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One thing we could do is make a tally of each one's kills, but I think in the end it's going to be more about the prominence and widespread impact of the kill(s) than the number. Ancalagon was the mightiest of the dragons, but Glaurung's indirect "kills" are kind of more relevant to us since we're given a more detailed account of what he did. He might not have killed Túrin or Nienna directly, but his actions significantly contributed to their deaths. Gothmog killed 2 High Kings of the Noldor, Fëanor and Fingon. Mount Doom "killed" Gollum and the Ring, which ushered the end of an age. Eowyn killed the Witch King, an act that most people then probably thought impossible, not to mention it crippled Sauron's forces and psychological edge somewhat. Gandalf...is a lot of things, but I'm personally not as ready to associate deadly with him as with the others on the list. I will unabashedly admit that I cannot remember who Forweg was.
Based on this, it's Glaurung, Gothmog, and Mount Doom for me (in no particular order - at least for now). More thoughts when I wake up.
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