Mark Watches ‘Supernatural’: S05E20 – The Devil You Know

In the twentieth episode of the fifth season of Supernatural, Sam is stunned when Dean agrees to ally with a demon. Intrigued? Then it’s time for Mark to watch Supernatural. 

Like I said in the opening of my review of “The Song Remains the Same,” retcons are a tricky thing. I don’t think that “The Devil You Know” introduces Brady quite as well as the show wrote the angels into Mary Winchester’s past, but ultimately, I’m okay with what’s done here. Well, more than okay, as this is a thrilling episode that deals with an emotionally-charged Sam respectfully. Which is important to me! I like Crowley a lot PROBABLY MORE THAN I SHOULD, but I quickly recognized what a minefield of awful it was that Dean was agreeing to work with a demon after spending more than a year criticizing Sam for doing the same thing. Thankfully, the show openly acknowledges this in the text, and Sam is given a means to engage with his own disappointment and sadness.

It gets a little weird in the middle, though. Well, wait, let me back up first before I start talking about that. The set-up is crucial here because I feel like there are a lot of intentional references to Ruby here, even if they’re not outright stated. The writers cleverly reverse the dynamic from the last season and feature Dean dealing with a demon. It’s out of desperation, and we’re never allowed to forget that. Despite that they now have a loose plan to stop Lucifer, this is still a last-minute shot that will probably fail. They know it! And hell, once Crowley gets involved, it’s not like he’s prone to thoughts of grandeur or illusion. He knows it’s a slim chance to stop Lucifer, but it’s a chance, and these goobers are gonna take it!

Still, it’s heartbreaking to watch Sam’s face as Dean agrees to Crowley’s plan to track down the demon closest to Pestilence. This is the first of many ways that the show reminds us of what Sam went through, not just because of Ruby, but due to the fallout from trusting her. Simply put, Dean put Sam through the ringer, mistrusting him and second-guessing him. So I get why Sam is so hurt by all this. I think that deep down, he understands why Dean is doing this, but it still rubs him raw, you know?

Of course, throughout this, we’re meant to question Crowley’s loyalty. Is this Ruby 2.0? Historically, demons are not to be trusted, and Crowley is no exception to that. He openly trolls Sam and Dean for his own amusement, but is that his endgame? Is he just using them as pawns? Or is he actually telling the truth? His story – that this entire plan is self-preservation for him – does fit within the framework of the demon mythology in the show. Demons are inherently selfish, so it makes sense that one would do anything within his power to serve his own interests. That’s where a lot of the tension in “The Devil You Know” comes from. I half expected Crowley to turn on Dean at every opportunity, but… it doesn’t happen. Well, it hasn’t happened, I should say.

Again, Crowley toys with Dean! We can’t deny that. He sends Dean into Brady’s office without the right information so Dean will genuinely screw up the negotiating, allowing Crowley to capture Brady. And this is where it got weird. I actually suspected that this was the con Crowley was pulling because it seemed too coincidental. In a clever bit of retconning, Brady turns out to have been Sam’s college buddy and a demon for most of that time. He is the one who introduced Sam to Jess and he was the demon who actually murdered her. (That’s a tad confusing, because I thought Azazel admitted to killing Jess? Well, I did call it a retcon.) Initially, I thought that introducing this was a little too last-minute for me. And then I was super confused by Dean actually taking Brady back to Sam! Like, Dean gets furious with Sam for trying to do anything to Brady, but YOU BROUGHT HIM HERE, DEAN. WHAT DID YOU EXPECT.

This is why I assumed this was a con. It fell together too perfectly. But I think it’s safe to say that this isn’t the case at all. Crowley seems to have genuinely tried to get the location of Pestilence in this episode, at great risk to his own life. I can’t find a hole in his story or a flaw in his motivations. Hell, even his little trick about spreading the rumor that he and Brady are lovers in league against Satan still keeps Crowley in the crosshairs of Lucifer and the other demons. SO… is this not a trick?

I mentioned in the video for this episode that this season’s tagline should be changed to MARK FEELS BAD FOR SAM WINCHESTER. Because this was just agonizing to watch, y’all. How conflicted must Sam have felt about Brady? On the one hand, Sam has been haunted by demons his entire life. Azazel, Ruby, Lilith, and now Brady. They’ve pushed his life in directions meant to break him and his spirit. And as horrible as it was to lose Jess, Brady still introduced them, and it’s clear that Sam still views his time with Jess as a good part of his life. So the test for him here is whether or not killing Brady will be worth it. If Brady is their only means of getting the location of Pestilence, killing Brady could damn the entire earth. Sam puts aside his need for closure for the whole world. THE WHOLE WORLD.

That’s not to say that I wasn’t happy that Sam eventually did get to kill Brady. I really do think that was an act of closure, for what it’s worth. If Brady was responsible for part of Sam’s despair, then killing him helps Sam move on. I actually thought that scene in the alley was visually meaningful, too, since we’ve got Dean in the background, looking over his younger brother silently. He knows that this is not his battle, so he stands back and lets it unfold. It’s a way to communicate Dean’s desire to start trusting Sam and stop viewing him as a child, you know? Sam has to take care of his own demons, literally speaking.

So, with the location of Pestilence, we’re ready to move to the next step in the plan, right? HAHAH HOW ABOUT THE NEXT TWO STEPS? Holy shit, the final scene in “The Devil You Know” is just unreal, and I’M SO EXCITED TO SEE WHAT’S GOING TO HAPPEN. Can we trust Crowley? Is his promise to return Bobby’s soul after using it for a spell real??? I actually don’t think Bobby is going to turn Crowley down, given how he’s felt about his own life the past year. We’re getting down to the end, and Bobby is just as desperate as the Winchesters. BUT??? IS THIS REAL LIFE???

The video for “The Devil You Know” can be downloaded here for $0.99.

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About Mark Oshiro

Perpetually unprepared since '09.
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