|“||It's the archangel! I'll hold him off! I'll hold them all off! Just stop Sam!||”|
|“||I learned that from my friend Cass you son of a bitch!||”|
After going to Hell, hunter Dean Winchester inadvertently began The Apocalypse by breaking the first of the 66 Seals. Dean was eventually rescued by the angel Castiel and began working to attempt to stop the demon Lilith from bringing about the Apocalypse by breaking the remaining seals.
With only one final seal left to break, Dean was kidnapped to the Green Room by Castiel and his superior Zachariah. There, Dean learned that the angels actually intended to allow the Apocalypse to happen in order to achieve paradise on Earth through the final defeat of Lucifer by the archangel Michael. Due to the carnage this battle would cause, Dean appealed to Castiel to help him stop the angels' plan. Castiel eventually rebelled, banishing Zachariah and revealing to Dean that killing Lilith would break the final seal. Unaware of the location of the last seal, Castiel decided to take Dean to the home of Prophet Chuck Shurley who would have seen it due to his nature as a Prophet.
Arriving at Chuck's house, Dean and Castiel learn from Chuck's latest manuscript that Lilith will be at St. Mary's Convent. Chuck warns that the two aren't supposed to be there as "you aren't in this story," but Castiel tells Chuck that they are making it up as they go along.
As they look over the book, the house begins shaking and is filled with bright light. Realizing what's happening, Castiel warns Dean that the archangel protecting Chuck is coming. Promising to "hold them all off," Castiel teleports Dean to St. Mary's Convent while remaining behind with Chuck to face Raphael. Ultimately, Castiel proves to be no match for Raphael and is blown apart on the molecular level by Raphael, killing Castiel and leaving Chuck's house a mess.
After failing to stop the Raising of Lucifer, the Winchesters return to Chuck's house in search of Castiel and find it to be a mess. As they search for Chuck, Sam is hit in the head by him out of fear of who Sam initially is. Chuck expresses surprise that Sam is okay since his last vision where Sam killed Lilith had Sam's eyes turn black and Sam gain a body temperature of 150 and a heartrate of 200. Sam admits that he didn't know that his eyes had turned black when Lilith died.
Dean asks about Castiel's fate and learns that Castiel is dead as "the archangel smote the crap out of him." Sam notices that Chuck has one of Castiel's molars in his hair and points it out to him, leading to Chuck freaking out about it while Dean mourns Castiel's sacrifice. As the Winchesters argue, Chuck senses the angels coming.
Moments after Chuck senses them, Zachariah appears with two other angels. Zachariah tells Dean that "playtime is over" and that its time for Dean to come with them. However, Dean orders Zachariah to keep his distance. Dean angrily states that the angels jumpstarted Judgement Day, but Zachariah, while admitting that they let it happen, deflects the full blame for the Apocalypse beginning on Sam. Zachariah tells Dean that they need to set aside their differences with the Apocalypse having begun and that they have a common enemy as the angels want Dean to kill Lucifer.
Dean refuses to side with Zachariah because of his manipulations as the angel warns that Lucifer is "powerful in ways that defy description" and that they must strike hard and fast to get Lucifer before he can find his vessel. Sam is surprised to learn that Lucifer needs a vessel, but Zachariah reminds him that Lucifer is still an angel "and them's the rules." Zachariah warns the brothers of the destruction Lucifer will wreak upon the Earth once he "touches down" and states that Dean can still stop him, but he will need the angels' help. However, Dean still refuses stating that he doesn't want "jack squat" from the angels.
Zachariah advances on Dean angrily but stops short after seeing that Dean has a bleeding hand. Dean comments that its an "insurance policy" he created in case the angels showed up and reveals a hidden angel banishing sigil on a sliding door. As Zachariah moves to stop him, Dean uses the sigil to banish the three angels from the house. "I learned that from my friend Cass you son of a bitch!"
Following the encounter with Zachariah and his men, Sam creates hex bags to hide them from both the angels and the demons. Despite this, Zachariah manages to lure them into a trap using a false prophecy he implanted in Chuck's mind. However, the trap is foiled by a resurrected Castiel who brands the Winchesters with sigils that hide them from all angels. Its eventually revealed that following his death at Raphael's hands during the battle, Castiel was resurrected by God to help stop the Apocalypse.
- During this skirmish, Dean Winchester uses an angel banishing sigil to get rid of Zachariah and his men. This is the first of many times that the Winchesters will come to use the sigil as an effective defense against angels.
- Dean states that he learned the angel banishing sigil from Castiel, presumably referring to when Castiel used it to banish Zachariah in Lucifer Rising. However, this is not the first time Dean has seen the sigil used as Anna Milton previously used it in Heaven and Hell to banish Castiel and Uriel.
- During both Lucifer Rising and Sympathy for the Devil the archangel involved in this skirmish that killed Castiel is unnamed. During Free To Be You and Me its revealed to be Raphael.
- This fight is the first of five times on the series that Castiel dies and is ultimately resurrected.
- Unknown to the Winchesters or Castiel, the Prophet Chuck Shurley whose house the fight took place at and who was with Castiel when he died was actually God in disguise as revealed in Don't Call Me Shurley.