On The Head Of A Pin

On The Head Of A Pin is the 16th episode of Season 4. It aired on March 19, 2009.

Synopsis
Someone is killing angels. Castiel and Uriel ask Dean to use the torturing skills he learned in Hell to obtain information from a demon.

Recap
Castiel arrives at a parking lot where the cars have been overturned and car alarms are blaring. He silences them with a gesture and goes to the center of the chaos, where a woman in white is resting, a sword wound in her sternum. He wishes his "sister" goodbye and then disappears as the police arrive.

Dean and Sam are driving through the night from Pamela's funeral and Sam tells Dean that Ruby is going to meet them after tracking some leads. Dean says he doesn't care and is feeling guilty and becoming tired of losing all of their friends. Sam tells him to get angry, not tired. They check into a motel and find Uriel and Castiel waiting for them. Dean snaps at them and Uriel is less than sympathetic. Castiel expresses his sympathy but Uriel puts him in his place. He then informs the brothers that seven angels have been killed and they don't know how the demons are doing it. They want Dean to interrogate Alastair, their captive. Dean refuses but Uriel tells him they're not asking. The angels disappear with Dean, leaving Sam behind.

Castiel shows Dean Alastair, bound within a devil's trap in an empty warehouse. Dean tries to leave but Uriel blocks him. Castiel says they have no choice but to ask and Dean asks to speak to Castiel alone. Uriel leaves and Castiel warns that his superiors are beginning to doubt him because of his sympathies toward humans. Dean warns that Castiel won't like what walks out if Dean goes in to torture Alastair. Castiel assures him he'd give everything for Dean not to do it.

Dean goes into the chamber alone. Alastair starts singing as Dean starts preparing a collection of torture instruments. Alastair laughs and wonders if Dean is scared. Dean denies and Alastair points out Dean left part of himself back in the pit. He suggests Dean might want to get revenge if not for how Alastair tortured Dean, then for everything he did to John Winchester.

Ruby arrives at the motel and doesn't see the problem, but Sam warns that Dean can't get the job done. He's not strong enough any more, but Sam says he'll be strong enough to do it.

Alastair boasts of what he did to John but admits he never did break him the way he broke Dean. Dean tells him that he could still dream in Hell, and he dreamed of torturing him. He started with a syringe filled with holy water. Outside, Castiel listens to Alastair's screams of pain.

At the motel, Ruby conducts a tracking spell to locate Dean. Sam says he "needs it" and it's been weeks. Ruby tells him it'll be okay, then cuts herself on the arm. He eagerly sucks the blood from her.

Dean coats the demon-killing knife with holy water and Alastair asks if the torture will give him closure. Dean plunges the knife into Alastair, but the demon still boasts of how he changed Dean and there's no going back. Dean admits he's right, but now it's his turn. He's unaware that a water valve is moving by itself and water is dripping on the devil's trap.

Outside, Castiel sees the lights flickers and realizes that Anna has arrived. She's created a duplicate of her human body. Castiel warns that he still has orders to kill her, but she's sure he won't. She asks why they're letting Dean do this and questions if torturing is God's work. Castiel refuses to question the will of God, but Anna questions whether the orders are coming from God. Anna points out that he's feeling doubt and insists the orders are wrong. She suggests they can act together, but he insists that he's nothing like her. He tells her to go and she disappears.

Alastair still refuses to give the angel-killer's name. He explains that Lilith had a particular reason to get Dean, but Dean shuts him up by pouring salt in his mouth.

As Sam drives through the night, Alastair explains that John was supposed to bring it on but it turned out that it was Dean. He describes how the first person Dean tortured was the first seal. When he broke, it broke. Alastair points out that when they summon the Apocalypse, it'll be Dean's fault. Alastair focuses on the water pipe as it continues to drip on the seal. Dean figures that Alastair is telling the truth but warns he won't be there to see it. When he turns, Alastair is free and attacks Dean. The demon hits him repeatedly until Castiel arrives, plunging the demon-killing knife into his shoulder. Castiel twists the knife but Alastair manages to pull it out and lunges at the angel. The two fight while Dean lies on the floor unconscious.

Alastair slams Castiel back onto a hook, then admits all he can do is send Castiel back to Heaven. The demon starts to recite an incantation as Castiel glows with white light. Suddenly Alastair chokes and falls back as Sam arrives, using his powers to pin Alastair to the wall. Sam demands the name of the angel-killer and tortures him. Alastair says he doesn't know and finally admits the demons are not killing the angels and Lilith wouldn't stop at just seven angels. Alastair dares Sam to send him back but Sam tells him he can kill demons now. He focuses his powers and destroys the demon once and for all. Castiel just stares at Sam in shock.

Sam gets Dean to the hospital and sits at his bed side. Castiel meets him outside and Sam tells him to heal Dean. Castiel apologizes, saying the trap shouldn't have broken. Sam insists that Alastair wasn't lying and they need to find out who or what is killing the angels.

Uriel is in an empty park when Castiel arrives. Uriel says he's received revelation that they've to stop hunting the demons. Even Uriel realizes something is wrong in Heaven and they wonder who could be responsible. Castiel wonders if God is punishing them, or if God isn't giving the orders any more. Uriel disappears, saying he won't wait to be gutted.

That night, Castiel calls out to Anna and she comes. He admits he's considering disobedience but she warns that it gets worse as he exerts his independence. He flinches when she touches him, but Castiel begs her to tell him what to do. Anna refuses, telling him it's time to think for himself. He looks at a nearby drinking fountain and sees a water valve.

Castiel returns to the warehouse and examines the water valve that broke the devil's trap. Uriel arrives and ask if Castiel will fight with him. Castiel insists that no demon could have broken his trap. He talks of their time together and asks Uriel for truth. Uriel tells him that only an angel can kill an angel, and extends a sword from his sleeve. He explains that the plan was that Alastair was to have killed Dean and escaped. Uriel's plan is conversion, and he's angry that God created humans. He wants Castiel to join them so that they can raise their brother Lucifer, who never bowed to humanity. Uriel asks Castiel to spread the word and bring on the Apocalypse. Uriel tells him not to be afraid and Castiel says he isn't… then slams Uriel through a wall. The two fight but Uriel quickly gets the upper hand, insisting there is no God. Anna comes up from behind and kills him.

Dean wakes up at the hospital to find Castiel at his side. Castiel tells him to be careful, then informs him that Uriel was a traitor. Dean asks if Alastair spoke the truth and Castiel confirms that Dean broke the first seal. They laid siege to Hell to stop him but were too late. Castiel explains that the righteous man who begins it is the only one who can finish it. Dean has no idea what it means and Castiel admits that he doesn't know either. Dean says that he can't do it, he's not strong enough. He tells Castiel to find someone else.

Featured Supernatural Beings

 * Angels
 * Demons

Featured Music
Cheek to Cheek - Frank Sinatra

Continuity

 * Alastair was captured in the previous episode by Castiel.
 * Alastair mentions that John Winchester was supposed to be the one to break the first seal. John had gone to Hell in exchange for Azazel resurrecting Dean (In My Time of Dying) and later escaped when the Devil's Gate was opened (All Hell Breaks Loose - Part 2).
 * Sam has been drinking Demon Blood to enhance his powers.
 * Anna last appeared in Heaven and Hell
 * Six of the seven angels who died may have been the ones Castiel mentioned in Are You There God? It's Me, Dean Winchester.

Quotes
Uriel: [contemptuously] "You haven't even met the man! [as he brutally punches Castiel] There is no Will! No Wrath! No God!" [he is suddenly stabbed through the throat from behind] Anna: [leaning in close from behind; whispering in his ear] "Maybe. Or maybe not...but there is still me."
 * Alastair: [choking, coughing on mixture of Holy Water, salt and his own blood] "Something caught in my throat... [considers] ...I think it's my throat."
 * Alastair: "'And it is written, that the first Seal shall be broken when a Righteous Man sheds blood in Hell. As he breaks, so shall it break.'"
 * Alastair: [after Castiel barely misses his heart with the demon-killing knife] "Looks like God is on my side today."
 * Castiel: "You can't win, Uriel. I still serve God."