On the Head of a Pin
Production information
Season : 4
Episode : 16
Original airdate : 19 March, 2009
Directed by : Mike Rohl
Written by : Ben Edlund
Preceded by : Death Takes a Holiday
Followed by : It's a Terrible Life

On the Head of a Pin is the sixteenth episode of Season 4 of Supernatural.


"Can torture be God's work? After seven angels are mysteriously murdered, Castiel and Uriel demand that Dean use the agony-inducing skills he learned in Hell to extract information from Alastair."[1]

Full synopsisEdit

Castiel is investigating a mysterious phenomenon occurring on Earth: angels are being killed by a mysterious method which leaves their vessels dead, surrounded by mild destruction, with angel wings burned into the ground where they fell. Castiel and Uriel go to Sam and Dean, who are just recovering from Pamela's death, for help. Castiel says that they want Dean to torture Alastair, who has proven impervious to all their tortue methods, to learn from him how the demons are killing angels, based on the torturing skills Dean learned under Alastair in Hell. When Dean intends to refuse, they take him away anyway and leave Sam behind.

Castiel and Uriel take Dean to an abandoned warehouse where Alastair is being held by iron chains and a powerful old-Enochian devil's trap. Dean wants to speak to Castiel alone, and Uriel leaves. Castiel tells Dean that his superiors are beginning to doubt him because of his emotional attachment to Dean and sympathies towards humans, and have even demoted him to rank underneath Uriel because of it. Dean warns Castiel one last time that if he goes in there he won't like what'll come back out, and Castiel can only say that he'd give anything not to see Dean have to do this.

Dean goes into the chamber alone. As he prepares a collection of torture instruments, Alastair taunts Dean, not taking him to be a threat that'll break him. Alastair also suggests that if Dean doesn't want revenge on him for all the things he did to him in Hell, then perhaps he'll want revenge for what Alastair did to John Winchester when he was in Hell. Alastair boasts, but admits that John never did break, even after a century in Hell-time, like Dean did after 30 years. Dean declares to Alastair that even in Hell he could still dream, of torturing Alastair in so many ways, then begins the torture with a syringe filled with holy water.

Meanwhile, Ruby arrives at the motel where Sam and Dean were staying, and she and Sam concoct a locating spell to find where the angels have Dean. After they successfully get the location, Sam insists that they go in to deal with Alastair, saying that Dean isn't strong enough but he can be now. Sam also says that he "needs it" and it's been weeks. Ruby tells him it'll be okay, then cuts herself on the arm... an lets Sam suck her blood.

Back at the warehouse, Dean continues torturing Alastair with brutal creative methods. But unbeknownst to Dean, a water valve is being telekinetically moved as Alastair focuses on it, to cause water to slowly drip onto the chalk-drawn devil's trap. Outside, as Castiel listens to Alastair's agonised screams, Anna arrives; having called in a favour to get her original human bdy rebuilt after it was destroyed when she regained her grace. Anna is confident that Castiel won't kill her here and now, and she's come to talk to him about what Dean is doing right now: she insists that torture can't be God's work, and suggests that whoever their orders are coming from, it's not him; and probably hasn't been for a long time. Castiel refuses to question what he believes to be God's will, but Anna notes that he's conflicted and feeling doubts before she leaves.

As Dean continues torturing Alastair, he refuses to say who's killing the angels, but he does taunt Dean over the reason why Lilith was so fixed on going after him and sending him to Hell: Alastair reveals, to Dean's shock, that when Dean broke and took up torturing in Hell, he broke the first seal (a righteous man breaking in Hell) and set all this off. The demons had originally intended to break John to break the first seal, but when that failed, it instead fell to Dean. Dean figures that Alastair is telling the truth, and doesn't deny his taunts that it'll be all his fault when Lucifer and the demons bring the Apocalypse, but Dean does say that Alastair won't live to see it. However, before Dean can finish Alastair, the latter breaks free as the water finally breaks the devil's trap, and attacks. Alastair beats Dean unconscious before Castiel comes in and fights him; however, Alastair manages to overpower Castiel and tries to use an angel-exorcising chant to send him back to Heaven. Before Alastair can complete the chant, Sam comes in and pins Alastair with his powers. Alastair finally breaks under the immensity of Sam's demon-torturing abilities; he reveals that the demons don't know how to kill angels and aren't behind the killings. Sam then focuses his powers, which have gotten a lot stronger than just exorcising demons now, and successfully destroys Alastair as a shocked Castiel watches.

After Sam gets Dean to hospital, he talks with Castiel; insisting that Alastair definitely wasn't lying before he killed him, and that they need to find whomever is behind the angel-killings. Castiel's doubts in Heaven are only further increased when he goes to talk to Uriel, and is told that the hunt for the angel-killer has been called off. Thinking on Anna's words about the angels' orders not being coming from God, Castiel goes to see her, and admits that he's now considering rebelling. Anna comforts Cass, telling him that his independence doesn't get easier, but she refuses to tell him what to do and encourages him to think for himself, then leaves.

Upon working out how Alastair escaped from the devil's trap with the water valve, Castiel returns to the scene at the warehouse, and calls Uriel over. Castiel points out that Alastair's powers couldn't have broken while the trap was intact even in the least, so it wasn't him who was turning the water valve that broke the trap. He then turns to Uriel and demands the truth. Uriel unsheathes a silvery blade from his sleeve, and admits that he is indeed the one who has been killing the angels, and that he freed Alastair so that he could kill Dean, escape, and still be chased as the prime suspect. Uriel explains that he has been converting other angels to his secret cause and beliefs, and killing the ones who said no: he thinks that God betrayed angelkind when he created humanity, and he supports Lucifer's original ideals that angels shouldn't bow to humans and intends to see Lucifer freed to purge the Earth of humans. Uriel softly asks Castiel to join him. Castiel considers, decides, then fights Uriel. Uriel quickly gets the upper-hand in the fight, and declares that there is no God and prepares to land the killing blow with his blade... when Anna suddenly catches him from behind and stabs the blade through his throat, killing him.

When Dean wakes up in recovery in hospital, Castiel is there by his bedside, and informs him of Uriel's treachery. Dean asks if Alastair was telling the truth when he said that Dean broke the first seal, and Cass confirms that he did; he also reveals that the one who started this also will yet end it, and neither of them understand exactly what that means. However, Dean tells Castiel to find someone else, saying he's not strong enough to do this.








  • Castiel was originally slated to be killed off in this episode and his role over the rest of the season filled by Anna, but he was kept alive due to his immense popularity with fans.


  1. Supernatural: The Complete Fourth Season DVD episode guide
Supernatural Season 4
Lazarus RisingAre You There, God? It's Me, Dean WinchesterIn the BeginningMetamorphosisMonster MovieYellow FeverIt's the Great Pumpkin, Sam WinchesterWishful ThinkingI Know What You Did Last SummerHeaven and HellFamily RemainsCriss Angel Is a DouchebagAfter School SpecialSex and ViolenceDeath Takes a HolidayOn the Head of a PinIt's a Terrible LifeThe Monster at the End of This BookJump the SharkThe RaptureWhen the Levee BreaksLucifer Rising

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