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When Cas and Dean narrowly escape from the Empty, it's abundantly clear their freedom is marred with tragedy. The angel reveals he's been cursed by the vengeful Shadow, and is now becoming a Prince of Hell. Urging Dean to spend time with Cas on his terf at Needham Asylum, Sam hopes the change in setting will allow his brother to gather useful intel leading to a solution. Dean must reprise his infamous role as Alistair's star pupil if he is to gain Cas's trust and continue searching for a means of saving him.
Making an unannounced trip to the asylum, Sam confirms that Dean's method acting is no longer a reluctant performance, but a full blown descent into darkness. He recruits Jack and Rowena for a critical "all hands on deck" situation. When the plan backfires spectacularly, they're forced into making a series of swift, unfathomable choices to avoid losing Dean and Cas forever. The dark ingenuity will require extreme violations of free will and the consequences of the cure might be worse than the curse itself.