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===[[4.09 I Know What You Did Last Summer]]===
Alastair leaves [[Hell]] and [[Possession|possesses]] a pediatrician to capture and interrogate [[Anna]]. He follows [[Sam]] and [[Dean]] from Anna's house to the her father's church Anna is hiding at, where she fled to after her escape. [[Ruby]] tries to get Sam, Dean, and Anna to leave as quickly as possible to avoid Alastair, but realizes that it is too late when signs of his approach break out, including a statue of the virgin Mary weeping blood. Although she convinces Sam to [[exorcise]] Alastair with his powers, they have little effect on Alastair, who uses [[telekinesis]] to fling Sam down the staircase before attacking and beating Dean. He taunts Dean about their "closeness" in Hell, prompting Dean to finally recognize Alastair, even in his [[meatsuit]]. Sam returns to stab Alastair in the shoulder with [[Ruby's knife]], but much to the Winchesters' horror, the [[demon]] does not dieis undeterred by the knife wound. As Alastair pulls the knife out, Sam and Dean flee from him by jumping out the church window and he allows them to escape so that he can use them to lead him to Anna again.
===[[4.10 Heaven and Hell]]===
Alastair is described by [[Ruby]] as a master torturer who is "practically the Grand Inquisitor" in [[Hell]], whom she is more scared of him than even the [[angels]]. After her suggestion to abandon [[Anna]] and run from Alastair gets rejected, she tries to get [[Sam]] to resume drinking her [[Demon blood|blood]] so that he can successfully [[exorcise]] Alastair. Sam refuses this as well. Later on, Alastair reappears when Ruby leaves to fulfill her part in Sam's plan, burning her [[hex bag]] and letting Alastair find her at a [[crossroads]]. Alastair derides her, a fellow [[demon]], for protecting Anna, an [[angel]](albeit without her grace), and rejects her offer to trade him Anna for the safety of herself, Sam, and [[Dean]]. He just insults her again before having his minions capture her and he begins torturing her with [[Ruby's knife|her own knife]] to simply make her to tell him where Anna is. While torturing her, Alastair reveals that he actually vastly prefers Hell to Earth (which he loathes), having only left it because he must deal with "this nasty ghastly angel business." Eventually, Ruby agrees to lead him and his minions to Anna - she is unwilling to simply tell him what he wants to know because she knows that he would just kill her afterwards. Alastair and his minions accompany her and find that [[Castiel]] and [[Uriel]] are also at the site, about to execute Anna. Contrary to the terror other [[demons]] showed of angels, Alastair dismisses Castiel's warnings that they will be killed if they do not leave and even trades insults with Uriel before leading his forces to fight the angels and stop them from killing Anna so that he may capture and torture her. Although his minions are quickly killed by Uriel, Alastair proves too powerful for Castiel to smite and overpowers the angel, which shocks the latter. When Dean hits him over the head with a crowbar, Alastair shifts his attentions to him and Sam and launches a [[Telekinesis|telekinetic]] attack on their hearts while chastising Dean about his lost "potential." He tries to intervene when he sees Anna regain her [[grace]], only to get his meatsuit vaporized instead, leaving behind only Ruby's knife. Later, Dean tearfully reveals to Sam that after every day of torture in Hell, Alastair would offer to stop if Dean agreed to torture other souls. Although Dean held out for the first thirty years (three months on Earth), he eventually gave in because he couldn't take it anymore and spent the last ten years of his time there (one month on Earth) torturing other souls under Alastair's instruction.[[File:Alistair with Death's weapon.Jpg|350px|thumb|left|Alastair in his new [[meatsuit]], preparing to break one of [[the 66 Seals]].]]
[[File:Alistair with Death's weapon.Jpg|350px|thumb|left|Alastair in his new [[meatsuit]], preparing to break one of [[the 66 Seals]].]]
===[[4.15 Death Takes a Holiday]]===
Alastair is once again made to leave [[Hell]] and assist in starting the [[Apocalypse]], much to his dissatisfaction. Now in a new [[meatsuit]], he is attempting to break one of [[the 66 Seals]] by killing two [[reaper]]s under a solstice moon. He confronts [[Dean]] and [[Sam]] in a cemetery, revealing that he had survived his encounter with [[Anna]], though the pediatrician he had been [[possessing]] did not, and gloating that the latter's wife is still looking for her husband and unaware he is dead, which he finds hilarious. Trying again to kill them, Alastair telekinetically throws Dean into a gravestone and injures him, but finds that Sam is now immune to his powers. He flees when Sam tries to [[exorcise]] him with his powers, and later returns in yet another meatsuit. When the boys become non-corporeal to better find the demons holding the reapers hostage, they track Alastair down at a funeral home warded in [[Enochian]] script against [[angels]]. As they have made themselves subject to [[ghost]]ly weaknesses in their spiritual state, Alastair traps them with an [[iron]] chain and toys with them by shooting them with rock [[salt]] as he sends a minion to kill their unconscious bodies. While their ally [[Pamela Barnes]] is able to hold off Alastair's servant for a time and thwart this aspect of Alastair's plan, she is fatally wounded by Alastair's servant in the process and later dies. Meanwhile, Alastair begins breaking the seal and succeeds in killing one [[reaper]] with [[Death's scythe]], though the boys help [[Tessa]] escape and ultimately save the seal before fleeing. Alastair later tracks Dean down alone as Sam is fighting off Alastair's minion in an attempt to save Pamela. As he begins closing in on Dean, Alastair is struck by lightning and vanishes again as he is captured by [[Castiel]].
===[[4.16 On the Head of a Pin]]===
[[File:AlastairKilled.jpg|thumb|right|350px|Alastair is killed by [[Sam]].]]
Alastair has held captive by [[Castiel]] and [[Uriel]] and imprisoned in a [[devil's trap]] since the previous episode, but he refuses to tell them anything about the slain [[angel]]s. [[Dean]] is recruited as an interrogator because he was formerly Alastair's student during his time in [[Hell]]. Amused by the idea, Alastair taunts him over the course of the torture session, though he concedes that reality is "too concrete" compared to Hell for Dean to adequately torture him. Dean instead tortures Alastair with [[holy water]] injected into his veins, [[salt]] poured down his mouth, and mutilation from [[Ruby's knife]], as he admits to an unnerved Alastair he'd dreamed of doing in Hell. Instead of giving Dean the information he asks for regarding the angel murders, Alastair messes with Dean by claiming that he tortured Dean's father [[John]] in Hell and even made him the same offer he'd made Dean, but that unlike his son, John was a "hero" who steadfastly refused and ultimately escaped after 100 years (one year ten months on Earth) of Alastair's torture. Alastair gloats that when Dean accepted the offer in 30 years (30 months) and began torturing souls, he broke the first of [[the 66 Seals]] and enabled [[demons]] to begin breaking the rest of them. Having kept an eye on the devil's trap he's caught in being compromised - later revealed to be Uriel's doing, to let Alastair kill Dean and escape to make the angels keep thinking the demons are responsible for the angel murders when it is really Uriel himself committed - Alastair escapes when a devastated Dean turns his back, then begins savagely beating Dean again. He is about to finish Dean off and send him back to Hell, telling him he has a lot to learn, when he becomes distracted by Castiel intervening. Castiel throws embeds Ruby's knife and embeds it in Alastair's chestshoulder and uses telekinesis to twist the blade, but Alastair simply pulls the knife out and fights Castiel. He again overpowers Castiel and while he is unable to kill the angel as he admits he wishes he could, he reveals that all he can do is send him back to [[Heaven]]. Alastair begins an angel [[exorcism]], but he is stopped by [[Sam]], who has become strong enough through his consumption of [[Ruby]]'s [[demon blood]] to overpower even him with ease. Agonized by Sam's psychic torture, Alastair finally reveals that he knows none of the demons, including himself and [[Lilith]], are responsible for the angel deaths. Knowing that Sam can psychically [[exorcise]] demons, he challenges Sam to exorcise him back to Hell, where he wants to be, but is shocked when Sam instead uses his enhanced power to kill him.
===[[4.18 The Monster at the End of This Book]]===

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