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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>.
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>
Alastair is sent to Earth to capture and interrogate [[Anna Milton]] on what she hears other angels saying. However, he
fails 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 captures Alastair to interrogate him on who has been killing members of his [[angel garrison]].<ref name="four16" /> Alastair proves 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 tortures 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" />