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Exodus 20

Sam and Rowena

I don't care about anything enough to take my own life. Not you, your brother -- not even the world. But I believe in prophecy. I believe in magic. And I'm here and you're here and everything we need to end this right is in our hands. I know this in my bones -- it has to be this way. Do it! Kill me, Samuel! I know we've gotten quite fond of each other, haven't we? But will you let the world die, let your brother die, just so I can live?
Rowena convinces a reluctant Sam to kill her.
in The Rupture

Sam Winchester and the witch Rowena MacLeod have a complicated relationship. Starting out as mortal enemies, they evolved into friends and even something of a mentor-student relationship. The complicated nature of this relationship is highlighted by the fact that Sam was fated to be Rowena's one true killer.

Background

The relationship between Sam and Rowena is a complicated one in general. Due to Rowena's evil nature originally, the two often found themselves at odds and only reluctantly working together for situations of mutual benefit. As Rowena proves to be untrustworthy, Sam often works with her under supervision and iron chains.

Following her Rowena's death at the hands of Lucifer and her subsequent resurrection, a situation in which she had betrayed the Winchesters and Crowley to help Lucifer, their alliance became somewhat less reluctant and more willing in nature with Rowena helping the Winchesters against Lucifer and the Darkness to save the world. With Rowena having a change of heart following the war with the Darkness, she became more of a willing ally, coming to the Winchesters aid against the Loughlin Family and helping with her grandson Gavin after Sam calls upon Rowena for help. In both cases, she had something to gain for herself, but also put herself into danger against the Loughlin's to help save Dean.

After Rowena's second death at the hands of Lucifer and subsequent resurrection, her relationship with Sam became closer due to the two sharing traumatizing experiences at the hands of the archangel, giving them a greater understanding of each other. As a result, Sam gave Rowena the ritual she needed to remove the bindings on her powers so that she could protect herself. Not long later, the relationship took on a whole new dimension when Sam and Rowena learned that every version of her final fate had Sam as Rowena's one true killer. Despite this, Rowena couldn't bring herself to kill Sam and began seeking redemption at his suggestion, becoming more selfless in her actions and helping while asking for nothing in return. Following the death of Mary Winchester, Rowena attempted to help bring her back because of how devastated Sam and Dean were, even creating a resurrection spell for the job as was later revealed. In addition, Rowena and Sam's relationship took on a more mentor-student turn with Sam learning various things about the practice of witchcraft from Rowena. During the Sanetur Acre Vulnus spell, Rowena called Sam the closest thing they had to a witch besides her and trusted Sam to act as her assistant in casting the spell.

At the end of Rowena's life, Sam and Rowena had changed from mortal enemies to close friends who cared deeply about each other. When Rowena ultimately met her fate at Sam's hands, it was at her own request so she could sacrifice herself to save the world, a request that drove Sam to tears. When Sam fatally stabbed Rowena, he hugged her at the same time as a final gesture of comfort. Rowena's death had a profound impact on Sam who continued to reel from her loss for some time afterwards.

Sam would be later be called Rowena's protégé by Dean while it was implied that Rowena intended for Sam alone to inherit her magical stash, including the journals chronicling Rowena's lifelong spellwork. Rowena's journals helped Sam again by allowing him to use one of her spells to resurrect old friend Eileen Leahy. At the same time, Sam was able to kill a witch using a powerful spell and hex bag he created, something Sam credited as having learned from the best, Rowena.

Season 10

In Girls, Girls, Girls, Rowena first comes to Sam's attention when she kills the demon Raul with the Defigere Et Depurgare spell. Sam identifies Rowena as the culprit as she is the only witch to know that particular spell. The meeting between the two is brief before Rowena casts the Attack Dog Spell on Elle and runs off chased by Dean, leaving Sam to fight off the girl who ultimately dies from the spell. Subsequently, in About a Boy, the Winchesters learn from Katja that she was sent by the Grand Coven to hunt Rowena.

In Book of the Damned, Sam is surprised to learn that Rowena is Crowley's mother and had revealed that the Mark of Cain was a curse. After being unable to decode the Book of the Damned, Sam seeks out Rowena's help at the end of Book of the Damned and the beginning of The Werther Project. Rowena offers Sam a deal to help remove the Mark of Cain in exchange for Sam killing Crowley which he accepts, but becomes frustrated when she reveals that she can't currently read the Book of the Damned. Following Rowena's instructions, Sam searches for Nadia's Codex which can be used to read the Book of the Damned, seeking Rowena's advice for a disenchantment spell, but rejecting her help otherwise. Sam's hallucinations under the Werther Box take the form of Rowena supposedly helping and encouraging him. After getting the codex, Sam brings it to Rowena, but chains her up until she can find the spell as he doesn't trust her.

In Dark Dynasty, Sam becomes frustrated when Rowena reveals that she can't read the codex and assembles a team to help her, but has to spend time away due to Dean's growing suspicions.

In The Prisoner, following the death of Charlie Bradbury, Sam prepares to end the ongoing efforts on Dean's orders and makes it clear to Castiel that he intends to kill Rowena. However, after getting an email from Charlie containing her decoder, Sam changes his mind when Rowena confirms that she can use it to read the Book of the Damned. However, Rowena forces Sam to keep up his end of the deal by refusing to do so until Sam kills Crowley. Sam attempts to kill Crowley with the Defigere Et Depurgare spell as per Rowena's instructions, but fails and Rowena refuses to do anything until Sam succeeds.

In Brother's Keeper, Sam creates the witch-killing bullets to try to threaten Rowena into helping, but she is unthreatened as she knows that Sam needs her help and can't actually kill her. Instead, Rowena negotiates for her freedom and the codex which Sam accepts when she confirms that she knows which spell she needs. Sam helps with planning for assembling the ingredients, but has to leave to deal with Dean. Rowena subsequently removes the Mark of Cain, but casts the Attack Dog Spell on Castiel, forcing him to attack Crowley while she escapes with the Book of the Damned.

Season 11

In The Bad Seed, Sam captures Rowena to force her to break the Attack Dog Spell on Castiel, making a deal with her to do so in exchange for her freedom. Sam is frustrated however when they only recover Charlie's decoder and Nadia's Codex from Rowena's belongings, but not the Book of the Damned. When Castiel escapes due to the spell overtaking him again, Rowena reveals her deal with Sam to Dean while they search for him though she fails to drive a wedge between the Winchesters. When they find Castiel, Sam holds Rowena at gunpoint with witch-killing bullets to ensure her cooperation, but she disarms him and escapes afterwards. Despite Rowena's escape, Sam is still left pleased as they got Castiel back to normal and without the decoder and codex, Rowena's use of the Book of the Damned should be more limited.

In O Brother, Where Art Thou?, Sam, Dean and Crowley are forced to seek out Rowena's help to speak to Lucifer in Hell. Though Sam allows Rowena access to the decoder and codex so she can translate the spell in the Book of the Damned, he's careful to keep her on task and away from reading the other spells. While Rowena succeeds in helping Sam speak to Lucifer, the warding suddenly fails and Sam is captured by the archangel. In The Devil in the Details, its revealed that Rowena betrayed them and was working with Lucifer the whole time to help Lucifer escape the Cage with Sam as his vessel. Using a Witchcatcher, Dean and Crowley force Rowena to help them send Lucifer back into the Cage, but are left unaware that he took Castiel as his vessel and escaped before killing Rowena.

In Hell's Angel, Crowley reveals Rowena's death to the Winchesters while negotiating with them for a Hand of God in exchange for helping to get rid of Lucifer. Sam is annoyed as they need both Rowena and the Book of the Damned to lock Lucifer away again as Crowley wants and they have neither. Sam is the first to notice a resurrected Rowena's message as Dean and Crowley argue. While preparing to combat Lucifer, Sam and Rowena don't interact much, but he seems uncomfortable with her presence and not totally pleased to see her.

In We Happy Few, Sam is the one to suggest seeking out Rowena's help against the Darkness, calling Rowena "a snake," but a powerful witch who has the Book of the Damned on her side. Sam is the one to approach Rowena for help and get her and Clea on board with the plan. In Alpha and Omega, after God is mortally wounded by the Darkness, the Winchesters and Rowena continue their alliance as they try to save the universe from destruction. Rowena helps build the Soul Bomb to kill the Darkness and remains with Sam, Crowley and Castiel until they see the sun being restored, showing Dean's success.

Season 12

In LOTUS, the Winchesters, Crowley, Castiel and Rowena team up to exorcise Lucifer out of the President and return him to Lucifer's Cage in Hell. By this point, Sam, Dean and Rowena's interactions have taken on a less antagonistic quality due to Rowena's change of heart following the war with the Darkness. Together, they apparently succeed in sending Lucifer back to Hell. However, Crowley and Rowena flee immediately afterwards, leaving Sam and Dean to deal with the aftermath and the Secret Service.

In Regarding Dean, Sam and Rowena's relationship has improved to the point that Sam is able to call for help when Dean is cursed by a witch. Though Sam originally only sought Rowena's advice, she shows up in person to help and identifies the culprit as Gideon Loughlin. Sam becomes suspicious of Rowena's supposed altruism until she reveals that they need the Black Grimoire to break the curse, causing Sam to believe that she only wants the spellbook for herself. Dean's deteriorarting condition forces Sam to put aside his mistrust and accept her help, but he refuses to trust Rowena enough to take her along, instead leaving Rowena to guard Dean while he forces the Loughlin Family to reveal the reversal spell over the phone to her. However, things go bad and Sam is captured. Instead of abandoning him and Dean, Rowena goes to help herself, though its revealed that she and the Loughlin's have a bad history. Rowena is nearly killed by Catriona Loughlin in the process, but is saved by Dean who kills Catriona and Boyd. Afterwards, Rowena breaks the curse and tries to leave with the Black Grimoire. Though Sam stops her, he admits that they owe Rowena for her help.

In Family Feud, Sam contacts Rowena again when he and Dean learn they must find Rowena's grandson Gavin MacLeod for help with dealing with a vengeful spirit. Rowena did not want to partake in the matter until Sam promised compensation for her help and then told her about Gavin. With Gavin's help, Sam and Dean were able to identify the ghost and find a solution on how to stop it - by sending Gavin back in time. Rowena shared their view that Gavin should return, and even helped the brothers keep Gavin away from his father Crowley, who did not want to lose Gavin. Rowena tweaks the spell for Sam and Dean to be able to send Gavin back to his time, but later admits to Crowley that her actions were in part to get revenge for Crowley forcing her to murder Oskar to remove the Mark of Cain.

In All Along the Watchtower, the Winchesters seek Rowena's help again after learning that Lucifer is still on the loose in the body of Nick. However, Rowena is revealed to have been brutally murdered by Lucifer. Sam is visibly furious about this, especially since he had intended to use Rowena to lock up Lucifer for good, this being the very reason Lucifer had killed Rowena in the first place. After this, Sam and Dean believe that Rowena is truly dead, even telling Crowley as much as Lucifer had crushed Rowena's head and burned her body.

Season 13

In Various & Sundry Villains, Rowena is revealed to be alive, having been resurrected again following her death at Lucifer's hands. Rowena reveals that she is seeking the Black Grimoire to unbind her full powers to protect her from Lucifer who she believes will inevitably come back. Sam and Rowena briefly bond over their shared trauma of seeing Lucifer's true face and the torture they suffered at his hands. Though Rowena briefly betrays them again, she also saves the Winchesters from the Plum sisters. Sam refuses to let Rowena take the Black Grimoire, but silently gives her the page she needs when Rowena pleads with him as Sam knows from personal experience where her fear comes from. Sam admits to Dean that if Rowena plans to backstab them again he will hunt her down and shoot her himself but he also hopes that if Rowena ever reencounters Lucifer, she will make the archangel suffer. Thanks to Sam, Rowena is able to regain her full power.

In Funeralia, after Rowena goes about killing people, Sam feels guilty since he let her obtain her full power. It is revealed by Jessica, that according to every version of Rowena's final fate, Sam is the one to permanently kill Rowena and he is shocked to learn this. When Rowena calls them and tells them she wants her son back, Sam asks her to stop while Dean threatens her with the revelation of Sam being the one to permanently kill her which leaves her mildly surprised and interested. After failing to convince Rowena to stop, Sam reluctantly tries and fails to kill Rowena with a witch-killing bullet, shocking Rowena that he would actually go through with trying to kill her. Rowena captures Sam and threatens his life in an attempt to bargain with Death, using Sam's fate as her true killer to her advantage. Though Billie still refuses to resurrect Crowley, Rowena can't bring herself to harm Sam. In the aftermath, Sam encourages Rowena to try to change her fate and seek redemption, an idea she finds appealing even though Rowena isn't sure that its possible. However, Rowena is comforted by the fact that with Sam being fated to be her true killer, she knows Lucifer ultimately can't permanently harm her.

In Beat the Devil, the Winchesters, Castiel, Rowena and Gabriel work together to open a rift to Apocalypse World and finally rescue Mary and Jack, capturing Lucifer to act as a power source for the rift. However, Sam is disgusted along with the others when Rowena and Gabriel almost have sex with each other. After Rowena accidentally blasts Lucifer through the rift, she finds herself unable to abandon Sam and the others and remains to try to keep the rift open long enough for them to return.

In Exodus, Rowena keeps the rift open long enough for the Winchesters and Apocalypse World refugees to return to the main universe. While everyone is celebrating, Sam and Rowena talk and he congratulates Rowena for holding the rift open long enough to get everyone back. Sam admits that they owe her one and Rowena tells him that she plans to collect on it eventually, but smiles at Sam as she says it and the two share a drink.

Season 14

In Unhuman Nature, Sam contacts Rowena for help after Jack falls ill, lying to her that it is Dean that needs her help. Rowena is less than pleased to learn that Sam lied to her and that it is Lucifer's son that requires her help, but her compassion for Jack causes her to stay and help. Rowena is able to diagnose Jack's condition using a spell from the Book of the Damned and is distressed when the attempt to save Jack fails and she has to report that all they can do is be there for Jack as he dies.

Fine. Don't tell me. But using dangerous, mysterious magic, regardless of the cost. That's a very on-brand 'me' thing to do.
Well, thank you.
Of course, Samuel. Until very recently, I was the villain.
— Rowena and Sam discuss Sam's secrets regarding Jack.
in Ouroboros

In Ouroboros, Rowena aids Team Free Will 2.0 on a case and works closely together with Sam. Together, Sam and Rowena determine that they are dealing with a gorgon and work with Jack to get the anti-venom Rowena needs to create an antidote for gorgon venom. After detecting the magic that is keeping Jack alive, Rowena is disturbed and concerned by what she senses and confronts Sam about it. Sam brushes off her concerns which Rowena accepts, admitting that using dangerous off-brand magic is a very her thing to do before reminding Sam that until recently, she had been the bad guy. It is the Apocalypse World Michael's threats against Sam and Dean that ultimately get Rowena to consent to being his vessel, something that horrifies Sam to see. However, she is saved when Jack taps into the power of his soul, exorcises Michael from Rowena and kills the archangel.

In Absence, after Mary Winchester is accidentally killed by a soulless Jack, the Winchesters contact Rowena who determines that Mary is nowhere on Earth and effectively confirms their mother's death for Sam and Dean. At their request, Rowena looks for a way to resurrect Mary using the Book of the Damned, going so far as to help Jack with his efforts to use the Necromantiorum despite her concerns about his state of mind. However, after learning that Jack lacks Mary's body, Rowena refuses to perform the spell out of concern that something will go wrong and warns Sam and Dean. As is later revealed, Rowena began working on creating another resurrection spell to get around the lack of a body limitation, but stopped when she found out that Mary was happy in Heaven.

Season 15

In Raising Hell, Rowena helps the Winchesters, Castiel, Belphegor and Arthur Ketch deal with the ghosts released from Hell by God, creating a Soul Catcher at their request. Despite the efforts of Francis Tumblety, Rowena traps the escaped ghosts, but becomes concerned when even more escape from Hell as her Soul Catcher isn't enough to stop them.

In The Rupture, Rowena becomes despondent after the failure of the Rafforza l'incantesimo spell, leaving Sam greatly concerned over her state. When Belphegor offers a solution using Lilith's Crook, Rowena is reinvigorated, offering up the Sanetur Acre Vulnus spell as a solution to closing the Rupture to Hell. As part of the spell, Rowena reveals that she needs Sam's help as her assistant, calling Sam the closest thing they have to a witch besides herself. Rowena helps Sam focus on the task at hand and together they successfully cast the spell, causing the rupture to begin to seal.

However, when the souls stop being pulled back into Hell after Castiel kills Belphegor and inadvertently destroys the Crook, Sam becomes alarmed when Rowena cuts out her last Resurrection Seal. Rowena reveals the existence of a spell that she can use to draw all of the escaped souls and demons into her own body so she can cast them back into Hell. However, the spell requires the sacrifice of her own life and Rowena demands that Sam kill her to his shock. Rowena knows that she doesn't love anything enough to kill herself to save the world and all versions of her ultimate fate have Sam as her one true killer so he must be the one to do it. At Rowena's urging, a crying Sam pulls her into a hug before fatally stabbing Rowena in the abdomen, pleasing her. As Rowena casts herself and the souls and demons back into Hell, she says a final goodbye to her friends. Sam is left devastated by Rowena's death which is compounded by the news of Arthur Ketch's loss shortly thereafter.

In Atomic Monsters, Sam is shown to still be reeling from the loss of Rowena. While encouraging Sam not to give up, Dean lists Rowena as one of the people who have believed in them over the years who they should continue fighting for.

In Golden Time, in order to create a Soul Catcher to hold the ghost of Eileen Leahy, Dean sends Sam to Rowena's apartment to find her magical stash, calling Sam "Rowena's protégé" due to all Sam had learned from her. With the help of Eileen, Sam finds Rowena's magical stash and her journals containing all of Rowena's spellwork throughout her life. Sam becomes noticeably emotional at the reminder of his lost friend, causing Eileen to realize that Sam misses Rowena. Sam briefly explains the complicated circumstances behind Rowena's death before finding a resurrection spell Rowena had been creating to bring back Mary Winchester before learning that Mary was happy in Heaven. Sam realizes that Rowena's spell can be used to resurrect Eileen instead of condemning her to an eternity in a Soul Catcher or Hell. Sam is captured by the Witch Mother and Emily shortly thereafter and the Witch Mother reveals that Rowena placed a powerful curse on her apartment that kills anyone who enters aside from Sam, suggesting that Rowena intended for Sam alone to inherit her magical stash. While talking with Emily, Sam displays his admiration and respect for Rowena, calling Rowena possibly the most powerful witch to ever live.

Rowena's teaching of Sam over the years ultimately comes in handy against the witches, allowing Sam to create his own hex bag using her stash and kill the Witch Mother with a spell, something Sam credits to having learned from the best, Rowena. Rowena's magic helps Sam once again as he is able to complete her resurrection spell and bring Eileen back to life.

In Our Father, Who Aren't in Heaven, Sam discovers that Rowena has become the new Queen of Hell. Rowena assures Sam that she is happy and he did the right thing in killing her, greatly relieving him.

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