Fool me once, shame on you. Fool me twice...
After the loss of Mary Winchester, the hunters gather to say their goodbyes but the time for grieving is short. With Jack still out there, Bobby refuses to sit around and plans on doing everything he can to track the Nephilim down. In his determination to save him, Castiel reaches out to heaven and meets with Duma. It's then that he tells her everything that has happened and asks for her help finding Jack. Duma agrees to help but after finding Jack, she has her own plans to manipulate the most powerful person in the universe or the good of heaven. Back at the bunker, Dean has a plan that Sam doesn't like one bit. He plans on luring Jack into the archangel box and trapping him there forever; the catch is that he needs Sam to lie to Jack to make it happen. Not being a heartless monster – Sam is torn. He knows that Jack is dangerous but can he live with the guilt of condemning Jack to a waking death, trapped inside of a box for the rest of eternity? It's either that or leave the most powerful being in existence without a conscious to do as he pleases.
More of strong setup than a story unto itself, Jack in the Box's crawling pace does little to drive the plot of season fourteen towards an exciting conclusion. To start the episode with Mary Winchester's eulogy was a nice touch and showed that her life impacted people around her besides her sons. Where that goes off the rails is Bobby's dramatic entrance in killing the wraith and then serving as the voice that thinks that Jack needs to be put down. After that moment, Bobby vanishes from the story in the search of answers for Jack. This has become a pattern for Supernatural this season, having characters make a big entrance only for them to be almost entirely forgotten. Remember when Ketch showed up in a video several months ago? After that, things improved quite a bit over the course of Jack in the Box as Sam and Dean struggled to determine what they should do next. Dean's logic was sound as he now sees Jack as any other monster and something that must be put down. Castiel wants to do everything in his power to save his son from his current path and Sam is caught in the middle. Whatever happens next week in the season finale, it's a safe guess that Sam will play an important part in it.
As exciting as the final moments of Jack in the Box were, most of the middle with Jack and Duma didn't have the intended impact. Jack visit to Professor Tate was interesting but turning him into a pillar of salt didn't do anything that we haven't seen before. It's been established again and again that Jack has lost his soul. He turned his pet snake into dust, burned Nick from the inside out and kill Mary. Having him kill the professor and the pastor didn't top that in any way and only felt weak by comparison. The exciting part was that Jack was able to easily create more angels and called back to what heaven and Naomi originally planned when Jack was discovered.
Overall, Jack in the Box was an average episode of Supernatural that hopefully leads us to an exciting conclusion. What it established is that there may be nothing that can truly end Jack's life – he might be more powerful than Amara. We'll see what the Winchesters do in next week's season finale, Moriah.