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Ray Sutton (David Gallagher)
We loved him because: Who wouldn't love Simon Camden? Ray, a werewolf, was quite a trooper. Stefan and Klaus murdered his friends, then tortured him in a bar full of compelled patrons until Ray finally spilled the location of his other wolf pals.
We lost him because: Klaus killed Ray and turned him into a hybrid, but the transformations was pretty ugly. Bleeding-from-the-eyes ugly. Ray went all rabid and found Damon in the woods, but just as he was about to go in for the kill, Stefan ripped his heart out, proving that he still loves his big bro. Awww.