|“||I'm killing everyone you've ever saved. The damsels in distress, the innocent whippersnappers, the would-be vampire chow -- all of them... I'm going to gut one person every 12 hours until you bring me the demon tablet and stop this whole... Trials nonsense... About now you'll be thinking of ways to stop me -- you won't be able to. But you'll try, because that's what you do, you... you try... What's the line? "Saving people, hunting things – the family business." Well, I think the people you save, they're how you justify your pathetic little lives. The alcoholism, the collateral damage, the pain you've caused – the one thing that allows you to sleep at night, the one thing is knowing that these folks are out there, still out there happy and healthy because of you, you great, big, bloody heroes! They're your life's work, and I'm going to rip it apart piece by piece because I can, because you can't stop me, and because when they're all gone, what will you have left? You want to keep those people alive. I want complete and utter surrender. The tablet, the Trials – you'll give them up, or we'll keep doing this dance. Your choice, my darlings.||”|
After escaping from Crowley, Prophet Kevin Tran learns from the demon tablet that there is a way to seal the Gates of Hell forever. He passes this knowledge onto the Winchesters after they find him. However, shortly thereafter, Crowley manages to steal the demon tablet back and learns of the demon tablet containing the information on how to seal the Gates of Hell as well.
After the Winchesters and the Seraphim Castiel retrieve half of the demon tablet from Crowley, Kevin sets to work on translating the tablet and eventually locates three Trials that once completed will seal the Gates of Hell forever. Sam Winchester is able to complete the first two Trials to seal the Gates of Hell, but not before Crowley puts together what he is up to and recaptures Kevin.
Using Winchester imposters, Crowley is able to trick Kevin into giving up the fact that there are three Trials to close the Gates of Hell and that the Winchesters are up to the Third Trial. Kevin eventually sees through the trick and is rescued by the Scribe of God, Metatron. When Kevin leaves, he steals Crowley's half of the demon tablet which has the third and final Trial upon it.
As a tactic to get the Winchesters to stop the Trials, Crowley decides to begin targeting the people they've saved over the years. Correctly deducing that the Third Trial likely needs a demon to work, Crowley decides to keep his demons away from the Winchesters and instead use spells to kill his targets. In order to best choose his targets, Crowley reads the Supernatural books which depict the Winchesters adventures in novel form.
In Lost Creek, Colorado, Tommy Collins, the young man the Winchesters saved from a wendigo visits a cabin with his girlfriend Shelly. Tommy is nervous about being back in the area due to the trauma from the wendigo attack he suffered. Suddenly, Tommy hears a growl that Shelly can't and becomes convinced that its a wendigo, not a bear. As Tommy grabs a torch to kill the wendigo he believes he hears, he suddenly experiences extreme pain and starts bleeding from the ears. Tommy begins bleeding from his eyes as well before his head violently explodes, killing Tommy and splattering Shelly with his blood.
As the Winchesters prepare to perform the Third Trial on a captive Abaddon, they receive a call from Crowley. After the Winchesters step away from Abaddon and put Crowley on the phone, he tells them that they should read the Denver Times from the day before, calling it "side-splitting." Crowley also texts the Winchesters an address that he states they should check out.
Looking at the Denver Times online, Dean finds an article on Tommy Collins' death. Sam recognizes Tommy as a young man they'd saved from a wendigo "forever ago." Dean realizes that Crowley likely blew Tommy's head off and is confused if they are dealing with "some kind of demon-wendigo team-up." While Dean decides to "pour one out for Tommy later" and ignore Crowley as they have everything they need to lock down Hell, the Winchesters discover that Abaddon has escaped.
After finding the devil's trap bullet used to bind Abaddon on the floor, Sam gets a text from Crowley with an address in Prosperity, Indiana. Dean remembers that they once worked a case there involving witches and baked goods. The Winchesters realize that Crowley must be going after someone in Prosperity now, though Dean points out that it has to be a trap. Sam acknowledges this, but reminds that a trap means demons and they need to capture another one for the Third Trial since Abaddon is gone.
Arriving at the address, the Winchesters find the power out and a bunch of cupcakes sitting on the counter. Searching further, Dean finds the burned body of Jenny Klein, a young woman they had saved from a witch's hex, facedown in her oven. The Winchesters recognize Jenny and Dean solemnly tells her "you were a great gal, Jenny Klein."
Sam receives a call from Crowley who explains that "I'm killing everyone you've ever saved. The damsels in distress, the innocent whippersnappers, the would-be vampire chow -- all of them." While looking at the Supernatural books, Crowley explains he knows who they've saved because of his "sources" and "a cracking research team." Crowley threatens to kill someone they've saved every 12 hours until the Winchesters give him the demon tablet and stop the Trials. While Sam attempts to claim that Kevin Tran took the demon tablet, Crowley tells them that he took Kevin but someone took him back. Since he knows it wasn't the angels, Crowley knows it had to have been the Winchesters.
Crowley warns that if Kevin isn't with them, they'd better find him "because time, she is a wasting. About now you're thinking of ways to stop me. You won't be able to. But you'll try, because that's what you do, you... you try. So, time for an object lesson: Indianapolis, the Ivy Motel, Room 116. You have 57 minutes." Crowley then hangs up on the Winchesters who rush off.
Arriving at the Ivy Motel, Sam is shocked to find Sarah Blake, the young woman he had saved years earlier from a ghost and was romantically interested in. While happy to see Sam, Sarah quickly realizes that something is terribly wrong from the look on his face. Sam informs Sarah of the fact that Crowley is coming to kill her at midnight which is sixteen minutes away after Sam finishes explaining.
Dean enters with a bag full of weapons and Sam reassures Sarah that they are going to protect her. The Winchesters have holy water, an exorcism on Sam's phone ready to play on a loop and they intend to put up warding around the room and devil's traps. As the Winchesters load their shotguns with rock salt shells, the promise to keep Sarah safe and she takes them at their word as they have succeeded in doing so in the past. As the Winchesters protect the room, Sarah and Sam catch up briefly and joke about their past together and how Sam has grown up since then.
With five seconds left until midnight, Crowley calls the room phone and counts down the seconds as the Winchesters and Sarah arm themselves for the expected demon attack. Instead, when it hits midnight, Sarah collapses to the ground, struggling to breathe. Crowley explains that he is the "son of a witch" and that "my mommy taught me a few tricks." Sam realizes that they are dealing with a spell and the Winchesters frantically begin searching for the hex bag. As the Winchesters desperately search for the hex bag, Crowley explains that while he had thought about sending his demons in to kill Sarah, he realized that the first two Trials were both Hell-related so he has decided to keep everything Hell-related away from the Winchesters, including demons. "Plus I just thought it seemed fitting: from what I understand, Sammy took that bird's breath away."
As Sarah struggles to breathe and the Winchesters struggle to find the hex bag, Crowley gives a speech about how he believes that the people the Winchesters have saved are their life's work and what allows them to live with themselves and what they have done. Crowley threatens that he now intends to destroy their life's work by killing everyone the Winchesters have ever saved and they won't be able to stop him. Crowley gives the Winchesters an ultimatum: their complete and utter surrender as well as turning over the demon tablet and stopping the Trials in exchange for his stopping his attack on all of the people they've saved. If they refuse, Crowley will continue killing everyone the Winchesters have ever saved. As Sarah dies, Crowley tells them that its their choice and hangs up.
The Winchesters are left devastated by their inability to save Sarah's life. In a fit of rage, Dean flings the handset to the phone across the room, smashing it. The Winchesters see too late that the hex bag they had been looking for was in the phone the whole time.
Crowley eventually targets Sheriff Jody Mills through the guise of a blind date, but the Winchesters pretend to acquiesce to Crowley's demands in exchange for Jody's life. Crowley stops his attempt to kill Jody after the Winchesters surrender and negotiate a deal where they stop the Trials of God and exchange the demon tablet for the angel tablet that is in Crowley's possession. However, this proves to be a trap and the Winchesters use the opportunity to capture Crowley himself for the Third Trial.
- While going after Sarah Blake, Crowley comments that he learned the magic he was using from his mother and that he's the son of a witch. This is the first reference to Rowena MacLeod who goes on to appear in seasons 10, 11, 12 and 13.
- Crowley is revealed to be using the Supernatural books to choose his victims. However, Jenny Klein was saved in season 7's Shut Up, Dr. Phil which is after the books were finished being written. Fan Fiction later confirms that the books ended with season 5's Swan Song.
- The people Crowley targets are Tommy Collins from Wendigo, Jenny Klein from Shut Up, Dr. Phil and Sarah Blake from Provenance. He also targets Jody Mills but stops before killing her as the Winchesters make a deal to trick him.
- Crowley's distraction of the Winchesters by calling them about Jenny Klein distracts them from where they are holding the reconstituted Knight of Hell Abaddon prisoner. As a result, she is able to escape. His phone call also interrupts them as they are about to perform the Third Trial upon Abaddon.
- Crowley quotes the line "saving people, hunting things, the family business" while taunting the Winchesters. Ironically this line first appeared in Wendigo while the Winchesters were rescuing Tommy Collins, the first person Crowley targeted.
- While Tommy and Sarah are clearly killed by spells, it is unclear how Jenny was ultimately killed. As the Winchesters only found that she was cooked in her own oven, she may have been compelled to do so by a spell cast by Crowley or he may have sent his demons to do it as he knew the Winchesters weren't anywhere nearby.