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	Demon (White-Eyed) Grand Inquisitor of Hell
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 4.21 When the Levee Breaks (hallucination)

You know the problem with your generation? Instant gratification. It's all now, now, now. No patience, no craftsmanship. But I do have to say... This knife of yours... It's an exquisite piece. You must tell me where you found it. 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. So, the sooner you cooperate, the sooner I can finish up with this ghastly angel business and return home to my studies. But no rush. Let's take our time... Relish the moment. Now, I'm going to remove this, but don't you go smoking out of that meat. You won't get very far. – Alastair, 4.10 Heaven and Hell

History

Alastair was a 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", whether the title was official or not is unknown. He also claimed to be an "old friend" of Death's, who had been imprisoned since Biblical times. 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. In Hell, Alastair took Meg as his apprentice and trained her at some point prior to his demise in 2009..

Alastair was charged with breaking the first of the 66 Seals by forcing "The Righteous Man" to torture other souls 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. A year later, Alastair receives John's son Dean Winchester from Lilith as a replacement for John. 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. 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.

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. 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, the last of whom captured Alastair to interrogate him on who has been killing members of his angel garrison. 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.

Characteristics

Potestas inferna, me confirma. Potestas inferna, me confirma. Potestas inferna, me confirma! – Alastair, 4.10 Heaven and Hell

Alastair has white eyes (including pupils and irises). His presence caused statues to weep blood and was noted as an expert interrogator and torturer, 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. Alastair possessed an extensive knowledge of the occult as well as Enochian spells and rituals, including an incantation with an unknown negative effect on angels, as well as another incantation that expels an angel from his vessel and sends him back to Heaven, and spell-work to incapacitate reapers.

Alastair survives being stabbed with Ruby's knife.

Powers and abilities

• Arcane knowledge – Being a white-eyed demon and presumably among the first created, Alastair possessed old and powerful knowledge, such as an exorcism ritual that could 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.
• Telekinesis – 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.
• Teleportation – As a high-level demon, Alastair had the ability to teleport.
• Superhuman strength and durability – Alastair could overpower angels, though he did not possess the power to kill them and could be overpowered sufficiently distracted, but had also shown to resistant to the smiting powers of angels, though their grace could destroy his meatsuit. His durability also extended to a high resistance to the demon-killing knife.

Weaknesses

• 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.
• Holy water – Holy water was shown to steams on Alastair weaker and didn't burned his skin like regular demons.
• 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.

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 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 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 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 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.

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 reapers 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 ghostly 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

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 angels. 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 (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 Uriel 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.

Alastair is killed by Sam.

Castiel embeds Ruby's knife in Alastair's shoulder 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 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

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 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.

15.01 Back and to the Future

Belphegor mentions Dean's time in Hell, where he was tortured by Alastair, until after 30 years Dean accepted Alastair's deal that he would stop the torture if Dean himself would take his place. Belphegor says he got to watch Dean "work" and describes the things he did to people as not torture but "art," calling himself a fan of Dean's work. Dean simply states that it was a long time ago.

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