Anna Milton

Anna Milton originally appeared as an amnesiac angel who had been reincarnated in human form and was being pursued by demons and angels alike. With the help of the Winchesters, she regained her grace and became a rogue angel, helping where she could in stopping the Apocalypse, but she was eventually captured by angels with the help of Castiel, and imprisoned in Heaven.

After the release of Lucifer, Anna attempted to kill Sam Winchester to prevent Lucifer from using him as a vessel, thus effectively stopping the Apocalypse. She was killed by the archangel Michael.

Member of the Heavenly Host
Created by God before the creation of humans, Anna was a fairly high-ranking angel. She commanded a garrison that included "brothers" Castiel and Uriel, and possibly Balthazar, Hester, and Inias. It is implied that Anna and Castiel were once quite close.

Anna was stationed on Earth for 2000 years while invisibly and silently observing humans, waiting for orders, and longing to return home to Heaven; during this time, she came to believe that angels were cold, unfeeling, and without any will of their own when compared to humans.

Losing her grace
Out of the desire to experience life as a human, Anna removed her grace in March 1985, which caused her and her grace to separately fall to Earth as meteorites. She was born as a human child to infertile couple Richard and Amy Milton in northwestern Ohio in December 1985. Meanwhile, Anna's grace landed in Kentucky in a barren field that it caused to flourish, even creating an oak tree in six months that appeared centuries old.

When Anna was a toddler, she repeatedly told Rich that he was not her real father and that her real father was angry at her and was going to kill her. She panicked when Rich even came near her. The Miltons took her to a child psychologist for therapy. As she grew up, she repressed her memories of her true heritage to the point that she genuinely believed she was a normal human. She attended college as a journalism major; according to her psychiatrist, she was happy and well-adjusted with many friends and a bright future.

Hunted
Anna started hearing angels talking in her head on September 18, 2008--the day Dean Winchester was resurrected from Hell. The first message she heard was "Dean Winchester is saved." She heard the angels talk about hunters Dean and Sam Winchester constantly, causing her feel as though she already knew them: she learned that some believed that Dean could save them while some "didn't like" Sam at all. She tried to warn people about the oncoming Apocalypse but was dubbed insane and admitted to the Connor Beverly Behavioral Medicine Center for schizophrenia. She drew pictures of the seals Lilith broke and scribbled messages pertaining to them in a sketchbook as she heard angels talk about them.

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 in November in "I Know What You Did Last Summer" when a demonically-possessed nurse tried to capture her; instead she noticed the demon's true face and knocked it unconscious by telekinetically throwing a dresser at it. She then took refuge at the church Rich worked at as deacon because she was too afraid to return home to the Miltons.

Dean and Sam tracked Anna to the church after Ruby tipped them off about her. Anna asked them about her parents, unaware of that they had already been killed by demons. Before the brothers could tell her, Ruby arrived to warn them that Alastair was coming to take Anna. The brothers fended Alastair off while Ruby used the distraction to discretely take a frightened Anna from her hiding place and take her to safety at a remote cabin. Anna and Ruby reunited with Dean and Sam later. Anna learned about her parents when she asked if she could call them so they wouldn't worry about her, becoming quite distraught and questioning why this was all happening.

Anna sensed the approach of a threat so the Winchesters and Ruby hid her in another room and prepared to take on the unknown enemy: Castiel and Uriel, who had orders to kill her both to prevent demons from extracting information from her and as punishment for falling. However, she banished her brothers in "Heaven and Hell" by slitting her wrists and using the blood to draw out and activate an Enochian sigil. She did not know how she knew to do so.

Regaining her grace
The four of them went to Bobby Singer's house so Anna could be protected in the demon-proofed panic room. Dean called Pamela Barnes for help in figuring out more about Anna's past and why she could hear angels. Pamela put Anna into a hypnotic trance. Although it seemed that Anna went through a mental breakdown that almost destroyed the room, the hypnosis worked; she finally remembered her origins and decided to regain her grace to save herself from both demons and other angels.

Anna argued with Dean about whether or not humanity was better than being an angel. She explained how unhappy she had been while stationed on Earth and awaiting orders from a father she had never even met, something that Dean sympathized with due to his experiences with his own father.

Sam managed to determine find where Anna's grace had landed, but when the group arrived, Anna discovered that it was gone--it had already been taken by Uriel. 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. Believing that she deserved to be punished for disobeying as Lucifer had, she resigned herself to her fate.

Anna revealed to Dean 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. She 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 they 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 pit them against each other.

Castiel and Uriel confronted Anna and the Winchesters in a barn. Although Anna forgave Dean for "betraying" her, she did not forgive her brothers for their actions. Regardless, she ordered her former soldiers to execute her quickly. The angels were stopped by Ruby bringing Alastair and two other demons to the barn.

While Uriel was distracted by killing the demons, Anna noticed he had her grace. She managed to grab it, broke the container it was in, and painfully absorped it back into her body. She ordered the Winchesters and Ruby to shut their eyes before her body was destroyed in a bright, white light that also destroyed Alastair's host body.

Afterward, Castiel and Uriel departed. While Sam believed Anna would be happier as an angel, Dean remembered her earlier conversations with him and knew she was not.

Renegade angel
Although Anna's body was destroyed when she regained her grace, she managed to get it restored through "favors" owed to her by an unspecified entity. She used it as her vessel out of sentimentality.

Anna came to speak with Castiel in "On the Head of a Pin". He warned her that he still had orders to kill her for her disobedience, but she brushed it off, saying, "Somehow, I don't think you'll try." They discussed the orders he was following by making Dean torture Alastair to learn who killed seven angels from their garrison; Anna suspected that God was not the one giving such cruel orders (and was later proven right) 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 considering disobedience. She sympathized with his confusion and terror; however, she was upset because he still regarded her as "a walking blasphemy". He wanted her to give him orders to follow again, but she refused so that he could learn to exercise free will.

Uriel revealed that he had been killing the other angels and prepared to kill Castiel when the latter refused to join him in following Lucifer. Anna intervened by stabbing Uriel through the neck with a sword, killing him and saving Castiel. She and Castiel watched on together as Uriel died.

Castiel eventually had a change of heart that led to his being brought into Heaven for reconditioning. Dean and Sam tried to protect his depossessed vessel, Jimmy Novak, from demons, but Jimmy fled to reunite with his family. Anna teleported into the backseat of the Impala to inquire about Jimmy's whereabouts, nearly causing Dean to crash the car in shock at her sudden appearance. She deflected Dean's flirting and noted, troubled, that Sam seemed "different". When she learned that Castiel had wanted to tell Dean something important, she urged Dean and Sam to find Jimmy but feared that he was already dead.

Anna was horrified and angered when Castiel released Sam from Bobby's panic room during demon blood detox in "When the Levee Breaks". She confronted Castiel, but was captured by two other angels and taken to Heaven in the process. She henceforth developed a grudge against Castiel for betraying her to the Heavenly Host.

Imprisonment
Anna was imprisoned in Heaven for the remainder of the fourth season and the majority of the fifth.

Like Castiel, Anna was tortured extensively. It is unclear whether she was tortured because the other angels were trying to punish her for disobeying, to break her and make her revert into being a willing member of the Heavenly Host again, or both.

Mission to prevent Sam's birth
Anna either escaped or was released from Heaven in "The Song Remains the Same". To stop Lucifer from using him as his vessel, she tried to kill Sam then scatter his cells across the universe in order to prevent Lucifer from resurrecting him.

Anna was unable to simply teleport to the Winchesters due to Enochian sigils Castiel had carved into their ribcages, forcing her to invade Dean's dreams and give him an address to meet her at to lure him and Sam to a warehouse. At the warehouse, she was confronted by Castiel, who had convinced the Winchesters to stay behind because he did not trust her. When pressured, she confessed her plans to kill Sam to prevent the Apocalypse. He 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 go back in time to 1978 after Dean had been conceived so that she could prevent Sam's birth altogether by killing John. However, the effort it took to go back in time weakened her. She 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. However, Castiel had brought Dean and Sam back in time to stop her. Dean and his mother held Anna off long enough for Sam to banish her with a blood sigil.

Anna enlisted the help of the Uriel of 1978. He recognized that she was not the Anna of 1978, but she lied 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.

Anna and Uriel 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 by stabbing him in the stomach with a fixture she ripped from a wall. Afterward, she apologized to a shocked Mary.

Death
After Anna had thrown John through the wall and into the backyard, he gave his consent to Michael for possession in exchange for Mary's safety. Michael approached Anna, laid his hand on her shoulder, and set her ablaze from within. She screamed in agony before dying.

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.

After removing her grace, Anna became a mostly normal human. 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 high stress situations.


 * Super-strength: It took four men to restrain her.
 * Clairaudience: She telepathically heard angels' conversations.
 * Telekinesis: She was able to throw a dresser with her mind.
 * Clairvoyance: She could see the demonic true faces of a possessed nurse and Ruby.
 * Precognition: Her drawings from her time in the psychiatric ward may indicate that she could see into the future.
 * Clairsentience: She 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 she didn't know what it is was, she knew to create a sigil out of her blood that could temporarily banish angels.

After reclaiming her grace, Anna regained the rest of her angelic abilities.


 * Angelic possession: Her original human body was destroyed by the restoration of her grace. She had it recreated and used it as her human vessel.
 * Teleportation: Like all angels, Anna can teleport but can do so silently if she wishes as shown when she teleported behind Uriel and caught him by surprise.
 * Time travel: She successfully travelled back to 1978, although as soon as she arrived she spat out blood and went unconscious.
 * Voice mimicry: While on the phone with John, she altered her voice to sound like his (male) boss.
 * Extreme endurance: When Mary Winchester stabbed her with a crowbar, Anna seemed unfazed, spitting up a small amount of blood and pulling the crowbar out of her chest without much effort.

Name
Ironically, Anna's first name meant "grace". In fandom, her name before she fell is often changed to a variation of "Anael". There is an archangel in Jewish lore known as Haniel, Hanael, Anael, or Aniel who is associated with love and beauty. The writers of Supernatural may have also named Anna for the fallen angel Ananiel who is mentioned in the Book of Enoch as a Watcher.

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.

Season 4

 * "I Know What You Did Last Summer"
 * "Heaven and Hell"
 * "On The Head Of A Pin"
 * "The Rapture" (cameo)
 * "When the Levee Breaks" (cameo)

Season 5

 * "The Song Remains the Same"