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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 considered 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" /> His presence caused statues to weep blood<ref name="four09" /> and was noted as an expert interrogator and torturer,<ref name="four10" /> and was also incredibly resilient to being tortured himself; according to [[Castiel]], he had an exceptionally strong will, allowing him to withstand extended torture from both [[angels]] and one of his own apprentices.<ref name="four16" /> Alastair possessed 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" />
[[File:AlastairKnife416.jpg|thumb|350px|Alastair survives being stabbed with [[Ruby's knife]].]]
* [[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 a powerful demon Alastair must be trapped and bound into a special old-Enochian devil's trap.<ref name="four16" />
* [[Holy water]] – Holy water has an affect on Alastair like most demons, however he
is able to shrug off the effects quicker than typical demons.<ref name="four16" />
* [[Salt]] – Ingestion of salt mixed with holy water was able to cause great discomfort.
* [[Special Children]] – Alastair was killed by [[Sam]]'s powers after Sam had consumed a sufficient amount of [[demon blood]].<ref name="four16" />
===[[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]].]]