Don't fear the reaper.
As Chuck was the man behind the curtain pulling the strings all along, the plan is in pieces and Jack is a bomb of divine energy waiting to go off. The Winchesters and Castiel are running out of time with no way to contain the destruction when suddenly Billie appears. They explain how the plan was doomed to failure and she is none too pleased. She sends Jack away to the Empty, unsure if he or the Empty will survive the blast. Besides coming to see if the plan succeeded, Billie is there for the book on Chuck that Sam stole and mentions that she will bring Jack back for the book. With no options and no guarantees they hand the book over who reads the latest changes to the book's story. Something hits her like a revelation and she quickly pulls Jack from the clutches of the Empty. With Jack back and safe, Billie changes the terms of the deal and has a new plan for Jack but Dean won't let her taken him and manages to take her scythe and wound Billie before she can escape. Elsewhere, Charlie Bradbury is eating breakfast with her partner, Stevie. It's a great morning with plans for a fun date involving a shifter hideout when suddenly Stevie disappears without a trace. Sam and Dean answer Charlie's call and come to investigate and reach one conclusion – Death is wrapping up loose ends of removing everyone that came back or crossed over. People they care about are going to disappear unless they do something and fast; leaving Sam to protect everyone he saved from the apocalypse world while Dean and Castiel have plans to reap the reaper and end it.
As a send off to multiple, long running characters on Supernatural, Despair had its share of highs and lows. Picking up immediately from the events of last week, Jack's condition worsening gave the episode a true sense of...despair (had to do it) and that all hope was lost. This momentum was immediately dismantled when Jack was brought back moments later by Billie. Picking up from there, Dean attacking Billie brought true excitement and finally set everything up for the confrontation with Death...again. For all of the good will that Despair built up early on, the pacing took a hit by introducing the storyline with Charlie and having Stevie disappear. Ultimately, the plot gave Sam a reason to feel as broken as Dean by the end of the episode but if that is the last we'll see of some characters (I doubt it), that was easily Supernatural's weakest send off – maybe ever. Adding to that, it wasn't Billie that was making all of this happen – so it didn't make the battle with her feel as impactful as it needed to be. In the end, Billie was barely a character in Supernatural and always just an obstacle or foil to further the plot whenever it was convenient. Even when confronted by Sam about her plan to assume power, Billie barely acknowledged it and just kept going. Her plan was to become the next god, but she didn't care that it didn't happen and all of her efforts failed. As much as Despair showed the importance of some characters, it showed just how unimportant others were. As a fan of the show since the beginning, that made me kinda sad.
Eleven seasons ago, Supernatural introduced a character that would become one of the defining aspects of Supernatural – an angel named Castiel. With a gravely voice and unmatched condescension, he pulled Dean from perdition and would go on to become a series regular fans have come to adore. Played by Misha Collins, Castiel sacrificed himself to save Dean. The moment was pure and done for love as he was embraced by the empty and taken along with Billie. Dean is broken, I'm broken, you're probably broken too. With Castiel's goodbye, Supernatural has never felt more like it was ending than it did in that moment. Throughout the series, Collins played the character remarkably well and Castiel was a character that changed, grew and finally understood what it is to be happy. How the Winchesters go on without him after all this time?
For all of Despair's faults, they can't help but be overshadowed by the death of Castiel and how wonderfully acted and genuine that scene was. We've all seen the videos of the cast having fun together at cons and truly becoming friends. It felt like Misha Collins was saying goodbye to Jensen Ackles after all of this time.
We'll see how the Winchesters carry on without him in Supernatural's second last episode, Inherit the Earth.