Alastair

Name	Alastair
Actor	Mark Rolston (4.09 & 4.10) Andrew Wheeler (4.15) Christopher Heyerdahl (4.15, 4.16 & 4.21)
Dates	???? - 2009 (killed by Sam Winchester)
Location
Occupation	White-Eyed Demon
Episode(s)	4.09 I Know What You Did Last Summer 4.10 Heaven and Hell 4.15 Death Takes a Holiday 4.16 On the Head of a Pin 4.18 The Monster at the End of This Book (mentioned) 4.20 The Rapture (mentioned) 4.21 When the Levee Breaks (hallucination) 4.22 Lucifer Rising (mentioned) 6.10 Caged Heat (mentioned) 6.20 The Man Who Would Be King (mentioned)

You know... I haven't been up here since Poland '43. Truth is, I loathe it. It's chilly. No stink of blood or sizzle of flesh or the wet flap of flayed skin. I don't know how you stand it. – Alastair, 4.10 Heaven and Hell

Characteristics

Alastair is a white-eyed demon responsible for torturing human souls in Hell. He is held in high esteem by many of his demon comrades, he is referred to by Ruby as "practically the Grand Inquisitor downstairs." He possesses an extensive knowledge and awareness of the universe, having occult knowledge, usage of spells cast in Enochian as well as rituals.

Alastair was initially immune to Sam's psychic abilities, although, ironically, he is eventually killed by them. His durability seems to exceed that of most demons' as Ruby's knife, a weapon that can kill demons, only greatly damaged him without killing him.

As a torturer, he is an expert interrogator in that regard; according to Castiel, he had an exceptionally strong will, allowing him to sustain himself while being tortured. Meg was an apprentice of his before his death, giving her a similar strength when facing torture. He tortured both Dean and John Winchester, and in both instances offered to end the torment if they would become torturers themselves. Alastair reveals that the first seal was broken when Dean accepted this offer after thirty years of torture, although John resisted him for over a century.

He may also be able to send an angel back to Heaven by expelling it from its vessel (he was interrupted in doing so when h tried to perform that ritual, but his age suggests that this ability may simply not be well-known). Alastair has shown to be resistant to an angel's power of exorcism. He possess knowledge of the Four Horsemen of the Apocalypse and has demonstrated power to overwhelm a reaper.

Episodes

4.09 I Know What You Did Last Summer

Alastair leaves Hell and possesses a pediatrician to capture and interrogate Anna. He follows Sam and Dean from Anna's house to the church Anna is hiding at. 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 overpowering Dean. He taunts Dean about their "closeness" in Hell, prompting Dean to finally recognize Alastair, even in his meatsuit. Sam returns to stab Alastair with Ruby's knife, but much to the Winchesters' horror, the demon does not die. 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 in his new meatsuit, preparing to break one of the 66 Seals.

Ruby tells Sam that Alastair is "practically the Grand Inquisitor" in Hell and that she more scared of him than even angels. She suggests that he resume drinking demon blood so that he can exorcise Alastair, but Sam refuses. Later on, Ruby fulfills her part in Sam's plan by letting Alastair find her. Alastair derides her for protecting Anna, an angel, when she is a demon, and rejects her offer to trade him Anna for the safety of herself, Sam, and Dean, instead capturing her and torturing her with her own knife to force 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 angel business." Eventually, Ruby leads 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 find that Castiel and Uriel are also at the site and are about to execute Anna. Dismissing Castiel's warnings that they will be killed if they do not leave, the demons fight the angels to stop them from killing Anna. Although Alastair's minions are quickly killed by Uriel, Alastair proves too powerful for Castiel to smite and overpowers the angel. When Dean hits him over the head with a crowbar, Alastair shifts his attentions to him and Sam and launches a telekinetic attack on their internal organs while chastising Dean about his lost "potential." He tries to intervene when he sees Anna regain her grace, but gets 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 initially refused, he eventually gave in because he couldn't take it anymore.

4.15 Death Takes a Holiday

Now in a new meatsuit (his previous one having been destroyed by Anna), Alastair is attempting to break one of the 66 Seals by killing two reapers under a solstice moon. He confronts Dean and Sam in a cemetery, and injures Dean, but Sam is resistant to his powers and fights back, revealing that he survived his last encounter with Anna. He flees when Sam tries to exorcise him with his powers and later returns in yet another meatsuit. When the boys become non-corporeal, and therefore subject to ghostly weaknesses, they track Alastair down at a funeral home and he traps them with an iron chain. He kills one reaper, but the boys rescue Tessa, preventing the seal from being broken. Later as he confronts Dean, Alastair is captured by Castiel.

4.16 On the Head of a Pin

Alastair is captured by Castiel and Uriel and imprisoned in a devil's trap, but he refuses to tell them anything about the slain angels. Dean is recruited as an interrogator because he was formerly Alastair's student during his time in Hell. After extensive torture, Alastair breaks free Uriel having sabotaged the devil's trap to prevent his role in the angelic deaths being revealed. He almost kills Dean, but is stopped by Castiel, who throws Ruby's knife and embeds it in Alastair's chest. Alastair pulls the knife out and fights Castiel. He manages to trap him against a pillar, and admits that while he is unable to kill the angel, he will send him back to Heaven. Alastair begins to chant, but he is stopped by Sam, who has become strong enough to overpower him with ease. Sam forces Alastair to talk, then kills him via his abilities.

Alastair survives being stabbed with Ruby's knife.

Alastair is killed by Sam.

4.18 The Monster at the End of This Book

Dean reveals that Castiel has told him about Sam torturing and killing Alastair with ease. Dean thinks that this is one of the signs that Sam is going dark-side.

4.20 The Rapture

Dean points out that Sam's powers used to be strong enough to kill Alastair but are now not even strong enough to kill a low-level demon.

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. Sam hallucinates that he is strapped down and tortured by Alastair with a knife, but eventually Alastair disappears and Sam realizes that he is hallucinating.

4.22 Lucifer Rising

Ruby reveals that not even Alastair had known that she was working undercover 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 the following episode.

6.20 The Man Who Would Be King

Crowley mentions Alastair when listing off those who underestimated the threat the Winchesters pose and paid the price for it.

Alastair in Lore

The character Alastair may be a reference to the demon Alastor in Christian demonology. Alastor is the chief executioner and torturer for the monarch of Hell. He is an exceptionally cruel demon. The name "Alastor" became a common place term in reference to evil spirits or foul tempered individuals.

Trivia

• The name "Alastair" is the anglicized form of the Scottish Alasdair, which is the Scottish (Gaelic) version of Alexander. The latter is the English form of the ancient Greek name Alexandros, which has the meaning "protector of men" in Greek.
• The character may be a reference to British occultist Aleister Crowley, who during his day was dubbed "the wickedest man in the world" by the press. At one point, Led Zeppelin guitarist Jimmy Page developed an interest in Crowley. Page once owned Boleskine House, Crowley's estate on the shores of Loch Ness.
  • In addition, another demon named Crowley later appears.

External links

• Interview with Mark Rolston