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Crowley

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Evil Doer

Crowley (Supernatural)

Real Name:
Fergus MacLeod
Aliases:
Crowley, King of the Crossroads, Lucky the Leprechaun
Origin:
Supernatural
Occupation:
King of the Crossroads (originally), The King of Hell (as of Season 6)
Skills & Abilities:
Vast demonic powers, Possession, Charismatic, High authority within Hell, High intellect (possibly genius-level)
Hobbies:
Making Faustian deals, Drinking Craig, Renovating Hell
Goals:
Get rid of Lucifer (Season 5), Break into Purgatory (Season 6), See Sam, Dean, and Dick Roman kill each other (Season 7), Make Sam and Dean suffer, stop them from closing the Gates of Hell, obtain the demon and angel tablet's power (Season 8), kill Abaddon (Season 9), deal with Demon Dean and his mother, Rowena (Season 10)
Villain Type:
Deal Maker, Damned Souls

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 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. Because when they're all gone, what will you have left?
~ Crowley threatening Sam and Dean, "Clip Show"

Crowley is an antagonist appearing on the TV series Supernatural. He is the most recurring villain of the series. He appears as an anti-hero for most of the series, but he was one of the main antagonists in Season 6 and the main antagonist in Season 8.

He is played by Mark Sheppard, who also played Jim Sterling in Leverage.

History

Season 5

Crowley is first mentioned in the Season 5 episode "The Real Ghostbusters" as being the demon to whom Lilith handed the Colt over after obtaining the weapon from Bela Talbot, in addition to possibly being Lilith's lover.

Crowley first appears in the subsequent episode "Abandon All Hope...," where Dean and Sam Winchester infiltrate his mansion on a mission to retrieve the Colt so they can kill Lucifer and stop the Apocalypse. They corner Crowley, but are captured by two of his henchmen. Crowley then draws the Colt and proceeds to shoot his henchmen dead, then leads the brothers into his office. He offers to give the Colt to the Winchesters, stating that Lucifer will eradicate all demons after he wipes out humans. Crowley then disappears to what he calls "all points nowhere," but not before insulting the brothers after Dean asks what will happen to him if he's discovered to have helped the Winchesters.

Crowley a la Mark Sheppard

Crowley always ready to make a deal.

Crowley returns in "The Devil You Know," suddenly appearing in the Impala's backseat. After avoiding being stabbed by an irate Sam (who initially believes that Crowley gave them the Colt knowing it wouldn't work on Lucifer), Crowley reveals that Lucifer knows he (Crowley) wants him dead and that he (Crowley) has been in hiding for the past few months. He then offers to help the Winchesters obtain the remaining two Horsemen rings and aids Dean in capturing Brady, Pestilence's servant. Later, when a hellhound approaches, Crowley disappears but returns shortly after with his own, larger hellhound, whom he sics on the other hellhound to allow the Winchesters to escape with Brady. At the end of the episode, Crowley approaches Bobby Singer with an offer to reveal Death's location in exchange for Bobby's soul.

In "Two Minutes to Midnight," Crowley appears just after Bobby reveals Death's location to the Winchesters and Castiel, and Bobby and Crowley's deal comes to light (along with the fact that the two men kissed to seal the deal). Crowley reveals that he bought Bobby's soul as leverage against the Winchesters, whom he believes will kill him. Later, Crowley gives Dean Death's scythe so he can use it to kill Death, and accompanies Dean to Chicago, where Death currently is. Crowley finds the Horseman in a restaurant.

Season 6

Crowley serves as one of the four main antagonists of the season (along with Raphael, Eve, and Castiel). In "Weekend at Bobby's," he refuses to return Bobby's soul as agreed, but is eventually forced to return it when Sam and Dean threaten to burn his human bones.

It is later revealed that Crowley only wanted Lucifer removed so that he could take his place as the King of Hell. After ascending to the throne of Hell, he changed Hell so that everyone there had to stand in line endlessly, going to the back of the line when they finally reached the front.

Crowley also resurrected Sam and Dean's maternal grandfather, Samuel Campbell, and got him to work for him in his quest to find Purgatory, in exchange for bringing Samuel's daughter Mary (Dean and Sam's mother) back to life. Samuel and his relatives captured monsters, which Crowley tortured to find Purgatory's location. Crowley forces Sam and Dean to work for him as well, saying that he will return Sam's soul if they do, claiming to have that kind of power as he is now King of Hell. Eventually, Sam and Dean work together with Meg to force Crowley to return Sam's soul, but Crowley admits that he can't return Sam's soul, leading Castiel to seemingly burn his bones and destroy him.

After the death of Eve, however, it is revealed that Castiel and Crowley faked the latter's death, as Crowley and Castiel are working together to find Purgatory so Castiel can win his war against Raphael in Heaven. However, in the Season 6 finale, Castiel betrays and tricks Crowley, and opens Purgatory on his own, absorbing all the souls there. Castiel kills Raphael, but allows Crowley to escape, saying that he has plans for him.

Season 7

After the events of Season 6, Crowley goes into hiding from Castiel, only to be found by the angel-turned-deity soon afterwards. Instead of killing the King of Hell, Castiel lets Crowley continue his work in Hell under his supervision, stating he still needs a place to punish his enemies; Crowley reluctantly agrees.

After Castiel is dethroned, so to speak, and the Leviathans are set free, Crowley tries to ally with their leader Dick Roman, only to be rejected and have his entire race threatened. Fearing for his life, he later makes an uneasy alliance with the Winchesters and Castiel. The season ends with Dick's death and Crowley kidnapping the newly-called prophet Kevin Tran.

Season 8

In "Clip Show," Crowley begins killing the people Sam and Dean saved from supernatural menaces over the years, using Chuck Shurley's Supernatural books to find said people.

In "Sacrifice," Crowley goes on a date with Sheriff Jody Mills, a friend of the Winchesters. When Jody begins choking on her own blood as a result of a hex bag made by Crowley, the Winchesters call Crowley and agree to stand down if he agrees to stop killing people they've saved. Later, Crowley meets with the Winchesters at Singer Scrap Yard, where Crowley displays an extremely long contract. Dean seizes the opportunity to handcuff Crowley to himself with shackles bearing a devil's trap, preventing Crowley from abandoning his human host.

Dean and Sam then take Crowley to an abandoned church, intending to use him as the third and final trial to close Hell forever (said trial calls for the one completing the trials to cure a demon). Crowley is bound to a chair, and Sam regularly injects him with his purified blood. Crowley manages to send out a message for help, and Abaddon arrives. However, rather than help, Abaddon tries to kill Crowley so she can take the throne of Hell.

Following Sam defeating Abaddon for the moment, he continues the process and it begins to work. As Crowley starts to become human, he begins expressing regret for his actions, asking Sam where does he start to confess. He also reveals he has always had a desire to be respected and loved, implying all his power-grabbing and egocentric actions are driven by this desire being twisted and perverted by his transformation into a demon.

However, Dean stops Sam before he can fully cure Crowley, as he's discovered the process will cause Sam to die.

Season 9

In the season premiere "I Think I'm Gonna Like It Here," after the angels apparently refuse to answer his prayer to save Sam, Dean decides to turn to Crowley, whom he has locked in the Impala's trunk. He asks for Crowley to knock once for "yes" and twice for "no," then asks him if he's still alive. At first Crowley does nothing, but eventually answers "yes." However, before Dean can do anymore, an angel shows up and interrupts him and as Ezekiel offers his help afterwards, he no longer needs Crowley's help.

In "Devil May Care," Dean reveals to Sam that, instead of killing Crowley, he has him trapped in the Impala's trunk under a devil's trap as he believes Crowley will be useful. The brothers take Crowley to the Bunker, where they lock him in the dungeon and question him as to the names of the demons on Earth, pointing out that he had previously been close to being human again. Crowley, however, is unimpressed with their questions and tells them that they can't torture him more than he already tortures himself all the time. Sam and Dean then lock the dungeon and shut the lights to leave Crowley to reflect, which he does, remembering how he nearly became human.

Hearing Kevin in the next room getting a file, Crowley taunts him, causing Kevin to beat him with his fists and a sledgehammer. Crowley claims to Kevin that he never killed his mother like he earlier claimed, and that he will lead Kevin to her if he releases him. Crowley also tells Kevin that the Winchesters will use him and then discard him as there will always be more prophets. While Kevin considers releasing Crowley, he decides not to and leaves him in the dungeon.

When Sam and Dean return to the Bunker, Crowley reveals the names of two demons to them that he claims they would be doing him a favor by killing. Crowley offers them a deal: he has the names they want and they have the ability to help him with the things he wants. If they help him, he'll help them. He also tells them that he told them the names because he got enjoyment out of Kevin's predicament. Dean has Sam check on the names Crowley gave them while he stops Kevin from leaving, telling him that even if Crowley was telling the truth, his mother is dead in all the ways that matters.

Sam gives Crowley a pen and paper for more demon names, but Crowley refuses unless he can stretch his legs. Sam just leaves the paper and pen with Crowley and leaves.

In "Slumber Party," when the Wicked Witch of the West escapes, she finds Crowley and he has her write what she wants on the paper. When she writes "key," Crowley tells her that the Winchesters keep the keys in the kitchen. When Sam and Dean find him, he agrees to tell them what the Witch wanted in exchange for being allowed to stretch his legs. Sam releases him from the collar keeping him in his chair, but he stalls so Dean shoots him. Crowley shows them the paper and tells them what he told the Witch. Sam and Dean then leave him alone.

After the Wicked Witch is killed, Sam secures Crowley to his chair again and puts a pen and paper in front of Crowley again. When Crowley tries to get more out of him, Sam leaves without ever saying a word, leaving the paper for Crowley. Annoyed, Crowley mutters "bollocks."

In "Heaven Can Wait," Kevin tells Sam there is some smudging on the tablet, as if the scribe didn't want anyone to read it. Neither one of them cannot translate it, so Sam suggests they get Crowley to translate the tablet, but Crowley refuses. When Sam tries to reason with him, Crowley crumples the paper up and throws it in Sam’s face. Sam then threatens to give Crowley up to Abaddon, and Crowley asks for one phone call.

Crowley proves that he can read the translation, and Sam decides to let him have one phone call. Kevin says letting the King of Hell and Abaddon communicate with each other is a terrible idea. Since the phone call involves drawing blood, Sam starts to do it but Crowley demands Kevin’s blood, saying he's had enough of Sam’s blood and wants something fresh. After some coaxing, Kevin agrees and fills a syringe with his blood. With the blood bubbling in a bowl, Crowley contacts Hell; when he says he is their King, he is put on hold.

Crowley reaches Abaddon, who gleefully tells him that she has doubled his projections by voiding his contracts and bringing more souls to Hell. She then insults Crowley and tells him she will soon replace him. Crowley yells that she can't rule Hell with chaos and she will burn, to which Abaddon snarls she can't wait. Crowley passes the bowl back to Sam and asks for the transcripts, saying that he keeps his promises. He then reads the transcripts and gives Sam and Kevin the bad news: the angel-banishing spell is irreversible.

When Sam is washing out the bowl of blood, he notices something amiss with the set of syringes. Opening it, he finds one gone and realizes that Crowley palmed one of the syringes. Heading to Crowley, Sam sees Crowley injecting himself with Kevin’s blood and leaning back, sighing with relief.

In "Road Trap," after Gadreel takes complete control of Sam, kills Kevins, and leaves with the tablets, Dean asks Castiel for help, and Castiel reminds him of how the demons were able to dig into the angel Samandriel's mind, and tells Dean they might be able to bypass Gadreel and talk directly to Sam to get him to expel the angel possessing his body.

Dean then tries to bargain for Crowley’s help and offers him a syringe of human blood, believing Crowley has a craving for it, but Crowley refuses and asks for a massage by Kevin. After Castiel informs him that Kevin is dead, Crowley then taunts Dean, saying that people who get close to him get killed. He agrees to help Dean and Castiel crack open Gadreel in exchange for allowing him a little field trip with the chains still on. Castiel and Dean get into an argument about accepting Crowley's deal, and when Crowley then suggests asking for Sam's opinion, he sees Dean's reaction to Sam's name and deduces that it's Sam who's in trouble. Dean then agrees to the deal.

Crowley, Dean, and Castiel drive to a NSA listening post where Cecily, a demon who can track anything, is employed. Cecily insists on meeting Crowley alone in a warded room, thus making Castiel unable to listen in, then updates Crowley on the high points of the months he's missed; she admits that Hell is in chaos and that Abaddon hasn't yet taken over. She also implies that she is not totally loyal to Crowley, but that she is playing both sides. She then locates the Impala for Crowley.

Once Gadreel is captured, Crowley begins to access Gadreel's "programming" and is able to make the angel reveal his identity, but Crowley is still unable to bypass the angel and talk directly to Sam. Dean then asks for Castiel to posses Sam and help him kick Gadreel out, but Castiel can't possess a vessel without permission. Crowley then offers to do it if they remove the chains and set him free. Dean agrees and releases Crowley from his bindings, allowing him to jump into Sam's body. Once in Sam's mind, Crowley convinces him that an angel is possessing his body and he is tucked away in a small, dark corner of his mind, but then Gadreel finds them and a fight ensues. Sam expels Gadreel from his body, and Crowley leaves voluntarily.

As Sam starts to wake up, Abaddon arrives, and Crowley tells the Winchesters and Castiel to leave. Dean then says that this doesn't make them square and if he sees Crowley again, he is dead, Abaddon orders her demons to kill Crowley, but they refuse and Crowley points out she does not yet rule all demons. Abaddon wants to fight, but Crowley likens their conflict more to an election; whoever wins over the demons will rule Hell.

In "First Born," Crowley, searching for the First Blade, the only weapon that can kill Abaddon, approaches Dean for help, revealing that the only demon who knew about the Blade was captured by Dean's father John Winchester before Crowley could get to him. Following a clue in John's journal, Dean and Crowley travel to John's lock-up where they find a file on an old case that John worked with a hunter named Tara where he interrogated and exorcised the demon who mentioned the Blade.

Crowley and Dean then find Tara, who recognizes Crowley as a demon and initially refuses to help until she is told about Abaddon. After Tara reveals that the last ingredient of a locator spell for the Blade is essence of kraken, Crowley takes off to get it. Using the spell, Dean and Crowley are able to track the Blade to Missouri. Upon arriving at the location the spell indicated, Crowley is terrified to find Cain, who silences him and keeps him from fleeing.

Cain reveals that he created the Knights of Hell and slaughtered them (which Crowley knew and didn't tell Dean), but refuses to give them the Blade. Four demons arrive to attack and Crowley kills one with an angel blade while Dean kills the rest. As an army of demons arrive, Cain agrees to help, gives Dean the Mark of Cain (the source of the Blade's power) and tells Dean and Crowley that the Blade itself is in the ocean. Cain then teleports the two outside as he takes on the demon army and they flee. Dean realizes that Crowley was actually using him all along, having known the truth about the Blade and Cain the whole time. Crowley confirms it, saying that while Cain wouldn't help him, he knew he'd help Dean. While Dean threatens to kill Crowley once they've dealt with Abaddon, the two are forced to work together for the time being as Crowley is the only one who can find and retrieve the Blade.

In "Blade Runners," Crowley has grown addicted to human blood and relies on a beautiful demon named Lola to get it, not knowing that she is betraying his secrets to Abaddon. After discovering Lola's betrayal and killing her, Crowley calls in Sam and Dean, who force him to detox from the blood. Crowley reveals that he tracked the Blade down from where it was retrieved from the bottom of the Marianas Trench years earlier, and helps the brother find who it was sold to by possessing the man sent to meet with them briefly. Sam and Dean learn that a man going by the alias "Magnus" got the Blade and realize he was one of the Men of Letters. Crowley reveals that "Magnus," actual name Cuthbert Sinclair, was a rogue member whom he had been trying to track down but lost track of.

Sam and Dean learn that Sinclair was once the Men of Letters' spellmaster and manage to convince him to let them into his secret lair, but Crowley is left behind. After Sam is sent back outside without Dean when Sinclair decides to add Dean to his collection of monsters and artifacts, Sam and Crowley work together to get inside Sinclair's lair. Once inside, though he is powerless, Crowley avoids capture and frees Dean, allowing him to kill Sinclair with the First Blade. However, knowing Sam and Dean will likely betray and try to kill him, Crowley steals the Blade from them until such time that they track down Abaddon and use it to kill her.

In "Mother's Little Helper," after Dean calls him and then hangs up, Crowley tracks him down at a bar and tries to convince him to embrace the Mark of Cain and the killer instinct that comes with it, but Dean refuses. While Crowley is using the bathroom, Dean stops a hunter from going after him and confronts Crowley as he believes Crowley was shooting up again with human blood. Crowley doesn't deny it, instead believing that Dean is hunting Abaddon so that he can touch the First Blade again and get the rush it gives him. Dean denies it, telling him he's focused on killing Abaddon and can't worry about the consequences of using the Blade, though Crowley is unconvinced. Crowley agrees to bring Dean the Blade when he finds Abaddon, but meets with the "hunter" Jake who was supposedly after him. It's revealed that Jake is actually a demon working for Crowley, who used him to test Dean to see if Dean would save him. Crowley is pleased, stating that he knew Dean would as they're "besties" and that Dean is "ready."

In "King of the Damned," Abaddon pulls Crowley's son Gavin MacLeod to the present to use his lingering humanity and affection for his son against him to force him to help her kill the Winchesters. After Abaddon causes Gavin great pain, Crowley agrees and informs the Winchesters of where to find the First Blade, calling off a hellhound guarding it. He then tells them where to find him and that he has found Abaddon, but tells Dean "Poughkeepsie," the code word Dean taught him that means "drop everything and run" to warn him of the trap.

To keep Crowley from interfering, Abaddon shoots him in the shoulder with a bullet engraved with a devil's trap, binding his powers and trapping him. When Dean arrives, Crowley tells him that Abaddon is close, then warns him with his eyes of an attacking demon. Dean kills the demon and faces off against Abaddon while Crowley watches, immobile. As Crowley watches, Dean displays immunity to Abaddon's powers, allowing him to gain the upper hand and kill Abaddon.

Afterwards, Crowley uses a knife to dig out the bullet, annoyed that Sam and Dean won't help him. Sam informs him that they are letting him live and he should be happy with that. Crowley is amused to find out that Dean didn't tell Sam that he'd warned them it was a trap and is upset that Sam and Dean insist on sending Gavin back to his own time as Crowley doesn't want him to die. Pretending to say goodbye to his son, Crowley teleports Gavin to a park where he tells him of his fate and that he should build a new life in the present.

In the season finale "Do You Believe in Miracles?", having regained his post as King of Hell, Crowley is summoned by Dean, who's trapped inside the Bunker's dungeon by Sam and Castiel. He then informs Dean that the Mark of Cain's side effect is that the more you kill, the better you feel; the less you kill, the worse you feel. When Dean states that Cain was not affected like this, Crowley reminds him that Cain is a demon and that a human body is not strong enough to handle the Mark's power before telling Dean that, unless he keeps killing, he will die. Crowley helps Dean escape the Bunker, retrieve the First Blade and start hunting down Metatron.

During a brief stop in a restaurant, where Crowley insists that Dean order some food so that the waitress will get a bigger tip, he asks Dean if he ever wonders if "this" is all there is, and whether or not Dean has ever just wished to abandon it all and "go howl at the moon." He also states that he's kicked his human blood addiction, and that Hell is secure but complicated, to which Dean tells him that it's him that's complicated, not Hell. Before Dean can ask what they are, two of Crowley's demons enter the restaurant and inform him of Metatron's recent actions. Both Dean and Crowley leave, though Crowley asks Dean if he plans to eat his food, to which Dean replies that he isn't hungry.

Tracking down a woman that Metatron resurrected, both Crowley and Dean find Sam outside her house. Sam implores Dean to work with him instead of Crowley, to which Dean agrees and tells Crowley to go, causing Crowley to sarcastically quip that he's been "Winchester'd" and tell the brothers he would wish them good luck if he thought it would actually do anything.

After Dean has died from a fatal knife wound, Sam attempts to summon Crowley, not knowing that Crowley is already inside the Bunker with Dean's corpse. Crowley tells Dean's corpse that he has never lied to him, but he did omit certain truths or only half-tell them. He then says there is another story about Cain, that one day he realized what the Mark was doing to him and in desperation took his own life, but the Mark would not let him die. He then tells Dean's lifeless body that he isn't really dead but is entering a new life, where he will see what Crowley sees and feel what Crowley feels. He encourages Dean to open his eyes, which Dean does, revealing that he has become a demon.

Season 10

In the season premiere "Black," Crowley is with Dean at a bar called the Black Spur. After Dean has sex with a waitress named Ann Marie, Crowley walks in on the two of them in his bed, and is upset with them for "soiling" his room. Later, Dean and Crowley play foos-ball with two people at the bar. They lose, and Dean blames Crowley for interrupting him while playing. When Dean almost kills a man who was harassing Ann Marie outside the bar, Crowley watches the whole fight silently.

When looking through the phone of an Abaddon loyalist by the name of Neely, Sam discovers a text that had alerted the demon of Dean's presence and whereabouts. When Sam calls the number, Crowley answers, revealing that he has been sending the "Abaddon loyalists" after Dean the whole time. Sam promises Crowley that he will save his brother or die trying, but Crowley tells Sam that he's jealous of the fact that Crowley and Dean are best friends now, and that his brother is not just possessed, but has been twisted into a demon by the Mark of Cain.

In "Reichenbach," Sam tracks Crowley using the phone number in the text message, which Crowley anticipates. Back at the Black Spur, Crowley tells Dean about Sam and that they have to leave immediately, but Dean doesn't agree. He then urges Dean to be his second-in-command and tells him that they could rule Hell together and be unstoppable. When Dean still refuses, Crowley admits that he sent that Abaddon loyalists, knowing Dean would make quick work of them, and that Dean needed to "feed" the Mark of Cain by fulfilling his newfound lust for killing. Crowley then tells Dean that he must decide if he really wants to rule Hell with him or not.

In "Soul Survivor," Crowley has gone back to ruling Hell, including sentencing to death demons that were loyal to Abaddon, as well as any demon that annoy him. When a demon questions Crowley's ability and competence in light of his time with Dean before immolating himself in front of Crowley and the other demons with holy oil, Crowley is shocked by the turn of events.

Crowley later learns of the angel Adina attacking Castiel (whom Crowley's been keeping tabs on) and Hannah, and he arrives at the gas station before Adina is about to kill Hannah. He slices Adina's throat and steals her grace before fatally stabbing her, then gives Castiel her grace, allowing him to power up again. Crowley tells Castiel the reason he helped him was because he wants Castiel to help fix the problem that is Dean Winchester.

In "Girls, Girls, Girls," Crowley is angered to learn that two of his demon minions, Gerald and Raul, went behind his back to create a demonic brothel to increase the number of souls in Hell by having people sell their souls for sex with hookers, as he finds it tacky rather than evil. After learning that Raul was killed, Gerald convinces Crowley to go after the witch that killed Raul. Later, Gerald reports to Crowley, saying that while their alpha team were killed by the Winchesters, the beta team caught the witch responsible. Crowley enters the dungeon to confront her and is shocked to find that the witch, Rowena, is his mother.

In "The Things We Leave Behind," Crowley is venting to Gerald about how horrible Rowena was as a mother when Gerald asks him why he just doesn't kill her, to which he answers he has his reasons. Gerald then offers to kill Rowena for Crowley, telling him he would have no problem with it as he killed his own mother over burning him with cigarettes, though Crowley doesn't give him an answer.

When Crowley finally decides to see Rowena, he berates her for being a terrible mother to him, but Rowena deflects that by saying she was motivating him for bigger things. When he brings up she abandoned him when he was eight years old, she tells it was because she ran afoul of the locals and had to flee. Rowena then tells Crowley she wishes to be a family again, and that he can trust her, unlike the demons who will turn on him at the first chance.

After their chat, Crowley and Gerald escort Rowena back to the dungeon. It's there that Rowena accuses Gerald of smuggling demons out of Hell, to which another demon, Trish, confirms. Gerald denies the accusations and begins to strangle Rowena. When he doesn't listen to Crowley's repeated orders to stop, Crowley stabs Gerald through the neck with an angel blade, killing him. As Crowley leaves the cell, he asks Rowena if she's coming, and she smiles and follows him out the door.

In "The Executioner's Song," Crowley presides over his court, extremely bored and playing games while a Crossroads Demon complains about not getting enough credit. While Crowley initially decides to give the demon the credit he wants, he instead takes Rowena's suggestion of cutting the demon in two. Afterwards, Rowena approaches him to help her eliminate one of her rivals, Olivette, which Crowley ultimately agrees to despite knowing her help before was so she could manipulate him into helping her with Olivette.

As Crowley plans an attack on Olivette with his mother, he is called by Dean, who tells that Cain is killing again and that he needs the First Blade to stop him. Crowley refuses at first until Dean tells him that Cain wants Crowley dead too. Crowley then retrieves the First Blade and goes to meet with the Winchesters and Castiel despite Rowena's objections that the Winchesters are using him and they are not his friends.

At a barn in Ohio, Crowley refuses to turn over the First Blade until they have Cain where they want him. Crowley, Sam and Castiel use Rowena's illusion spell to draw Cain into a devil's trap to weaken him for Dean to fight. Crowley then reluctantly turns over the First Blade to Dean after being promised its return if Dean returns in a sound state of mind. After Dean kills Cain, he hands the First Blade over to Castiel instead of Crowley, who is shocked that Dean lied to him. He is even more shocked when Dean reveals that he lied about Cain coming after Crowley, and Crowley disappears without a word.

Back at his palace, Crowley finds Rowena preparing to leave and she tells him he is no longer a king but the Winchesters' "lap dog" and "bitch," something that he is left considering.

In "Inside Man," after Rowena attempts to kill Dean and tries to deceive Crowley into thinking Dean beat her in hope of her son retaliating, Crowley ignores her and tells her she deserved what she got for going up against Dean.

Later, Crowley finds Dean and the two have a drink together. Dean schools Crowley about the meaning of family, saying it's not whether they're a blood relative or not, but how they treat you that matters. Crowley reveals to Dean that Rowena knows the Mark of Cain is a curse. He then returns to Hell and forces Rowena to leave, stating that the only reason she is clinging to him is because he is being useful to her. Rowena then packs and leaves her son's palace.

Quotes

I only have one rule: Make a deal, keep it. The reason we don't call our chits in early--consumer confidence. This isn't Wall Street; this is Hell! We have a little something called "integrity!"
~ Crowley, about Faustian Deals, "Season Seven, Time for a Wedding!"

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