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|actor= [http://www.imdb.com/name/nm0001679/ Mark Rolston] ([[4.09 I Know What You Did Last Summer|4.09]] & [[4.10 Heaven and Hell|4.10]])<br>[http://www.imdb.com/name/nm0923766/ Andrew Wheeler] ([[4.15 Death Takes a Holiday|4.15]])<br>[http://www.imdb.com/name/nm0382216/ Christopher Heyerdahl] ([[4.15 Death Takes a Holiday|4.15]], [[4.16 On the Head of a Pin|4.16]] & [[4.21 When the Levee Breaks|4.21]])
- 2009 (killed by [[Sam Winchester]])
|occupation= [[Demon]] ([[White-eyed Demon|White-Eyed]])<br>Grand Inquisitor of Hell
Alastair was a [[Demonology|white-eyed demon]] and possibly the second demon ever made whose past is unknown, but implied to be almost as long as [[Lilith]]'s. He
was considered by the centuries-old [[Ruby]] to be "young" and believed that her generation's style of torturing is amateurish compared to his methods. Ruby called him the "Grand Inquisitor",<ref name="four10">[[4.10 Heaven and Hell]]</ref> whether the title was official or not is unknown. He also claimed to be an "old friend" of [[Death]]'s,<ref name="four15">[[4.15 Death Takes a Holiday]]</ref> who had been imprisoned since Biblical times.<ref name="five10">[[5.10 Abandon All Hope...]]</ref> Alastair was present for World War II, at which time he is involved with the concentration camps in Poland. He returned to [[Hell]] after 1943 and does not resurface on Earth again until 2008, as he prefers to spend his time in Hell, torturing [[souls]], only heading topside when it is absolutely necessary.<ref name="four10" /> In Hell, Alastair took [[Meg]] as his apprentice and trained her at some point prior to his demise in 2009.<ref name="six10">[[6.10 Caged Heat]]</ref>.
Alastair was charged with breaking the first of [[the 66 Seals]] by forcing "
The Righteous Man" to torture other [[soul]]s in Hell. He first attempted to break this seal by torturing [[John Winchester]]'s soul from 2006 to 2007, promising to stop only if John agrees to torture other souls. However, John continually refuses the offer for 100 years (10 months) and eventually escaped Alastair's clutches through the [[Devil's Gate in Wyoming]].<ref name="four16">[[4.16 On the Head of a Pin]]</ref><ref name="two22">[[2.22 All Hell Breaks Loose: Part Two]]</ref> A year later, Alastair receives John's son [[Dean Winchester]] from Lilith as a replacement for John.<ref name="four16" /> Although Alastair expected similar resistance from Dean that he got from John, he succeeded in getting Dean to agree to the offer in 30 years (3 months). Once Dean breaks the first seal, this allowed the rest of the seals to be broken.<ref name="four16" /> Impressed by Dean's potential, Alastair keeps training him as an apprentice until an army of [[angels]] rescued Dean, including [[Castiel]] who personally pulled him out.<ref name="four09">[[4.09 I Know What You Did Last Summer]]</ref > Alastair is then sent to Earth to capture and interrogate [[Anna Milton]] on what she hears other angels saying. However, he failed due to the combined efforts of [[Sam]], Dean, Ruby, and Anna herself.<ref name="four10" /> He is sent back up to Earth once again to participate in breaking more seals. His attempt to sacrifice two [[reapers]] during the winter solstice is thwarted by Sam, Dean, and Castiel,<ref name="four15" /> the last of whom captured Alastair to interrogate him on who has been killing members of his [[angel garrison]].<ref name="four16" /> Alastair proved too strong-willed for the angels to break and they call Dean in to torture his old tormentor, but to no avail. Alastair only gives up the information when Sam tortured him with his [[demon blood]]-enhanced powers; after Alastair reveals that he only knows that no demons are behind the murders, he becomes the first demon killed by Sam's growing powers.<ref name="four16" />
Alastair has white eyes (including pupils and irises).<ref name="four09" />
He is noted as an expert interrogator and torturer,<ref name="four10" /> and is also incredibly resilient to being tortured himself; according to [[Castiel]], he has an exceptionally strong will, allowing him to withstand extended torture from both [[angels]] and one of his own apprentices.<ref name="four16" /> Alastair possesses an extensive knowledge of the occult as well as [[Enochian]] spells and rituals, including an incantation with an unknown negative effect on [[angel]]s<ref name="four10" /> as well as another incantation that expels an angel from his [[vessel]] and sends him back to [[Heaven]],<ref name="four16" /> and spell-work to incapacitate [[reapers]].<ref name="four15" /> His presence causes statues to weep blood.<ref name=" four09" />
===Powers and abilities===
* Arcane knowledge
- Being a [[white-eyed demon]] and presumably among the first created, Alastair possesses old and powerful knowledge, such as an [[exorcism]] ritual that can eject an angel from its [[vessel]] and send it back to [[Heaven]]. * [[Possession]] - Like all demons, Alastair was capable of possessing any humans not in possession of an [[anti-possession symbol]].<ref name="four09" /><ref name="four15" />* [[Telekinesis]] <ref name="four09" /><ref name="four15" /> - Alastair can moves anything with a thought. The power also extends to being able to telekinetically inflict damage onto humans's hearts with a gesture.<ref name="four10" />* [[Teleportation]] - As a high-level demon, Alastair has the ability to teleport.<ref name="four10" />* Superhuman strength and durability .<ref name="four10" /><ref name="four16" /> - Alastair can overpower [[angels]],<ref name="four10" /> though he does not possess the power to kill them and they can overpower him if he is sufficiently distracted, but had also shown to resistant to the smiting powers of [[angel]]s, though their [[grace]] can destroy his [[meatsuit]].<ref name="four10" /> .<ref name="four16" /><ref name="four15" /> His durability also extends to a high resistance to the [[demon-killing knife]].<ref name="four09 " /><ref name="four16" />
* [[Demon-killing knife]]
- While Alastair had survived being stabbed with the knife twice, it's use still caused him great pain.* [[Devil's traps]] - As powerful as Alastair was, he was still vulnerable to devil's traps.<ref name="four16" />* [[Holy water]]<ref name="four16" /> - Holy water was shown to burn Alastair like all demons.* Psychic powers - Alastair was killed by [[Sam]]'s powers if Sam has recently consumed [[demon blood]].<ref name="four16" /> * [[Salt]] - Alastair was incapable of crossing a salt line, ingestion of salt mixed with holy water was able to cause great discomfort.
===[[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 her father's church, 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]] is 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 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 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 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]].]]
===[[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
===[[4.16 On the Head of a Pin]]===
[[File:AlastairKilled.jpg|thumb|right|350px|Alastair is killed by [[Sam]].]]
===[[4.18 The Monster at the End of This Book]]===
Alastair's death is brought up by
[[Dean ]], who reveals that [[Castiel ]] has told him about [[Sam ]] using his powers to torture and kill Alastair with ease. Dean thinks that Sam being able to do so is another sign that he is going dark -side.
===[[4.20 The Rapture]]===
Alastair is again mentioned by
[[Dean ]], who is in disbelief that [[Sam ]]'s powers were strong enough to kill Alastair but are now not even strong enough to kill a low-level [[demon ]]. The reason, unknown to Dean at the time, is that Sam has not recently fed on [[demon blood ]] due to a prolonged absence from [[Ruby ]].
===[[4.21 When the Levee Breaks]]===
While undergoing forced withdrawal from
[[demon blood ]], [[Sam ]] has several hallucinations, the first of which is Alastair inexplicably returning in his last meatsuit. Finding Sam locked in [[Bobby's Panic Room]] alone with him, Alastair tortures him with a knife. Eventually Alastair disappears and Sam realizes that he had hallucinating both Alastair and the torture.
===[[4.22 Lucifer Rising]]===
Alastair is the only
[[demon ]] explicitly mentioned by [[Ruby ]] when she is explaining that none of the others besides herself and [[Lilith ]] had known of her undercover mission for [[Lucifer]] and Lilith.
===[[6.10 Caged Heat]]===
To prove that she is capable of making [[Crowley]] give into her demands, [[Meg]] reveals that she had apprenticed under Alastair in [[Hell]] like [[Dean]] had, and Dean grudgingly concedes that this means she can make Crowley do whatever she wants
. Meg doesn't reveal when she undertook this apprenticeship, but it must have been before Alastair's capture in [[4.15 Death Takes a Holiday]], as he was killed in [[4.16 On the Head of a Pin|the following episode]]. She is known to have been in Hell in the time between her [[exorcism]] in [[1.22 Devil's Trap]] and her return for revenge against the Winchesters in [[2.14 Born Under a Bad Sign]]; if his words in [[4.16 On the Head of a Pin]] were true, he would have also been working on torturing and trying to tempt [[John]]'s [[soul]] at the time. Alternately, Alastair may have taught her previously in Hell at some point [[pre-series]].
===[[6.20 The Man Who Would Be King]]===
Alastair is mentioned by
[[Crowley ]] when listing off those who underestimated the threat the Winchesters pose and paid the price for it, along with [[Lucifer]], [[Michael]], [[Lilith]], and [[Azazel]] .
==Alastair in Lore==