Alastair

Alastair 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 ease. His stature to Lilith remains unclear. Dean first encounters Alastair in Hell and is the one in charge of torturing him. Each day, for 40 years (or 4 months in Earth time), 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.

Post Season 4
In Hell, Alastair was assigned to torture Dean. He did so for 40 years, he broke him within 30 years.

Season 4
Alastair resurfaces on Earth to try to capture Anna Milton and use her gift for their gain. 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 later vanishes after Anna regains her grace.

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 one 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. 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 protege 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. Alastair managed to break free from the Devil's Trap he was bound in through water dripping from a pipe. 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 where not behind the angel killings. Alastair then challenged Sam to excorcise 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 hallucinating from his detox of demon blood. In this hallucination, Alastair is torturing Sam.

Family / Relations

 * Lucifer (Father/Creator)
 * Lilith (Superior/Leader)
 * Demons (students/brothers and sisters)
 * Meg (student)
 * Dean Winchester (student/victim)

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 reasonable 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 a content for angels, 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 is one of the most powerful demons, also he, as the grand torturer of Hell, he is a great in torture.


 * Possession- Like all demon's, 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". Oddly, all of his vessels speak with the same "accent".


 * Telekinesis- Like all higher-level demons, Alastair possesses the ability to move objects with his mind. He has show great skill, usually pinning people to walls.


 * Superhuman Strength - Alaster is incredibly strong, able to casualy overpower humans, Reapers and even angels.
 * Overpowering- Alaster was strong enough to over power two reapers, who as servants of Death are themselves very powerful, and even a celestial being, Castiel.
 * Invulnerability- Little could damage him, he couldn't be killed by the Knife, nor could the Killing Touch of average angels.
 * Superhuman Stamina/Endurance - Alastair doesn't tire, being able to literally do profuse torturing without tiring; he tortured Dean for 30 years. He continuously searched for Anna, which only ended when she regained her grace.
 * White Light (presumably)
 * Teleportation - Alaster 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.

Skills

 * Master of Torture: Alastair was very proficient in torture.


 * Magical Knowledge: Alastair is shown to have vast knowledge in heavyweight spellwork. It is shown that he can expel angels from their vessels and that he can enhance his demonic strength with the help of the infernal powers.

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)