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Zach Salvatore (Chris William Martin)
We loved him because: "Blood only runs so deep when you're related to vampires." Zach was related to Stefan and Damon -- we're not sure how, exactly, but they were close enough that he lived in their house and knew the "family secret." Despite his family loyalty, he had a good head on his shoulders -- and a good crop of vervain growing in the basement.
We lost him because: Remember when Damon was a bad guy? Zach helped Stefan lock Damon in the basement, effectively starving him for days. A hungry Damon is a mean Damon, and when he got out of the basement and tried to have Caroline for dinner, Zach got in his way. Damon snapped his neck and later, used his absence to infiltrate the council.