Ruby was a character that was shrouded in mystery for quite some time as fans never really knew where her loyalties lied. Do the fact that she was a demon the Winchesters at first thought of her as an enemy, but Sam slowly over time eased up to her and the two became a pseudo-couple. Dean never felt that he could trust her as he felt that Ruby was becoming a bad influence on Sam that was bringing him down a dark path that would soon consume his life to the point that Dean might lose his brother forever. She gained their loyalties for a brief amount of time when she presented the boys with a demon killing knife and for saving them on a few occasions. She even helped Bobby Singer fix the colt as it ran out of magical bullets. In her previous life she was a witch when the plague was big as she says, and due to her prolonged stay in Hell it slowly burned away her humanity making her into the demon she is today. However, her true allegiances are shown in the season four finale Lucifer Rising after she had delivered Sam to Ilchester, Maryland at St. Mary's Convent where he killed Lilith. This in fact was the final seal that would break Lucifer out of his cage, and effectively showing her devout allegiance to Lucifer. Ruby was played by a few different actresses but most notably Katie Cassidy in season three, and Genevieve Padalecki in season four. Sometime after her character had been killed off it was announced that Genevieve and Jared Padalecki were getting married as the show seemed to have sparked a romance between the two. Even more interesting was the fact that in season three, Katie Cassidy had more chemistry with Dean (Jensen Ackles) although her character was there more for Sam. In season four, Genevieve clearly had more on-screen chemistry, and off, with Jared Padalecki.
Ruby first appeared in the third season premiere "The Magnificent Seven," where the seven deadly sins had been running amok around town. The Winchester, Bobby and two other hunters attempted to take down the monsters but as things began to look bleak for the boys a mysterious blonde haired girl with a special knife came in and saved Sam Winchester. Her knife was able to kill a demon in one swing of the knife. She then again appears to Sam in the following episode as she explains to him that he is special and that it has always been about him, vague, yes I agree. She tells him to dig up information on his mother's friends, and when he does he notices all of them are dead. Sam questions her as to why she knows so much about his past to which she reveals that she is in fact a demon and that he simply fascinates her. She even goes one step further to explain that she knows of a way to save Dean from going to hell considering in the previous season, Dean made a deal with a crossroad demon to bring some back to life in return for Dean's soul in a year. In return for Sam's trust in her, she explains that she will break Dean's deal. Sam tells Dean about Ruby, to which Dean asks why his brother didn't kill her once she revealed herself to be a demon. While Sam feels it is necessary to exhaust all resources possible to break Dean's deal, even if it means working with a demon. In the episode "Malleus Maleficarum," she helps the boys take down a coven of witches who just so happens to have a demon among themselves. The demon was named Tammi, and was the witch that Ruby sold her soul to long ago. Tammi is about to kill Ruby, but Dean is able to get free from her death grip and lunges for Ruby's knife where he uses it to kill Tammi. The following night, Ruby explains to Dean that she remembers what it means to be human and that all demons were once human. She also tells him that she cannot save him from Hell but she needs him to be able to prepare Sam for life without his brother as Sam will need to be more like Dean when the time comes.
Ruby shows up two more times in season three, once in "Jus in Bello," when she barges into the police station that the boys are locked up in with demons on the prowl. She explains that the demons that are present are devout followers of Lilith, who is Sam's rival, due to the fact that she does not believe Azazel expected him to be a leader of a demonic army. Lilith wants Sam and Dean dead, and she is being aggressive about it. Ruby explains that they are completely outnumbered by the demons outside and that the only way to ensure a safe victory is a special spell that calls upon the sacrifice of a virgin. Dean laughs, as he is sure there are no virgins in the vicinity, except Nancy the receptionist in the station reveals herself to be. She agrees to do the spell as long as Ruby promises her that no one will be hurt in the process. She asks if the people that are being possessed by the demons outside will be safe after the spell, to which Ruby says yes. Sam also is okay with doing the spell, but Dean does not want to win a war by sacrificing virgins. Instead, Dean convinces Sam that they simply open the doors and fight off every last one of the demons. Ruby, shocked at the boys dismissal of her plan leaves in a hurry. The boys are able to expel all of the demons out of their human hosts and in the process their names are cleared by the police. When they leave the station to celebrate at their hotel, Ruby breaks up the celebration and tells them to turn on the news. They turn it in to find out that the police station they were just at had been leveled by what seemed to have been described as a bomb. Ruby explains that Lilith showed up shortly after they left, and killed their precious virgin. Ruby appears once again in season three for the season finale, it starts with Sam summoning Ruby searching for ways to defeat Lilith as they have found out that she holds Dean's contract. The boys are desperate for answers, but Dean is adamant against getting help from Ruby. Ruby explains that Sam has the power within him to be able to take down Lilith due to what Azazel did to him that fateful night. She explains that his power is simply lying dormant waiting for him to call upon it one more time. Dean intervenes and lures Ruby into a devil's trap where the boys leave her as they go to where Lilith is hiding out. Ruby eventually gets out and tracks them down before they get into Lilith's house and when time is running out for Dean, Sam turns to Ruby asking for help but she explains it is too late. The hellhounds then come for Dean and he quickly realizes that Ruby is no longer who she says she is and that Lilith had taken over her human host. Lilith explains that she sent Ruby "far, far away."
Clearly Ruby wasn't sent to far away because she is back in the first episode of season four, in a different human host of a woman who was essentially a vegetable. Over the summer that Dean was gone in hell, Sam and Ruby got closer as Sam was in a bad place and wanted revenge on Lilith for killing his brother. Ruby helped him learn how to use his psychic abilities as he was now able to pull demons out of people. The two also had sex on occasion. Sam began to really trust her despite his brother's frustration with his allegiance to her. Dean has moments where he begins to trust her when they are faced with Alastair while protecting Anna Milton. Ruby allows herself to be taken by Alastair as she and the Winchesters bring Heaven and Hell together to fight over Anna. The two forces cancel each other out, and Anna is then able to get her angelic grace back allowing her to repel both forces. Ruby comes back into play when Alastair resurfaces in the episode "On the Head of A Pin," when the angels see Dean as the candidate to stop Lilith from breaking the seals. Sam explains to Ruby that Dean is weak after his stay in Hell, and is somewhat broken. He goes further and says that he needs to be strong, to which then it is revealed that he had been getting stronger by drinking demon blood from Ruby. Ruby uses the knife to cut into her skin and Sam begins to drink from her. The following scene Sam easily dispatches Alastair, but doesn't just send him back to Hell, he kills him with his mind.
Sam loses contact with Ruby for sometime after this and begins to breakdown as he is in remission from demon blood and is clearly addicted to it. Dean and Bobby throw him into Bobby's Panic Room to sober up from the effects that the demon blood has had on him to which he eventually breaks out of and meets up with Ruby in a hotel. She lets him feed on her and she explains to him that Lilith is the only one that can break the final seal to free Lucifer. This in fact renews his desire to kill Lilith and Ruby tells him that she is narrowing down where Lilith will be. As the two are about to head out for Lilith, Dean interrupts and attempts to kill Ruby. Sam overpowers Dean and the two fight as Dean tells him that Ruby has essentially turned Sam into a monster, the very thing that they would hunt. Sam, filled with demonic blood, is too much for Dean to handle in a fight and the two go their separate ways. In season finale, Ruby helps Sam capture Lilith's minion who reveals where she is. Ruby continues to push Sam to get to where Lilith is and even explains that he will need more than she can provide him in order to kill Lilith. She means that he will need to drain a demon dry of their blood, and a human in the process. Sam has reservations of it at first, but when he gets a falsified message from Dean calling him a monster, he goes through with it. Sam goes into the St. Mary's Convent in Ilchester, Maryland where Lilith is held up and uses his ability to kill her. After she falls her mouth opens and blood pours out of it creating a giant circle that acts as a door for Lucifer to come out of. Ruby finally shows her true colors as her allegiance was always to Lucifer. She reveals to him that only Lilith knew of her true allegiance and that the two of them had been working together all along. She also explains that he never needed the demon blood as he always had it in him. Sam asks "Why me?" to which she once again answers, "It had to be, it always had to be you." That mirrors what Azazel told him previously in the season two finale as Azazel zeroed in on him once he found out that his mother was a hunter. More so, the fact her name was Mary and Lucifer's cage was below St. Mary's Convent. Ruby then meets her maker in Dean when he charges through the locked door with her knife and Sam grabs her from behind so that Dean can kill her with the knife.
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