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The dragon who destroyed Gondolin vs. the man who attacked Valinor.
This is a difficult one.
However, Glaurung's actions were done out of spite and malice, whereas Ar-Pharazon's were done out of hubris. I'll have to side with the purer evil on this one.
++Glaurung
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Even as fog continues to lie in the valleys, so does ancient sin cling to the low places, the depression in the world consciousness.
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