It looks like the British Men of Letters are teaming up with Mary and Castiel, or at the very least, offering up some advice on how to get Sam and Dean out of prison. Though, they look pretty smug. Anyone smell a double cross?
Sam must be pondering how he and Dean could have been captured. After all, the brothers have fought demons, Lucifer, Leviathan, and even the Darkness. Looks like he’ll just wait to be escorted to his cell.
With Sam and Dean locked up, that means Mary and Castiel are taking the lead. And Castiel should be thankful he doesn’t have to partner with Crowley anymore. Wonder what Mary’s corresponding “Agent” name will be?
Guns are down, so that's good. Sam and Dean must be asking about the president and if the Secret Service know if something weird has been going on with the president.
It looks like the Secret Service have their guns drawn. But what is Dean looking at from behind? Something more dangerous? Perhaps a President Lucifer?
When Lucifer decides he has no plan and no rules to follow, Crowley might be worried that Lucifer is going to come after him next. He doesn't look too pleased with his current conversation, so he hasn't found a way to take down the rogue villain.
Why do they call this place The Empty? It's full. It's full of sorrow and despair playing over and over again of angels and demons dreaming about their regrets. Forever.