No Sympathy For A Devil Part I: A Closer Look at Ruby Revisited

Editor’s Note: To celebrate Genevieve Padalecki’s birthday, I went looking through our archives for articles about her Supernatural character, Ruby. This 2-part analysis of Ruby was first published in December of 2011. It traces Ruby’s motivations and impact on Sam and Dean from her introduction in season 3 through her death in season 4. It goes deeper than anything else I’ve seen on the subject, providing insight into not only her role in the apocalypse but also her personal story, how she was able to influence Sam so completely and orchestrate the schism between the brothers, and what might have happened had she not been killed. When this was originally published, Ruby’s character was highly controversial (as you will infer from the author’s comments). Genevieve was also not yet married to Jared, so she was not yet the beloved part of the SPNFamily that she is now. I hope you enjoy this character study, which is as penetrating now as it was 8 years ago. 

 

So I tend to think about Supernatural when I should be thinking about, and writing about, other things. Such as the four final papers that are coming due for Grad school. This week. But what the hey right? This is Supernatural. Priorities.
 
Anyway, some of that thinking has led me to the dangerous territory surrounding Ruby. I blame it on Crowley. From what I can tell, I am in the minority when it comes to disliking Crowley. He gets under my skin in a way I won’t explain here since I don’t want to piss anyone off more than I might by writing about Ruby. What Crowley did was to cast a different light on Ruby. His scummy, despicable, self centered, smarmy, slimy, gut turning self…*breathe* caused me to unwillingly compare him to my other least favorite demon, Ruby. And standing in that company, she doesn’t look as bad.

Before anyone gets riled up, this is not about defending the black eyed bitch or trying to tribute her in any way. Nope, still hate her. So why write? I don’t know. Maybe because I want to honor the boys by examining the skills of their enemy. Maybe because “there are heroes in evil as well as in good.”  Maybe because time and distance have blunted some of my initial revulsion. Whatever the reasons, what I write is an opinion piece. That’s it. These are the speculations my mind has wandered down, so don’t go thinking I’m trying to make my own imagination canon.
 
Sadly, I feel I must address an issue concerning the actresses who have played Ruby. Four different women have taken the role, two briefly and two for longer periods. I am aware that there has been discord in fandom over the two who mostly played her. I ask, I beg and plead and use Sammy puppy dog eyes and pouty Dean lips, no attacks on any of these women? Let’s keep our grown up pants on and be polite. I am perfectly ok with anyone expressing a preference for a certain actress’s portrayal. That’s cool, everyone’s entitled to their opinion. But please remember, these were women simply doing a job they were hired to do. 
 
Beginning at the beginning

So we know that Ruby was a witch back when the plague was big. In Supernatural, there appears to be a couple different kinds of witches. Those who think they are smart enough to outwit the demon they are getting their power from but end up in hell, and those who have found a way to use their power to keep living VERY long lives and their souls out of hell. And then there are those who are the ‘just plain ignorant/stupid’ category of witch. My guess is that Ruby fell in the first category but probably wanted to be in the second. 

In seeing the interaction between Ruby and her prior mistress “Tammy” in Malleus Maleficarum, I got the impression that as a human, she knew what she was getting into. This tells me that even as a person, she was attracted, intelligently attracted no less, to things of evil. She was most likely not a nice person. At all. 

So she dies and ends up in hell where her soul begins to be twisted into a demon. And not just any demon, but one that remembers being human. I believe this was a plan of Lilith’s. Hell and heaven both had a long view on planning, and they planned for contingencies. I think they sometimes experimented just in case it might come in handy down the road. Lilith had plenty of time in the pits of hell to toy with many ideas. I doubt that Ruby was the only demon on the experimental rack.
 
I must admit, I am curious as to the making of the demon Ruby. A memory of her humanity had to remain intact, but she must be obsessively loyal to Hell’s cause. She had to be intelligent (not a common demon quality), devious, but not strong enough to be considered a serious threat to other demons. How many botched trials before the perfect mixture of cunning, reliability, and pure, black evil were made? Were Meg and her brother attempts made by Azazel?

Fast forward several centuries (and who knows how many millennia in hell) to Azazel escaping the pit and Lilith sending him on his path to create the perfect vessel for Lucifer and to open the Devil’s Gate. The plan is in motion, finally. Then John arrives in the pit and Alistair goes to work. I wonder at what point Lilith really began to prime Ruby for her role. After all, no one else but Lilith (and probably Lucifer) knew of Ruby’s involvement. What secret keepings and whispers and meetings behind flayed bodies went on between the two demon bitches? Did Ruby sneak in to overhear John’s screams? Did she eavesdrop and learn what she could about Sam and Dean? Did she participate?

Oh, and what the hell did that conversation between Lilith and Ruby look like? I mean seriously. Ruby must have been terrified of Lilith, but I don’t believe it was terror that drove all of her actions. No, she was in it fully, willingly and without reservation. She was to be a double agent behind enemy lines. A spy hated and disowned by her peers, hunted by her superiors and renounced by Lilith herself. Alone, truly and without recourse, alone. And she knew she was going to be alone ahead of time! Say what you will (and what I do) about Ruby, that took some serious guts. 

Of course it doesn’t appear that she ever really had friends, or whatever the equivalent of a friend is in hell. Other demons, from their comments, appeared to know her, or at least of her. The cross roads demon nearly spat out her name, other demons knew her on sight, and not with affection. Her retention of human memories could not have endeared her to the other hell spawn. Rather a brilliant stroke on Lilith’s part, to truly have Ruby’s one hope of any form of happiness be dependent on the release of Lucifer. Her very self interest, want for power or whatever it was she desired, rested on the opening of the cage’s door. 

Then Dean sold his soul and how Hell must have rejoiced. Azazel probably sent word to prepare, the Gate would open soon! (Did John hear this rumor? Was hell in such a confusion of preparation to flee through the Gate that he was able to step off the rack?) Ruby’s orders? Get Sam Winchester to drink demon blood and have him kill Lilith. The Gate finally opens, go Ruby, sick him.
 
Out of Hell, into a Blonde

That must have been quite the free for all from hell’s viewpoint, all those demons, clawing their way out of the pit into freedom. Ruby was among them, as was Lilith, the seven deadly sins, perhaps even Crowley was in that dark cloud. We know John was able to fight his way out.
 
I can’t help but wonder if it was Lilith’s demon smoke that broke the iron rails of Samuel Colt’s devil’s trap. It seems that there was a shared moment of greeting, when the smoke caused the rails to curl up and old Yellow Eyes passed through. And if anyone, Lilith definitely had the juice to break iron.

I find it slightly…well, weird I guess to think of the end of Season 2. Out of all the seasons, it is perhaps the most cheerful of cliffhangers. Yes, Dean had sold his soul, yes the demon army had been released. But Yellow Eyes was dead, John was out of hell and there was hope to be seen in Dean’s confidant smirk. Yay boys! Little did I know that the unusual pall of cheer was a smoke screen for the tragedy’s to come. It was the last time we knew the boys without Ruby intruding on the picture. She was free, she was on the mission of the Winchester hunt. 

“What are the demons waiting for?” 
“Beats me.”
“It’s driving me crazy. I tell you, if it’s gonna be war, I wish it’d just start already.”
“I don’t know man. Careful what you wish for.”

Indeed. The start of war is rarely out and out conflict. First spies and other agents are infiltrated behind the lines. 

Ruby’s first move was to find someone to possess. Who does she choose? A blonde like Mary and Jessica were blondes. It seems a similar strategy as the demon who possessed the girl Meg, also a blonde. Psychological warfare? We don’t know anything about Ruby’s first possessed girl, not even her name. Or at least I assume Ruby was Ruby’s name and not the girls. Other demons seemed to know her by Ruby, as they knew Lilith as Lilith and Azazel as Azazel. It makes sense I guess, since Ruby was allowed to remember her humanity.

Anyway, Ruby slides her smoke into a pretty blonde chosen on the basic information she knows about Sam Winchester. What fun! A human meat suit to control and a human soul to toy with. Now what? Here she is, finally up top, free to work the havoc her dark nature craves. And at first she gets it. Or at least I assume that it was her who killed all of Mary’s family and acquaintances. Ruby also somehow gets her hands on the demon killing knife. Where did she get that thing?! Hello! Show? Will you answer this please?
 
Next move, find the Winchesters and look for an opening to introduce herself. That’s when we first see her, materializing out of the shadows, assessing the situation, stalking Sam, thinking, considering, hovering at the fringes and planning her entrance. It must have been somewhat daunting. Here she was, a hated demon and her task was to turn Sam Winchester into her lapdog. And the biggest obstacle to this? Dean. Dean, Dean, Dean. Ruby must have had some faith in Sam. He was Lucifer’s chosen after all. But Dean was in the way and a direct attack on Dean meant closing the door to Sam forever. If Sam even scented a whiff of violence toward Dean, Ruby would be SOL. Mission failed.

And the brothers were so solid. Yes, there was tension over Dean’s deal and his refusal to fight for his life, yes there was some questions in Dean’s mind about Sam returning whole from the dead. But they were joined shoulder to shoulder without a hairsbreadth of mistrust between them. This united front was what Ruby faced. Pretty damn discouraging if you ask me. Just give it up Ruby, go back to hell. Please?

No such luck.

She chose the persona of a kick ass, smart mouthed, manipulative, sensuous and intelligent woman with a give a crap attitude covering an intense drive. First opportunity, she jumped in with both feet, knife carving up demons, know-it-all smirk at the ready. Sam, meet Ruby. Interest piqued? 

I also have to take this moment to again ponder how before Ruby entered the scene, Pride had Sam by the throat. Literally. I mean literally. Sure, Pride was ganked a minute later, but Ruby didn’t come to save the day until after Pride had a minute to strangle Sam. Coincidence? I think not!

“If you want a troubling question, I’ve got one for you.”
“What’s that?”
“If we let out the seven deadly sins, what else did we let out?”

Oh Sam, why didn’t you listen to yourself?! 

Now that she had his attention, she needed to keep his attention. She needed something, anything, to grab onto and Ruby wasn’t taking chances. She approached the problem from multiple directions. She presented as a sexy, mysterious hunter chick, offered knowledge about his past and family, acted as a helpful, conscious driven demon and lastly as someone who could help Dean out of his deal. That is the one that hooked Sam in and she did not let go. Dean was both her largest impediment and her one way in, complicated problem. 

The bait was dangled, the bait was taken but it must have felt a little like having the tiger by the tail. Her hold was so incredibly tenuous. But bonus points, she got to witness up close and personal the deep and controlled anger Sam is capable of. 

“Because demon, that’s why. The second you find out this Ruby chick is a demon you go for the holy water, you don’t chat!”
“No one was chatting Dean!”
“Oh yeah, then why didn’t you send her ass back to hell?”

Dean was very much in the way. It must have been so frustrating to circle the perimeter of the Winchester brothers, waiting for the rare opportunity to get Sam alone. She needed, she desperately needed, a way to earn Sam’s trust and to add doubt to Dean’s certainty. Her method was an incredibly risky one. Approach Bobby and offer to fix the Colt, a gun that could easily kill her. Ruby decided to risk her life further, really put things on the line, by giving the power of the Colt back into the Winchester’s hands. 

Now this is about Ruby, but it’s nearly impossible to look at Ruby’s methods without examining Lilith’s role. So I don’t doubt for a minute that she first consulted Lilith on this decision. The Colt was a game changer. It could kill Lilith before Dean ever went to hell to break the first seal. My guess, Ruby received permission and reassurances that her boss would find a way to remove the Colt from Winchester possession, without implicating Ruby. (Bella, you tool.)

So it went, Ruby trying to snatch moments alone with Sam, manipulating, endeavoring to herd Sam in the direction she wanted him to go, dangling the bait of saving Dean, sprinkling her lies with enough truth to seem a least a little genuine. It was working, but not very well. Sam and Dean still walked in lock step, and honestly, Ruby’s approach to Sam was not all that effective. He did not like her, thought she could be useful, but not likable. She was bossy, condescending and impatient. Ew. Not likely he was going to latch onto a vein of hers.

Ruby didn’t have that many cards to play. She couldn’t save Dean and even if she could, she wouldn’t. It was a thin thread and one that began to wear rapidly. She needed more leverage, and that was hard to come by. Distance from Dean meant keeping her life, distance from Sam could mean losing her fragile hold. Let them in on information about Lilith would mean putting Lilith in danger. Options were limited. Her best bet was to bide her time, wait for Dean to be dragged to hell and then set Sam’s sights on Lilith. In the meantime, show her face once in a while to keep it in Sam’s mind that she was an ally to trust.

Then the damn crossroads demon interfered and told Sam that there was a big bad to chase. That must have been infuriating. One more piece of precious knowledge Ruby no longer controlled. And then Sam killed the demon? If I were Ruby, I would have been tasting fear. One hint gets to Sam about her game plan and she’d be dead. In fact, Ruby disappeared for a while. It wasn’t until the boys hunted the witch coven and her old demon mistress “Tammy”, that she returned. And it was a fantastic opening, a golden opportunity to reveal her past humanity, some vulnerability and feelings, and become a little more likable. It was an opportunity good enough that she chanced a face to face with Dean, and it almost was the death of her. 

And the chance paid off, not only did she learn that Sam was willing to protect her, had her ‘loyalty’ to the Winchesters confirmed by another demon, but she exploited that crack in Dean’s solid armor, Sam. That conversation with Dean in the motel parking lot, it must have been both fun and annoying. Ruby never liked Dean. He was the thorn in her side and there she was, having to make polite conversation with him. She certainly threw quite a mixture of truth and lies at his head. “I don’t believe in the devil.” (Ha!) And then the admission that she couldn’t save him? Both said with equal conviction. 

That episode had their relationship go through some fast changes. Dean went from shooting the Colt at her, to turning his back on her (with the Colt in hand) while she stared him down with black eyes, to chatting with her in the parking lot. Ruby must have laughed herself silly. Of course, not being a fool, it was soon after this that Bella found an opportunity to take the Colt. My thought is that Ruby had a vote in the timing.
 
“She’s here to help us.”

‘Jus in Bello’ is a fantastic episode. I mean wow, but whenever I look at it from the strategic point of view of the demons, I get a little, wait, a lot pissed at Ruby…and feel a little admiration. Dammit. 

The demon plan, Lilith’s plan, was bold, risky and did not have a lot of room for error. The plan had to sell it to Sam, Dean, and all the rest of the demons, that Lilith wanted Sam dead. That meant that Lilith had to be commanding, threatening and insistent to her minions to kill the Winchesters. All the while, in reality, she needed Sam alive. Talk about walking a razor’s edge. 

Word comes in that the Winchester’s are on lock down in a jail cell. Lilith sends her demons to kill them, and Ruby to save them. I know that what I’ve been saying makes it seem like I believe that Ruby and Lilith were in constant communication. That’s not what I really believe, mostly Ruby had to act under her own initiative. After all, if word got out that the two were in cahoots, the plan would implode. But I also think that Ruby, being on her own so much, under cover and ducking other demons, sometimes had to get news and orders from her boss. Ruby’s very own blood bowl perhaps? 

So Ruby needed to get in the station, where Dean was with his distrustful and homicidal thoughts, dangle false information about Lilith and then offer herself up as a sacrifice. Ruby already knew the Colt was stolen. She knew. Bitch. But because she knew, I can’t help but admire her nerve and dedication. 

Now I don’t really believe that Ruby really believed Dean would allow her to sacrifice a virgin. (Or for that matter, did the spell even exist in reality?) But I also think that if it came down to the wire, she would have martyred herself with the knowledge that Lilith would have someone else lined up in the wings to take her place. She was quite literally willing to die for the cause, and not a hero’s death either. No other demon would know of her sacrifice. She was in it to win it, not for the accolades. 

Of course, Dean being Dean, there was no sacrifice and Ruby skedaddled. I can’t help but wonder about how fast she got out of there. Ruby was 100% invested in Sam, but she left them to pull off their iffy and dangerous gamble? She didn’t even hand over the knife! So I wonder if there was a backup plan. Maybe if the boys were really about to die, Lilith had a way to pull her demons back. Or maybe she had a deal in the works to bring Sam back from the dead again. Who knows? That wasn’t the way it went down because the Winchesters are smart, bad ass and determined. 

Instead, Lilith simply showed up to clean up the mess and to drive the point home that Sam needed to focus on a bigger picture. (Miss you Hendrickson!) And Ruby again walked that razor edge of throwing truth and lies in their face. 

“You strike fast and don’t leave any survivors, so no one can go running to tell the boss.” 

If you think about it, she was basically putting up a neon sign that said “You had better kill me now!” But because it was so obvious, so clearly in their face, they didn’t follow her advice. She had to take these risks, or else Sam wouldn’t believe her to be sincere.
 
She wasn’t seen again until Sam summoned her. Ruby steered clear of the Winchesters, probably biding her time until Dean got dragged to hell. She wanted Sam all to herself. But when Sam called her in, she exploited the moment. She snatched the opportunity to plant the seed about Sam’s power. Again she sprinkled truth and lies together. Yes, Sam had the power to save Dean. But no, he couldn’t have been ready to kill Lilith so quickly. Look how long it took to ‘train’ him up to it when he did kill her! He had to drink the blood that Ruby could afford and drain the nurse dry. No, Ruby was manipulating yet again. Even if Dean hadn’t walked in on them in that barn, I just don’t believe Sam could have brought himself to blood drinking. He was desperate, but not broken, vengeful, and grief crazed. 
 
“You are one ugly broad.”

That barn scene, it’s one of the very few times we saw Ruby without her cloak of lies. She was just pure Ruby. Her frayed temper snapped, her hatred and disgust exploded outward and she tackled Dean and Sam both. It was a mistake. She became trapped, she raged, but it did no good. Ruby had screwed up, the boys had the knife, and now Lilith was in danger.

She never should have indulged her tantrum. The next time Sam saw her; he threatened her with the knife and called her bitch.

Progress definitely was lost. And not just progress but she disappointed Lilith. I don’t doubt that Ruby warned Lilith of the Winchester’s coming, but that doesn’t change the fact that Ruby screwed up. So off to hell she went to be punished. Of course this served multiple purposes. It taught Ruby not to be so self-indulgent, it reinforced to the rest of hell that Ruby and Lilith were not allies, Lilith got to use Ruby as an example to keep the rest of her army in line, and it could be used as leverage for Ruby to win her way back into Sam’s favor.  

Lilith was able to use Ruby’s mistake to her advantage. By placing herself visually in front of Sam, by opening the doors to the Hellhounds herself, by laughing while Dean was ripped apart in front of Sam’s eyes, Lilith dug her way into being even more of a priority on Sam’s revenge list. She basically was jumping up and down in front of him screaming “Hate me! Hate me!” And then she got to put proof in the pudding that yes, Ruby was right. Sam himself, all by himself, was a danger to her. “Come and get me Sam. I’m afraid of you Sam. You can do it Sam.” Taunting him, tempting him, taking the smallest minutia of openings to lure him down the path to Lucifer’s waiting arms.

Keep Going with Part 2!