Anna Milton

"I was stationed on Earth 2,000 years...just...watching. Silent...invisible...out on the road...sick for home...waiting on orders from an unknowable father I can't begin to understand."

- Anna to Dean

Anna Milton was a fallen angel who became the human daughter of Richard and Amy Milton by removing her grace. Due to her newly reawakened ability to hear angels speaking, she was pursued by demons and angels alike. Sam and Dean protected her until she managed to regain her grace and fend off her pursuers herself, even briefly becoming lovers with Dean. Due to Castiel's betrayal, the Host of Heaven eventually captured Anna and took her back to Heaven. She returned to Earth in "The Song Remains the Same" with the intent to prevent The Apocalypse from having occurred by killing John and Mary Winchester to retroactively erase Sam and Dean Winchester from existence. She was killed by Michael to protect the Winchesters.

Background
Created by God before the creation of the human race, Anna served as the superior of Castiel and Uriel, and presumably Balthazar, Hester, Bartholomew and Inias. Anna was particularly close to Castiel, who noted that they had "been through much together." Anna never met, saw, or heard from God, but initially followed what she believed to be his orders out of pure faith and fruitlessly awaited his return to Heaven.

Anna observed humans and became loving of them for their emotions particularly loyalty, forgiveness and love, coming to believe that her own kind were emotionless and without any will of their own in comparison. She also became fond of the idea of chocolate cake and sex. Wanting to experience life as a human herself, she removed her grace in March 1985 through an agonizing process she compared to cutting out one's own kidneys using a butter knife. Anna and her grace fell separately to Earth at high speeds; to onlooking humans, they resembled meteorites.

Anna was reborn as the human daughter of infertile couple Richard and Amy Milton in northwestern Ohio in December 1985 with the new name Anna Milton. Because Amy had not been able to get pregnant before conceiving Anna, she called Anna her "little miracle." When Anna was a toddler, she panicked in Richard's presence because she believed that her "real" father would kill her for her disobedience. Her outbursts were such that the Miltons took her to a child psychologist for therapy. Anna gradually repressed her memories of her origins, and convinced herself that she was a normal human. As a young woman, she attended college as a journalism major.

On September 18, 2008, the day Castiel resurrected Dean Winchester from Hell, Anna heard an angel say "Dean Winchester is saved" inside her head. After that, she started to hear other angels talking. They talked so often about Dean and Sam Winchester that Anna felt as though she personally knew the Winchester brothers; she learned that some believed that Dean could save them while some "didn't like" Sam at all. Anna became hysterical when trying to warn people about the oncoming Apocalypse and had to be subdued by four men. She was subsequently committed to the Connor Beverly Behavioral Medicine Center with a diagnosis of schizophrenia. She drew pictures of the seals Lilith broke and scribbled messages pertaining to them in a sketchbook.

"I Know What You Did Last Summer"
When demons learned about Anna's knowledge of the seals and her ability to hear angels, they began hunting her down in order to torture her for information. She fled from Connor Beverly when a possessed orderly tried to capture her; instead she noticed the demon's true face and knocked it unconscious in order to flee. She sought refuge at her father's church because she was too afraid to go home. Having been tipped off by Ruby, Dean and Sam tracked Anna down, but were followed by Alastair. The brothers fended Alastair off while Ruby took advantage of the distraction to take a frightened Anna to safety at a remote cabin, where they were later rejoined by Sam and Dean. Much to Anna's distress, she learned that her parents had been murdered by the demons looking for her. When Anna sensed the approach of a threat, the Winchesters and Ruby hid her in another room and prepared to take on the unknown enemy. The threat turned out to be Castiel and Uriel, who had orders to execute her for falling.

"Heaven and Hell"
Anna banished her brothers in a moment of panicked instinct by slitting her wrists and using the blood to draw out and activate an angel banishing sigil. Ruby bandaged Anna's wounds, and the four of them went to Bobby Singer's house so Anna could be protected in the demon-proofed panic room. She was angered to find out that Sam and Dean were digging into her past without asking her questions directly, but admitted that she did not know why these things were happening, so Sam and Dean called in Pamela Barnes to put her into a hypnotic trance in the hopes that she might be able to remember something important. As the hypnotized Anna was questioned, she became distressed and her powers went haywire. However, she finally remembered her origins by the time Pamela woke her up. Anna then decided to regain her grace so that she could protect herself from both demons and other angels. Despite this, she did not truly want her grace back, as she privately confided in Dean that she preferred humanity to living as a "perfect, unfeeling" angel.

Sam managed to piece together that Anna's grace had landed in a field in Kentucky, but when the group arrived, Anna discovered that it was gone. She received a message from the angels, who threatened to cast Dean's soul back into Hell if she was not handed over to them. She began wondering if she even deserved to be saved, reasoning that she had disobeyed like Lucifer had and this meant she might deserve to be punished. Dean, however, rejected this idea. Anna revealed to him that she knew that he had tortured other souls in Hell. She tried to comfort him by telling him that it wasn't his fault and he should forgive himself, then kissed him. After reminding him that it was her last night on Earth, she had sex with him in the backseat of The Impala. Unbeknownst to Anna, Uriel invaded Dean's dreams after the latter fell asleep. When threatening to cast Dean into Hell didn't convince him to betray Anna, Uriel threatened to kill Sam. Dean reluctantly told Uriel their location to protect his brother at the same time a captured Ruby was tortured by Alastair into leading them to Anna; secretly, however, this was part of a larger plan concocted by Sam to lure the angels and demons into the same room to put them against each other.

Castiel and Uriel confronted Anna and the Winchesters in a barn. With Ruby having failed to arrive with the other demons in tow, Anna resigned herself to her fate and forgave Dean for "betraying" her, though she still did not forgive Castiel and Uriel for their actions. She ordered them to execute her quickly, but they were interrupted by Ruby finally bringing Alastair and two other demons to the barn. While Uriel was distracted by killing the demons, Anna noticed that he had her grace. She broke the container it was in and painfully reabsorbed it as she shouted for the Winchesters and Ruby to shut their eyes. Her transformation back into an angel destroyed Alastair's vessel and sent him back to Hell, and Anna vanished.

"On The Head Of A Pin"
Anna came to speak with Castiel, brushing off his warning that he still had orders to kill her. They discussed the orders he was following by making Dean torture Alastair to learn who had killed seven angels from their garrison; Anna suspected that God was not the one who had given the orders, and begged her brother to stop Dean before the torture went too far. At her suggestion that Castiel become her ally, he pulled away from her and told her to leave, which she reluctantly did. After Castiel learned that demons were not responsible for the deaths of his siblings, he summoned Anna for advice because he was having doubts and was considering disobedience. She sympathized with him, but was hurt by the realization that he still regarded her as "a walking blasphemy." When he begged her to give him orders to follow, she refused because she believed that he needed to learn to make his own choices. However, she kept an eye on him and intervened to save him from the treacherous Uriel by stabbing Uriel through the neck with an Angel Blade. She and Castiel watched on together as Uriel died.

"The Rapture"
Anna teleported into the backseat of the Impala to inquire after Jimmy Novak once she learned that Castiel had been taken back to Heaven to be punished for almost rebelling. Dean was surprised by her sudden arrival and nearly crashed the car. She deflected his flirting and noted, troubled, that Sam seemed "different," though Sam tried to play it off. When she learned that Castiel had wanted to tell Dean something important, she sensed that it had been important and grew agitated. Despite her urging Dean and Sam to find Jimmy, she feared that he was already dead.

"When the Levee Breaks"
Anna was horrified when Castiel released Sam from Bobby's panic room during Demon Blood detoxification. She confronted Castiel and demanded to know why he had done it, but ended up getting captured by two other angels and taken to Heaven as Castiel looked on in guilt.

Interim
For the remainder of Season 4 and over half of Season 5, Anna was imprisoned in Heaven, where she was tortured extensively by other angels. It is unconfirmed how she got out; Castiel believed that the Host of Heaven released her once she rejoined them, but Anna herself insisted that she had escaped on her own power and remained her own agent.

"The Song Remains the Same"
To stop Lucifer from using his true vessel, Anna planned to kill Sam and then scatter his cells across the universe to prevent Lucifer from simply resurrecting him. Unable to simply teleport to the Winchesters due to Enochian sigils Castiel had carved into their ribcages, she invaded Dean's dreams and gave him an address to meet her at to lure him and Sam to a warehouse. At the warehouse, she was instead confronted by Castiel, who had convinced the Winchesters to stay behind because he did not trust her. After Anna revealed her plans, Castiel refused to let her kill Sam and threatened to kill her if she tried, regardless of their history. With Castiel guarding the brothers in the present, Anna decided to prevent the Apocalypse from having occurred altogether. She went back in time to 1978 to kill John and Mary Winchester so that Sam and Dean wouldn't be born to break the first and final seals. Castiel and the Winchesters figured out her plan and went back in time to stop her.

Anna killed John's boss, Mr. Woodson, at the garage John worked at. She then called John up while posing as Mr. Woodson, and lured him to the garage to kill him. When she was attacking him, she got distracted by Dean and then Mary attacking her with angel blades. They managed to hold her off long enough for Sam to banish her. Realizing that she was outnumbered, Anna summoned the Uriel of 1978 for backup. He recognized that she was not the Anna of 1978, but to enlist his aid in her mission, she claimed that she was still his superior, that the Winchesters killed him in the future, and that she was giving him the opportunity to kill them first. Together, the angels destroyed the Enochian sigils, made the holy oil vanish, and broke the windows and lights in the house that the Winchesters were hiding in. They attacked the family, with Anna fighting and eventually killing Sam. However, the archangel Michael himself, having gained John's consent to be possessed by him in exchange for Mary's safety, killed the frightened Anna by burning her alive with a touch, reducing her to ashes as she screamed.

Appearance
Anna's true form was composed of bright light that blinded and could even kill humans upon direct eye contact; she also had wings, as seen when right before she vanished after regaining her grace. Her human body was that of a pale-skinned young woman who was 5'6" with long red hair, wide hazel eyes, and small moles on her cheeks. Her hair was a very dark, vivid shade of red in Season 4 which had lightened to auburn by the time she reappeared in Season 5. Anna wore a pair of white and blue scrubs at Connor Beverly Behavioral Medicine Center. Once she escaped the mental institution, she began wearing a frilly button-down white shirt and jeans with a green jacket, the last of which she later swapped out in favor of a navy coat that went down to mid-thigh. Her body was destroyed by her grace in "Heaven and Hell", but she had it restored by calling in "favors" from an unknown entity and used it as her earthly vessel until her death.

Personality
Anna was earnest, compassionate, and trusting to a fault: despite the horror she felt at Ruby's true face, she accepted that Ruby was indeed different from other demons and treated her in a friendly manner after she saved Anna's life, and repeatedly tried to protect and guide Castiel despite the fact that he had orders to kill her, because she did not believe he would even try. She held a bitter grudge against anyone who broke that trust or otherwise hurt her, though she would still willing to help that person. Anna was initially timid, distressed, and uncertain when the brothers met her, but became more authoritative and reserved upon regaining her memories and even more so when she regained her grace. She was extremely dedicated to any cause she pledged herself to, as Castiel noted that the only way of stopping her would be killing her. Like Gabriel, she enjoyed sex and sweets.

Anna was dissatisfied with her existence as an angel. She disliked the strict rules governing her, and also admitted to not understanding God. While at first she longed to return to Heaven during her station on Earth, she grew hungry for humanity and risked the wrath of her family by falling for the sake of her own happiness; this shows that Anna had a certain recklessness and selfishness. She feared punishment for her disobedience to such a degree that she had to go to a psychiatrist as a child, but once she repressed her true identity, she became happy and well-adjusted with many friends and a promising future. She resented her siblings for their treatment of her as an abomination, but also wanted their companionship and actively encouraged them to join her. Unlike many other angels, Anna viewed humans as superior to her own kind; she especially valued their capacity for emotions. Her attachment to humanity was one of her strongest traits: she tore out her own grace to experience life as a human, she confessed to Dean that she would have preferred not to turn back into an angel, and she betrayed Sam and Dean in attempt to stop The Apocalypse, which would save billions of lives and preserve free will.

Anna was willing to commit extreme actions for the greater good. She killed her brother Uriel to prevent him from serving Lucifer, as well as to save Castiel. In her desperation to stop the Apocalypse, she decided first to kill Sam to prevent Lucifer from using him as a vessel and then to undo the Apocalypse entirely by killing John and Mary to prevent from Sam and Dean from existing in the first place, despite her alliance with Sam and Dean and her affection for Dean in particular. However, although Anna could not be swayed once she made her decision, she regretted doing what she saw as necessary in attacking the Winchesters, and repeatedly apologized to them.

Powers and Abilities
Anna was implied to have been a powerful angel when at full strength due to her having once been the superior of Castiel and Uriel, who were both formidable in their own right. When Dean challenged them to go after her at the end of "Heaven and Hell", he implied that they were too frightened by her to do so. Whereas Castiel was unable to smite Alastair, Anna's power was such that she destroyed the demon's vessel and sent him back to Hell as a mere side-effect of regaining her grace.

Anna became essentially human without her grace. It seems as though her remaining power only reactivated once Castiel manifested on Earth to save Dean from Hell in "Lazarus Rising", as she is not mentioned as having shown any powers (such as the ability to hear angels) before that time. However, she could not fully control her abilities and tapped into her suppressed potential only under highly stressful situations. When having a mental breakdown in "Heaven and Hell" from remembering her true origins, she caused a door to swing shut without her touching it and made the lights above her short-circuit.

Powers as an angel

 * Chronokinesis - Anna traveled back to 1978, although the effort it took weakened her to the point that she spat out blood and fell unconscious as soon as she succeeded. She also briefly suffered a bout of dizziness while fighting Mary.
 * Clairsentience - She was able to detect that Sam was drinking demon blood, saying that he looked "different".
 * Dream Walking - Anna contacted Dean in "The Song Remains the Same" by appearing in the middle of an erotic dream he was having and causing the strippers he was dreaming about to vanish. As soon as she finished passing on her message, she had Dean wake up to go meet her.
 * Immortality - She is immune to age & illness as well as most forms of physical harm on earth. She has been alive for over 2000 years.
 * Invisibility - Although Anna did not demonstrate this power on-screen, she mentioned that she used to watch over humans invisibly during her station on Earth.
 * Limited Cosmic Awareness - Being an angel she had a greater understanding of the universe than humans, monsters and most demons. She knew of the angel banishing sigil, some of the oldest demons and also the demons plans for the apocalypse.
 * Possession - Anna's original human body was destroyed by the restoration of her grace. She had it recreated by an unknown entity and used it as her human vessel.
 * Invulnerability - Sam noted that both standard weaponry (i.e. knives and guns) and common anti-demon measures (i.e. devil's traps, iron, salt, and holy water) would not kill Anna or even slow her down, and would probably only irritate her. When Mary stabbed her with a crowbar, Anna seemed mostly unfazed, only spitting up a small amount of blood and pulling the crowbar out of her chest.
 * Teleportation - Anna could instantly transport herself to anywhere on Earth. She could do so silently if she wished, as shown when she appeared behind Uriel and caught him off-guard to kill him.
 * Voice Mimicry - Anna imitated John's boss when speaking to John over the phone.
 * Smiting - Even after she fell, she retained the ability to smite, which she did with Mr. Woodson.

Powers as a human

 * Super Strength - It took four human men to restrain Anna. During a moment of panic, she flung Dean across Bobby's Panic Room and into a wall by hitting him with one arm. After regaining her grace, her strength increased to superhuman levels as she had the physical strength necessary to throw adult humans across the room without effort. Once she was an angel again, she was stronger than humans, spirits, monsters, angels and demons.
 * Telekinesis - Anna consciously threw a dresser with her mind with enough force to knock out a possessed human, and unconsciously made the door to the panic room slam shut and lock.
 * Telepathy - Anna heard other angels' conversations in her mind.
 * Astral Perception - Anna saw the true forms of a demonically possessed nurse and of Ruby. She also sensed Castiel and Uriel's approach towards the end of "I Know What You Did Last Summer", though she did not recognize or identify them.
 * Magical Knowledge - Although at that time Anna did not know what it was, she knew how to create an Enochian sigil out of her blood that could temporarily banish angels.

Weaknesses

 * Angel banishing sigil - Like all angels, she could be banished by the sigil.
 * Holy Fire - As an angel, Anna could be trapped or killed by holy fire.
 * Angel Blades - An angel blade could kill her.
 * Higher Angels - An archangel could smite Anna.

Killed By
As Anna tried to kill Mary Winchester in an attempt to prevent Sam Winchester from being born and thus the Apocalypse, the archangel Michael took John Winchester as his vessel. Approaching Anna in the form of John, Michael set Anna ablaze, burning her to ashes and killing her. dean and castiel fuck a anna 5x21
 * Michael

Quotes

 * Anna: Look... I get it. You think I'm nuts. If I were you, I'd think I was nuts. But it's all true.
 * Anna's doctor: It's okay. You can tell me. I'm here to listen.
 * Anna: The end is coming. The Apocalypse.
 * Anna's doctor: "The Apocalypse". Like in the Bible?
 * Anna: Kind of. I mean, same bottom line. This demon, Lilith, is trying to break the 66 seals to free Lucifer from Hell. Lucifer... will bring the Apocalypse. So... smoke 'em if you got 'em.


 * Dean: So, they lock you up with a case of the crazies when really you were just... tuning in to angels radio?
 * Anna: Yes. Thank you.


 * Sam: The angels said you were guilty of something. Why would they say that?
 * Anna: You tell me. Tell me why my life has been leveled—why my parents are dead. I don't know, I swear. I would give anything to know.


 * Anna: Thank you, Pamela. That helps a lot. I remember now.
 * Sam: Remember what?
 * Anna: Who I am.
 * Dean: I'll bite. Who are you?
 * Anna: I'm an angel.


 * Anna: My grace. It's... energy. Hacked it out and fell. My mother, Amy, couldn't get pregnant—always called me her little miracle... she had no idea how right she was.


 * Dean: Why would you fall? Why would you want to be one of us?
 * Anna: You don't mean that.
 * Dean: I don't? A bunch of—of miserable bastards. Eating, crapping, confused, afraid.
 * Anna: I don't know. There's loyalty... forgiveness... love.
 * Dean: Pain.
 * Anna: Chocolate cake.
 * Dean: Guilt.
 * Anna: Sex.
 * Dean: Yeah, you got me there.
 * Anna: I mean it. Every emotion, Dean, even the bad ones... it's why I fell. It's why—why I'd give anything not to have to go back. Anything.


 * Anna: I was stationed on Earth two thousand years. Just... watching. Silent, invisible. Out on the road, sick for home, waiting on orders from an unknowable father I can't begin to understand.


 * Castiel: I'm sorry.
 * Anna: No. You're not. Not really. You don't know the feeling.


 * Castiel: You shouldn't be here. We still have orders to kill you.
 * Anna: Somehow, I don't think you'll try.


 * Anna: The father you love. You think he wants this? You think he'd ask this of you? You think this is righteous? ... What you're feeling? It's called doubt.


 * Castiel: Anna, I don't know what to do. Please tell me what to do.
 * Anna: Like the old days? No. I'm sorry... it's time to think for yourself.


 * Uriel: There is no will! No wrath! ... No God.
 * [Anna appears behind Uriel and kills him with an Angel Blade.]
 * Anna: Maybe. Maybe not. But there's still... me.


 * [Anna suddenly appears in The Impala's backseat.]
 * Anna: Hey, guys.
 * [Dean shouts in surprise and nearly crashes the car.]
 * Anna: Smooth.
 * Dean: You ever try calling ahead?
 * Anna: I like the element of surprise.


 * Castiel: Anna, whatever they sent you here to do—
 * Anna: They didn't send me; I escaped.
 * Castiel: No one escapes.
 * Anna: All this time, and you're underestimating me now?


 * Castiel: We'll find another way.
 * Anna: How's that going? How's the Colt working out? Or the search for God? Is anything working? If you want to stop the Devil, this is how.

Name
Ironically, Anna's first name means "grace". The writers of Supernatural may have also named Anna for Anahita (linked to the earth and harvest), Anauel (of wealth), Ananchel (of grace, believed to put people in a state of religious ecstasy to better praise God), the fallen angel Ananiel (mentioned in the Book of Enoch as a Watcher), or even Haniel (an archangel in Jewish lore who inspires harmony in love). Haniel is sometimes known as Anael, the name of another angel that appeared in Season 13.

Anna's surname alludes to the famous poet John Milton, whose epic work Paradise Lost influences Supernatural, particularly in later seasons concerning angels and Lucifer.

Appearances

 * Season 4
 * I Know What You Did Last Summer
 * Heaven and Hell
 * On The Head Of A Pin
 * The Rapture
 * When the Levee Breaks
 * Season 5
 * The Song Remains the Same

Trivia

 * Anna was intended to replace Castiel, who was supposed to be killed by Alastair in "On The Head Of A Pin", as Dean's angelic guide. Due to Castiel's immediate popularity with critics and fans alike, much of Anna's role was given to him instead. Instead, Anna was the one to be killed off.
 * Anna shared some traits with legendary female warrior Joan of Arc, as both believed they could hear angels speaking, participated in battles as commanders and warriors, and were burned alive.
 * Anna was the first angel to lose her grace and become human, also the first one to be reborn as a human. Her case is unlike or inconsistent with other angels who go through the same process in the future such as Castiel and Metatron, who simply become human and bound to their vessels as their bodies while she was reborn as a human infant and gained her own body.