Well the Winchesters usually kill the big demons because I am dealing with heaven problems but I would have to say personally Lilith because she was trying to break Lucifer out of hell I didn't get to kill her though my friend Sam did.
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RandomHello Sam said I should do this well I am recovering from Rowena spell so this book while be about me I don't really understand this website so please bare with me anyways I hope you enjoy.