Crowley is certainly the most unlikely member of the team, but he again manages to deliver. Forget the joy he brings Bobby. His info about Pestilence is good as is his trick to find Death's location. Still, his behavior is a bit strange when taking Dean to find Death. His hint about getting some pizza is the clue that he and Death covertly arranged for Dean to come to him. Interesting too that it had to be Dean but I assume that is the case so that death could get assurances that he wouldn't stop Sam. How else would Death know about about Sam's plan? Crowley is the only link I see, especially the slick way the sickle is returned. A bargain was made. That makes me wonder what Crowley is asking for in return.
Then there are the captains of Team Freewill themselves. These are not good times for the Winchesters. Both are trying to plug on with calmer heads, but the burdens they carry underneath are still too raw to share openly. They both know, as well as Bobby and Castiel, that this is all going to end very badly for them. They say it only with troubled expressions though. They find themselves with two grave predicaments, stopping the Croatoan virus from distribution and finding Death. Sam takes the lead on one, Dean the other. As the time comes for them to part, their weariness over the tasks ahead says it all.
“Alright, well, good luck stopping the whole Zombie Apocalypse.”
“Yeah, good luck killing Death.”
When Sam reminiscences about the good ole days when they only had to hunt Wendigos, that reminds us just how much these two have taken on since season one. It’s stunning.
Yes, Dean has a right to be really upset when he first hears of Sam's plan. He knows what the consequences mean. Its suicide or worse for his brother, but no one else can do it. Sure, it also means that Dean isn't ready to make the choice of the world over his brother, but he’s strong armed into it anyway by Death. By the end scene he’s actually contemplating what could happen if caught lying to Death. Now we're left to wonder if he'll make good on his promise when the time comes. I'm also wondering how he'll live with himself if he does watch Sam take on that horrible fate. It's a no-win for him as well.