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That's why the Apocalypse is coming. That's why the angels are losing. That's why we're all going to die!
~ Anna predicts that Heaven will lose the Apocalypse whilst at the hospital

Anna Milton is a supporting character appearing in the fourth and fifth season of the TV series Supernatural.

She was portrayed by Julie McNiven.

History

Backstory

Initially, Anna was an angel and was Castiel and Uriel's garrison leader, as well as Castiel's friend. She was posted to watch Earth for over two thousand years. However, Anna became disillusioned with her role. Thousands of years of waiting without an answer from God led her to believe He didn't exist. She also became curious about human life, which seemed so happy and full of emotion in comparison to the stoic angelic ideal. Because of this, she tore out her grace and fell from Heaven in what witnesses saw as a meteor shower. She created a new tree upon her fall and was reborn as a human.

Anna lived an unremarkable life with a loving human family, but she did have nightmares about her Father wanting her dead and how her siblings were going to kill her. After the first seal was broken, she was placed in a mental asylum for saying the Apocalypse would begin and she could hear angels.

Season 4

In "I Know What You Did Last Summer," Anna is in an asylum having nightmares about the end of the world. Castiel tells Sam and Dean that, if she can hear angels, then demons will go to any lengths to capture her to hear what Heaven is doing.

Anna is almost taken by a demon but escapes and meets Sam and Dean, who takes her to a barn, but then demons led by Alastair arrive and try to abduct her. Just then, Castiel and Uriel show up to kill her.

In "Heaven and Hell," Anna remembers an essential angelic weakness, a special sigil can banish angels. With the help of a psychic, Pamela Barnesk, the Winchesters remind her of who she truly is and embark on a quest to retake her grace. They find where her grace hit, but discover it is gone, as Uriel took it earlier to prevent Anna from regaining her powers.

While still human, Anna's shares an intimate moment with Dean and the two have sex in the back of Dean's car. She also tells Dean about problems in Heaven, how angels simply answer orders and have never actually seen God. Anna surrenders to the angels; however, Castiel is reluctant to kill his former friend. Before they can carry on, however, Alastair bursts in and a fight breaks out. Anna manages to steal back her grace from Uriel. Doing so destroys her body and the blast also destroys Alastair's vessel.

Anna returns in "On the Head of a Pin," appearing in her human form (she was able to call in a few favors to get her own body recreated to act as her vessel). She comes to talk to Castiel, who is suffering from a conflict of allegiances, as his love of humanity is making him question a few orders. She recommends he join her, but Castiel angrily refuses and orders her to leave. Later, however, she saves him from Uriel and kills the traitorous angel.

In "The Rapture," Anna appears in the backseat of the Impala to talk to Sam and Dean, and they tell her that Castiel has been forcibly taken back to Heaven; she advises them not to trust angels anymore because they are planning something very bad and it will affect everyone.

In "When the Levee Breaks," Anna appears to Castiel and demands to know why he let Sam out of Bobby Singer's demon panic room. Castiel simply replies that Anna shouldn't have come, at which point two angels appear and capture Anna, taking her away to Heaven.

Season 5

In "The Song Remains the Same," Anna manages to escape from Heaven and, desperate to stop the Apocalypse, plans to kill Sam and scatter his atoms across the universe so Lucifer can't use him as his true vessel. This would theorectically end the Apocalypse before it even started. She appears to Dean in a dream and tells him to meet her somewhere since she can't find him via normal means because of the Enochian sigil on his ribs. Castiel goes instead and hears her plan but refuses to let her kill Sam, since Sam is his friend. She is surprised by his new change in allegiance and seemed proud of him. With Castiel guarding the Winchesters, Anna travels back through time to the year 1978, intending to kill John and Mary Winchester so they won't be able to conceive Sam. With Castiel's help, Dean and Sam travel back to the same year and manage to thwart Anna's first attempt to kill their parents.

Anna summons Uriel for assistance and tricks him into believing that it is Sam and Dean who will kill him in the future and gives him the chance to save himself. The two angels track down the boys and their parents to their hideout. Uriel restrains Dean while Anna succeeds in killing Sam. Anna then advances on Mary. However, she hesitates to apologize for what she believes must happen, only to be stopped by Michael, who is possessing John (who was thrown out the window moments earlier). Michael puts his hand on Anna and burns her to death, then sends Uriel away. After a conversation with Dean in which he informs him that the Apocalypse is inevitable, he sends Sam, fully healed, back to the present along with Dean.   

Trivia

  • Anna desired the Apocalypse to be derailed, which coincidentally was the same thing Sam and Dean wanted, but Anna's methods of doing so were more rash and cold and set her against her former allies.
  • Anna's surname was a reference to the poet John Milton, who wrote Paradise Lost, which was an inspiration for Supernatural.
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