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|dates= ???? - 2009 (killed by [[Sam Winchester]])
|occupation= [[Demon]] ([[White-eyed Demon|White-Eyed]])<br>Grand Inquisitor of Hell
|episodes= [[4.09 I Know What You Did Last Summer]]<br>[[4.10 Heaven and Hell]]<br>[[4.15 Death Takes a Holiday]]<br>[[4.16 On the Head of a Pin]]<br>[[4.21 When the Levee Breaks]] (hallucination)
Alastair is 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 considers the centuries-old [[Ruby]] to be "young" when compared to himself and believes that her generation's style of torturing is amateurish compared to his methods.Ruby calls him the "Grand Inquisitor."<ref name="four10">[[4.10 Heaven and Hell]]</ref> He also claims 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 is present for World War II, at which time he is involved with the concentration camps in Poland. He returns 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" /> Alastair takes [[Meg]] as his apprentice and trains her at some point prior to his demise in 2009.<ref name="six10">[[6.10 Caged Heat]]</ref>.
Alastair is charged with breaking the first of [[the 66 Seals]] by forcing "The Righteous Man" to torture other [[soul]]s in Hell. He first attempts 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 and eventually escapes Alastair's clutches through the [[Devil's Gate in Wyoming|Devil's Gate]].<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|Dean]] from Lilith as a replacement for John.<ref name="four16" /> Although Alastair expects similar resistance from Dean that he got from John, he succeeds in getting Dean to agree to the offer in a third of the time John resisted it. Once Dean breaks the first seal, this allows 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]].<ref name="four09">[[4.09 I Know What You Did Last Summer]]</ref>

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