| Before humanity - 1985 (fell)
1985 - 2010 (killed by Michael)
| 4.09 I Know What You Did Last Summer
4.10 Heaven and Hell
4.16 On the Head of a Pin
4.20 The Rapture
4.21 When the Levee Breaks
5.13 The Song Remains the Same
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, so don't tell me that...
– Anna Milton, 4.10 Heaven and Hell
Anna Milton is an angel who removed her grace, fell to Earth, and was born human. As a human child Anna still remembered being an angel, however the older she got and the longer she stayed human she ultimately forgot who and what she really was. Anna was able to live a normal life, becoming a journalism major. Until 2008 when she began to hear the angels speak to each other and had what her parents assumed was a psychotic break and was institutionalized at the Connor Beverley Behavioral Medicine Center on 9th September 2008. Upon regaining her grace, all of her angelic abilities were restored, but her human body was destroyed. It was later regenerated, after Anna called in some "old favors" so that she could inhabit it as her vessel.
Without her grace, Anna could hear angels communicating in Heaven, move objects with her mind, exhibit superhuman physical strength, see the true faces of demons, and draw upon her hidden angelic knowledge to draw an angel banishing sigil.
Anna's abilities as an angel were similar to those of other angels. Anna was able to easily overpower humans, and can telekinetically move objects and people. Looking on Anna's true form could burn out a human's eyes, her true voice was piercing to the human ear and her angelic presence could shatter lights. Anna was able to teleport herself through time and space, including silently if necessary. Anna, like all other angels, was vulnerable to an angel blade.
Anna Milton is being held in a psychiatric institution (Connor Beverley Behavioral Medicine Center) because she has been trying to warn people that the apocalypse is coming, and that the voices she hears told her so. She actually does hear voices - those of the angels. She knows that Lilith is trying to break the 66 Seals and release Lucifer. When a demon tries to kill her she manages to escape, using some form of psychic power in the process. She takes refuge in the church in which her father was a deacon.
Ruby alerts Sam and Dean to her plight and they track her down. At her house, they find her parents dead. They then discover Anna at her church. She recognizes them, and says she has heard the angels talking about Dean, as the one who may save them. She reveals that some of them don't like Sam. The demon Alastair then appears. He is immune to Sam's powers, and beats Dean, who had encountered him in Hell. In the chaos, Ruby takes Anna to safety, even though Anna is scared because she can see Ruby's demon face. Later, Sam and Dean meet up with Ruby and Anna. Castiel and Uriel arrive at their hideout to take Anna, with Castiel announcing "She has to die."
While the Winchesters and Ruby attempt to fight off Castiel and Uriel, Anna slits her wrists and draws an angel banishing sigil in blood that casts the angels "far away." When asked, she states that she does not know how she knew what to do. Later, with the help of Pamela Barnes, who places Anna in a hypnotic trance, Anna is revealed to be an angel. She is the former superior of Castiel and Uriel, who chose to rip out her grace and fall to Earth, where she was born as a human. Her disobedience is why the angels want to kill her.
Anna suggests that if she has her grace restored she will be able to protect herself. Sam determines where Anna's grace fell to earth by analyzing signs from the time of Anna's conception on Earth. It was mistaken for a meteor, and created a massive oak tree when it touched down. But when Anna, Ruby, and the Winchesters get there they find that the grace has been taken. Anna then gets a messages from the angels demanding that she be turned over to them by midnight or Dean will be returned to Hell.
She speaks to Dean of her frustrations with being an angel, particularly the blind obedience to God and the lack of emotion. Anna explains that she has never seen God, and that in fact only four angels have. She reveals that she knows what Dean did in Hell and encourages him to forgive himself. She then kisses him, and they have sex in the Impala. Later Uriel appears to Dean in a dream and reveals the he is carrying Anna's grace in a vial around his neck. He reiterates the ultimatum, and adds that either Anna will die, or Sam will.
When Castiel and Uriel appear in person the next morning, it seems that Dean has betrayed Anna and is handing her over. In fact, it is part of a ruse to bring the angels and demons (in the form of Alastair and his hench-demons) together to rid the Winchesters of both. A fight ensues, during which Anna steals her grace back from Uriel. She breaks the vial and shouts to Dean, Sam and Ruby to close their eyes. Her transformation back into an angel involves an overpowering white light, and destroys her human form and causes Alastair to disappear. When the light subsides, Anna is gone, presumably back to Heaven, where Dean imagines she is not happy.
As Dean is torturing Alastair, Anna appears and challenges Castiel about what he is doing and why he thinks God would order torture. Cas is reluctant to listen to her as she is still wanted dead and she encourages disobedience. Anna also explains that she managed to get her human body restored to act as her vessel. She encourages him to rebel, but he rejects the offer. Later as his doubts grow, he calls on Anna and asks her for guidance, but she says he must choose his own course of action. After Uriel's treachery is revealed, Castiel refuses to "convert" and follow Uriel's plan and the two fight. Uriel wins, but Anna sneaks up behind Uriel and kills him with his own angel blade.
Anna visits Dean and Sam and tells them that Castiel was sent back to Heaven, and that Castiel knew something important. His vessel, Jimmy Novak, may know it too, and she encourages Sam and Dean to find him.
Anna appears in a dream to Dean. She tells him she has been held prisoner and tortured in Heaven because Castiel turned her in. Because of the Enochian sigils on his ribs, she can't find Dean and asks him to meet her. Castiel arrives instead, and suggests that she has been sent on a mission from Heaven, which is the only way she could have been released. She denies this initially, insisting she is following her own agenda. Anna eventually confesses that she intends to kill Sam to prevent Lucifer taking him as his vessel. Castiel protests, pointing out that Sam is not Lucifer's only Vessel, but Anna states that Nick is falling apart as she and Castiel speak, and Sam is the only potential Vessel that matters. Castiel says he is willing to kill Anna to protect Sam.
When Castiel refuses to help her kill his friend, Anna vanishes, and travels back to 1978 intending to kill Sam's parents and prevent his birth. She is injured when she arrives in the past, indicating that she did not have the power of Heaven behind her when she time traveled. When Castiel takes Sam and Dean back in time to stop her, she lures John Winchester away from them by posing as his boss in a phone call. At the garage where John works, the body of a young man whose eyes were mysteriously burned out is found, implying that this human had spied on Anna’s true form, and was killed as a result. Anna is unsuccessful in her first attempt on John and Mary's lives, and is temporarily banished with the angel banishing sigil.
Anna next enlists the help of a younger Uriel to kill the Winchesters. However Michael arrives from the future, killing Anna for trying to interfere with his plans, and sending Uriel back to Heaven. In this episode, Anna wielded a blade with which she intended to kill Sam; Castiel pointed out it was not a blade that could kill angels. This knife was knocked from her hand during one of the fights. She instead pulled a pipe from a hole in the wall and used that to stab Sam. He was severely injured. However, Sam was healed when Michael returned the brothers to present day after Anna's death, so her mission was not accomplished.
- There is a discrepancy as to when Anna was born: on the patient history form Sam looks at, it says that Anna's date of birth is April 13, 1985. However, later in the episode Sam says, In March '85, a meteorite vanished in the night sky over northwestern Ohio. It was sighted nine months before Anna was born and she was born in that part of Ohio, which would put her birthday in December of 1985.
- When Anna removed her grace and was reborn human on Earth, she didn’t inhabit a human; she had her own body. When she reclaimed her grace, her human body was destroyed, which forced her to call in some favors to have her human body reconstructed so that she could occupy it.
- Her surname, Milton, may be a reference to the writer John Milton who wrote the epic poem Paradise Lost. The poem describes the fall of man, the tempting of Adam and Eve, and their being banished from the Garden of Eden. Milton also made reference to fallen angels, Lucifer, the war in Heaven, and the relationship between Heaven and Hell.
- Anna was given the same name as an infant that she had as an angel, which indicates that Richard and Amy Milton were supernaturally influenced - possibly by Anna herself - in the choice of their newborn daughter's name.
- Julie McNiven suggested that Anna's full angelic name was actually Anael, who is an angel in real-world lore, which would make "Anna" a nickname for her by other angels, similar to "Cas" for Castiel. Fans have speculated that Anna was one of the angels in lore with "Ana-" names ever since the reveal of her true nature; Anael just so happened to be the most common pick. This is dispelled with the appearance of Danneel Ackles' character Anael in 13.13 Devil's Bargain.
- Canon timeline discrepancy: In 4.09 I Know What You Did Last Summer, Anna states that she was institutionalised after she began hearing the angels' voices. She then goes on to state that she first heard these voices on September 18th 2008 when she heard "Dean Winchester is saved". However, in 4.10 Heaven and Hell, on her patient history form from Connor Beverly Behavioral Medicine Center, it states she was admitted to the hospital on "09/10/08" (10th September 2008).
Anna in Fandom
- @GracelessAngel_ - Twitter Roleplaying account.
- A Haven for Anna Fans - LiveJournal community
- RP Tumblr blog - AU, Narrative, Gen
- Mitovich, Matt. 2008. Supernatural Angels Want Mad Men's Hildy Dead. TV Guide, November 13; archive link
- Sablegreen. 2011. Sablegreen's Exclusive Interview With Julie McNiven. The Winchester Family Business, May 26; archive link
- Illustrated meta on Anna by tirra-lyrra (July 2009); archive link
- Okay so I’m about to talk about Anna Milton and why I think people should reconsider their dislike of her, or at least respect her as a character by potterstyles (September 2012); archive link
- Anna’s reincarnation into the same vessel by cinemeta (July 2013); archive link
- Anna Milton Meta: The Lioness, the Leader, the Sacrificial Lamb by arcadianambivalence (October 2013); archive link
- Cas/Anna and Hael/Cas parallels by beespatellas (November 2013); archive link
- Comparing the Deaths of Anna and Rachel by arcadianambivalence (March 2014); archive link
- The Frustrating Saga of Anna’s Growing Influence on the Show Going Unacknowledged by mrsbluebertgreggleson (April 2015); archive link
- They could have said Gadreel learned of Dean and Cas' mission from Anna while they were both in Heaven jail (Untitled) by larinah, mrsbluebertgreggleson (April 2015); archive link
- "There's Still Me": A Truly Massive Anna Milton Meta by susurrantpetrichor (May 2013-14); archive link