(Contains references through Supernatural episode 4.07 “Yellow Fever”)

Witches have a hard go of it everywhere. Remember those witches in Oz who were so mad to wear the enchanted ruby slippers? Wear those shoes too long, and a house falls on you, or a bucket of water melts your sister. Then some whiny Dorothy steals the family shoes!

The Ruby shoes, er meatsuits, on Supernatural have a similarly tough gig. What’s a misfit demongirl to do when she just won’t forget her humanity? Does she take the rebel road and play the Good Witch when her wicked sisters won’t invite her in to hell’s heavy clambakes? How’s a Good Witch fit in with the evil doer in-crowd? Maybe Ruby’s not a bad evil thing; maybe she’s just drawn and shoed that way.

Ruby once told Dean she’d been in hell since the plague was big. Didn’t some evil rub off after seven centuries down in the pit? Yet for someone evil, she’s been awful helpful to the Winchester brothers.

Ruby first appears from the shadows and helps Sam kill three of the Seven Deadly Sin demons with her Demon Killing Ginsu. She meets up again with Sam for French fries and shares the news that Sam’s still special to Team Evil.

Ding dong the demon’s dead
Ruby likes Sam for his sole survivor status among the PsychicKids; and because he’s tall. Sam’s still a big deal, what with all that happened to Mary’s friends and family, but she gives no freebie details… though she does leave her phone number.

When Sam does call, Ruby says it’s the “God’s honest truth” that she wants to help Sam. When pushed about why, she says that not all demons are the same. Ruby wants to help Sam in a big way since she could help save Dean. But only if Sam will be nice to her even when she’s a sarcastic bitch.

Ruby next emerges from the shadowy trees and helps Bobby test the rebuilt Colt, by provoking him into shooting her. To thank Bobby’s kindness, Ruby magically fixes the Colt off screen (but not quite). Why help them? She tells Bobby she wants peace on earth and a new shirt.

After bonding over weaponry, Ruby brings Bobby and the Colt to exactly the right spot, just in time, for Sam to use the Colt to blow away the two Sin City demons (Casey and her demon lover Father Gil), and thus save Dean. Yeah, this chick’s a menace; and super convenient for plot devices.

Ruby congratulates Sam for shooting the two demons. He calls her a cold bitch, since Sam’s upset about killing two possessed humans. Ruby demands some respect for helping him. Sam pulls the Colt on her, but can’t pull the trigger. The possibility Ruby can save Dean from hell is the only thing stopping him. Ruby shows insight into Sam. She says Sam has to go against his gentle nature to win the demon war, and she’ll be there. Stalker!

Ruby next appears on a shadowy road to tell Sam to get out of town because the demon behind the witches coven is more than he can handle. Dean refuses the advice; and tries to shoot her with the Colt but Sam stops him. The demon, Tammy, is a lot to handle. She plants a hex bag somewhere to kill Dean. Sam tries to shoot Tammy and finds the Colt doesn’t kill her. Ruby appears from nowhere again to save Dean again from dying by the demon’s hex bag.

After bonding with Dean over witchcraft, Ruby then follows him to the witch’s house and tries to rescue them from Tammy by getting close enough to stab her. Tammy is too fast, and starts kicking Ruby’s butt. She pauses to explain Ruby is a lying whore and she knows because she is Ruby’s ex-DemonPimp. Tammy begins to exorcise Ruby just by latinating! But the human witch distracts Tammy with a mouthful of pins, giving Dean the opening to stab Tammy several times with Ruby’s Knife. Now that’s teamwork!

Ruby appears from the shadows to Dean again. (Stalker!) He asks if the devil may care about humans after all. Ruby claims she doesn’t believe in the Devil. She chattily drops the intel that hell is forgetting who you are as the fire burns away your humanity in unimaginable agony. Ouch! Poor Dean. Oh, and Dean cannot be saved from the pit. When Dean asks why she’s helping them, this time Ruby says she remembers what it’s like to be human.

Ruby appears from the shadows yet again, killing demons in her path as she breaks into jail to help Sam and Dean survive the demon assault on precinct 13. She tells them Lilith has her minions coming to kill Sam, and they need the Colt to survive. Ruby berates Sam and Dean for losing the Colt, and shuts Sam up when he tries to explain.

Ruby the Rescuer offers a witchy solution to the siege problem with a spell that will take out all the demons. Sam is willing to consider her plan, but Dean rejects due to the virgin sacrifice part of the plan. Ruby says she was going to kill herself to help Sam win, (but only on her terms) and Dean’s plan won’t work, so she bails. She’s not angry with Sam, she’s just disappointed. The Winchester plan mostly succeeds and the possessed humans mostly live. One demon gets away to report back to Lilith. Lilith kills everyone left alive at the police station, including that sweet virgin.

Ruby appears to watch TV with the brothers and rub Sam and Dean’s nose in their failure. She yells at them about how she’s fighting a war and they can’t win one little battle. Then all is forgiven and she gives both Sam and Dean special hex bags to hide them from Lilith. So net overall, Ruby gives some evidence that she is a DemonWhore with a heart of gold.

All her good works and rescuing begs the question about how Ruby knows to appear at the right time all the time? She just clicks her heels and says “there’s no place like Sam”? No, that’s right, she’s a mystery (i.e. for the writers’ convenience, there will be no explanation, but makes the character a cardboard plot device).

Once Sam learns Ruby told Dean there was no way to save him from hell, Sam stops calling her; plus Dean is so stubborn about talking to demons. As Dean’s time runs down, Sam does call. Ruby appears from the shadows and says they have a true blue window to take out Lilith. And yes, she did lie to Dean, because manipulative is something that did rub off after all her time in hell. Ruby also admits she knows Sam is willing to do anything to save Dean. Dean stops Slutty Yoda from getting further with Sam’s training by baiting her into a fight and stealing the Demon Killing Ginsu. In thanks for the knife, Dean leaves her locked up in a Devil’s trap. Both Dean and Sam use the Knife to kill some of Lilith’s watchdogs on their way to New Harmony. More teamwork!

Ruby appears in New Harmony, somehow escaping from the Devil’s Trap, to get back her Knife. Sam won’t give it back, so she tags along on their assassination attempt on Lilith. Lil outsmarts them though and steals Ruby’s shoes (and meatsuit), sending Ruby far far away. Lilith is the Wicked Witch of the West! She releases the hell hounds on Dean. Before Sam can stab Lilith with the Knife, Lilith abandons the meatsuit, which is dead from Bobby’s test firing the Colt point-blank into her chest.

Jerking Your Chain Down the Road

Ruby proved useful by saving Sam’s bacon a few times, offering him intel, and even saving Dean in order to build a truce (if not a trust). Ruby said that manipulative was in the demon job description. She convinced Sam she could help break Dean’s deal. But she never actually did anything to prove her claim. Sam never demanded proof either. The idea that she could help nicely drives a wedge between Dean and Sam. Ruby told Dean the awful truth that he couldn’t get out of the Deal and that nicely opened the wedge further between Dean and Sam.

Dean didn’t recognize the true threat of Ruby. If he had, he would have exorcised her after trapping her in No Rest For the Wicked. Dean didn’t understand why Sam was listening to Ruby or why Sam had any connection to her. Did Dean’s preoccupation with the impending hell ride cloud his focus on protecting Sam? Very likely. But Dean also hoped that Sam’s powers were gone.

Ruby never had any intention of stopping Dean from going to hell. All through season 3, Ruby wanted Sam to embrace his powers. She used Dean’s Deal as the way to get close to Sam. Ruby dangled hope that she could help Dean. She dangled the Knife that could kill demons. And she offered sympathy with Sam’s situation, reinforcing the idea that Dean doesn’t understand Sam. Ruby nearly got Sam to use his powers, but Dean intervened.

Ruby connects with Sam in a way Dean cannot. She understands Sam’s yearning to be normal. Ruby states how Sam feels – how he hates when Dean looks at him like he’s a freak. She knows that Sam doesn’t like to be different. Ruby’s not exactly Miss Popular amongst demon kind. She’s still too human compared to the average demon. Ruby is probably as lonely as Sam.

To get close to Sam, Ruby needed Dean out of the way. She couldn’t take Dean out herself, so Dean’s deal was an excellent opportunity. It would make Sam vulnerable to her influence as he grew desperate and could lure Sam to embrace his powers. What better way than to get Lilith to make the hit on Dean? Ruby gets rid of Dean, who stood between her and Sam, and motivates Sam like no other way to take out Lilith in revenge. For some as-yet unexplained reason, Ruby wants to help Sam use his powers to Kill Lil. That’s probably just the beginning of what Ruby really wants.

Sam told Dean that he was using Ruby, not trusting her. He says he still doesn’t trust her in the season 4 episode Lazarus Rising, even after she’s taught him to exorcise demons with his mind. Wherever Lilith sent her, and however Ruby came back from Far Far Away, the journey changed Ruby’s personality, as a docile and dull Ruby2 appears to Sam in the diner.

Somehow in the five months that Dean was in hell, Ruby got close enough to Sam to teach him to use his powers. Perhaps it was the journey and not the destination that Ruby wanted. The journey for revenge is what started turning Sam into Anakin. What will happen now that Dean is back, scar free and recently deflowered? The mission now is not just stopping Lilith so much as stopping the Apocalypse.

Ruby2 should be worried with Dean back, and his new angelic BFF is the most powerful being anyone’s encountered. That could be used to her advantage, if Dean neglects his watchful Sammy duties. There’s a scab of resentment in Sam that Ruby2 might start picking. Maybe Ruby can take advantage of Castiel’s scary powers to drive Sam and Dean further apart.

Ruby wants Lilith dead. But she never says why. Maybe Ruby wants Lucifer to stay sealed up for her own reasons? If Lucifer comes out, does that mean the lazy good times are over for hell’s residents and it’s mandatory overtime and no more shore leave?

Ruby’s shoes are a tough fit. Ruby1 was introduced as a bitchier Buffy. She made no effort to be liked by Sam (and Dean was never a consideration.) Her tactics were to lure Sam with his deepest need – to save Dean from going to hell. Failing that, Ruby2 is a whole new character, and not just a new meatsuit. (Though in both cases, Ruby chose meatsuits with the DILF packaging and the Mediocre Actress option.)

Ruby2 is a supportive coach, though Dean’s label, Slutty Yoda, is funnier. She tells Sam in the diner that she doesn’t want to come between him and Dean, though clearly she knows that she already has. She seems to be Sam’s confidante, as they sit in the booth talking amongst the dead victims. They appear pretty comfortable, which is ya know, disturbing. Remember back when Sam would have stopped and buried those people?

Ruby2 no longer sneers at Sam, but gives him a support? Ruby-the-Rescuer is now the maybe-not-so powerful sidekick taking Sam’s direction? What are Ruby’s above-average demon powers? How is she staying alive without the Demon Killing Ginsu?

What does Ruby need Sam for other than to be the trigger man for Lilith? Casey told Dean she was going to line up with Sam, but Sam never stepped up to take the job. She also said she believed in Lucifer, though she’d never seen it. What does Ruby believe in? We have no idea why Ruby became a witch. Maybe peer pressure by the teens in the Middle Ages? (She turned me into a toad once! I got better. )

As big bads go, Ruby is not even as scary or menacing as Meg, who was just a mid-level demon in Azazel’s family crew. Tammy could kick Ruby’s butt and nearly exorcised her. Ruby’s not more powerful than Lilith, and Lilith’s just a little girl. But she got out of Deans’ devil’s trap somehow. Ruby got back from Far Far Away somehow.

Maybe hell is full of all the red tape that Azazel implied. Maybe Ruby is as powerful as Lilith, but due to some loophole or bureaucratic rules, she can’t take Lilith out directly? Is Ruby a Made Demon and you have to get permission from the DemonDon to take out another Made Demon?

One thing is clear, in hell’s hierarchy Ruby is middle management. More powerful forces are emerging - Sam, Castiel, Lilith and God knows who else can all stop her as needed. Whether Ruby’s good or evil, no witch (or actress) can wear the ruby slippers for long.