Alastair

"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

Alastair (occasionally spelled "Alistair") was a white-eyed demon who was Hell's grand torturer, and Meg apprenticed under him in the field of torture. He was able to travel from Hell and Earth with incredible ease, something he shares with Azazel. His stature to Lilith is vague, but the way he grudgingly followed her orders indicates that she at the very least out-ranked him. Dean first encounters Alastair in Hell and is the one in charge of torturing him.

During the 40 years (or 4 months in Earth time) that Dean was in Hell, each day Alastair would ask Dean if he wanted to trade his place for another soul. For 30 years, he refused and, each day, was chopped and killed and then placed back together, only for the cycle to continue. He couldn't bear the pain much longer and, for 10 years, tortured souls. This makes Alastair directly responsible for triggering the Apocalypse.

Personality
Alastair was cruel, even for a Demon, he enjoyed dishing out pain to others. The more pain he could cause the happier he was, not just physical pain, he was equally capable at giving mental torture and stress, he was also reasonably patient, criticizing Ruby, stating that young demons were always so impatient and willing to run into things.

As well as enjoying dishing out pain, Alastair also enjoyed taking it, showing he was masochistic, he seemed to enjoy being tortured, almost as much as he enjoyed torturing others, however even he had a limit to how much he could take. For these reasons, he is the only demon, who doesn't just like Hell, he likes it more than Earth, dismissing the Earth as a "craphole" and several times expressing the wish to return down. He did however obey Lilith, and would never disobey her.

He also held contempt for Angels, referring to them as "fanatics" and "pricks", and enjoyed hurting them, even more than he enjoyed humans, souls and demons, he also wished he knew how to kill them, rather than just being able to send them back to heaven. Alastair also had a twisted sense of humor, and never missed a chance to exploit something he considered funny or ironic.

Powers and Abilities
As a White-Eyed Demon, Alastair was one of the most powerful demons in existence, his mere presence caused statues to literally weep blood and as Grand Torturer of Hell, he was a master in torture. It's unknown however if was as strong as Azazel who was the previous leader of Hell. It is confirmed that he is Lilith's subordinate.


 * Possession - Like all demons, Alastair requires the use of a vessel on earth, although he prefers to be in his true form, as he calls Earth a "crap hole".
 * Voice Mimicry - Two of his three shown vessels spoke with the same accent.
 * Invulnerability - Even by a demon's standards, Alistair was extremely difficult to kill, he was resistant to various demonic weaknesses such as holy water, salt and iron, although they caused him pain, he barely noticed them. He was also able to walk on Holy ground with ease, something most demons can't do. He was also immune to Ruby's Knife (though he still found it painful) and the killing touch of a lower-level angel. He could only be killed by Sam's powers, and only after the latter had consumed a large quantity of demon blood. He was also presumably vunerable to the Colt.
 * Immortality - Alastair could potentially live forever, before the seals began to break, he hadn't been on earth since 1943.
 * Advanced Telekinesis - Like all higher-level demons, Alastair possesses the ability to move objects with his mind. He has shown great skill, usually tossing people over large distances.
 * Super strength - Alastair is incredibly strong, able to casually overpower humans, Reapers and likely other lower-level demons. Even in a weakened state from the injuries he sustained from the prolonged torture at Dean's hands, he could still overpower a lower-level angel such as Castiel which is very impressive since even low-level angels are usually much more powerful than demons.
 * Enhanced Endurance - Alastair possesses a very large pain threshold and a strong will as he was able to withstand extreme torture from both Dean and the angels without giving up any information. However, when up against Sam who had recently consumed a large amount of demon blood, he broke within a few seconds as Sam's powers proved to be too much for him to bear.
 * Teleportation - Alastair could teleport from one place to another. He could even travel from Hell to Earth with no trouble.
 * Healing - He was able to heal others of any wound, an ability he used in torture, allowing him to torture others to the limit, and then heal them and start again. He could only do this in Hell.
 * Torturing - As Hell's grand master of torture, Alistair has a profuse and in-depth knowledge of torture, being capable of inflicting maximum pain to an individual, both physically and mentally and can withstand great amounts of torture to himself as well.
 * Spell Casting - Alastair is shown to have vast knowledge in heavyweight spellwork. It is shown that he can expel angels from their vessels, and knew a spell to restrain Reapers. He also knew enochian symbols that could ward off a building from angels. He also had knowledge of the 66 seals and how to break them.
 * Biokinesis - Like Azazel, Alastair could inflict pain and damage mentally, he once used this ability on both Sam and Dean at once.

Early Life
Nothing is known about Alastair's life as a human, nor is it known how he became Hell's Grand Torturer. What is known is that while in Hell, he gained a reputation for being cruel and sadistic - a reputation which made even other demons fear him. He also became one of the few demons who actually enjoyed life in Hell more than life on Earth. At some point in his career, he trained Azazel's "daughter" Meg in the art of torture.

Some time during John Winchester's imprisonment in Hell, Alastair took command in attempting to break him in the name of the first seal; however, John endured for a century before being freed during the events of All Hell Breaks Loose. At the end of No Rest for the Wicked he encountered Dean in Hell, and resumed the same duty as before.

Pre-Season 4
In Hell, Alastair was assigned to torture Dean. He did so for 40 years, he broke him within 30 years. In doing so, the first of the 66 Seals was broken.

Season 4
Alastair resurfaces on Earth to try to capture Anna Milton and use her gift for their gain. During this time, he re-encountered his favorite student Dean who remembered him from Hell. Although his initial attempt was unsuccessful, he manages to get a hold of Ruby's magical knife. Later, he returns and strikes a deal with Ruby, who promises Anna for the safety of the Winchesters and herself. Alastair, after torturing Ruby, accepts. Unknowingly, however, he falls into a trap set by the Winchesters and is confronted by two Angels, Castiel and Uriel. He and his demonic minions get into a fight with the Angels, although his minions are easily killed, Alastair proves to be a stronger opponent, and causally knocks about Castiel, and during the battle, Anna regains her Grace and lets loose of a blast of light that disintegrates Alastair's vessel.

He returned a short while later, possessing a new body. He was behind the abduction of a reaper in a small town. He encountered Sam and Dean and fought them, before escaping when Sam revealed that he's immune to his power. He gained a new vessel soon after and abducted a second Reaper named Tessa who Dean knew. He planned to kill the two reapers on the night of the solstice moon to break another of the 66 Seals that needed to break in order to free Lucifer. Sam and Dean, in their astral forms, used their new ghost abilities to fight Alastair; however, he was able to trap them in an iron chain, mocking them about how they often did the same to spirits. However, through a combination of their new abilities, they managed to bring the chandelier down on him, breaking the ring and freeing Tessa. He failed, only being able to kill one reaper, and was captured by the angels.



After seven angels were killed, Castiel recruited Dean to torture information out of Alastair. Alastair simply mocked the fact that his former protégé would be the one to try and break him. Alastair revealed that the first seal was broken when Dean gave in in Hell and began torturing people. This explained why the angels had rescued Dean from Hell. With some help from Uriel, Alastair managed to break free from the Devils Trap he was bound in through water dripping from a pipe and washing away a portion of the symbol.

"You should talk to your plumber about the pipes"

-- Alastair to Dean before disfiguring his face with a single punch

He quickly beat up Dean and nearly banished Castiel to Heaven until Sam arrived and pinned Alastair against a wall using telekinesis. He tortured Alastair until the demon revealed that the demons were not behind the angel killings. Alastair then challenged Sam to exorcise him, but Sam, now being more advanced with his powers, simply used his abilities to kill Alastair in a similar fashion to what the Colt or Ruby's knife would do. It was later shown that Uriel  was behind the angel killings.

He also appears when Sam is hallucinating from his detox of demon blood. In this hallucination, Alastair is torturing Sam.

Appearances

 * Season 4
 * I Know What You Did Last Summer
 * Heaven and Hell
 * Death Takes a Holiday
 * On the Head of a Pin
 * When the Levee Breaks (Appears as hallucination)