Quote:
Originally Posted by Legate of Amon Lanc
Effectively, any arguments especailly in his, Glaurung's or the Mouth's favor might make me decide.
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I would say that Ted Sandyman does not seem particularly selfish to me. Close-minded before Frodo leaves the Shire and drunk with power afterwards, maybe, but I don't know that he best fits malicious.
The Mouth of Sauron could definitely be seen as malicious, but is limited to what his master commands. He does not have a name nor, it seems, much of a sense of self (beyond apparently desiring to be Lord of Isengard), so I don't know that he could achieve as much maliciousness as possible.
Glaurung, on the other hand, is about as malicious as they come. He had the opportunity to kill Turin, but instead played games with him. He also, discovering Nienor's availability, actively sought her out to, again, play malicious games with Turin and Nienor. He, destroyer of armies, had no need of this underhanded trickery, so the fact that he used it indicates that he enjoyed it - malicious to his heart.
So, while all three are good candidates, for me, Glaurung is by far the most malicious.