Metatron has a spy in his camp and he's only fighting fire with fire.
The next day, the Winchesters pull up to the hotel and Dean suggests that they check out the place first. He says that Crowley told him there might be some demons in the basement, takes the First Blade, and says that he'll check out the main floor while Sam checks the basement. Once inside, Dean goes to the penthouse and finds Crowley sitting down, clutching at his shoulder wound. He moves in, First Blade drawn, and a demon charges out at him. Dean easily kills him, but Abaddon slams him against the wall.
In the basement, Sam looks around and finds nothing.
Abaddon tells Dean that she'll kill him first, then Gavin, then Crowley. Focusing on the First Blade, Dean pulls himself away from the wall and advances on Abaddon. She manages to knock him back again, breaking his grip on the Blade. As Abaddon chokes him, Dean stares at the blade and it flies up into his hand. Sam comes in just as Dean stabs Abaddon, killing her. She drops to the ground and Dean stabs her corpse over and over again. Sam tells him to stop and Dean finally gains control of himself.
Crowley borrows a knife to cut the bullet out of his shoulder while Sam wraps up the First Blade. The demon points out that they owe him because he warned them, and Sam has no idea what he's talking about. Crowley realizes that Dean lied to his brother, and Dean says that Gavin has to go back to his own time. The demon says that his son died in a storm during the crossing, and the Winchesters say that they have no choice. Before they take Gavin back to the bunker, Crowley asks for a moment with his son. However, he then teleports Gavin away.
In Scotland, Crowley tells Gavin what will happen to him in his future and suggests that he stay in the 21st century. Gavin realizes that he has no choice, but Crowley tells his son that they won't meet again. When Gavin tries to hug him, Crowley backs up and advises him not to tell anyone that he's a Prince of Hell.
As the Winchesters drive off, Dean explains that he didn't tell Sam about Crowley's warning because he knew Sam would want to go with him. Sam says that they're partners and demands an explanation, and Dean finally tells him that as soon as he touched the First Blade, he knew he would kill Abaddon alone. He insists that they couldn't afford Abaddon taking Sam hostage, and Sam warns his brother that the Blade might be doing something else to him as well. Sam suggests that they should store the Blade somewhere distant, and Dean refuses.