Suggested by iKnowledge Sam has returned once more. Randall Flagg is one of those characters who has a lot of vague cosmic abilities but rarely actually does things. Occasionally he does have some physical feats though like surviving a fatal gun wound and catching a bullet. The guy is definitely pretty tough, but I’d say that this is one demonic threat that Sam can overcome. His own abilities are quite versatile and potent. I don’t believe Randall will be able to keep up. Sam Winchester wins.
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You maybe underestimating Randall Flagg, for he’s a Stephen King villain so evil he makes King Joffrey look like BJ from Barney and Friends, and Percy Wetmore, for all his punchability, a Buddhist Arhat (One who has achieved Enlightenment) by comparison. It would be a fight for the ages among Fantasy/Horror fans, truth be told. It took one of Flagg’s former trusted men to take him down.
He is definitely super evil so I’m with you there. Part of what makes him dangerous is how he corrupts everyone. I don’t think it will be that useful against Sam though since he has even resisted Lucifer in the past