Supernatural Season 4, Episode 16 recap: Dean tortures a demon

In one of the saddest episodes of Supernatural Season 4, Dean has to torture a demon for the angels. Meanwhile, Sam straddles the line between good and evil.

Supernatural Season 4, Episode 16 sees Dean have to torture a demon. And it’s not just any demon. He tortures the demon that taught him everything he knows about torture. The student attempts to become the master, but it’s not going to be that easy.

In an episode that had us on the edges of our seats and ending in a heartbreaking way, we got to see that angels aren’t all united. There’s a gray to good and bad. Here’s a look at everything that happened in “On the Head of a Pin.”

Dean is summoned

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Opening with Castiel saying goodbye to his “sister” and then Dean and Sam driving from Pamela’s funeral, the episode quickly gets into the main storyline. Uriel and Castiel need information about how demons have killed seven angels so far. Remember they’d captured Alastair in the last episode and now they need Dean to torture the demon for answers.

Of course, Dean doesn’t want to but this isn’t a request. The angels take Dean against his will to an empty wawrehouse, where Alastair is bound in a devil’s trap. When Dean tries to leave, Uriel prevents him. it’s clear that Dean doesn’t have a choice.

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Throughout the torture session, Alastair taunts Dean with the knowledge that John never broke. Dean is the weaker of the two Winchesters. Despite being tortured and in pain, Alastair continues to taunt Dean.

While this happens, Dean doesn’t realize that a water valve moves on its own and water starts dripping onto the devil’s trap. It continues to drip water, breaking the trap. But this doesn’t happen until Alastair gets to impart some wisdom on Dean. When Dean started torturing people, he broke the very first seal.

Once the devil’s trap is broken, Alastair gets free and starts beating Dean. Castiel is the one to step in and save Dean, stabbing Alastair in the shoulder. When Alastair pins Castiel to a hook, he uses an incantation that threatens to send Castiel back to Heaven.

Ruby pushes Sam further

Meanwhile, Ruby turns up at the motel to see Sam. She doesn’t get what the problem is about the angels taking Dean. It means Sam can become strong enough to get the job done.

Ruby scrys with a map and fire to find a way to locate Dean. That’s when Sam says he “needs it,” and Ruby cuts her arm to allow Sam to drink her blood.

Sam gets to Dean’s location just in time. He sees Alastair start to send Castiel back to Heaven and uses his own powers to pin Alastair down. All he wants is to know who is killing the angels.

Alastair doesn’t know. In fact, it’s not demons that are killing angels, and Lilith isn’t going to stop at seven. With that knowledge, Sam kills Alastair with his powers. All Castiel can do is look in shock.

Castiel starts to doubt his orders

For the first time ever, Castiel begins to question the orders he’s given. Anna appears to hint that the orders may not have come from God. She’s there if he ever wants to work with her and then she disappears.

It’s not until the end that Castiel learns the full truth. Uriel received a revelation to stop hunting demons. Castiel starts to wonder if God is punishing them or if it’s even God. After another visit from Anna, who he admits to about considering disobedience, Castiel visits the warehouse again.

He realizes how the devil’s trap broke and Uriel shows back up. Sure enough, it was Uriel who had caused the water valve to open. He wanted Alastair to kill Dean and escape. He’s angry at God for creating humans and wants to raise Lucifer to get rid of them all.

This is also when we learn that angel blades exist and only angels can wield them to kill angels. As it looks like Uriel will kill Castiel and believes there is no God, Anna turns up with her own blade and kills Uriel.

Dean refuses to fight

At the very end, Castiel goes to see Dean in the hospital, sharing the news that Uriel was a traitor. What Dean wants to know is whether he really was the first seal.

Castiel confirms the truth, sharing that they’d tried to break Dean out of Hell earlier but was too late. Only a righteous man could start it and Dean is now the only person who can finish it. However, Dean isn’t going to do it, claiming he’s not strong enough. It’s time for Castiel to find someone else.

What did you think of Uriel’s betrayal? What were your thoughts about Alastair’s statement of Dean being the one to start it all? Share your thoughts in the comments below.

Supernatural airs Thursdays at 8/7c on The CW.